TOMOPENEM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H35N7O6S
Molecular Weight	537.632
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12[C@@H](C)C(S[C@H]3C[C@H](N(C)C3)C(=O)N4CC[C@@H](C4)NC(=O)CNC(N)=N)=C(N1C(=O)[C@]2([H])[C@@H](C)O)C(O)=O

InChI

InChIKey=KEDAXBWZURNCHS-GPODMPQUSA-N

InChI=1S/C23H35N7O6S/c1-10-17-16(11(2)31)21(34)30(17)18(22(35)36)19(10)37-13-6-14(28(3)9-13)20(33)29-5-4-12(8-29)27-15(32)7-26-23(24)25/h10-14,16-17,31H,4-9H2,1-3H3,(H,27,32)(H,35,36)(H4,24,25,26)/t10-,11-,12+,13+,14+,16-,17-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C23H35N7O6S
Molecular Weight	537.632
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21844314 | https://adisinsight.springer.com/drugs/800014654 | https://www.ncbi.nlm.nih.gov/pubmed/18519723

Tomopenem (formerly CS-023) is a 1β-methylcarbapenem with improved activity against diverse hospital pathogens, including Pseudomonas aeruginosa and methicillin-resistant Staphylococcus aureus (MRSA), and has a half-life about twice longer than the half-lives of other carbapenems such as imipenem (IPM) and meropenem (MEM). In vitro activity of tomopenem is comparable to that of IPM against most isolates of Gram-positive pathogens and similar to that of MEM against Gram-negative pathogens. Furthermore, tomopenem displayed improved activity against not only P. aeruginosa but also MRSA compared to IPM and MEM. In addition to the improved activity, tomopenem showed a half-life about twice longer than that of IPM or MEM in humans. The affinity of tomopenem for penicillin-binding protein (PBP) 2a might be higher than that of IPM. Tomopenem had been in phase II clinical trial for the treatment of Gram-positive and Gram-negative bacterial infection. However, this development was discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
Gateways to clinical trials.	2007 Apr	17520107
In vivo efficacy and pharmacokinetics of tomopenem (CS-023), a novel carbapenem, against Pseudomonas aeruginosa in a murine chronic respiratory tract infection model.	2008 Dec	18835805
Multidrug-resistant Gram-negative bacterial infections: the emerging threat and potential novel treatment options.	2008 Feb	18246520
Lack of age and gender effects on single-dose pharmacokinetics of tomopenem (RO4908463/CS-023), a novel carbapenem.	2009 Apr	19371322
Current status of carbapenem antibiotics.	2010	20615191
In vitro postantibiotic effects of tomopenem (CS-023) against Staphylococcus aureus and Pseudomonas aeruginosa.	2010 Apr	20093378

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:30:48 UTC 2023` Edited by `admin` on `Fri Dec 15 15:30:48 UTC 2023`
Record UNII	1654W9611T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TOMOPENEM

Official Name

English

R-1L5685

Code

English

tomopenem [INN]

Common Name

English

CS-023

Code

English

TOMOPENEM [USAN]

Common Name

English

RO4908463

Code

English

R-1558

Code

English

Tomopenem [WHO-DD]

Common Name

English

RO-4908463

Code

English

R-115685

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C260