cefprozil   Click here for help

GtoPdb Ligand ID: 12219

Synonyms: BMY-28100 | Cefzil®
Approved drug
cefprozil is an approved drug (FDA (1991))
Compound class: Synthetic organic
Comment: Cefprozil is a semisynthetic, second generation cephalosporin belonging to the β-lactam class of antibacterial compounds. We show the cis-isomer which has greater antibacterial activity in vitro than the trans form [1].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 4
Rotatable bonds 6
Topological polar surface area 158.26
Molecular weight 389.43
XLogP -1.57
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CC=CC1=C(C(=O)O)N2[C@H](SC1)[C@@H](C2=O)NC(=O)[C@@H](c1ccc(cc1)O)N
Isomeric SMILES C(=O)(O)C1=C(CS[C@H]2N1C(=O)[C@H]2NC(=O)[C@H](N)c1ccc(O)cc1)C=CC
InChI InChI=1S/C18H19N3O5S/c1-2-3-10-8-27-17-13(16(24)21(17)14(10)18(25)26)20-15(23)12(19)9-4-6-11(22)7-5-9/h2-7,12-13,17,22H,8,19H2,1H3,(H,20,23)(H,25,26)/t12-,13-,17-/m1/s1
InChI Key WDLWHQDACQUCJR-PBFPGSCMSA-N
References
1. Naito T, Hoshi H, Aburaki S, Abe Y, Okumura J, Tomatsu K, Kawaguchi H. (1987)
Synthesis and structure-activity relationships of a new oral cephalosporin, BMY-28100 and related compounds.
J Antibiot (Tokyo), 40 (7): 991-1005. [PMID:3624077]
2. Tomatsu K, Ando S, Masuyoshi S, Kondo S, Hirano M, Miyaki T, Kawaguchi H. (1987)
In vitro and in vivo evaluations of BMY-28100, a new oral cephalosporin.
J Antibiot (Tokyo), 40 (8): 1175-83. [PMID:3500158]