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Identification
NameErythromycin
Accession NumberDB00199  (APRD00953)
TypeSmall Molecule
GroupsApproved
Description

Erythromycin is a macrolide antibiotic produced by Streptomyces erythreus. It inhibits bacterial protein synthesis by binding to bacterial 50S ribosomal subunits; binding inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins. Erythromycin may be bacteriostatic or bactericidal depending on the organism and drug concentration.

Structure
Thumb
Synonyms
SynonymLanguageCode
(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dioneNot AvailableNot Available
3''-O-demethylerythromycinNot AvailableNot Available
AbomacetinNot AvailableNot Available
EritromicinaNot AvailableNot Available
ErythromycinNot AvailableNot Available
Erythromycin ANot AvailableNot Available
Erythromycin CNot AvailableNot Available
ErythromycineNot AvailableNot Available
ErythromycinumNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Akne-mycinointment20 mg/gtopicalCoria Laboratories1985-01-102015-06-30Us 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ery-pedsuspension400 mg/5mLoralArbor Pharmaceuticals, Inc.2012-06-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ery-pedsuspension200 mg/5mLoralArbor Pharmaceuticals, Inc.2011-07-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
E.e.sgranule, for suspension200 mg/5mLoralArbor Pharmaceuticals, Inc.2011-04-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
E.e.sgranule, for suspension200 mg/5mLoralArbor Pharmaceuticals, Inc.2011-04-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
E.e.sgranule, for suspension200 mg/5mLoralA S Medication Solutions Llc2011-04-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycincapsule, delayed release pellets250 mgoralMidlothian Laboratories2013-07-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erybidtablet500 mgoralAmdipharm LimitedNot AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Pcetablet333 mgoralAmdipharm LimitedNot AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Erythromycinsolution20 mg/mLtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.1997-09-30Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycingel20 mg/gtopicalE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.1997-09-30Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycincapsule, delayed release250 mgoralKAISER FOUNDATION HOSPITALS2012-04-26Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ery-tabtablet, delayed release333 mgoralKAISER FOUNDATION HOSPITALS2009-08-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythra-dermsolution20 mg/mLtopicalPaddock Laboratories, Inc.1988-02-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ilotycinointment5 mg/gophthalmicPaddock Laboratories, LLC2014-10-08Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycinointment5 mg/gophthalmicPaddock Laboratories, LLC2014-05-08Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycincapsule, delayed release250 mgoralStat Rx USA1986-12-22Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ery-tabtablet, delayed release333 mgoralSTAT Rx USA LLC2011-04-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycinointment5 mg/gophthalmicStat Rx USA1994-07-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycintablet, film coated250 mgoralSTAT Rx USA LLC1972-07-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycinointment5 mg/gophthalmicAkorn, Inc.1996-07-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycinointment5 mg/gophthalmicAkorn, Inc.2013-03-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycinointment5 mg/gophthalmicRebel Distributors Corp1994-07-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycin Base Filmtabtablet, film coated250 mgoralRebel Distributors Corp1972-07-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycin Base Filmtabtablet, film coated500 mgoralRebel Distributors Corp1972-07-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ery-tabtablet, delayed release333 mgoralRebel Distributors Corp1972-07-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycinointment5 mg/gophthalmicBausch & Lomb Incorporated1994-07-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycintablet, film coated250 mgoralArbor Pharmaceuticals, Inc.2011-09-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycintablet, film coated500 mgoralArbor Pharmaceuticals, Inc.2011-09-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycincapsule, delayed release250 mgoralArbor Pharmaceuticals, Inc.2012-01-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ery-tabtablet, delayed release250 mgoralArbor Pharmaceuticals, Inc.2011-04-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ery-tabtablet, delayed release333 mgoralArbor Pharmaceuticals, Inc.2011-04-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ery-tabtablet, delayed release500 mgoralArbor Pharmaceuticals, Inc.2011-04-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycin Basetablet, film coated500 mgoralLake Erie Medical DBA Quality Care Products LLC2011-09-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erygelgel20 mg/gtopicalPrestium Pharma, Inc.2014-01-27Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ery-tabtablet, delayed release333 mgoralSTAT Rx USA LLC2011-04-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
E.e.s.tablet, film coated400 mgoralPd Rx Pharmaceuticals, Inc.2010-12-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycinsolution20 mg/mLtopicalPerrigo New York Inc2011-12-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erysolution.8 mL/100mLtopicalPerrigo New York Inc2008-07-07Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycingel20 mg/gtopicalPerrigo New York Inc2008-06-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycinointment5 mg/gophthalmicFera Pharmaceuticals2010-01-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ilotycinointment.5 mg/gophthalmicFera Pharmaceuticals, LLC2010-10-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ery-tabtablet, delayed release500 mgoralREMEDYREPACK INC.2011-08-24Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ery-tabtablet333 mgoralREMEDYREPACK INC.2011-08-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycin Base Basetablet, film coated500 mgoralREMEDYREPACK INC.2013-03-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycin Base Filmtabtablet, film coated500 mgoralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2012-03-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycinointment5 mg/gophthalmicLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2010-01-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycin Base Basetablet, film coated250 mgoralREMEDYREPACK INC.2013-12-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycin Base Basetablet, film coated250 mgoralREMEDYREPACK INC.2013-03-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycinointment5 mg/gophthalmicREMEDYREPACK INC.2013-05-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycinointment5 mg/gophthalmicREMEDYREPACK INC.2013-12-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycinointment5 mg/gophthalmicH.J. Harkins Company, Inc.1994-07-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycingel20 mg/gtopicalAidarex Pharmaceuticals LLC2008-06-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycinointment5 mg/gophthalmicA S Medication Solutions Llc1996-07-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ery-tabtablet, delayed release333 mgoralA S Medication Solutions Llc2011-04-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycincapsule, delayed release250 mgoralA S Medication Solutions Llc2012-01-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycin Basetablet, film coated250 mgoralA S Medication Solutions Llc2011-09-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycin Basetablet, film coated500 mgoralA S Medication Solutions Llc2011-09-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ery-tabtablet, delayed release500 mgoralA S Medication Solutions Llc2011-04-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ery-tabtablet, delayed release250 mgoralA S Medication Solutions Llc2011-04-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycinointment5 mg/gophthalmicPhysicians Total Care, Inc.1994-09-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ery-tabtablet, delayed release333 mgoralPhysicians Total Care, Inc.1999-09-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycinsolution20 mgtopicalPhysicians Total Care, Inc.1996-03-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycin Base Filmtabtablet, film coated250 mgoralPhysicians Total Care, Inc.1995-07-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycin Base Filmtabtablet, film coated500 mgoralPhysicians Total Care, Inc.1996-12-09Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ery-tabtablet, delayed release500 mgoralPhysicians Total Care, Inc.2004-06-30Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycinointment5 mg/gophthalmicDispensing Solutions, Inc.1996-07-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycinointment5 mg/gophthalmicCardinal Health1996-07-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycin Base Filmtabtablet, film coated500 mgoralCardinal Health2011-09-08Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycinointment5 mg/gophthalmicCardinal Health1994-07-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycin Basetablet, film coated500 mgoralPd Rx Pharmaceuticals, Inc.2011-09-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycin Base Basetablet, film coated250 mgoralPd Rx Pharmaceuticals, Inc.2011-09-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
E.e.s.tablet, film coated400 mgoralPd Rx Pharmaceuticals, Inc.2010-12-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ery-tabtablet, delayed release500 mgoralPd Rx Pharmaceuticals, Inc.2011-04-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ery-tabtablet, delayed release333 mgoralPd Rx Pharmaceuticals, Inc.2011-04-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycinsolution20 mg/mLtopicalMorton Grove Pharmaceuticals, Inc.1987-10-23Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycinsolution20 mg/mLtopicalVersa Pharm Incorporated2010-08-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycinointment5 gophthalmicDIRECT RX2014-01-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycinointment5 mg/gophthalmicProficient Rx LP1996-07-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ery-tabtablet, delayed release250 mgoralCarilion Materials Management2011-04-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ery-tabtablet, delayed release333 mgoralCarilion Materials Management2011-04-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycin Basetablet, film coated250 mgoralCarilion Materials Management2011-09-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycinointment5 mg/gophthalmicPreferred Pharmaceuticals, Inc.1996-07-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycinointment5 mg/gophthalmicPreferred Pharmaceuticals, Inc.2014-07-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Erythromycinointment5 mg/gophthalmicPreferred Pharmaceuticals, Inc.2013-08-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
ErycHospira
IlosoneCipa
StaticinWestwood
T-statWestwood
Brand mixtures
Brand NameIngredients
Sans-Acne SolutionAlcohol Anhydrous + Erythromycin
Staticin LotAlcohol Anhydrous + Erythromycin + Laureth 4
Stievamycin Forte GelErythromycin + Tretinoin
Stievamycin GelErythromycin + Tretinoin
T-Stat LotAlcohol Anhydrous + Erythromycin
T-Stat Pad-LotAlcohol Anhydrous + Erythromycin
SaltsNot Available
Categories
CAS number114-07-8
WeightAverage: 733.9268
Monoisotopic: 733.461241235
Chemical FormulaC37H67NO13
InChI KeyULGZDMOVFRHVEP-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/s1
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)O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolides and analogues
Sub ClassNot Available
Direct ParentMacrolides and analogues
Alternative Parents
Substituents
  • Macrolide
  • Amino sugar
  • Desosamine
  • Amino saccharide
  • Oxane
  • Monosaccharide
  • Saccharide
  • Tertiary alcohol
  • Cyclic ketone
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Polyol
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • 1,2-diol
  • 1,2-aminoalcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor 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 to antitoxin in infections due to Corynebacterium diphtheriae, in the treatment of infections due to Corynebacterium minutissimum, intestinal amebiasis caused by Entamoeba histolytica, acute pelvic inflammatory disease caused by Neisseria gonorrhoeae, skin and soft tissue infections of mild to moderate severity caused by Streptococcus pyogenes and Staphylococcus aureus, primary syphilis caused by Treponema pallidum, infections caused by Chlamydia trachomatis, nongonococcal urethritis caused by Ureaplasma urealyticum, and Legionnaires' disease caused by Legionella pneumophila.
PharmacodynamicsErythromycin 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, low concentrations 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 serum drug levels reaching 5 - 20% of maternal serum concentrations. Erythromycin is not removed by peritoneal dialysis or hemodialysis.
Mechanism of actionErythromycin acts by penetrating the bacterial cell membrane and reversibly binding to the 50 S subunit of bacterial ribosomes 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 protein synthesis is inhibited. Erythromycin is effective only against actively dividing organisms. The exact mechanism by which erythmromycin reduces lesions of acne vulgaris is not fully known: however, the effect appears to be due in part to the antibacterial activity of the drug.
AbsorptionOrally administered erythromycin base and its salts are readily absorbed in the microbiologically active form. Topical application of the ophthalmic ointment to the eye may result in absorption into the cornea and aqueous humor.
Volume of distributionNot Available
Protein bindingErythromycin 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 recovered in the active form in the urine. Erythromycin is partially metabolized by CYP3A4 resulting in numerous drug interactions.

SubstrateEnzymesProduct
Erythromycin
norerythromycinDetails
Route of eliminationNot Available
Half life0.8 - 3 hours
ClearanceNot Available
ToxicitySymptoms of overdose include diarrhea, nausea, stomach cramps, and vomiting.
Affected organisms
  • Enteric bacteria and other eubacteria
  • Streptococcus pyogenes
  • Haemophilus influenzae
  • Staphylococcus aureus
Pathways
PathwayCategorySMPDB ID
Erythromycin Action PathwayDrug actionSMP00250
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5114
Blood Brain Barrier-0.9889
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.8098
P-glycoprotein inhibitor IInhibitor0.8564
P-glycoprotein inhibitor IINon-inhibitor0.5963
Renal organic cation transporterNon-inhibitor0.9222
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateNon-substrate0.9225
CYP450 3A4 substrateSubstrate0.6528
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 substrateNon-inhibitor0.907
CYP450 2D6 substrateNon-inhibitor0.923
CYP450 2C19 substrateNon-inhibitor0.9074
CYP450 3A4 substrateNon-inhibitor0.5744
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9391
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9335
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.2296 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9902
hERG inhibition (predictor II)Non-inhibitor0.8956
Pharmacoeconomics
Manufacturers
  • Hospira inc
  • Parke davis div warner lambert co
  • Warner chilcott inc
  • Abbott laboratories pharmaceutical products div
  • Barr laboratories inc
  • Stiefel laboratories inc
  • Altana inc
  • Merz pharmaceuticals llc
  • Perrigo co
  • Syosset laboratories inc
  • Akorn inc
  • Bausch and lomb pharmaceuticals inc
  • E fougera div altana inc
  • Pharmaderm div altana inc
  • Pharmafair inc
  • Dista products co div eli lilly and co
  • Dow pharmaceutical sciences inc
  • Paddock laboratories inc
  • Taro pharmaceuticals north america inc
  • Bioglan pharma inc
  • Alpharma us pharmaceuticals division
  • Eli lilly and co
  • Perrigo new york inc
  • Wockhardt eu operations (swiss) ag
  • Hi tech pharmacal co inc
  • Westwood squibb pharmaceuticals inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Orthoneutrogena
  • Versapharm inc
  • Ah robins co
  • Solvay pharmaceuticals
  • Watson laboratories inc
  • Life laboratories inc
  • Lilly research laboratories div eli lilly and co
  • Ross laboratories div abbott laboratories inc
  • Pharmacia and upjohn co
  • Naska pharmacal co inc div rugby darby group cosmetics
  • Wyeth ayerst laboratories
  • Abbott laboratories chemical and agricultural products div
  • Mylan pharmaceuticals inc
  • Elkins sinn div ah robins co inc
  • Abraxis pharmaceutical products
  • Baxter healthcare corp anesthesia and critical care
  • Teva parenteral medicines inc
  • Bristol laboratories inc div bristol myers co
  • Warner chilcott div warner lambert co
  • Lederle laboratories div american cyanamid co
  • Purepac pharmaceutical co
  • Bristol myers squibb co
  • Pfizer laboratories div pfizer inc
Packagers
Dosage forms
FormRouteStrength
Capsule, delayed releaseoral250 mg
Capsule, delayed release pelletsoral250 mg
Geltopical20 mg/g
Granule, for suspensionoral200 mg/5mL
Ointmentophthalmic.5 mg/g
Ointmentophthalmic5 g
Ointmentophthalmic5 mg/g
Ointmenttopical20 mg/g
Solutiontopical.8 mL/100mL
Solutiontopical20 mg
Solutiontopical20 mg/mL
Suspensionoral200 mg/5mL
Suspensionoral400 mg/5mL
Tabletoral333 mg
Tabletoral500 mg
Tablet, delayed releaseoral250 mg
Tablet, delayed releaseoral333 mg
Tablet, delayed releaseoral500 mg
Tablet, film coatedoral250 mg
Tablet, film coatedoral400 mg
Tablet, film coatedoral500 mg
Prices
Unit descriptionCostUnit
Benzamycin 5-3% Gel 46.6 gm Jar236.63USD jar
BenzamycinPak 60 5-3% Packets (2 Box Contains 60 Packets)142.45USD packet
Erythromycin 2% Gel 60 gm Tube46.8USD tube
Erycette 60 2% Pad Box30.99USD box
Erythromycin 2% Gel 30 gm Tube26.2USD tube
Erythromycin 2% Solution 60ml Bottle26.13USD bottle
Eryderm 2% Solution 60ml Bottle25.99USD bottle
Erythromycin 5 mg/gm Ointment Limited Supply Available.13.99USD tube
Benzamycin gel4.95USD g
Akne-mycin 2% ointment3.96USD g
PCE 500 mg Enteric Coated Tabs3.28USD tab
Pce 500 mg dispertab3.03USD tablet
PCE 333 mg Enteric Coated Tabs2.48USD tab
Erythromycin e.s. powder2.39USD g
Benzamycinpak gel2.37USD gel
Pce 333 mg dispertab2.3USD tablet
Romycin eye ointment1.98USD g
Erythromycin eye ointment1.44USD g
Pms-Erythromycin 0.5 % Ointment1.3USD g
Emgel 2% topical gel1.07USD g
Ery-Tab 500 mg Enteric Coated Tabs0.93USD tab
Ery-tab 500 mg tablet ec0.77USD tablet
Ery-Tab 333 mg Enteric Coated Tabs0.72USD tab
Erythro-rx powder0.72USD g
Erythromycin ec 500 mg tablet0.66USD tablet
Erythromycin Base 500 mg tablet0.61USD tablet
Eryc 333 mg Capsule (Enteric-Coated Pellet)0.6USD capsule
Apo-Erythro-S 500 mg Tablet0.57USD tablet
E-mycin 333 mg tablet ec0.54USD tablet
Eryc 250 mg Capsule (Enteric-Coated Pellet)0.54USD capsule
Erythromycin powder0.54USD g
Erythromycin 2% gel0.5USD g
Erythromycin Base 250 mg Enteric Coated Capsule0.5USD capsule
Erythromycin Base 250 mg tablet0.5USD tablet
Ery-tab ec 500 mg tablet0.46USD tablet
Apo-Erythro E-C 333 mg Capsule (Enteric-Coated Pellet)0.45USD capsule
Ery-Tab 250 mg Enteric Coated Tabs0.45USD tab
Erythromycin st 500 mg tablet0.44USD tablet
Apo-Erythro E-C 250 mg Capsule (Enteric-Coated Pellet)0.41USD capsule
Ery-tab 333 mg tablet ec0.4USD tablet
Apo-Erythro-Es 600 mg Tablet0.35USD tablet
Erythromycin 500 mg filmtab0.3USD tablet
Erythrocin 500 mg filmtab0.29USD tablet
Ery-tab 250 mg tablet ec0.27USD tablet
E.e.s. 400 filmtab0.25USD tablet
Erythromycin 250 mg filmtab0.25USD tablet
Erythromycin es 400 mg tablet0.25USD tablet
Apo-Erythro-S 250 mg Tablet0.22USD tablet
Apo-Erythro Base 250 mg Tablet0.19USD tablet
Erythrocin 250 mg filmtab0.16USD tablet
Novo-Rythro Ees 80 mg/ml Suspension0.15USD ml
Novo-Rythro Estolate 50 mg/ml Suspension0.13USD ml
Novo-Rythro Ees 40 mg/ml Suspension0.1USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point191 °CPhysProp
water solubility2000mg/L at 28°CEuropean Pharmacopeia
logP3.06MCFARLAND,JW ET AL. (1997)
Caco2 permeability-5.43ADME Research, USCD
pKa8.88 (at 25 °C)MCFARLAND,JW ET AL. (1997)
Predicted Properties
PropertyValueSource
Water Solubility0.459 mg/mLALOGPS
logP2.37ALOGPS
logP2.6ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)12.44ChemAxon
pKa (Strongest Basic)8.38ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area193.91 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity186.04 m3·mol-1ChemAxon
Polarizability78.21 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Takehiro Amano, Masami Goi, Kazuto Sekiuchi, Tomomichi Yoshida, Masahiro Hasegawa, “Process for preparing erythromycin A oxime or a salt thereof.” U.S. Patent US5274085, issued October, 1966.

US5274085
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
  2. Ogwal S, Xide TU: Bioavailability and stability of erythromycin delayed release tablets. Afr Health Sci. 2001 Dec;1(2):90-6. Pubmed
  3. Okudaira T, Kotegawa T, Imai H, Tsutsumi K, Nakano S, Ohashi K: Effect of the treatment period with erythromycin on cytochrome P450 3A activity in humans. J Clin Pharmacol. 2007 Jul;47(7):871-6. Pubmed
External Links
ATC CodesD10AF02J01FA01S01AA17
AHFS Codes
  • 08:12.12.04
  • 34:00.00
  • 52:04.04
PDB EntriesNot Available
FDA labelDownload (149 KB)
MSDSDownload (73 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. 23S rRNA

Kind: nucleotide

Organism: 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
  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
  3. Garza-Ramos G, Xiong L, Zhong P, Mankin A: Binding site of macrolide antibiotics on the ribosome: new resistance mutation identifies a specific interaction of ketolides with rRNA. J Bacteriol. 2001 Dec;183(23):6898-907. Pubmed

2. 50S ribosomal protein L22

Kind: protein

Organism: Escherichia coli O157:H7

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
50S ribosomal protein L22 P61177 Details

References:

  1. Halling SM, Jensen AE: Intrinsic and selected resistance to antibiotics 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
  2. Tu D, Blaha G, Moore PB, Steitz TA: Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance. Cell. 2005 Apr 22;121(2):257-70. Pubmed
  3. Rolain JM, Raoult D: Prediction of resistance to erythromycin in the genus Rickettsia by mutations in L22 ribosomal protein. J Antimicrob Chemother. 2005 Aug;56(2):396-8. Epub 2005 Jul 4. Pubmed
  4. Cagliero C, Mouline C, Cloeckaert A, Payot S: Synergy between efflux pump CmeABC and modifications in ribosomal proteins 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
  5. Schlunzen F, Harms JM, Franceschi F, Hansen HA, Bartels H, Zarivach R, Yonath A: Structural basis for the antibiotic activity of ketolides and azalides. Structure. 2003 Mar;11(3):329-38. Pubmed
  6. Davydova N, Streltsov V, Wilce M, Liljas A, Garber M: L22 ribosomal protein and effect of its mutation on ribosome resistance to erythromycin. J Mol Biol. 2002 Sep 20;322(3):635-44. Pubmed

3. 50S ribosomal protein L4

Kind: protein

Organism: Escherichia coli O157:H7

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
50S ribosomal protein L4 P60725 Details

References:

  1. Halling SM, Jensen AE: Intrinsic and selected resistance to antibiotics 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
  2. Tu D, Blaha G, Moore PB, Steitz TA: Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance. Cell. 2005 Apr 22;121(2):257-70. Pubmed
  3. O’Connor M, Gregory ST, Dahlberg AE: Multiple defects in translation associated with altered ribosomal protein L4. Nucleic Acids Res. 2004 Oct 27;32(19):5750-6. Print 2004. Pubmed
  4. Schlunzen F, Harms JM, Franceschi F, Hansen HA, Bartels H, Zarivach R, Yonath A: Structural basis for the antibiotic activity of ketolides and azalides. Structure. 2003 Mar;11(3):329-38. Pubmed

4. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

References:

  1. 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

5. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. Pubmed

6. Motilin receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Motilin receptor O43193 Details

References:

  1. Li JJ, Chao HG, Wang H, Tino JA, Lawrence RM, Ewing WR, Ma Z, Yan M, Slusarchyk D, Seethala R, Sun H, Li D, Burford NT, Stoffel RH, Salyan ME, Li CY, Witkus M, Zhao N, Rich A, Gordon DA: Discovery of a potent and novel motilin agonist. J Med Chem. 2004 Mar 25;47(7):1704-8. Pubmed

7. Potassium voltage-gated channel subfamily H member 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Potassium voltage-gated channel subfamily H member 2 Q12809 Details

References:

  1. Du LP, Tsai KC, Li MY, You QD, Xia L: The pharmacophore hypotheses of I(Kr) potassium channel blockers: novel class III antiarrhythmic agents. Bioorg Med Chem Lett. 2004 Sep 20;14(18):4771-7. Pubmed

8. Lanosterol 14-alpha demethylase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Lanosterol 14-alpha demethylase Q16850 Details

References:

  1. Ekins S, Mankowski DC, Hoover DJ, Lawton MP, Treadway JL, Harwood HJ Jr: Three-dimensional quantitative structure-activity relationship analysis of human CYP51 inhibitors. Drug Metab Dispos. 2007 Mar;35(3):493-500. Epub 2006 Dec 28. Pubmed

9. Serum albumin

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Serum albumin P02768 Details

References:

  1. Baneres-Roquet F, Gualtieri M, Villain-Guillot P, Pugniere M, Leonetti JP: Use of a surface plasmon resonance method to investigate antibiotic and plasma protein interactions. Antimicrob Agents Chemother. 2009 Apr;53(4):1528-31. doi: 10.1128/AAC.00971-08. Epub 2009 Jan 21. Pubmed

10. Multidrug and toxin extrusion protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Multidrug and toxin extrusion protein 1 Q96FL8 Details

References:

  1. Wittwer MB, Zur AA, Khuri N, Kido Y, Kosaka A, Zhang X, Morrissey KM, Sali A, Huang Y, Giacomini KM: Discovery of potent, selective multidrug and toxin extrusion transporter 1 (MATE1, SLC47A1) inhibitors through prescription drug profiling and computational modeling. J Med Chem. 2013 Feb 14;56(3):781-95. doi: 10.1021/jm301302s. Epub 2013 Jan 22. Pubmed

Enzymes

1. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
  3. Ekins S, Bravi G, Wikel JH, Wrighton SA: Three-dimensional-quantitative structure activity relationship analysis of cytochrome P-450 3A4 substrates. J Pharmacol Exp Ther. 1999 Oct;291(1):424-33. Pubmed
  4. Lexicomp

2. Cytochrome P450 3A7

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A7 P24462 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.

3. Cytochrome P450 3A5

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A5 P20815 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.

4. Cytochrome P450 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

5. Cytochrome P450 2B6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2B6 P20813 Details

References:

  1. Lexicomp

Transporters

1. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor inducer

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

References:

  1. Schuetz EG, Beck WT, Schuetz JD: Modulators and substrates of P-glycoprotein and cytochrome P4503A coordinately up-regulate these proteins in human colon carcinoma cells. Mol Pharmacol. 1996 Feb;49(2):311-8. Pubmed
  2. Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. Pubmed
  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
  4. Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. Pubmed
  5. Takano M, Hasegawa R, Fukuda T, Yumoto R, Nagai J, Murakami T: Interaction with P-glycoprotein and transport of erythromycin, midazolam and ketoconazole in Caco-2 cells. Eur J Pharmacol. 1998 Oct 9;358(3):289-94. Pubmed
  6. Kim RB, Wandel C, Leake B, Cvetkovic M, Fromm MF, Dempsey PJ, Roden MM, Belas F, Chaudhary AK, Roden DM, Wood AJ, Wilkinson GR: Interrelationship between substrates and inhibitors of human CYP3A and P-glycoprotein. Pharm Res. 1999 Mar;16(3):408-14. Pubmed
  7. Asakura E, Nakayama H, Sugie M, Zhao YL, Nadai M, Kitaichi K, Shimizu A, Miyoshi M, Takagi K, Takagi K, Hasegawa T: Azithromycin reverses anticancer drug resistance and modifies hepatobiliary excretion of doxorubicin in rats. Eur J Pharmacol. 2004 Jan 26;484(2-3):333-9. Pubmed
  8. Yasuda K, Lan LB, Sanglard D, Furuya K, Schuetz JD, Schuetz EG: Interaction of cytochrome P450 3A inhibitors with P-glycoprotein. J Pharmacol Exp Ther. 2002 Oct;303(1):323-32. Pubmed
  9. Dahan A, Sabit H, Amidon GL: The H2 receptor antagonist nizatidine is a P-glycoprotein substrate: characterization of its intestinal epithelial cell efflux transport. AAPS J. 2009 Jun;11(2):205-13. Epub 2009 Mar 25. Pubmed
  10. Sun H, Huang Y, Frassetto L, Benet LZ: Effects of uremic toxins on hepatic uptake and metabolism of erythromycin. Drug Metab Dispos. 2004 Nov;32(11):1239-46. Epub 2004 Jul 30. Pubmed

2. Multidrug resistance-associated protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Multidrug resistance-associated protein 1 P33527 Details

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 Agents Chemother. 2000 Jun;44(6):1697-700. Pubmed

3. Solute carrier organic anion transporter family member 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier organic anion transporter family member 1A2 P46721 Details

References:

  1. Cvetkovic M, Leake B, Fromm MF, Wilkinson GR, Kim RB: OATP and P-glycoprotein transporters mediate the cellular uptake and excretion of fexofenadine. Drug Metab Dispos. 1999 Aug;27(8):866-71. Pubmed

4. Solute carrier family 22 member 7

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 7 Q9Y694 Details

References:

  1. Kobayashi Y, Sakai R, Ohshiro N, Ohbayashi M, Kohyama N, Yamamoto T: Possible 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
  2. Kobayashi Y, Ohshiro N, Shibusawa A, Sasaki T, Tokuyama S, Sekine T, Endou H, Yamamoto T: Isolation, characterization and differential gene expression of multispecific organic anion transporter 2 in mice. Mol Pharmacol. 2002 Jul;62(1):7-14. Pubmed

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