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Details

Stereochemistry ABSOLUTE
Molecular Formula C13H16N2O8S.H2O
Molecular Weight 378.355
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RITIPENEM ACOXIL MONOHYDRATE

SMILES

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

InChI

InChIKey=ZZFMPSZLBDWBLH-UYQYSZDNSA-N
InChI=1S/C13H16N2O8S.H2O/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);1H2/t5-,8+,11-;/m1./s1

HIDE SMILES / InChI
Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C13H16N2O8S
Molecular Weight 360.34
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 0.076 nM [IC50]
Inhibitor
8504
Escherichia coli growth
23
Target ID: Escherichia coli growth
Inhibitor
8504
Staphylococcus aureus growth
27
Target ID: Staphylococcus aureus growth
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Preclinical
Unknown

Approved Use

Unknown
Curative
Preclinical
Unknown

Approved Use

Unknown
Curative
Phase II
1147
Unknown

Approved Use

Unknown
Curative
Preclinical
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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

AEs

AESignificanceDosePopulation
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

PubMed

TitleDatePubMed
Potent bacteriolytic activity of ritipenem associated with a characteristic profile of affinities for penicillin-binding proteins of Haemophilus influenzae.
1999-10
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
A study of the pharmacokinetics and tolerability of ritipenem acoxil in healthy volunteers following multiple oral dosing.
1997-08
Patents

Patents

JP2002541233A
406

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Can also be used intravenously https://www.ncbi.nlm.nih.gov/pubmed/2732142
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 Mon Mar 31 21:29:39 GMT 2025
Edited
by admin
on Mon Mar 31 21:29:39 GMT 2025
Record UNII
N25O8O59B3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RITIPENEM ACOXIL MONOHYDRATE
Common Name English
RITIPENEM ACOXIL HYDRATE
JAN  
Preferred Name English
(+)-(5R,6S)-ACETOXYMETHYL 3-CARBAMOYLOXYMETHYL-6-((1R)-1-HYDROXYETHYL)-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPT-2-ENE-2-CARBOXYLATE MONOHYDRATE
Systematic Name English
RITIPENEM ACOXIL HYDRATE [JAN]
Common Name English
Code System Code Type Description
PUBCHEM
76961639
Created by admin on Mon Mar 31 21:29:39 GMT 2025 , Edited by admin on Mon Mar 31 21:29:39 GMT 2025
PRIMARY
FDA UNII
N25O8O59B3
Created by admin on Mon Mar 31 21:29:39 GMT 2025 , Edited by admin on Mon Mar 31 21:29:39 GMT 2025
PRIMARY
Related Record Type Details
Structure of RITIPENEM ACOXIL
PARENT -> SALT/SOLVATE
Structure of RITIPENEM ACOXIL
ANHYDROUS->SOLVATE
Related Record Type Details
Structure of RITIPENEM
ACTIVE MOIETY
NIH
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