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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 of RITIPENEM

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency
0.076 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown
Curative
Unknown
Curative
Unknown
Curative
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
7.28 mg/L
500 mg 3 times / day steady-state, oral
RITIPENEM plasma
Homo sapiens
167 mg/L
1 g single, intravenous
RITIPENEM serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
11.24 mg × h/L
500 mg 3 times / day steady-state, oral
RITIPENEM plasma
Homo sapiens
41.5 mg × h/L
1 g single, intravenous
RITIPENEM serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
0.79 h
500 mg 3 times / day steady-state, oral
RITIPENEM plasma
Homo sapiens
0.8 h
1 g single, intravenous
RITIPENEM serum
Homo sapiens

Doses

AEs

PubMed

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
Record UNII
D4SL77931L
Record Status Validated (UNII)
Record Version