drugbank_ erythromycin (db00199)

8/12/2019 DrugBank_ Erythromycin (DB00199)

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3/3/2014 DrugBank: Erythromycin (DB00199)

http://www.drugbank.ca/drugs/DB00199 1/18

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Identification

Name Erythromycin

Accession Number DB00199 (APRD00953)

Type small molecule

Groups approved

Descriptio n Erythromycin is a macrolide antibiot ic produced b y Streptomyces erythreus. It inhibits bacterial protein synthesis bybinding to bacterial 50S ribosomal subunits; binding inhibits peptidyl transferase activity and interferes withtranslocation of amino acids during translation and assembly of proteins. Erythromycin may be bacteriostatic or bactericidal depending on the organism and drug concentration.

Structure

(http://structures.wishartlab.com/molecules/DB00199/image.png)

Synonyms

Synonym Language Code

3''-O-demethylerythromycin Not Available Not Available

Abomacetin Not Availab le Not Availab le

Erythromycin A Not Available Not Available

Erythromycin C Not Available Not Available

Salts Not Available

Brand names

Name Company

Akne-Mycin Not Availab le

Eryc Not Available

Erygel Not Available

Home (/) Browse (/drugs) Search (/drugs/DB00199) Downloads (/downloads) About (/about)

Help (/ doc ument at ion) Tools ( ht tp: // www. wishart lab. com/ web_servers ) Cont ac t Us ( /c ont ac t)

Identification Taxonom y Pharm acology ADMET Pharm acoeconom ics Properties Spectra References Interactions 0 Com ments

targets (3) (/drugs/DB00199#targets) enzymes (5) (/drugs/DB00199#enzymes ) transporters (4) (/drugs/DB00199#transporters)

Biointeractions (15) (/dru gs/DB00199/biointeracti ons)

MOL (/drugs/DB00199.mol) SDF (/drugs/DB00199.sdf) PDB (/drugs/DB00199.pdb) SMILES (/drugs/DB00199.smiles)

InChI (/drugs/DB00199.inchi) View 2D Structure (/drugs/DB00199/structure) View 3D Structure (/drugs/DB00199/structure?dim=3d)

10 records per page Search

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http://structures.wishartlab.com/molecules/DB00199/image.pnghttp://www.drugbank.ca/http://www.drugbank.ca/drugshttp://www.drugbank.ca/drugs/DB00199http://www.drugbank.ca/downloadshttp://www.drugbank.ca/abouthttp://www.drugbank.ca/drugs/DB00199/structure?dim=3dhttp://www.drugbank.ca/drugs/DB00199/structurehttp://www.drugbank.ca/drugs/DB00199.inchihttp://www.drugbank.ca/drugs/DB00199.smileshttp://www.drugbank.ca/drugs/DB00199.pdbhttp://www.drugbank.ca/drugs/DB00199.sdfhttp://www.drugbank.ca/drugs/DB00199.molhttp://www.drugbank.ca/drugs/DB00199/biointeractionshttp://www.drugbank.ca/contacthttp://www.wishartlab.com/web_servershttp://www.drugbank.ca/documentationhttp://www.drugbank.ca/abouthttp://www.drugbank.ca/downloadshttp://www.drugbank.ca/drugs/DB00199http://www.drugbank.ca/drugshttp://www.drugbank.ca/http://structures.wishartlab.com/molecules/DB00199/image.pnghttp://v3.drugbank.ca/http://www.drugbank.ca/unearth/q/advanced_search


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Ilosone Not Available

Staticin Not Available

T-stat Not Available

Brand mixtures

Brand Name Ingredients

Sans-Acne Solution Alcohol Anhydrous + ErythromycinStaticin Lot Alcohol Anhydrous + Erythromycin + Laureth 4

Stievamycin Forte Gel Erythromycin + Tretinoin

Stievamycin Gel Erythromycin + Tretinoin

T-Stat Lot Alcohol Anhydrous + Erythromycin

T-Stat Pad-Lot Alcohol Anhydrous + Erythromycin

Categories Gastrointestinal Agents (/mesh/gastrointestinal-agents) Anti-Bacterial Agents (/mesh/anti-bacterial-agents)Protein Synthesis Inhibitors (/mesh/protein-synthesis-inhibitors)

CAS number 114-07-8

Weight Average: 733.9268Monoisotopic: 733.461241235

Chemical Formula C H NO

InChI Key InChIKey=ULGZDMOVFRHVEP-RWJQBGPGSA-N

InChI InChI=1S/C37H67NO13/c1-14-25-37(10,45)30(41)20(4)27(39)18(2)16-35(8,44)32(51-34-28(40)24(38(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-36(9,46-13)31(42)23(7)48-26/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1Plain Text (/drugs/DB00199.inchi)

IUPAC Name (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione

SMILES CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)OPlain Text (/drugs/DB00199.smiles )

Mass Spec Not Available

Taxonomy

Kingdom Organic Compounds

Superclass Phenylpropanoids and Polyketides

Class Macrolides and Analogues

Subclass Not Available

Direct parent Macrolides and Analogues

Alternative pare nts Dihexoses; O-glycosyl Compounds; Amino Sugars; Oxanes; Tertiary Alcohols; Tertiary Amines; Ketones; 1,2-Diols;Secondary Alcohols; Carboxylic Acid Esters; Polyamines; Acetals

Substituents disaccharide; amino sugar; oxane; saccharide; tertiary alcohol; tertiary amine; 1,2-diol; secondary alcohol; carboxylicacid ester; ketone; polyol; acetal; ether; polyamine; carboxylic acid derivative; carbonyl group; amine; alcohol;organonitrogen compound

Classificationdescription

This compound belongs to the macrolides and analogues. These are organic compounds containing a lactone ring of atleast twelve members.

Pharmacology

Indication For use in the treatment of infections caused by susceptible strains of microorganisms in the following diseases:respiratory tract infections (upper and lower) of mild to moderate degree, pertussis (whooping cough), as adjunct toantitoxin in infections due to Corynebacterium diphtheriae , in the treatment of infections due to Corynebacteriumminutissimum , intestinal amebiasis caused by Entamoeba histolytica , acute pelvic inflammatory disease caused byNeisseria gonorrhoeae , skin and soft tissue infections of mild to moderate severity caused by Streptococcus pyogenes




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http://www.drugbank.ca/drugs/DB00199.smileshttp://www.drugbank.ca/drugs/DB00199.inchihttp://www.drugbank.ca/mesh/protein-synthesis-inhibitorshttp://www.drugbank.ca/mesh/anti-bacterial-agentshttp://www.drugbank.ca/mesh/gastrointestinal-agents


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, ,trachomatis , nongonococcal urethritis caused by Ureaplasma urealyticum , and Legionnaires' disease caused byLegionella pneumophila .

Pharmacodynamics Erythromycin is produced by a strain of Streptomyces erythraeus and belongs to the macrolide group of antibiotics. After absorption, erythromycin diffuses readily into most body fluids. In the absence of meningeal inflammation, lowconcentrations are normally achieved in the spinal fluid, but the passage of the drug across the blood-brain barrier increases in meningitis. Erythromycin is excreted in breast milk. The drug crosses the placental barrier with fetal serumdrug levels reaching 5 - 20% of maternal serum concentrations. Erythromycin is not removed by peritoneal dialysis or hemodialysis.

Me chanism of action Erythromycin acts by penetrating the bacterial cell membrane and reversibly binding to the 50 S subunit of bacterialribosomes or near the P or donor site so that binding of tRNA (transfer RNA) to the donor site is blocked.Translocation of peptides from the A or acceptor site to the P or donor site is prevented, and subsequent proteinsynthesis is inhibited. Erythromycin is effective only against actively dividing organisms. The exact mechanism by whicherythmromycin reduces lesions of acne vulgaris is not fully known: however, the effect appears to be due in part to theantibacterial activity of the drug.

Absorption Orally administered erythromycin base and its salts are readily absorbed in the microbiologically active form. Topicalapplication of the ophthalmic ointment to the eye may result in absorption into the cornea and aqueous humor.

Volume of distribution Not Available

Protein binding Erythromycin is largely bound to plasma proteins, ranging from 75 - 95% binding depending on the form.

Metabolism Hepatic. Extensively metabolized - after oral administration, less than 5% of the administered dose can be recoveredin the active form in the urine. Erythromycin is par tially metabolized by CYP3A4 resulting in numerous druginteractions.

Substrate Enzymes

ErythromycinCytochrome P450 3A4(/bio_entities/BE0002638)

norerythromycin(/metabolites/DBMET00365)

Details (/reactions/367)

Route of elimination Not Available

Half life 0.8 - 3 hours

Clearance Not Available

Toxicity Symptoms of overdose include diarrhea, nausea, stomach cramps, and vomiting.

Affected organisms Enteric bacteria and other eubacteria

Pathways Pathway Category SMPDB ID

Erythromycin ActionPathway

Drugaction

SMP00250 (http://www.smpdb.ca/view/SMP00250?reset=true&highlight[DB00199]=true)

SNP Me diated Effects Not Available

SNP Me diatedAdverse DrugReactions

Not Available

ADMETPredicted ADMETfeatures

Property Value Probability

Human Intestinal Absorption + 0.5114

Blood Brain Barrier - 0.9889

Caco-2 permeable - 0.8957

P-glycoprotein substrate Substrate 0.8098

P-glycoprotein inhibitor I Inhibitor 0.8564

P-glycoprotein inhibitor II Non-inhibitor 0.5963

Renal organic cation transporter Non-inhibitor 0.9222

CYP450 2C9 substrate Non-substrate 0.7898

CYP450 2D6 substrate Non-substrate 0.9225

CYP450 3A4 substrate Substrate 0.6528

CYP450 1A2 substrate Non-inhibitor 0.9045
http://www.drugbank.ca/metabolites/DBMET00365http://www.drugbank.ca/bio_entities/BE0002638http://www.smpdb.ca/view/SMP00250?reset=true&highlight[DB00199]=truehttp://www.drugbank.ca/reactions/367


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Prepak Systems Inc. (http://www.prepaksys.com)Prescription Dispensing Service Inc.Proter SPAQualitest (http://www.worldoftest.com)Rebel Distributors Corp. (http://www.rebelrx.com)Redpharm DrugRemedy Repack (http://www.remedyrepack.com)Resource Optimization and Innovation LLCSandhills Packaging Inc. (http://www.sandhillspackaging.com)Sandoz (http://www.sandoz.ca)Sanofi-Aventis Inc. (http://www.sanofi-aventis.com)Seneca Pharmaceuticals Inc.Southwood Pharmaceuticals (http://www.southwoodhealthcare.com)St Mary's Medical Park PharmacyStat Rx Usa (http://statrxusa.exporterus.com)Tolmar Inc. (http://www.tolmar.com)Tya PharmaceuticalsValeant Ltd. (http://www.valeant.com)Veratex Corp.Wa Butler Co.Wilson Ophthalmic Corp. (http://www.hilco.com)Wockhardt Ltd. (http://www.wockhardtin.com)X-Gen Pharmaceuticals (http://www.x-gen.us)

Dosage forms

Form Route Strength

Capsule, coated Oral

Liquid Dental

Liquid Oral

Ointment Ophthalmic

Powder Intravenous

Powder Oral

Powder, for solution Intravenous

Powder, for solution Oral

Powder, for suspension Oral

Suspension Oral

Prices

Unit description Cost Unit

Akne-mycin 2% ointment 3.96USD g

Apo-Erythro Base 250 m g Tablet 0.19USD tablet

Apo-Erythro E-C 250 mg Capsule (Enteric-Coated Pell et) 0.41USD capsul e

Apo-Erythro E-C 333 mg Capsule (Enteric-Coated Pell et) 0.45USD capsul e

Apo-Erythro-Es 600 m g Tablet 0.35USD tablet

Apo-Erythro-S 250 mg Table t 0.22USD tablet

Apo-Erythro-S 500 mg Table t 0.57USD tablet

Benzamycin 5-3% Gel 46.6 gm Jar 236.63USD jar

Benzamycin gel 4.95USD g

BenzamycinPak 60 5-3% Packets (2 Box Contains 60 Packets) 142.45USD packet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents Not Available

Properties


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State solid

ExperimentalProperties

Property Value Source

melting point 191 C PhysProp

water solubility 2000mg/L at 28C European Pharmacopeia

logP 3.06 MCFARLAND,JW ET AL. (1997)

Caco2 permeability -5.43 ADME Research, USCD

pKa 8.88 (at 25 C) MCFARLAND,JW ET AL. (1997)

Predicted Properties Property Value Source

water solubility 4.59e-01 g/l ALOGPS (http://www.vcclab.org/lab/alogps/)

logP 2.37 ALOGPS (http://www.vcclab.org/lab/alogps/)

logP 2.6 ChemAxon(http://www.chemaxon.com/products/calculator-plugins/property-predictors/#logp_logd)

logS -3.2 ALOGPS (http://www.vcclab.org/lab/alogps/)

pKa (strongest acidic) 12.44 ChemAxon(http://www.chemaxon.com/products/calculator-

plugins/property-predictors/#pka)

pKa (strongest basic) 8.38 ChemAxon(http://www.chemaxon.com/products/calculator-plugins/property-predictors/#pka)

physiological charge 1 ChemAxon(http://www.chemaxon.com/products/calculator-plugins/property-predictors/#pka)

hydrogen acceptor count 13 ChemAxon(http://www.chemaxon.com/products/calculator-plugins/property-calculations/#h_bond)

hydrogen donor count 5 ChemAxon

(http://www.chemaxon.com/products/calculator-plugins/property-calculations/#h_bond)

polar surface area 193.91 ChemAxon(http://www.chemaxon.com/products/calculator-plugins/property-calculations/#topolgical_surface)

rotatable bond count 7 ChemAxon(http://www.chemaxon.com/products/calculator-plugins/property-calculations/#topology_analysis)

refractivity 186.04 ChemAxon(http://www.chemaxon.com/products/calculator-plugins/property-calculations/#refractivity)

polarizability 78.21 ChemAxon(http://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarization)

number of rings 3 ChemAxon(http://www.chemaxon.com/products/calculator-plugins/property-calculations/#topology_analysis)

bioavailability 0 ChemAxon(http://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarization)

rule of five No ChemAxon(http://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarization)

Ghose filter No ChemAxon(http://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarization)
http://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarizationhttp://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarizationhttp://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarizationhttp://www.chemaxon.com/products/calculator-plugins/property-calculations/#topology_analysishttp://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarizationhttp://www.chemaxon.com/products/calculator-plugins/property-calculations/#refractivityhttp://www.chemaxon.com/products/calculator-plugins/property-calculations/#topology_analysishttp://www.chemaxon.com/products/calculator-plugins/property-calculations/#topolgical_surfacehttp://www.chemaxon.com/products/calculator-plugins/property-calculations/#h_bondhttp://www.chemaxon.com/products/calculator-plugins/property-calculations/#h_bondhttp://www.chemaxon.com/products/calculator-plugins/property-predictors/#pkahttp://www.chemaxon.com/products/calculator-plugins/property-predictors/#pkahttp://www.chemaxon.com/products/calculator-plugins/property-predictors/#pkahttp://www.vcclab.org/lab/alogps/http://www.chemaxon.com/products/calculator-plugins/property-predictors/#logp_logdhttp://www.vcclab.org/lab/alogps/http://www.vcclab.org/lab/alogps/


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Veber's rule No ChemAxon(http://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarization)

MDDR-like rule Yes ChemAxon(http://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarization)

Spectra

Spectra Not Available

References

Synthesis Refe rence Takehiro Amano, Masami Goi, Kazuto Sekiuchi, Tomomichi Yoshida, Masahiro Hasegawa, Process for preparingerythromycin A oxime or a salt thereof. U.S. Patent US5274085, issued October , 1966.

US5274085 (https://www.google.com/?tbm=pts#q=5274085&tbm=pts)

General Reference 1. Kanazawa S, Ohkubo T, Sugawara K: The effects of grapefruit juice on the pharmacokinetics of erythromycin.Eur J Clin Pharmacol. 2001 Jan-Feb;56(11):799-803. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/11294369)

2. Ogwal S, Xide TU: Bioavailability and stability of erythromycin delayed release tablets. Afr Health Sci. 2001Dec;1(2):90-6. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/12789122)

3. Okudaira T, Kotegawa T, Imai H, Tsutsumi K, Nakano S, Ohashi K: Effect of the treatment per iod witherythromycin on cytochrome P450 3A activity in humans. J Clin Pharmacol. 2007 Jul;47(7):871-6. Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/17585116)

External Links Resource Link

KEGG Drug D00140 (http://www.genome.jp/dbget-bin/www_bget?drug:D00140)

KEGG Compound C01912 (http://www.genome.jp/dbget-bin/www_bget?cpd:C01912)

PubChemCompound

12560 (http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=12560)

PubChemSubstance

46508487 (http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46508487)

ChemSpider 12041 (http://www.chemspider.com/Chemical-Structure.12041.html)

ChEBI 48923 (http://www.ebi.ac.uk/chebi/searchId.do?chebiId=48923)ChEMBL CHEMBL532 (http://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL532)

TherapeuticTargets Database

DAP000111 (http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DAP000111)

PharmGKB PA449493 (http://www.pharmgkb.org/drug/PA449493)

HET ERY (http://www.ebi.ac.uk/msd-srv/chempdb/cgi-bin/cgi.pl?FUNCTION=getByCode&CODE=ERY)

Drug ProductDatabase

2237041 (http://205.193.93.51/dpdonline/searchRequest.do?din=2237041)

RxList http://www.rxlist.com/cgi/generic/erithrom.htm (http://www.rxlist.com/cgi/generic/erithrom.htm)

Drugs.com http://www.drugs.com/cdi/erythromycin-ointment.html (http://www.drugs.com/cdi/erythromycin-ointment.html)

PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/ery1163.shtml(http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/ery1163.shtml)

Wikipedia Erythromycin (http://en.wikipedia.org/wiki/Erythromycin)

ATC Codes D10AF02D DERMATOLOGICALS (/atc/D)D10 ANTI-ACNE PREPARATIONS (/atc/D10)D10A ANTI-ACNE PREPARATIONS FOR TOPICAL USE (/atc/D10A)D10AF Antiinfectives for treatment of acne (/atc/D10AF)

J01FA01J ANTIINFECTIVES FOR SYSTEMIC USE (/atc/J)J01 ANTIBACTERIALS FOR SYSTEMIC USE (/atc/J01)J01F MACROLIDES, LINCOSAMIDES AND STREPTOGRAMINS (/atc/J01F)J01FA Macrolides (/atc/J01FA)

S01AA17S SENSORY ORGANS /atc/S
http://www.drugbank.ca/atc/Shttp://www.drugbank.ca/atc/J01FAhttp://www.drugbank.ca/atc/J01Fhttp://www.drugbank.ca/atc/J01http://www.drugbank.ca/atc/Jhttp://www.drugbank.ca/atc/D10AFhttp://www.drugbank.ca/atc/D10Ahttp://www.drugbank.ca/atc/D10http://www.drugbank.ca/atc/Dhttp://en.wikipedia.org/wiki/Erythromycinhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/ery1163.shtmlhttp://www.drugs.com/cdi/erythromycin-ointment.htmlhttp://www.rxlist.com/cgi/generic/erithrom.htmhttp://205.193.93.51/dpdonline/searchRequest.do?din=2237041http://www.ebi.ac.uk/msd-srv/chempdb/cgi-bin/cgi.pl?FUNCTION=getByCode&CODE=ERYhttp://www.pharmgkb.org/drug/PA449493http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DAP000111http://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL532http://www.ebi.ac.uk/chebi/searchId.do?chebiId=48923http://www.chemspider.com/Chemical-Structure.12041.htmlhttp://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46508487http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=12560http://www.genome.jp/dbget-bin/www_bget?cpd:C01912http://www.genome.jp/dbget-bin/www_bget?drug:D00140http://www.ncbi.nlm.nih.gov/pubmed/17585116http://www.ncbi.nlm.nih.gov/pubmed/12789122http://www.ncbi.nlm.nih.gov/pubmed/11294369https://www.google.com/?tbm=pts#q=5274085&tbm=ptshttp://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarizationhttp://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarizationhttp://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarization


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S01 OPHTHALMOLOGICALS (/atc/S01)S01A ANTIINFECTIVES (/atc/S01A)S01AA Antibiotics (/atc/S01AA)

AHFS Code s 34:00.0008:12.12.0452:04.04

PDB Entrie s Not Available

FDA label show (/system/fda_labels/DB00199.pdf?1265922812)(149 KB)MSDS show (/system/msds/DB00199.pdf?1265922748)(73 KB)

Interactions

Drug Interactions Drug

Acenocoumarol(/drugs/DB01418)

The macrolide, erythromycin, may increase the anticoagulant effect of acenocoumarol.

Alfentanil (/drugs/DB00802) The macrolide, erythromycin, may increase the effect and toxicity of alfentanil.

Alprazolam(/drugs/DB00404)

The macrolide, erythromycin, may increase the effect of the benzodiazepine,alprazolam.

Aminophylline(/drugs/DB01223) The macrolide, erythromycin, may increase the effect and toxicity of the theophyllinederivative, aminophylline.

Amiodarone(/drugs/DB01118)

Increased risk of cardiotoxicity and arrhythmias

Anisindione(/drugs/DB01125)

The macrolide, erythromycin, may increase the anticoagulant effect of anisindione.

Aprepitant(/drugs/DB00673)

Erythromycin, a moderate CYP3A4 inhibitor, may increase the effect and toxicity of aprepitant.

Artemether (/drugs/DB06697)

Additive QTc-prolongation may occur. Concomitant therapy should be avoided.

Astemizole(/drugs/DB00637)


Atorvastatin(/drugs/DB01076)

The macrolide, erythromycin, may increase the toxicity of the statin, atorvastatin.

Avanafil (/drugs/DB06237) Co-administration with the moderate CYP3A4 inhibitor erythromycin resulted in anapproximate 3.6-fold increase in AUC0-inf and 2.0- fold increase in Cmax of avanafil.

Bendamustine(/drugs/DB06769)

Decreases metabolism, thus decreasing the effects of bendamustine.

Bretylium (/drugs/DB01158) Increased risk of cardiotoxicity and arryhthmias

Bromazepam(/drugs/DB01558)

Erythromcyin may increase the serum concentration of bromazepam by decreasing itsmetabolism. Consider alternate therapy or monitor for changes in the therapeutic and

adverse effects of bromazepam if erythromycin is initiated, discontinued or dosechanged. Dosage adjustments may be required.

Bromocriptine(/drugs/DB01200)

Erythromycin increases serum levels of bromocriptine

Buspirone(/drugs/DB00490)

The macrolide, erythromycin, may increase the effect and toxicity of buspirone.

Cabergoline(/drugs/DB00248)

Erythromycin increases serum levels and toxicity of cabergoline

Carbamazepine(/drugs/DB00564)

The macrolide, erythromycin, may increase the effect of carbamazepine.

Cerivastatin(/drugs/DB00439)

The macrolide, erythromycin, may increase the toxicity of the statin, cerivastatin.

Cilostazol (/drugs/DB01166) Erythromycin increases the effect of cilostazol

Cinacalcet(/drugs/DB01012)

The macrolide, erythromycin, may increase the serum concentration and toxicity of cinacalcet.

Cisapride (/drugs/DB00604) Increased risk of cardiotoxicity and arrhythmias
http://www.drugbank.ca/drugs/DB00604http://www.drugbank.ca/drugs/DB01012http://www.drugbank.ca/drugs/DB01166http://www.drugbank.ca/drugs/DB00439http://www.drugbank.ca/drugs/DB00564http://www.drugbank.ca/drugs/DB00248http://www.drugbank.ca/drugs/DB00490http://www.drugbank.ca/drugs/DB01200http://www.drugbank.ca/drugs/DB01558http://www.drugbank.ca/drugs/DB01158http://www.drugbank.ca/drugs/DB06769http://www.drugbank.ca/drugs/DB06237http://www.drugbank.ca/drugs/DB01076http://www.drugbank.ca/drugs/DB00637http://www.drugbank.ca/drugs/DB06697http://www.drugbank.ca/drugs/DB00673http://www.drugbank.ca/drugs/DB01125http://www.drugbank.ca/drugs/DB01118http://www.drugbank.ca/drugs/DB01223http://www.drugbank.ca/drugs/DB00404http://www.drugbank.ca/drugs/DB00802http://www.drugbank.ca/drugs/DB01418http://www.drugbank.ca/system/msds/DB00199.pdf?1265922748http://www.drugbank.ca/system/fda_labels/DB00199.pdf?1265922812http://www.drugbank.ca/atc/S01AAhttp://www.drugbank.ca/atc/S01Ahttp://www.drugbank.ca/atc/S01http://www.drugbank.ca/atc/S


10/18



Citalopram(/drugs/DB00215)

Possible serotoninergic syndrome with this combination

Clozapine(/drugs/DB00363)

Erythromycin increases the effect of clozapine

Colchicine(/drugs/DB01394)

Severe colchicine toxicity can occur

Cyclosporine(/drugs/DB00091)

The macrolide, erythromycin, may increase the effect of cyclosporine.

Diazepam(/drugs/DB00829)

The macrolide, erythromycin, may increase the effect of the benzodiazepine, diazepam.

Dicoumarol(/drugs/DB00266)

The macrolide, erythromycin, may increase the anticoagulant effect of dicumarol..

Digoxin (/drugs/DB00390) The macrolide, erythromycin, may increase the effect of digoxin in 10% of patients.

Dihydroergotamine(/drugs/DB00320)

Possible ergotism and severe ischemia with this combination

Disopyramide(/drugs/DB00280)


Docetaxel(/drugs/DB01248)

Erythromycin may increase the serum levels and toxicity of docetaxel.

Dofetilide (/drugs/DB00204) Increased risk of cardiotoxicity and arrhythmias

Dyphylline(/drugs/DB00651)

The macrolide, erythromycin, may increase the effect and toxicity of the theophyllinederivative, dyphylline.

Eletriptan (/drugs/DB00216) The macrolide, erythromycin, may increase the effect and toxicity of eletriptan.

Eltrombopag(/drugs/DB06210)

Affects hepatic CYP1A2 metabolism, increases Eltrombopag level or affect.

Eplerenone(/drugs/DB00700)

This CYP3A4 inhibitor increases the effect and toxicity of eplerenone

Ergonovine(/drugs/DB01253)


Ergotamine(/drugs/DB00696)


Erlotinib (/drugs/DB00530) This CYP3A4 inhibitor increases levels/toxicity of erlotinib

Everolimus(/drugs/DB01590)

The macrolide, erythromycin, may increase the serum concentration and toxicity of everolimus.

Felodipine(/drugs/DB01023)

Erythromycin increases the effect of felodipine

Fluoxetine(/drugs/DB00472)


Gefitinib (/drugs/DB00317) This CYP3A4 inhibitor increases levels/toxicity of gefitinib

Grepafloxacin(/drugs/DB00365)


Imatinib (/drugs/DB00619) The macrolide, erythromycin, may increase the serum concentration of imatinib.

Indacaterol(/drugs/DB05039)

Strong inhibitors of CYP3A4 may increase levels of indacaterol. Monitor closely for adverse events.

Itraconazole(/drugs/DB01167)

The macrolide, erythromycin, may increase the effect and toxicity of itraconazole.

Ivacaftor (/drugs/DB08820) Moderate CYP3A4 inhibitors may increase levels of ivacaftor. Consider dose reduction.

Levofloxacin(/drugs/DB01137)


Lincomycin(/drugs/DB01627)

Possible antagonism of action with this combination.

Lovastatin(/drugs/DB00227)

The macrolide, erythromycin, may increase the toxicity of the statin, lovastatin.
http://www.drugbank.ca/drugs/DB00227http://www.drugbank.ca/drugs/DB01627http://www.drugbank.ca/drugs/DB01137http://www.drugbank.ca/drugs/DB08820http://www.drugbank.ca/drugs/DB01167http://www.drugbank.ca/drugs/DB05039http://www.drugbank.ca/drugs/DB00619http://www.drugbank.ca/drugs/DB00365http://www.drugbank.ca/drugs/DB00317http://www.drugbank.ca/drugs/DB00472http://www.drugbank.ca/drugs/DB01023http://www.drugbank.ca/drugs/DB01590http://www.drugbank.ca/drugs/DB00530http://www.drugbank.ca/drugs/DB00696http://www.drugbank.ca/drugs/DB01253http://www.drugbank.ca/drugs/DB00700http://www.drugbank.ca/drugs/DB06210http://www.drugbank.ca/drugs/DB00216http://www.drugbank.ca/drugs/DB00651http://www.drugbank.ca/drugs/DB00204http://www.drugbank.ca/drugs/DB01248http://www.drugbank.ca/drugs/DB00280http://www.drugbank.ca/drugs/DB00320http://www.drugbank.ca/drugs/DB00390http://www.drugbank.ca/drugs/DB00266http://www.drugbank.ca/drugs/DB00829http://www.drugbank.ca/drugs/DB00091http://www.drugbank.ca/drugs/DB01394http://www.drugbank.ca/drugs/DB00363http://www.drugbank.ca/drugs/DB00215


11/18



Lumefantrine(/drugs/DB06708)

Additive QTc-prolongation may occur. Concomitant therapy should be avoided.

Mesoridazine(/drugs/DB00933)


Methylergometrine(/drugs/DB00353)


Methylprednisolone(/drugs/DB00959)

The macrolide, erythromycin, may increase the effect of corticosteroid,methylprednisolone.

Methysergide(/drugs/DB00247)


Midazolam(/drugs/DB00683)

The macrolide, erythromycin, may increase the effect of the benzodiazepine,midazolam.

Moxifloxacin(/drugs/DB00218)


Oxtriphylline(/drugs/DB01303)

The macrolide, erythromycin, may increase the effect and toxicity of the theophyllinederivative, oxtriphylline.

Pazopanib(/drugs/DB06589)

Affects CYP3A4 metabolism therefore will decrease levels or effect of pazopanib.Consider alternate therapy.

Pimozide (/drugs/DB01100) Increased risk of cardiotoxicity and arrhythmiasPitavastatin(/drugs/DB08860)

Erythromycin decreases metabolism of pitavastatin. Do not exceed 1 mg per day of pitavastatin or use alternative therapy.

Quetiapine(/drugs/DB01224)

The macrolide, erythromycin, may increase the effect and toxicity of quetiapine.

Quinidine (/drugs/DB00908) Increased risk of cardiotoxicity and arrhythmias

Quinidine barbiturate(/drugs/DB01346)


Quinupristin(/drugs/DB01369)

This combination presents an increased risk of toxicity

Ranolazine(/drugs/DB00243)

Increased levels of ranolazine - risk of toxicity

Repaglinide(/drugs/DB00912)

The macrolide, erythromycin, may increase the effect of repaglinide.

Rifabutin (/drugs/DB00615) The rifamycin, rifabutin, may decrease the effect of the macrolide, erythromycin.

Rifampicin(/drugs/DB01045)

The rifamycin, rifampin, may decrease the effect of the macrolide, erythromycin.

Ritonavir (/drugs/DB00503) Increased toxicity of both agents

Roflumilast(/drugs/DB01656)

Increases roflumilast levels.

Saxagliptin(/drugs/DB06335)

Erythromycin is an inhibitor of CYP3A4 which increases exposure of saxagliptin.Decrease dose of saxagliptin to 2.5 mg per day.

Sertraline(/drugs/DB01104)


Sibutramine(/drugs/DB01105)

Erythromycin increases the effect and toxicity of sibutramine

Sildenafil (/drugs/DB00203) The macrolide, erythromycin, may increase the effect and toxicity of sildenafil.

Silodosin (/drugs/DB06207) Erythromycin is a moderate inhibitor of CYP3A4 and inhibits P-glycoprotein thusincreasing the potential for adverse effects

Simvastatin(/drugs/DB00641)

The macrolide, erythromycin, may increase the toxicity of the statin, simvastatin.

Sirolimus (/drugs/DB00877) The macrolide, erythromycin, may increase the serum concentration of sirolimus.

Sotalol (/drugs/DB00489) Increased risk of cardiotoxicity and arrhythmias

Sparfloxacin(/drugs/DB01208)

http://www.drugbank.ca/drugs/DB00864http://www.drugbank.ca/drugs/DB01208http://www.drugbank.ca/drugs/DB00489http://www.drugbank.ca/drugs/DB00877http://www.drugbank.ca/drugs/DB00641http://www.drugbank.ca/drugs/DB06207http://www.drugbank.ca/drugs/DB00203http://www.drugbank.ca/drugs/DB01105http://www.drugbank.ca/drugs/DB01104http://www.drugbank.ca/drugs/DB06335http://www.drugbank.ca/drugs/DB01656http://www.drugbank.ca/drugs/DB00503http://www.drugbank.ca/drugs/DB01045http://www.drugbank.ca/drugs/DB00615http://www.drugbank.ca/drugs/DB00912http://www.drugbank.ca/drugs/DB00243http://www.drugbank.ca/drugs/DB01369http://www.drugbank.ca/drugs/DB01346http://www.drugbank.ca/drugs/DB00908http://www.drugbank.ca/drugs/DB01224http://www.drugbank.ca/drugs/DB08860http://www.drugbank.ca/drugs/DB01100http://www.drugbank.ca/drugs/DB06589http://www.drugbank.ca/drugs/DB01303http://www.drugbank.ca/drugs/DB00218http://www.drugbank.ca/drugs/DB00683http://www.drugbank.ca/drugs/DB00247http://www.drugbank.ca/drugs/DB00959http://www.drugbank.ca/drugs/DB00353http://www.drugbank.ca/drugs/DB00933http://www.drugbank.ca/drugs/DB06708


12/18



Tacrolimus(/drugs/DB00864)

Additive QTc-prolongation may occur increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution. The macrolideantibiotic, erythromycin, may also increase the blood concentration of tacrolimus.

Tamsulosin(/drugs/DB00706)

Erythromycin, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Erythromycin is initiated, discontinued, or dose changed.

Telithromycin(/drugs/DB00976)

Telithromycin may reduce clearance of Erythromycin. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Erythromycin if Telithromycinis initiated, discontinued or dose changed.

Terfenadine(/drugs/DB00342)


Theophylline(/drugs/DB00277)

The macrolide, erythromycin, may increase the effect and toxicity of theophylline.

Thioridazine(/drugs/DB00679)


Thiothixene(/drugs/DB01623)

May cause additive QTc-prolonging effects. Increased risk of ventricular arrhythmias.Consider alternate therapy. Thorough risk:benefit assessment is required prior to co-administration.

Tolvaptan(/drugs/DB06212)

Erythromycin is a moderate inhibitor of CYP3A4 and will considerably increase tolvaptanserum concentrations

Topotecan(/drugs/DB01030)

The p-glycoprotein inhibitor, Erythromycin, may increase the bioavailability of oralTopotecan. A clinically significant effect is also expected with IV Topotecan.Concomitant therapy should be avoided.

Toremifene(/drugs/DB00539)

Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Consider alternate therapy. A thorough risk:benefit assessment is requiredprior to co-administration.

Tramadol (/drugs/DB00193) Erythromycin may increase Tramadol toxicity by decreasing Tramadol metabolism andclearance.

Trazodone(/drugs/DB00656)

The CYP3A4 inhibitor, Erythromycin , may increase Trazodone efficacy/toxicity bydecreasing Trazodone metabolism and clearance. Monitor for changes in Trazodoneefficacy/toxicity if Erythromycin is initiated, discontinued or dose changed.

Triazolam(/drugs/DB00897)

The macrolide, erythromycin, may increase the effect of the benzodiazepine, triazolam.

Trimipramine(/drugs/DB00726)

Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.

Valproic Acid(/drugs/DB00313)

The macrolide antibiotic, Erythromycin, may increase the serum concentratin of Valproicacid. Consider alternate therapy or monitor for changes in Valproic acid therapeutic andadverse effects if Erythromycin is initiated, discontinued or dose changed.

Vardenafil(/drugs/DB00862)

Erythromycin, a moderate CYP3A4 inhibitor, may reduce the metabolism and clearanceof vardenafil. Consider alternate therapy or monitor for changes in the therapeutic andadverse effects of vardenafil if erythromycin is initiated, discontinued or dose changed.

Verapamil(/drugs/DB00661) Erythromycin, a moderate CYP3A4 inhibitor, may increase the serum concentration of veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Monitor for changes in the therapeutic/adverse effects of verapamil if erythromycin is initiated,discontinued or dose changed.

Vinblastine(/drugs/DB00570)

Erythromycin, a CYP3A4 and p-glycoprotein inhibitor, may increase the vinblastineserum concentration and distribution in certain cells. Consider alternate therapy toavoid vinblastine toxicity. Monitor for changes in the therapeutic/adverse effects of vinblastine if erythromycin is initiated, discontinued or dose changed.

Vincristine(/drugs/DB00541)

Erythromycin, a CYP3A4 and p-glycoprotein inhibitor, may increase the Vincristineserum concentration and distribution in certain cells. Consider alternate therapy toavoid Vincristine toxicity. Monitor for changes in the therapeutic and adverse effects of Vincristine if Erythromycin is initiated, discontinued or dose changed.

Vinorelbine(/drugs/DB00361)

Erythromycin, a CYP3A4 and p-glycoprotein inhibitor, may increase the Vinorelbineserum concentration and distribution in certain cells. Consider alternate therapy toavoid Vinorelbine toxicity. Monitor for changes in the therapeutic and adverse effects of Vinorelbine if Erythromycin is initiated, discontinued or dose changed.

Vismodegib(/drugs/DB08828)

P-glycoprotein inhibitors may increase the chance of adverse drug reactions.
http://www.drugbank.ca/drugs/DB08828http://www.drugbank.ca/drugs/DB00361http://www.drugbank.ca/drugs/DB00541http://www.drugbank.ca/drugs/DB00570http://www.drugbank.ca/drugs/DB00661http://www.drugbank.ca/drugs/DB00862http://www.drugbank.ca/drugs/DB00313http://www.drugbank.ca/drugs/DB00726http://www.drugbank.ca/drugs/DB00897http://www.drugbank.ca/drugs/DB00656http://www.drugbank.ca/drugs/DB00193http://www.drugbank.ca/drugs/DB00539http://www.drugbank.ca/drugs/DB01030http://www.drugbank.ca/drugs/DB06212http://www.drugbank.ca/drugs/DB01623http://www.drugbank.ca/drugs/DB00679http://www.drugbank.ca/drugs/DB00277http://www.drugbank.ca/drugs/DB00342http://www.drugbank.ca/drugs/DB00976http://www.drugbank.ca/drugs/DB00706http://www.drugbank.ca/drugs/DB00864


13/18



Voriconazole(/drugs/DB00582)

Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of erythromycin by decreasing its metabolism. Erythromycin may increase the serumconcentration of voriconazole by decreasing its metabolism. Additive QTc prolongationmay also occur. Consider alternate therapy or monitor for QTc prolongation andchanges in the therapeutic and adverse effects of both agents if concomitant therapy isinitiated, discontinued or dose changed.

Vorinostat(/drugs/DB02546)

Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTcprolongation as this can lead to Torsade de Pointes (TdP).

Warfarin (/drugs/DB00682) The macrolide, erythromycin, may increase the anticoagulant effect of warfarin.

Zafirlukast(/drugs/DB00549)

Erythromycin may decrease the serum concentration and effect of zafirlukast.

Ziprasidone(/drugs/DB00246)

Additive QTc-prolonging effects may increase the risk of severe arrhythmias.Concomitant therapy is contraindicated.

Zopiclone(/drugs/DB01198)

The macrolide antibiotic, erythromycin, may increase the serum concentration of zopiclone. Consider alternate therapy or monitor for changes in the therapeutic andadverse effects of zopiclone if erythromycin is initiated, discontinued or dose changed.

Zuclopenthixol(/drugs/DB01624)

Additive QTc prolongation may occur. Consider alternate therapy or use caution andmonitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).

Zuclopenthixol acetate

(/drugs/DB08919)

Additive QTc prolongation may occur. Consider alternate therapy or use caution and

monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).

Zuclopenthixol decanoate(/drugs/DB08920)

Additive QTc prolongation may occur. Consider alternate therapy or use caution andmonitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).

Food Interactions Avoid alcohol.Take on empty stomach: 1 hour before or 2 hours after meals.Take with a full glass of water Avoid taking with grapefruit juice.

1. 23S rRNA (/bio_entities/BE0004800)

Kind: nucleotideOrganism: Enteric bacteria and other eubacteria

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details

References:1. Moazed D, Noller HF: Chloramphenicol , erythromycin, carbomycin and vernamycin B protect overlapping sites in the peptidyl transferase region of 23S

ribosomal RNA. Biochimie. 1987 Aug;69(8):879-84. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/3122849)2. Schlunzen F, Zarivach R, Harms J, Bashan A, Tocilj A, Albrecht R, Yonath A, Franceschi F: Structural basis for the interaction of antibiotics with the peptidyl

transferase centre in eubacteria. Nature. 2001 Oct 25;413(6858):814-21. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/11677599)3. Garza-Ramos G, Xiong L, Zhong P, Mankin A: Binding site of m acrolide antibiotics on the ribosome: new res istance mutation identifies a s pecific

interaction of ketolides with rRNA. J Bacteriol. 2001 Dec;183(23):6898-907. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/11698379)

2. 50S ribosomal protein L22 (/bio_entities/BE0002464)

Kind: protein

Organism: Escherichia coli O157:H7


Actions: inhibitor

Components


50S ribosomal protein L22 P61177 Details (/polypeptides/P61177)
http://www.uniprot.org/uniprot/P61177http://www.drugbank.ca/bio_entities/BE0002464http://www.ncbi.nlm.nih.gov/pubmed/11698379http://www.ncbi.nlm.nih.gov/pubmed/11677599http://www.ncbi.nlm.nih.gov/pubmed/3122849http://www.drugbank.ca/bio_entities/BE0004800http://www.drugbank.ca/drugs/DB08920http://www.drugbank.ca/drugs/DB08919http://www.drugbank.ca/drugs/DB01624http://www.drugbank.ca/drugs/DB01198http://www.drugbank.ca/drugs/DB00246http://www.drugbank.ca/drugs/DB00549http://www.drugbank.ca/drugs/DB00682http://www.drugbank.ca/drugs/DB02546http://www.drugbank.ca/drugs/DB00582http://www.drugbank.ca/polypeptides/P61177


14/18



. .

References:1. Halli ng SM, Jensen AE: Intrinsi c and selected resis tance to antibioti cs binding the ribosome: analyses of Brucella 23S rrn, L4, L22, EF-Tu1, EF-Tu2,

efflux and phylogenetic implications. BMC Microbiol. 2006 Oct 2;6:84. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/17014718)2. Tu D, Blaha G, Moore PB, Steitz TA: Structures of MLSBK antibioti cs bound to mutated large ribosom al subunits provide a structural explanation for

resistance. Cell. 2005 Apr 22;121(2):257-70. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/15851032)3. Rolain JM, Raoult D: Prediction of resi stance to erythromycin in the genus Rickettsia by mutations in L22 ribos omal protein. J Antimicrob Chemother.

2005 Aug;56(2):396-8. Epub 2005 Jul 4. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/15996971)4. Cagli ero C, Mouline C, Cloeckaert A, Payot S: Synergy between efflux pump CmeABC and modi fications in ribosomal protei ns L4 and L22 in conferring

macrolide resistance in Campylobacter jejuni and Campylobacter coli. Antimicrob Agents Chemother. 2006 Nov;50(11):3893-6. Epub 2006 Aug 28.Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/16940070)

5. Schlunzen F, Harms JM, Francesch i F, Hansen HA, Bartels H, Zarivach R, Yonath A: Structural basi s for the antibiotic activity of ketolides and azalides.Structure. 2003 Mar;11(3):329-38. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/12623020)

6. Davydova N, Streltsov V, Wilce M, Lilj as A, Garber M: L22 ribos omal protein and effect of its mutation on ribosome res is tance to erythromycin. J Mol Biol .2002 Sep 20;322(3):635-44. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/12225755)

3. 50S ribosomal protein L4 (/bio_entities/BE0002465)

Kind: protein

Organism: Escherichia coli O157:H7


Actions: inhibitor

Components


50S ribosomal protein L4 P60725(http://www.uniprot.org/uniprot/P60725)

Details (/polypeptides/P60725)

References:1. Halli ng SM, Jensen AE: Intrinsi c and selected resis tance to antibioti cs binding the ribosome: analyses of Brucella 23S rrn, L4, L22, EF-Tu1, EF-Tu2,

efflux and phylogenetic implications. BMC Microbiol. 2006 Oct 2;6:84. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/17014718)2. Tu D, Blaha G, Moore PB, Steitz TA: Structures of MLSBK antibioti cs bound to mutated large ribosom al subunits provide a structural explanation for

resistance. Cell. 2005 Apr 22;121(2):257-70. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/15851032)3. OConnor M, Gregory ST, Dahlbe rg AE: Multiple defects in trans lation ass ociated with altered ribosomal protein L4. Nucleic Acids Res . 2004 Oct

27;32(19):5750-6. Print 2004. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/15509870)4. Schlunzen F, Harms JM, Francesch i F, Hansen HA, Bartels H, Zarivach R, Yonath A: Structural basi s for the antibiotic activity of ketolides and azalides.

Structure. 2003 Mar;11(3):329-38. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/12623020)

1. Cytochrome P450 3A4 (/bio_entities/BE0002638)

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components


Cytochrome P450 3A4 P08684(http://www.uniprot.org/uniprot/P08684)


References:1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table (http://medicine.iupui.edu/clinpharm /ddis/table.asp). Indiana University School

of Medicine (2007). Access ed May 28, 2010.2. Preis sner S, Kroll K, Dunkel M, Senger C, Goldsobe l G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preis sne r R: SuperCYP: a comprehens ive

database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database iss ue):D237-43. Epub 2009 Nov 24. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/19934256)

3. Ekins S, Bravi G, Wikel JH, Wrighton SA: Three-dim ensional-quantitative structure activity relations hip analysis of cytochrome P-450 3A4 subs trates. JPharmacol Exp Ther. 1999 Oct;291(1):424-33. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/10490933)

4. Lexicomp
http://www.ncbi.nlm.nih.gov/pubmed/10490933http://www.ncbi.nlm.nih.gov/pubmed/19934256http://medicine.iupui.edu/clinpharm/ddis/table.asphttp://www.uniprot.org/uniprot/P08684http://www.drugbank.ca/bio_entities/BE0002638http://www.ncbi.nlm.nih.gov/pubmed/12623020http://www.ncbi.nlm.nih.gov/pubmed/15509870http://www.ncbi.nlm.nih.gov/pubmed/15851032http://www.ncbi.nlm.nih.gov/pubmed/17014718http://www.uniprot.org/uniprot/P60725http://www.drugbank.ca/bio_entities/BE0002465http://www.ncbi.nlm.nih.gov/pubmed/12225755http://www.ncbi.nlm.nih.gov/pubmed/12623020http://www.ncbi.nlm.nih.gov/pubmed/16940070http://www.ncbi.nlm.nih.gov/pubmed/15996971http://www.ncbi.nlm.nih.gov/pubmed/15851032http://www.ncbi.nlm.nih.gov/pubmed/17014718http://www.uniprot.org/uniprot/P61177http://www.drugbank.ca/polypeptides/P08684http://www.drugbank.ca/polypeptides/P60725


15/18




Kind: protein

Organism: Human


Actions: substrate inhibitor

Components





of Medicine (2007). Access ed May 28, 2010.


Kind: protein

Organism: Human


Actions: inhibitor

Components





of Medicine (2007). Access ed May 28, 2010.


Kind: protein

Organism: Human


Actions: inhibitor

Components




References:1. Preis sner S, Kroll K, Dunkel M, Senger C, Goldsobe l G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preis sne r R: SuperCYP: a comprehens ive

database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database iss ue):D237-43. Epub 2009 Nov 24. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/19934256)
http://www.ncbi.nlm.nih.gov/pubmed/19934256http://www.uniprot.org/uniprot/P05177http://www.drugbank.ca/bio_entities/BE0002433http://medicine.iupui.edu/clinpharm/ddis/table.asphttp://www.uniprot.org/uniprot/P20815http://www.drugbank.ca/bio_entities/BE0002362http://medicine.iupui.edu/clinpharm/ddis/table.asphttp://www.uniprot.org/uniprot/P24462http://www.drugbank.ca/bio_entities/BE0003612http://www.drugbank.ca/polypeptides/P05177http://www.drugbank.ca/polypeptides/P20815http://www.drugbank.ca/polypeptides/P24462


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5. Cytochrome P450 2B6 (/bio_entities/BE0003549)

Kind: protein

Organism: Human


Actions: substrate

Components


Cytochrome P450 2B6 P20813(http://www.uniprot.org/uniprot/P20813)


References:1. Lexicomp

1. Multidrug resistance protein 1 (/bio_entities/BE0001032)

Kind: protein

Organism: Human


Actions: substrate inhibitor inducer

Components


Multidrug resistance protein 1 P08183(http://www.uniprot.org/uniprot/P08183)


References:1. Schuetz EG, Beck WT, Schuetz JD: Modulators and substrates o f P-glycoprotein and cytochrome P4503A coordinately up-regulate these proteins in

human colon carcinoma cells. Mol Pharmacol. 1996 Feb;49(2):311-8. Pubm ed (http://www.ncbi.nlm.nih.gov/pubmed/8632764)2. Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein ass ays in drug dis covery.

J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/11602674)3. Ekins S, Kim RB, Leake BF, Dantzig AH, Schuetz EG, Lan LB, Yasuda K, Shepard RL, Winter MA, Schuetz JD, Wikel JH, Wrighton SA: Three-dimensional

quantitative structure-activity relationships of inhibitors of P-glycoprotein. Mol Pharmacol. 2002 May;61(5):964-73. Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/11961113)

4. Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of i n vitro P-glycoprotein screening ass ays: recomm endations for their use in drugdiscovery. J Med Chem. 2003 Apr 24;46(9):1716-25. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/12699389)

5. Takano M, Hasegawa R, Fukuda T, Yumoto R, Nagai J, Murakami T: Interaction with P-glycoprotein and trans port of erythromycin, midazolam andketoconazole in Caco-2 cells. Eur J Pharmacol. 1998 Oct 9;358(3):289-94. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/9822896)

6. Kim RB, Wandel C, Leake B, Cvetkovic M, Fromm MF, Demps ey PJ, Roden MM, Belas F, Chaudhary AK, Roden DM, Wood AJ, Wilkinson GR:Interrelationship between substrates and inhibi tors of human CYP3A and P-glycoprotein. Pharm Res . 1999 Mar;16(3):408-14. Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/10213372)

7. Asakura E, Nakayama H, Sugie M, Zhao YL, Nadai M, Kitaichi K, Shim izu A, Miyoshi M, Takagi K, Takagi K, Hasegawa T: Azithromycin reverses anticancer

drug resis tance and modifies hepatobiliary excretion of doxorubicin in rats. Eur J Pharmacol. 2004 Jan 26;484(2-3):333-9. Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/14744620)

8. Yasuda K, Lan LB, Sanglard D, Furuya K, Schuetz JD, Schuetz EG: Interaction of cytochrome P450 3A inhibitors with P-glycoprotein. J Pharmacol ExpTher. 2002 Oct;303(1):323-32. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/12235267)

9. Dahan A, Sabit H, Amidon GL: The H2 receptor antagonis t nizatidine is a P-glycoprotein subs trate: characterization of its intes tinal epitheli al cell effluxtransport. AAPS J. 2009 Jun;11(2):205-13. Epub 2009 Mar 25. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/19319690)

10. Sun H, Huang Y, Frassetto L, Benet LZ: Effects of uremic toxins on hepatic uptake and metaboli sm of erythromycin. Drug Metab Dispos. 2004Nov;32(11):1239-46. Epub 2004 Jul 30. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/15286055)

2. Multidrug resistance-associated protein 1 (/bio_entities/BE0000785)

Kind: protein

Organism: Human


Actions: inhibitor

Components
http://www.drugbank.ca/bio_entities/BE0000785http://www.ncbi.nlm.nih.gov/pubmed/15286055http://www.ncbi.nlm.nih.gov/pubmed/19319690http://www.ncbi.nlm.nih.gov/pubmed/12235267http://www.ncbi.nlm.nih.gov/pubmed/14744620http://www.ncbi.nlm.nih.gov/pubmed/10213372http://www.ncbi.nlm.nih.gov/pubmed/9822896http://www.ncbi.nlm.nih.gov/pubmed/12699389http://www.ncbi.nlm.nih.gov/pubmed/11961113http://www.ncbi.nlm.nih.gov/pubmed/11602674http://www.ncbi.nlm.nih.gov/pubmed/8632764http://www.uniprot.org/uniprot/P08183http://www.drugbank.ca/bio_entities/BE0001032http://www.uniprot.org/uniprot/P20813http://www.drugbank.ca/bio_entities/BE0003549http://www.drugbank.ca/polypeptides/P08183http://www.drugbank.ca/polypeptides/P20813


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Multidrug resistance-associated protein 1 P33527(http://www.uniprot.org/uniprot/P33527)


References:1. Terashi K, Oka M, Soda H, Fukuda M, Kawabata S, Nakatomi K, Shiozawa K, Nakamura T, Tsukamoto K, Noguchi Y, Suenaga M, Tei C, Kohno S:

Interactions of ofloxacin and erythromycin with the multidrug resistance protein (MRP) in MRP-overexpressing human leukemia cells. Antimicrob AgentsChemother. 2000 Jun;44(6):1697-700. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/10817732)

3. Solute carrier organic anion transporter family member 1A2 (/bio_entities/BE0003642)

Kind: protein

Organism: Human


Actions: inhibitor

Components


Solute carrier organic anion transporter family member 1A2 P46721(http://www.uniprot.org/uniprot/P46721)


References:1. Cvetkovic M, Leake B, Fromm MF, Wilkinson GR, Kim RB: OATP and P-glycoprotein transporters medi ate the cellular uptake and excretion of

fexofenadine. Drug Metab Dispos. 1999 Aug;27(8):866-71. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/10421612)

4. Solute carrier family 22 member 7 (/bio_entities/BE0003646)

Kind: protein

Organism: Human


Actions: inhibitor

Components


Solute carrier family 22 member 7 Q9Y694(http://www.uniprot.org/uniprot/Q9Y694)

Details (/polypeptides/Q9Y694)

References:1. Kobayashi Y, Sakai R, Ohshiro N, Ohbayashi M, Kohyama N, Yamam oto T: Poss ible involvement of organic anion transporter 2 on the interaction of

theophylline with erythromycin in the human liver. Drug Metab Dispos. 2005 May;33(5):619-22. Epub 2005 Feb 11. Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/15708966)

2. Kobayashi Y, Ohshiro N, Shibus awa A, Sasaki T, Tokuyama S, Sekine T, Endou H, Yamamoto T: Isola tion, characterization and differential geneexpression of multispecific organic anion transporter 2 in mice. Mol Pharmacol. 2002 Jul;62(1):7-14. Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/12065749)

Comments

Comments
http://www.ncbi.nlm.nih.gov/pubmed/12065749http://www.ncbi.nlm.nih.gov/pubmed/15708966http://www.uniprot.org/uniprot/Q9Y694http://www.drugbank.ca/bio_entities/BE0003646http://www.ncbi.nlm.nih.gov/pubmed/10421612http://www.uniprot.org/uniprot/P46721http://www.drugbank.ca/bio_entities/BE0003642http://www.ncbi.nlm.nih.gov/pubmed/10817732http://www.uniprot.org/uniprot/P33527http://www.drugbank.ca/polypeptides/Q9Y694http://www.drugbank.ca/polypeptides/P46721http://www.drugbank.ca/polypeptides/P33527


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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:08

(http://www.metabolomicscentre.ca)

(http://genomealberta.ca) (http://genomebc.ca) (http://genomecanada.ca)

This project is supported by TheMetabolomics Innovation Centre(TMIC)

(http://www.metabolomicscentre.ca/), a nationally-funded research and core facility that supports a wide range of cutting-edge metabolomicstudies. TMIC is funded by Genome Alberta (http://www.genomealberta.ca), Genome British Columbia (http://www.genomebc.ca/), and GenomeCanada (http://www.genomecanada.ca), a not-for-profit organization that is leading Canada's national genomics strategy with $900 million infunding from the federal government.

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drugbank_ erythromycin (db00199)

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