RITIPENEM ACOXIL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C13H16N2O8S
Molecular Weight	360.34
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12SC(COC(N)=O)=C(N1C(=O)[C@]2([H])[C@@H](C)O)C(=O)OCOC(C)=O

InChI

InChIKey=FZKGLCPKPZBGLX-ROXVQFJHSA-N

InChI=1S/C13H16N2O8S/c1-5(16)8-10(18)15-9(12(19)23-4-22-6(2)17)7(24-11(8)15)3-21-13(14)20/h5,8,11,16H,3-4H2,1-2H3,(H2,14,20)/t5-,8+,11-/m1/s1

HIDE SMILES / InChI

Description
Sources: http://adisinsight.springer.com/drugs/800000518
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/10508039 and http://www.genome.jp/dbget-bin/www_bget?dr:D09849

Ritipenem (FCE 22101), a penem antibiotic, penicillin binding protein inhibitor, is potent against both gram-positive and -negative bacteria, and its acetoxymethyl ester (FCE 22891; ritipenem-acoxil) is orally available. Ritipenem is manufactured by Tanabe Seiyaku in the ritipenem acoxil prodrug form, which can be taken orally. It is not FDA approved in the United States.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Bacterial penicillin-binding protein 233 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10508039	Inhibitor 8297	0.076 nM [IC50]
Peptidoglycan biosynthesis 20 Target ID: map00550 Sources: http://www.genome.jp/dbget-bin/www_bget?dr:D09849	Inhibitor 8297
Escherichia coli growth 23 Target ID: Escherichia coli growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/7473551	Inhibitor 8297
Staphylococcus aureus growth 27 Target ID: Staphylococcus aureus growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/7473551	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Chronic lower respiratory tract infections 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8935119	Curative	Preclinical	Unknown Approved Use Unknown
Bacterial pneumonia 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8721077	Curative	Preclinical	Unknown Approved Use Unknown
Urinary tract infections 205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8904144	Curative	Phase II 1132	Unknown Approved Use Unknown
Uncomplicated cystitis 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7756468	Curative	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
MEN 10700, a new penem antibiotic: in-vitro activity and its correlation with beta-lactamase stability, PBP affinity and diffusion through the bacterial cell wall.	1998 May	9630405
Potent bacteriolytic activity of ritipenem associated with a characteristic profile of affinities for penicillin-binding proteins of Haemophilus influenzae.	1999 Oct	10508039

Patents

Sample Use Guides

In Vivo Use Guide

Ritipenem-acoxil was orally administered at 200 mg for 14 days

Route of Administration: Oral

In Vitro Use Guide

Ritipenem inhibited Escherichia coli growth with MIC = 1ug/ml

Name

Type

Language

RITIPENEM ACOXIL

Common Name

English

RITIPENEM ACETOXYMETHYL ESTER [MI]

Common Name

English

(+)-RITIPENEM ACOXIL

Common Name

English

RITIPENEM ACETOXYMETHYL ESTER

Common Name

English

4-THIA-1-AZABICYCLO(3.2.0)HEPT-2-ENE-2-CARBOXYLIC ACID, 3-(((AMINOCARBONYL)OXY)METHYL)-6-(1-HYDROXYETHYL)-7-OXO-, (ACETYLOXY)METHYL ESTER, (5R-(5.ALPHA.,6.ALPHA.(R*)))-

Common Name

English

FCE-22891

Code

English

4-THIA-1-AZABICYCLO(3.2.0)HEPT-2-ENE-2-CARBOXYLIC ACID, 3-(((AMINOCARBONYL)OXY)METHYL)-6-((1R)-1-HYDROXYETHYL)-7-OXO-, (ACETYLOXY)METHYL ESTER, (5R,6S)-

Common Name

English

Code System Code Type Description

PUBCHEM

6918147