cefapirin   Click here for help

GtoPdb Ligand ID: 12191

Synonyms: Cefadyl® | cephapirin
Approved drug
cefapirin is an approved drug (FDA (1974))
Compound class: Synthetic organic
Comment: Cefapirin is a semisynthetic, first generation cephalosporin belonging to the β-lactam class of antibacterial compounds [1].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 176.5
Molecular weight 423.06
XLogP -2.25
No. Lipinski's rules broken 0
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Canonical SMILES O=C(N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)COC(=O)C)CSc1ccncc1
Isomeric SMILES CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)CSc2ccncc2)SC1)C(=O)O
InChI InChI=1S/C17H17N3O6S2/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25)/t13-,16-/m1/s1
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1974))
IUPAC Name Click here for help
(6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-pyridin-4-ylsulfanylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
2871 cefapirin
Synonyms Click here for help
Cefadyl® | cephapirin
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Cephapirin
Other databases
CAS Registry No. 21593-23-7 (source: Scifinder)
ChEBI CHEBI:554446
ChEMBL Ligand CHEMBL1599
DrugBank Ligand DB01139
DrugCentral Ligand 575
GtoPdb PubChem SID 472319313
PubChem CID 30699
Search Google for chemical match using the InChIKey UQLLWWBDSUHNEB-CZUORRHYSA-N
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UniChem Compound Search for chemical match using the InChIKey UQLLWWBDSUHNEB-CZUORRHYSA-N
UniChem Connectivity Search for chemical match using the InChIKey UQLLWWBDSUHNEB-CZUORRHYSA-N