cefozopran   Click here for help

GtoPdb Ligand ID: 12054

Synonyms: SCE-2787
Approved drug
cefozopran is an approved drug (Japan)
Compound class: Synthetic organic
Comment: Cefozopran is a fourth generation cephalosporin, belonging to the β-lactam class of antibacterial compounds. It has broad-spectrum activity and was developed by Takeda for parenteral treatment of infections caused by a range of Gram-positive and Gram-negative bacteria [1-2].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 10
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 237.65
Molecular weight 515.08
XLogP -2.04
No. Lipinski's rules broken 0
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Canonical SMILES CO/N=C(/c1nsc(n1)N)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])C[n+]1ccn2c1cccn2
Isomeric SMILES CO/N=C(/c1nsc(n1)N)\C(=O)N[C@H]1[C@@H]2N(C1=O)C(=C(CS2)C[n+]1c2cccnn2cc1)C(=O)[O-]
InChI InChI=1S/C19H17N9O5S2/c1-33-24-11(14-23-19(20)35-25-14)15(29)22-12-16(30)28-13(18(31)32)9(8-34-17(12)28)7-26-5-6-27-10(26)3-2-4-21-27/h2-6,12,17H,7-8H2,1H3,(H3-,20,22,23,25,29,31,32)/b24-11-/t12-,17-/m1/s1
1. Iwahi T, Okonogi K, Yamazaki T, Shiki S, Kondo M, Miyake A, Imada A. (1992)
In vitro and in vivo activities of SCE-2787, a new parenteral cephalosporin with a broad antibacterial spectrum.
Antimicrob Agents Chemother, 36 (7): 1358-66. [PMID:1510428]
2. Miyake A, Yoshimura Y, Yamaoka M, Nishimura T, Hashimoto N, Imada A. (1992)
Studies on condensed-heterocyclic azolium cephalosporins. IV. Synthesis and antibacterial activity of 7 beta-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)- alkoxyiminoacetamido]-3-(condensed-heterocyclic azolium)methyl cephalosporins including SCE-2787.
J Antibiot (Tokyo), 45 (5): 709-20. [PMID:1624373]