RITIPENEM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H12N2O6S
Molecular Weight	288.277
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H](O)[C@@H]1[C@H]2SC(COC(N)=O)=C(N2C1=O)C(O)=O

InChI

InChIKey=IKQNRQOUOZJHTR-UWBRJAPDSA-N

InChI=1S/C10H12N2O6S/c1-3(13)5-7(14)12-6(9(15)16)4(19-8(5)12)2-18-10(11)17/h3,5,8,13H,2H2,1H3,(H2,11,17)(H,15,16)/t3-,5+,8-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C10H12N2O6S
Molecular Weight	288.277
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 234 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10508039	Inhibitor 8504	0.076 nM [IC50]
Peptidoglycan biosynthesis 20 Target ID: map00550 Sources: http://www.genome.jp/dbget-bin/www_bget?dr:D09849	Inhibitor 8504
Escherichia coli growth 23 Target ID: Escherichia coli growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/7473551	Inhibitor 8504
Staphylococcus aureus growth 27 Target ID: Staphylococcus aureus growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/7473551	Inhibitor 8504

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 207 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8904144	Curative	Phase II 1147	Unknown Approved Use Unknown
Uncomplicated cystitis 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7756468	Curative	Preclinical	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
7.28 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9301999/	500 mg 3 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		RITIPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status:
167 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3378958/	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:		RITIPENEM serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
11.24 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9301999/	500 mg 3 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		RITIPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status:
41.5 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3378958/	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:		RITIPENEM serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.79 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9301999/	500 mg 3 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		RITIPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status:
0.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3378958/	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:		RITIPENEM serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
1 g 3 times / day multiple, oral Studied dose Dose: 1 g, 3 times / day Route: oral Route: multiple Dose: 1 g, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8031062/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FED Sources: https://pubmed.ncbi.nlm.nih.gov/8031062/	Disc. AE: Diarrhea... AEs leading to discontinuation/dose reduction: Diarrhea (6.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/8031062/

AEs

AE	Significance	Dose	Population
Diarrhea	6.7% Disc. AE	1 g 3 times / day multiple, oral Studied dose Dose: 1 g, 3 times / day Route: oral Route: multiple Dose: 1 g, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8031062/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FED Sources: https://pubmed.ncbi.nlm.nih.gov/8031062/

PubMed

Title	Date	PubMed
Potent bacteriolytic activity of ritipenem associated with a characteristic profile of affinities for penicillin-binding proteins of Haemophilus influenzae.	1999-10	10508039
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.	1998-05	9630405
A study of the pharmacokinetics and tolerability of ritipenem acoxil in healthy volunteers following multiple oral dosing.	1997-08	9301999

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

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:37:04 GMT 2025` Edited by `admin` on `Wed Apr 02 09:37:04 GMT 2025`
Record UNII	D4SL77931L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RITIPENEM

Official Name

English

RITIPENEM [MI]

Preferred Name

English

ritipenem [INN]

Common Name

English

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

Systematic Name

English

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

Systematic Name

English

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

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C260