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

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
Curative
Unknown

Approved Use

Unknown
Curative
Unknown

Approved Use

Unknown
Curative
Unknown

Approved Use

Unknown
PubMed

PubMed

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

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 Sat Dec 16 05:26:24 GMT 2023
Edited
by admin
on Sat Dec 16 05:26:24 GMT 2023
Record UNII
N25O8O59B3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RITIPENEM ACOXIL MONOHYDRATE
Common 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
RITIPENEM ACOXIL HYDRATE
JAN  
Common Name English
Code System Code Type Description
PUBCHEM
76961639
Created by admin on Sat Dec 16 05:26:24 GMT 2023 , Edited by admin on Sat Dec 16 05:26:24 GMT 2023
PRIMARY
FDA UNII
N25O8O59B3
Created by admin on Sat Dec 16 05:26:24 GMT 2023 , Edited by admin on Sat Dec 16 05:26:24 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
ANHYDROUS->SOLVATE
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ACTIVE MOIETY