Erythromycin Acistrate

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Basic information

CAS: 96128-89-1
Standard SMILES: CCCCCCCCCCCCCCCCCC(=O)O.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](N(C)C)[C@H]2OC(C)=O)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O
InChIKey: FPEVNWDVXZGKCD-SAVXWCSHSA-N
Molecular formula: C57H105NO16
Average molar mass: 1,060.4 g/mol
Monoisotopic mass: 1,059.74333626

Overview

See also: Erythromycin (has active moiety).

Names & identifiers

Preferred name: Erythromycin Acistrate
IUPAC: [(2S,3R,4S,6R)-4-(dimethylamino)-2-[[(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-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-2,10-dioxo-oxacyclotetradec-6-yl]oxy]-6-methyloxan-3-yl] acetate;octadecanoic acid
English name: ErythromycinAcistrate
Molecular formula: C57H105NO16
Molecular weight: 1060.46

Names & synonyms

Erythromycin acistrateErasis96128-89-1Acistrate d'erythromycineAcistrato de eritromicinaErythromycini acistras6383U5A1KEDTXSID9022992RefChem:137781DTXCID502992ErythromycinAcistrateErythromycin acistrate (USAN)

Show more names

[(2S,3R,4S,6R)-4-(dimethylamino)-2-[[(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-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-2,10-dioxo-oxacyclotetradec-6-yl]oxy]-6-methyloxan-3-yl] acetate

ERYTHROMYCIN ACISTRATE [USAN]UNII-6383U5A1KEErythromycin acistrate [USAN:INN]Erythromycini acistras [INN-Latin]Erasis (TN)Acistrate d'erythromycine [INN-French]Acistrato de eritromicina [INN-Spanish]Erythromycin 2'-acetate, stearate (salt)

Database identifiers

Properties

Computed structural properties

Topological polar surface area: 237 Å²
Hydrogen bond donors: 5
Hydrogen bond acceptors: 17
Rotatable bonds: 25
Heavy atoms: 74
Formal charge: 0
Complexity: 1,490

Physicochemical properties

FDA UNII: 6383 U5A1KE · 6383U5A1KE

Chemistry & industry

Applications · 2 items

DescriptionErythromycin acistrate is a prodrug of erythromycin with lowered liver toxicity, improved phmacokinetics, and greatly reduced gastro-intestinal side-effects. It is indicated for respiratory tract infections, skin infections and chlamydial urethritis.

UsesAntibacterial.

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Compound notes

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