cefazolin   Click here for help

GtoPdb Ligand ID: 10935

Synonyms: Ancef® | cephazolin | CEZ | Kefzol® | SK&F-41558
Compound class: Synthetic organic
Comment: Cefazolin is a β-lactam and first-generation cephalosporin antibacterial.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 11
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 234.93
Molecular weight 454.03
XLogP 0.28
No. Lipinski's rules broken 1
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Canonical SMILES O=C(N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nnc(s1)C)Cn1cnnn1
Isomeric SMILES O=C(N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nnc(s1)C)Cn1cnnn1
InChI InChI=1S/C14H14N8O4S3/c1-6-17-18-14(29-6)28-4-7-3-27-12-9(11(24)22(12)10(7)13(25)26)16-8(23)2-21-5-15-19-20-21/h5,9,12H,2-4H2,1H3,(H,16,23)(H,25,26)/t9-,12-/m1/s1
Classification Click here for help
Compound class Synthetic organic
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(6R,7R)-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
2991 cefazolin
Synonyms Click here for help
Ancef® | cephazolin | CEZ | Kefzol® | SK&F-41558
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Cefazolin
Reactome Drug Reactome logo R-ALL-9695413
Reactome Reaction Reactome logo R-HSA-9695415
Other databases
CAS Registry No. 25953-19-9 (source: WHO INN record)
ChEMBL Ligand CHEMBL1435
DrugCentral Ligand 530
GtoPdb PubChem SID 405560376
PubChem CID 33255
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