ceftizoxime alapivoxil   Click here for help

GtoPdb Ligand ID: 10786

Synonyms: AS-924 | AS924 | KY-020 | KY020
Compound class: Synthetic organic
Comment: Ceftizoxime alapivoxil is a third-generation cephalosporin antibiotic ester prodrug [1-2].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 12
Hydrogen bond donors 3
Rotatable bonds 14
Topological polar surface area 245.15
Molecular weight 568.14
XLogP 0.63
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES CO/N=C(\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC=C2C(=O)OCOC(=O)C(C)(C)C)/c1csc(n1)NC(=O)[C@@H](N)C
Isomeric SMILES CO/N=C(\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC=C2C(=O)OCOC(=O)C(C)(C)C)/c1csc(n1)NC(=O)[C@@H](N)C
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
InChI Key VOPANQNVVCPHQR-IVVGYLHBSA-N
References
1. Kasai M, Hatano S, Kitagawa M, Yoshimi A, Shirahase H, Nishimura K, Kakeya N. (1999)
AS-924, a novel bifunctional prodrug of ceftizoxime.
J Antibiot, 52 (5): 491-500. [PMID:10480574]
2. Mori N, Kodama T, Sakai A, Suzuki T, Sugihara T, Yamaguchi S, Nishijima T, Aoki A, Toriya M, Kasai M et al.. (2001)
AS-924, a novel, orally active, bifunctional prodrug of ceftizoxime: physicochemical properties, oral absorption in animals, and antibacterial activity.
Int J Antimicrob Agents, 18 (5): 451-61. [PMID:11711261]
3. Totsuka K, Shimizu K, Mori N, Sugihara T, Sakai A, Yamaji S, Michisuji Y, Shinohara Y, Kubo A, Tokuoka H. (2001)
Effect of antacid pretreatment on the pharmacokinetics of AS-924, a novel ester-type cephem antibiotic--comparison with cefteram-pivoxil.
Int J Antimicrob Agents, 18 (5): 477-82. [PMID:11711264]
4. Totsuka K, Shimizu K, Mori N, Sugihara T, Sakai A, Yamaji S, Michisuji Y, Shinohara Y, Kubo A, Tokuoka H. (2001)
Effects of food intake and age on the pharmacokinetics of AS-924, a novel ester-type cephem antibiotic. Comparison with cefpodoxime proxetil.
Int J Antimicrob Agents, 18 (5): 463-9. [PMID:11711262]