cefpiramide   Click here for help

GtoPdb Ligand ID: 12027

Synonyms: SM-1652 | WY-44635
Approved drug
cefpiramide is an approved drug (FDA (1989))
Compound class: Synthetic organic
Comment: Cefpiramide is a semisynthetic, third generation cephalosporin and belongs to the β-lactam class of antibacterial compounds.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 11
Hydrogen bond donors 5
Rotatable bonds 11
Topological polar surface area 263.1
Molecular weight 612.12
XLogP 2.24
No. Lipinski's rules broken 1
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Canonical SMILES Oc1ccc(cc1)[C@H](C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nnnn1C)NC(=O)c1c[nH]c(cc1=O)C
Isomeric SMILES Cc1cc(=O)c(c[nH]1)C(=O)N[C@H](c1ccc(cc1)O)C(=O)N[C@H]1[C@@H]2N(C1=O)C(=C(CS2)CSc1nnnn1C)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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1989))
IUPAC Name Click here for help
(6R,7R)-7-[[(2R)-2-(4-hydroxyphenyl)-2-[(6-methyl-4-oxo-1H-pyridine-3-carbonyl)amino]acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
5152 cefpiramide
Synonyms Click here for help
SM-1652 | WY-44635
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Cefpiramide
Other databases
CAS Registry No. 70797-11-4 (source: Scifinder)
ChEMBL Ligand CHEMBL1201204
DrugBank Ligand DB00430
DrugCentral Ligand 552
GtoPdb PubChem SID 464244168
PubChem CID 636405
Search Google for chemical match using the InChIKey PWAUCHMQEXVFJR-PMAPCBKXSA-N
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UniChem Compound Search for chemical match using the InChIKey PWAUCHMQEXVFJR-PMAPCBKXSA-N
UniChem Connectivity Search for chemical match using the InChIKey PWAUCHMQEXVFJR-PMAPCBKXSA-N