SANFETRINEM CILEXETIL

Details

Stereochemistry	EPIMERIC
Molecular Formula	C23H33NO8
Molecular Weight	451.51
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CO[C@H]1CCC[C@@H]2[C@@H]3[C@@H]([C@@H](C)O)C(=O)N3C(C(=O)OC(C)OC(=O)OC4CCCCC4)=C12

InChI

InChIKey=QFEICXCLIGZEJB-IRVPUMQPSA-N

InChI=1S/C23H33NO8/c1-12(25)17-19-15-10-7-11-16(29-3)18(15)20(24(19)21(17)26)22(27)30-13(2)31-23(28)32-14-8-5-4-6-9-14/h12-17,19,25H,4-11H2,1-3H3/t12-,13?,15+,16+,17-,19-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C23H33NO8
Molecular Weight	451.51
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	5 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://adisinsight.springer.com/drugs/800002101 | https://www.ncbi.nlm.nih.gov/pubmed/7840571https://www.ncbi.nlm.nih.gov/pubmed/9661036 | https://adisinsight.springer.com/drugs/800006681

Sanfetrinem cilexetil (formerly known as GV 118819), a beta-lactam antibiotic, is the oral prodrug of sanfetrinem. Experiments on rodents have revealed that sanfetrinem cilexetil had strong antibacterial activity in vitro and good pharmacokinetic behavior in mice. This drug was suitable for the treatment of infections caused by a variety of bacteria and participated in a phase II clinical trial. However, this study was discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
[Sanfetrinem, the member of trinems--in vitro activity against Klebsiella pneumoniae producing ESBL].	2006	16871970
Carboxylesterases, a key factor in evaluating potential genotoxicity of Trinem antibiotics.	2000-01	10640530
In-vitro activity of sanfetrinem against isolates of Streptococcus pneumoniae and Staphylococcus aureus.	1998-11	9848449
In vivo antibacterial activities of sanfetrinem cilexetil, a new oral tricyclic antibiotic.	1998-07	9661036
Sanfetrinem and sanfetrinem-cilexetil: disposition in rat and dog.	1997-07	9253146
In vitro activity of sanfetrinem (GV104326), a new trinem antimicrobial agent, versus Streptococcus pneumoniae, Haemophilus influenzae, and Moraxella catarrhalis.	1996-09	8950528
In vitro activity of the tribactam GV104326 against gram-positive, gram-negative, and anaerobic bacteria.	1994-10	7840571
Automated assay for GV104326, a novel tribactam antibiotic, in human plasma by high-performance liquid chromatography and solid-phase extraction.	1994-02-04	8148994

Sample Use Guides

In Vitro Use Guide

The activity of sanfetrinem was determined using a broth microdilution MIC method versus a large number of clinical isolates of Streptococcus pneumoniae, Haemophilus influenzae, and Moraxella catarrhalis obtained in a recent 30-center United States surveillance study. The sanfetrinem MIC50 and MIC90 values for these three organism groups were 0.015 and 0.5 microgram/ml, 0.25, and 0.5 microgram/ml, and 0.015 and 0.03, respectively.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:13:29 GMT 2025` Edited by `admin` on `Mon Mar 31 18:13:29 GMT 2025`
Record UNII	7322RJ9FZB
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SANFETRINEM CILEXETIL

Official Name

English

GV-118819X

Preferred Name

English

SANFETRINEM CILEXETIL [USAN]

Common Name

English

1-Hydroxyethyl (1S,5S,8aS,8bR)-1,2,5,6,7,8,8a,8b-octahydro-1-[(R)-1-hydroxyethyl]-5-methoxy-2-oxoazeto[2,1-a]isoindole-4-carboxylate, cyclohexyl carbonate (ester)

Common Name

English

GV118819X

Code

English

Sanfetrinem cilexetil [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C260