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Details

Stereochemistry ABSOLUTE
Molecular Formula C37H67NO13
Molecular Weight 733.9268
Optical Activity ( - )
Defined Stereocenters 18 / 18
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ERYTHROMYCIN

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]3O[C@H](C)C[C@@H]([C@H]3O)N(C)C)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O

InChI

InChIKey=ULGZDMOVFRHVEP-RWJQBGPGSA-N
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

HIDE SMILES / InChI

Molecular Formula C37H67NO13
Molecular Weight 733.9268
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 18 / 18
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Erythromycin is produced by a strain of Saccharopolyspora erythraea (formerly Streptomyces erythraeus) and belongs to the macrolide group of antibiotics. Erythromycin A is considered its major active component. It is used for the treatment of broad range of infections. In sensitive organisms, it inhibits protein synthesis by binding to 50S ribosomal subunits, namely by interaction with nucleotides in 23S rRNA domains II and V. This binding process inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins. Erythromycin does not affect nucleic acid synthesis.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
A CLINICAL STUDY OF ERYTHROMYCIN STEARATE AND ERYTHROMYCIN ETHYL SUCCINATE IN OFFICE PRACTICE.
1964 Sep
[Use in pediatrics of a new form of erythromycin: erythromycin ethyl succinate].
1969 Mar 5
A C-13 relaxation study on erythromycin A cyclic 11,12-carbonate.
1978 May
Comparison of the mechanism of action of cyclic 11,12-erythromycin A carbonate and erythromycin A.
1980
Comparison of oral erythromycin ethylsuccinate and ciprofloxacin in the treatment of acute respiratory tract infections.
1990 Oct
Drug-induced gallbladder disease. Incidence, aetiology and management.
1992 Jan-Feb
The in-vitro activity of two new quinolones: rufloxacin and MF 961.
1992 Jun
[Bacteriostatic activity and killing curves of eight antibiotics against seven strains of penicillin G-resistant pneumococci].
1992 May
[In vitro activity of sparfloxacin against mycoplasmas].
1992 May
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.
1992 Sep
Hepatotoxicity due to erythromycin ethylsuccinate.
1993 Jan 18
Evaluation of pertussis treatment with erythromycin ethylsuccinate and stearate according to age.
1994 Nov
Bioavailability and stability of erythromycin delayed release tablets.
2001 Dec
Massive venlafaxine overdose resulted in a false positive Abbott AxSYM urine immunoassay for phencyclidine.
2003
Mixed chimerism of erythro- and megakaryopoiesis following allogeneic bone marrow transplantation.
2003
Synthesis of (+)-aptosimon, a 4-oxofurofuran lignan, by erythro selective aldol condensation and stereoconvergent cyclization as the key reactions.
2003 Apr
Effects of amphotericin B and caspofungin on histamine expression.
2003 Aug
Iclaprim, a novel diaminopyrimidine with potent activity on trimethoprim sensitive and resistant bacteria.
2003 Dec 1
Effect of erythromycin on contractile response of uterine smooth muscle strips in non-pregnant rats.
2003 Jan-Feb
A novel enzyme, D-3-hydroxyaspartate aldolase from Paracoccus denitrificans IFO 13301: purification, characterization, and gene cloning.
2003 Jul
Ratio of erythro and threo forms of beta-O-4 structures in tension wood lignin.
2003 Nov
[Hantavirus-induced acute renal failure. A case report].
2003 Oct
A novel three-component reaction catalyzed by dirhodium(II) acetate: decomposition of phenyldiazoacetate with arylamine and imine for highly diastereoselective synthesis of 1,2-diamines.
2003 Oct 16
Isolation and antimicrobial susceptibility of Aeromonas salmonicida in rainbow trout (Oncorhynchus mykiss) in turkey hatchery farms.
2003 Sep
The relationship of physico-chemical properties and structure to the differential antiplasmodial activity of the cinchona alkaloids.
2003 Sep 1
erythro-1-Naphthyl-1-(2-piperidyl)methanol: synthesis, resolution, NMR relative configuration, and VCD absolute configuration.
2003 Sep 19
Straightforward synthesis of sphinganines via a serine-derived Weinreb amide.
2004 Apr 30
Bitterness evaluation of medicines for pediatric use by a taste sensor.
2004 Aug
Delayed Gastric Emptying in Functional Dyspepsia.
2004 Aug
Evidence of significant contribution from CYP3A5 to hepatic drug metabolism.
2004 Dec
Local mechanisms underlying the regulatory effect of Kropanol on hemopoiesis during paradoxical sleep deprivation.
2004 Feb
Dicloxacillin and erythromycin at high concentrations increase ICAM-1 expression by endothelial cells: a possible factor in the pathogenesis of infusion phlebitis.
2004 Feb
[3 + 2] Cycloreversion of bicyclo[m.3.0]alkan-3-on-2-yl-1-oxonium ylides to alkenyloxyketenes. Stereospecific aspect.
2004 Feb 20
Cytochrome P450/NADPH-dependent formation of trans epoxides from trans-arachidonic acids.
2004 Feb 23
Validation of a [3H]astemizole binding assay in HEK293 cells expressing HERG K+ channels.
2004 Jul
Highly diastereoselective reductive coupling of 2-bromo-2,3,3,3-tetrafluoropropanamide with aldehydes promoted by triphenylphosphine-titanium(IV) isopropoxide. An efficient route to the synthesis of erythro-alpha-fluoro-alpha-(trifluoromethyl)-beta-hydroxy amides.
2004 Jul 23
Effect of particle size on mixing degree in dispensation.
2004 Mar
Effect of mixing method on the mixing degree during the preparation of triturations.
2004 Mar
Conformational study of a guaiacyl beta-O-4 lignin model compound by NMR. Examination of intramolecular hydrogen bonding interactions and conformational flexibility in solution.
2004 Mar
Anti-proliferative effects of lichen-derived lipoxygenase inhibitors on twelve human cancer cell lines of different tissue origin in vitro.
2004 Nov
Comparative pharmacodynamics and plasma concentrations of d-threo-methylphenidate hydrochloride after single doses of d-threo-methylphenidate hydrochloride and d,l-threo-methylphenidate hydrochloride in a double-blind, placebo-controlled, crossover laboratory school study in children with attention-deficit/hyperactivity disorder.
2004 Nov
Enantiomeric separation of racemic neolignans on chiralcel OD and determination of their absolute configuration with online circular dichroism.
2004 Oct
Effects of colchicine on the maximum biliary excretion of cholephilic compounds in rats.
2004 Sep
In vitro and in vivo activities of macrolide derivatives against Mycobacterium tuberculosis.
2005 Apr
Standardization of bone marrow features--does it work in hematopathology for histological discrimination of different disease patterns?
2005 Apr
On the CH...Cu agostic interaction: chiral copper(II) compounds with ephedrine and pseudoephedrine derivatives.
2005 Aug 14
Randomised controlled multiple treatment comparison to provide a cost-effectiveness rationale for the selection of antimicrobial therapy in acne.
2005 Jan
High volume bioassays to assess CYP3A4-mediated drug interactions: induction and inhibition in a single cell line.
2005 Jan
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Desensitization of the human motilin receptor by motilides.
2005 Jun
Patents

Sample Use Guides

In Vivo Use Guide
Initial dose - 30 mg/kg, then 15 mg/kg every 12 hours.
Route of Administration: Oral; Topical
In Vitro Use Guide
At the concentration which stops polylysine synthesis by more than 80% (about 0.5 nM/100 pM of 70S ribosomes), the Erythromycin cyclocarbonate inhibited but slightly binding of phage f2 RNA to ribosomes.
Substance Class Chemical
Created
by admin
on Mon Oct 21 19:49:13 UTC 2019
Edited
by admin
on Mon Oct 21 19:49:13 UTC 2019
Record UNII
63937KV33D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ERYTHROMYCIN
EP   GREEN BOOK   HSDB   INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN  
Official Name English
ERYTHROMYCIN [USP]
Common Name English
ERYTHROMYCIN [MART.]
Common Name English
TORLAMICINA
Common Name English
ROBIMYCIN
Brand Name English
A/T/S
Brand Name English
ERYTHROMYCINUM [WHO-IP LATIN]
Common Name English
ERYTHROMYCIN [ORANGE BOOK]
Common Name English
ERYGEL
Brand Name English
E-SOLVE 2
Brand Name English
ERYTHROMYCIN [HSDB]
Common Name English
ERYCETTE
Brand Name English
ERYTHROMYCIN COMPONENT OF BENZAMYCIN
Common Name English
E-GLADES
Brand Name English
NSC-55929
Code English
ERYTHRA-DERM
Brand Name English
ERYTHROMYCIN-A
Common Name English
E-BASE
Brand Name English
ERYTHROMYCIN A
Common Name English
PCE
Brand Name English
ERYTHRO-STATIN
Brand Name English
ERY-TAB
Brand Name English
PANTOMICINA
Common Name English
ERYTHROMYCIN [WHO-IP]
Common Name English
R-P MYCIN
Brand Name English
ILOTYCIN
Brand Name English
ERYTHROMYCIN [GREEN BOOK]
Common Name English
ERYTHROMYCIN [INN]
Common Name English
ERYTHROMYCIN [EP]
Common Name English
T-STAT
Brand Name English
ERYTHROMYCIN [WHO-DD]
Common Name English
STATICIN
Brand Name English
ERYTHROMYCIN ESTOLATE IMPURITY, FREE ERYTHROMYCIN- [USP]
Common Name English
J01FA01
Code English
ERYDERM
Brand Name English
SANSAC
Brand Name English
EMGEL
Brand Name English
AKNE-MYCIN
Brand Name English
BENZAMYCIN COMPONENT ERYTHROMYCIN
Common Name English
ERYTHROMYCIN [VANDF]
Common Name English
ERYMAX
Brand Name English
ERYTHROMYCIN [MI]
Common Name English
ERYTHROMYCIN ESTOLATE SPECIFIED IMPURITY, FREE ERYTHROMYCIN [EP]
Common Name English
E-MYCIN
Brand Name English
ERYC
Brand Name English
ERYTHROMYCIN [USP-RS]
Common Name English
C-SOLVE-2
Brand Name English
Classification Tree Code System Code
NDF-RT N0000007529
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
WHO-ATC S01AA17
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
WHO-ATC D10AF52
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
LIVERTOX 367
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
WHO-ATC D10AF02
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
NDF-RT N0000175877
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
WHO-VATC QJ51RF02
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.2.2
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
CFR 21 CFR 520.823
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
WHO-VATC QD10AF02
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
WHO-VATC QS01AA17
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
NDF-RT N0000007529
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
NDF-RT N0000009982
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
NCI_THESAURUS C261
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
WHO-VATC QJ01FA01
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
WHO-VATC QJ51FA01
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
NDF-RT N0000175935
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
WHO-ATC J01FA01
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
CFR 21 CFR 522.820
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
CFR 21 CFR 526.820
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
CFR 21 CFR 556.230
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
CFR 21 CFR 558.248
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
NDF-RT N0000007529
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
Code System Code Type Description
ChEMBL
CHEMBL2110577
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
PRIMARY
ChEMBL
CHEMBL532
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
PRIMARY
PUBCHEM
12560
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
PRIMARY
IUPHAR
1456
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
PRIMARY
EVMPD
SUB06605MIG
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
PRIMARY
HSDB
114-07-8
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
PRIMARY
LactMed
114-07-8
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
PRIMARY
INN
39
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
PRIMARY
DRUG BANK
DB00199
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
PRIMARY
RXCUI
4053
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
PRIMARY RxNorm
WHO INTERNATIONAL PHARMACOPEIA
ERYTHROMYCIN
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
PRIMARY Description: White or slightly yellow crystals or powder; odourless or almost odourless.Solubility: Soluble in 1000 parts of water but less soluble in hot water; freely soluble in ethanol (~750 g/l) TS and ether R.Category: Antibacterial drug.Storage: Erythromycin should be kept in a tightly closed container, protected from light.Additional information: Erythromycin is slightly hygroscopic.Definition: Erythromycin is a mixture of substances produced by the growth of certain strains of Streptomyces erythreus. The main component of the mixture is erythromycin A with lesser amounts of erythromycins B and C.
EPA CompTox
114-07-8
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
PRIMARY
WIKIPEDIA
ERYTHROMYCIN
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
PRIMARY
MERCK INDEX
M5009
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
PRIMARY Merck Index
NCI_THESAURUS
C476
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
PRIMARY
CAS
114-07-8
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
PRIMARY
MESH
D004917
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
PRIMARY
ECHA (EC/EINECS)
204-040-1
Created by admin on Mon Oct 21 19:49:13 UTC 2019 , Edited by admin on Mon Oct 21 19:49:13 UTC 2019
PRIMARY
Related Record Type Details
TRANSPORTER -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
LABELED -> NON-LABELED
TRANSPORTER -> INHIBITOR
SUBSTANCE->BASIS OF STRENGTH
METABOLIC ENZYME -> INHIBITOR
IC50
LABELED -> NON-LABELED
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC POPULATION: ADULTS

MIC BIOLOGICAL SUSCEPTIBILITY: S. PNEUMONIAE, S. PYOGENES

MIC BIOLOGICAL SUSCEPTIBILITY: S. PNEUMONIAE, S. PYOGENES

Tmax PHARMACOKINETIC COMBINATION FORM: ERYTHROMYCIN ETHYLSUCCINATE

FOOD EFFECT: DELAYED Tmax

Biological Half-life PHARMACOKINETIC POPULATION: END-STAGE RENAL DISEASE

Volume of Distribution PHARMACOKINETIC
MIC BIOLOGICAL SUSCEPTIBILITY: S. AUREUS

MIC BIOLOGICAL SUSCEPTIBILITY: S. AUREUS

Tmax PHARMACOKINETIC FOOD EFFECT: DELAYED Tmax

COMBINATION FORM: ERYTHROMYCIN STEARATE

Tmax PHARMACOKINETIC FOOD EFFECT: BASE

COMBINATION FORM: ERYTHROMYCIN BASE

MIC BIOLOGICAL SUSCEPTIBILITY: S. PNEUMONIAE, S. PYOGENES

Biological Half-life PHARMACOKINETIC POPULATION: NEONATES (LESS THAN OR EQUAL TO 15 DAYS OF AGE)

MIC BIOLOGICAL SUSCEPTIBILITY: S. AUREUS