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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 of TOMOPENEM

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Substance Class Chemical
Record UNII
1654W9611T
Record Status Validated (UNII)
Record Version