Compound ID | 358

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Ceftizoxime alapivoxil (prodrug)

Synonym(s): AS 924  |  KY 020  |  Cefizox

Class: Beta-lactam

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Cell wall synthesis inhibitor
Description: Bifunctional prodrug of ceftizoxime (a third-generation cephalosporin); developed for oral administration
Institute where first reported: Astellas; Kyoto Pharmaceutical Industries; Asahi Kasei
Year first mentioned: 1983
Highest development stage: Approved by FDA in 1983
Development status: Withdrawn
Reason dropped: Was in pre-registration in Japan later on but seems to have been pulled out, this may be due to side effects
Chemical structure(s):
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Molecular weight: 568.63
Iso. SMILES: C[C@@H](C(=O)NC1=NC(=CS1)/C(=N/OC)/C(=O)N[C@H]2[C@@H]3N(C2=O)C(=CCS3)C(=O)OCOC(=O)C(C)(C)C)N
InChI Key: VOPANQNVVCPHQR-IVVGYLHBSA-N
Can. SMILES: C[C@@H](C(=O)NC1=NC(=CS1)/C(=N/OC)/C(=O)N[C@@H]2C(=O)N3C(=CCS[C@H]23)C(=O)OCOC(=O)C(C)(C)C)N
InChI: InChI=1S/C22H28N6O8S2/c1-10(23)15(29)26-21-24-11(8-38-21)13(27-34-5)16(30)25-14-17(31)28-12(6-7-37-18(14)28)19(32)35-9-36-20(33)22(2,3)4/h6,8,10,14,18H,7,9,23H2,1-5H3,(H,25,30)(H,24,26,29)/b27-13-/t10-,14+,18+/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/9578661
Guide to Pharmacology: ceftizoxime alapivoxil

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