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cefazolin   Click here for help

GtoPdb Ligand ID: 10935

Synonyms: Ancef® | cephazolin | CEZ | Kefzol® | SK&F-41558
Approved drug PDB Ligand
cefazolin is an approved drug (FDA (1973))
Compound class: Synthetic organic
Comment: Cefazolin is a β-lactam and first-generation cephalosporin antibacterial.

cefazolin is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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
InChI Key MLYYVTUWGNIJIB-BXKDBHETSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. US FDA (1973)
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
RCSB PDB Ligand X56
Search Google for chemical match using the InChIKey MLYYVTUWGNIJIB-BXKDBHETSA-N
Search Google for chemicals with the same backbone MLYYVTUWGNIJIB
Search PubMed clinical trials cefazolin
Search PubMed titles cefazolin
Search PubMed titles/abstracts cefazolin
UniChem Compound Search for chemical match using the InChIKey MLYYVTUWGNIJIB-BXKDBHETSA-N
UniChem Connectivity Search for chemical match using the InChIKey MLYYVTUWGNIJIB-BXKDBHETSA-N

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MedChemExpress
Cefazolin (links to external site)
Cat. No. HY-B1892