Drug/Small Molecule:
cefazolin

2D structure

Overview

Generic Names: CEZ; Cefazolin sodium; Cefazoline; Cephazolin
IUPAC Name: (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
Trade Names: Ancef
PharmGKB Accession Id: PA448839

Description

A semisynthetic cephalosporin analog with broad-spectrum antibiotic action due to inhibition of bacterial cell wall synthesis. It attains high serum levels and is excreted quickly via the urine. [PubChem]

Indication

Mainly used to treat bacterial infections of the skin. It can also be used to treat moderately severe bacterial infections involving the lung, bone, joint, stomach, blood, heart valve, and urinary tract. It is clinically effective against infections caused by staphylococci and streptococci species of Gram positive bacteria.

ATC Therapeutic Category

  • J01DB:First-generation cephalosporins

Pharmacology and Interactions

Mechanism Of Action

In vitro tests demonstrate that the bactericidal action of cephalosporins results from inhibition of cell wall synthesis. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins.

Pharmacology

Cefazolin (also known as cefazoline or cephazolin) is a semi-synthetic cephalosporin for parenteral administration. Cefazolin has broad-spectrum antibiotic action due to inhibition of bacterial cell wall synthesis. It attains high serum levels and is excreted quickly via the urine.

Absorption, Distribution, Metabolism, Elimination & Toxicity

Half Life

The serum half-life is approximately 1.8 hours following IV administration and approximately 2.0 hours following IM administration.

Chemical Properties

Chemical Formula:

C14H14N8O4S3

SMILES Code:

Cc1nnc(s1)SCC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)Cn4cnnn4)SC2)C(=O)O

(Format: OpenEye Isomeric)

Molecular Weight ( average / monoisotopic )

454.507 / 454.03

Curated Information

The following genes are in curated knowledge about this drug.

  Gene Relationship Evidence
Phenotype data available Genotype Data Available Literature annotations available Has annotations
TPMT
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  • PD
  •   
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  • GN
Publications

Non-Curated Information

A list of non-curated publications that mention this drug along with other genes is available.

Drug Targets

Curated Information

The following drugs are in curated knowledge about this drug.

  Drug Relationship Evidence
Phenotype data available Genotype Data Available Literature annotations available Not annotated
warfarin
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Publications

Non-Curated Information

A list of non-curated publications that mention this drug along with other drugs is available.

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB01327
KEGG Compound ID:
C06880
KEGG Drug ID:
D02299
PubChem Compound ID:
656510
PubChem Substance ID:
9097

Common Searches

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Non-Curated Publications

A list of non-curated publications that mention this drug is available.

PharmGKB integrates drug information from different sources: DrugBank, Open Eye Scientific Software.
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