Erythromycin Estolate

HCID 441371
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Basic information

CAS
3521-62-8
Standard SMILES
CCC(=O)O[C@H]1[C@H](O[C@@H]2[C@@H](C)[C@H](O[C@H]3C[C@@](C)(OC)[C@@H](O)[C@H](C)O3)[C@@H](C)C(=O)O[C@H](CC)[C@@](C)(O)[C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@]2(C)O)O[C@H](C)C[C@@H]1N(C)C.CCCCCCCCCCCCOS(=O)(=O)O
InChIKey
AWMFUEJKWXESNL-JZBHMOKNSA-N
Molecular formula
C52H97NO18S
Average molar mass
1,056.4 g/mol
Monoisotopic mass
1,055.64263626

Overview

Erythromycin estolate is an aminoglycoside sulfate salt and an erythromycin derivative. It has a role as an enzyme inhibitor. It contains an erythromycin A 2'-propanoate.

Names & identifiers

Preferred name
Erythromycin Estolate
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] propanoate;dodecyl hydrogen sulfate

Names & synonyms

ERYTHROMYCIN ESTOLATEIlosone3521-62-8EstomicinaRoxomicinaStellamicinaEriscelEritrogerNeo-erycinumErythromycin estorateerythromycin propionate lauryl sulfatePELS
Show more names
DTXSID1037224Propionylerythromycin lauryl sulfateErythromycin (as estolate)XRJ2P631HPErythromycin, 2'-propanoate, dodecyl sulfate (salt)Lauryl sulfate propionyl erythromycin esterNSC-263364Erythromycin propionate, compound with dodecyl sulfate

Database identifiers

CAS
3521-62-8
PubChem CID
441371
DTXSID
DTXSID1037224
ChEMBL
CHEMBL2218877
ChEBI
CHEBI:4846
UNII
XRJ2P631HP
EC Number
222-532-4

Properties

Computed structural propertiesFilling in

Topological polar surface area
272 Ų
Hydrogen bond donors
5
Hydrogen bond acceptors
19
Rotatable bonds
22
Heavy atoms
72

Experimental & physicochemical properties

LipidsPolyketides [PK] -> Macrolides and lactone polyketides [PK04]
Human Drugs · 2 items

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Collision Cross Section264.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P233, P260, P261, P264, P270, P271, P272, P280, P284, P301+P317, P302+P352, P304+P340, P321, P330, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 118 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationErythromycin, 2'-propanoate, dodecyl sulfate (salt): Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Other Safety InformationIMAP assessments - Erythromycin, 2'-propanoate, dodecyl sulfate (salt): Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (100%)

Toxicology

Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Erythromycin estolate

vMost-DILI-concern

5

Warnings & precautions

DOI:10.1016/j.drudis.2016.02.015

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 4 items

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.

Drugs used for their effects on the gastrointestinal system, as to control gastric acidity, regulate gastrointestinal motility and water flow, and improve digestion.

Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins.

Substances that inhibit the growth or reproduction of BACTERIA.

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Compound notes

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