Compound ID | 1911

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Cefpiramide

Synonym(s): SM-1652

Class: Beta-lactam (cephalosporin, third generation)

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. Active against Gram-positive bacteria and against many Enterobacteriaceae but vulnerable to extended-spectum beta-lactamases (ESBL)
Description: Semisynthetic Cephalosporine, derived from Cephalosporin C
Institute where first reported: Wyeth Ayerst
Year first mentioned: 1982
Highest developmental phase: Approved by FDA in 1989
Development status: Discontinued
Chemical structure(s):
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Molecular weight: 612.64
Iso. SMILES: CC1=CC(=O)C(=CN1)C(=O)N[C@H](C2=CC=C(C=C2)O)C(=O)N[C@H]3[C@@H]4N(C3=O)C(=C(CS4)CSC5=NN=NN5C)C(=O)O
InChI Key: PWAUCHMQEXVFJR-PMAPCBKXSA-N
Can. SMILES: CC1=CC(=O)C(=CN1)C(=O)N[C@H](C2=CC=C(C=C2)O)C(=O)N[C@@H]3C(=O)N4C(=C(CS[C@H]34)CSC5=NN=NN5C)C(=O)O
InChI: InChI=1S/C25H24N8O7S2/c1-11-7-16(35)15(8-26-11)20(36)27-17(12-3-5-14(34)6-4-12)21(37)28-18-22(38)33-19(24(39)40)13(9-41-23(18)33)10-42-25-29-30-31-32(25)2/h3-8,17-18,23,34H,9-10H2,1-2H3,(H,26,35)(H,27,36)(H,28,37)(H,39,40)/t17-,18-,23-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/636405
Guide to Pharmacology: cefpiramide
Citation: https://www.jiac-j.com/article/S1341-321X(00)71317-1/fulltext

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