Compound ID | 321

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Tomopenem

Synonym(s): CS-023  |  RO4908463  |  R-115685

Class: Beta-lactam (carbapenem)

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Binds to bacterial penicillin-binding proteins (PBP) and interferes with bacterial cell wall integrity and synthesis. Carbapenems bind to all PBPs, with PBP2 and PBP4 as the highest-affinity targets. Carbapenems have a very broad spectrum incl. non-fermenters and are not hydrolysed by most beta-lactamases with exception of carbapenemases.
Institute where first reported: Daiichi Sankyo Pharmaceutical; Hoffman-La Roche, Switzerland
Year first mentioned: 2000
Highest developmental phase: Phase 2
Development status: Inactive
Reason Dropped: Discontinued for unknown reasons (LS)
Chemical structure(s):
Click here for structure editor
Molecular weight: 537.63
Iso. SMILES: C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H](N(C3)C)C(=O)N4CC[C@@H](C4)NC(=O)CN=C(N)N)C(=O)O)[C@@H](C)O
InChI Key: KEDAXBWZURNCHS-GPODMPQUSA-N
Can. SMILES: C[C@@H]1[C@@H]2[C@@H]([C@@H](C)O)C(=O)N2C(=C1S[C@H]3C[C@@H](C(=O)N4CC[C@@H](C4)NC(=O)CN=C(N)N)N(C)C3)C(=O)O
InChI: 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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/9809656
Guide to Pharmacology: tomopenem
Citations:
  • https://academic.oup.com/jac/article/54/2/557/767405?login=false
  • https://www.jstage.jst.go.jp/article/dmpk/22/1/22_1_41/_article

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