PENAMECILLIN

U.S. Department of Health & Human Services Divider Arrow

National Institutes of Health Divider Arrow

NCATS

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H22N2O6S
Molecular Weight	406.453
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of PENAMECILLIN

Structure Search

SMILES

CC(=O)OCOC(=O)[C@@H]1N2[C@H](SC1(C)C)[C@H](NC(=O)CC3=CC=CC=C3)C2=O

InChI

InChIKey=NLOOMWLTUVBWAW-HLLBOEOZSA-N

InChI=1S/C19H22N2O6S/c1-11(22)26-10-27-18(25)15-19(2,3)28-17-14(16(24)21(15)17)20-13(23)9-12-7-5-4-6-8-12/h4-8,14-15,17H,9-10H2,1-3H3,(H,20,23)/t14-,15+,17-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.drugs.com/international/penamecillin.html | https://www.ncbi.nlm.nih.gov/pubmed/19108231 | https://www.ncbi.nlm.nih.gov/pubmed/4959939

Penamecillin is a semi-synthetic beta-lactamase sensitive penicillin. The compound is the acetoxymethyl ester of benzylpenicillin, which is rapidly hydrolysed to the latter by the action of non-specific esterases.

Approval Year

Patents

Patents

Name

Type

Language

WY-20788

Preferred Name

English

PENAMECILLIN

Official Name

English

WY-20,788

Code

English

PENAMECILLIN [USAN]

Common Name

English

penamecillin [INN]

Common Name

English

Hydroxymethyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate, acetate (ester)

Common Name

English

Penamecillin [WHO-DD]

Common Name

English

4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 3,3-DIMETHYL-7-OXO-6-((PHENYLACETYL)AMINO)-(2S-(2.ALPHA.,5.ALPHA.,6.BETA.))-, (ACETYLOXY)METHYL ESTER

Common Name

English

PENAMECILLIN [MI]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QJ01CE06

Created by admin on Mon Mar 31 17:52:00 GMT 2025 , Edited by admin on Mon Mar 31 17:52:00 GMT 2025

WHO-ATC

J01CE06

Created by admin on Mon Mar 31 17:52:00 GMT 2025 , Edited by admin on Mon Mar 31 17:52:00 GMT 2025

Code System Code Type Description

ECHA (EC/EINECS)

213-571-8

Created by admin on Mon Mar 31 17:52:00 GMT 2025 , Edited by admin on Mon Mar 31 17:52:00 GMT 2025

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USAN

Y-10

Created by admin on Mon Mar 31 17:52:00 GMT 2025 , Edited by admin on Mon Mar 31 17:52:00 GMT 2025

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ChEMBL

CHEMBL2106988

Created by admin on Mon Mar 31 17:52:00 GMT 2025 , Edited by admin on Mon Mar 31 17:52:00 GMT 2025

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WIKIPEDIA

Penamecillin

Created by admin on Mon Mar 31 17:52:00 GMT 2025 , Edited by admin on Mon Mar 31 17:52:00 GMT 2025

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DRUG CENTRAL

2077

Created by admin on Mon Mar 31 17:52:00 GMT 2025 , Edited by admin on Mon Mar 31 17:52:00 GMT 2025

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MESH

C016646

Created by admin on Mon Mar 31 17:52:00 GMT 2025 , Edited by admin on Mon Mar 31 17:52:00 GMT 2025

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FDA UNII

H0P1YE5581

Created by admin on Mon Mar 31 17:52:00 GMT 2025 , Edited by admin on Mon Mar 31 17:52:00 GMT 2025

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CAS

983-85-7

Created by admin on Mon Mar 31 17:52:00 GMT 2025 , Edited by admin on Mon Mar 31 17:52:00 GMT 2025

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INN

2057

Created by admin on Mon Mar 31 17:52:00 GMT 2025 , Edited by admin on Mon Mar 31 17:52:00 GMT 2025

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EPA CompTox

DTXSID10243547

Created by admin on Mon Mar 31 17:52:00 GMT 2025 , Edited by admin on Mon Mar 31 17:52:00 GMT 2025

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SMS_ID

100000082497

Created by admin on Mon Mar 31 17:52:00 GMT 2025 , Edited by admin on Mon Mar 31 17:52:00 GMT 2025

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PUBCHEM

10250769

Created by admin on Mon Mar 31 17:52:00 GMT 2025 , Edited by admin on Mon Mar 31 17:52:00 GMT 2025

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MERCK INDEX

m8460

Created by admin on Mon Mar 31 17:52:00 GMT 2025 , Edited by admin on Mon Mar 31 17:52:00 GMT 2025

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Merck Index

NCI_THESAURUS

C170307

Created by admin on Mon Mar 31 17:52:00 GMT 2025 , Edited by admin on Mon Mar 31 17:52:00 GMT 2025

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DRUG BANK

DB13739

Created by admin on Mon Mar 31 17:52:00 GMT 2025 , Edited by admin on Mon Mar 31 17:52:00 GMT 2025

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EVMPD

SUB09659MIG

Created by admin on Mon Mar 31 17:52:00 GMT 2025 , Edited by admin on Mon Mar 31 17:52:00 GMT 2025

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ACTIVE MOIETY


					H0P1YE5581