เซฟาโซลิน

Also known as Cefazoline, Cefazolinum, (6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, Cefazolina, Cefamezin, Cephazolidin, Cephazolin, Cephamezine

Cefazolin, also known as cefazoline and cephazolin, is a first-generation cephalosporin antibiotic used for the treatment of a number of bacterial infections. Specifically it is used to treat cellulitis, urinary tract infections, pneumonia, endocarditis, joint infection, and biliary tract infections. It is also used to prevent group B streptococcal disease around the time of delivery and before surgery. It is typically given by injection into a muscle or vein.

In the Vinony graph

Within Vinony's link graph, เซฟาโซลิน is referenced by 219 other articles, and connects out to antibiotic, urinary tract infection and intravenous infusion and defusion.

It sits within the topics Cephalosporin antibiotics, Drugboxes which contain changes to watched fields and Drugs with non-standard legal status.

Its subject is documented across 29 Wikipedia language editions.

Chemical data

Formula: C14H14N8O4S3
Molecular weight: 454.5 g/mol
IUPAC name: (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
SMILES: CC1=NN=C(S1)SCC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)CN4C=NN=N4)SC2)C(=O)O
InChIKey: MLYYVTUWGNIJIB-BXKDBHETSA-N
XLogP: -0.4
Polar surface area: 235 Å²
H-bond donors: 2
H-bond acceptors: 12
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1973
Admin. routes: parenteral
Indications: infection, cardiac arrhythmia, skin disease, bacteriemia

via ChEMBL · EBI

Research

7,445 papers

Cefazolin as a predictor of urinary cephalosporin activity in indicated Enterobacterales.Journal of clinical microbiology · 2024
Cefazolin.Annals of internal medicine · 1978
Cefazolin.Advances in clinical pharmacology · 1974
Cefazolin-induced hemolytic anemia: a case report and systematic review of literature.European journal of medical research · 2021
[Cefazolin].Acta clinica Belgica · 1975

via PubMed

Wikidata facts

Subclass of: cephalosporin antibiotic
Has part: carbon
Mass: 454.030014
Manufacturer: Pfizer
Has use: medication

Show 8 more facts

chemical formula: C₁₄H₁₄N₈O₄S₃
Commons category: Cefazolin
isomeric SMILES: CC1=NN=C(S1)SCC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)CN4C=NN=N4)SC2)C(=O)O
canonical SMILES: CC1=NN=C(S1)SCC2=C(N3C(C(C3=O)NC(=O)CN4C=NN=N4)SC2)C(=O)O
defined daily dose: 3
World Health Organisation international non-proprietary name: cefazolin
subject has role: bactericide
stylized name: ceFAZolin