Structure via PubChem · Public domain (PubChem)
cefazolin
Sign in to saveAlso 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.
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 Ų
- H-bond donors
- 2
- H-bond acceptors
- 12
- Formal charge
- 0
via PubChem
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
- Mass
- 454.030014
Show 7 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
- stylized name
- ceFAZolin
Sources (8)
via Wikidata · CC0
~9 min read
Article
15 sectionsContents
- Medical uses
- Bacterial susceptibility
- Spectrum of activity
- Non susceptible
- Special populations
- Pregnancy
- Newborns
- Elderly
- Additional considerations
- Side effects
- Mechanism of action
- Cost
- Trade names
- References
- External links
{{Drugbox | Watchedfields = changed | verifiedrevid = 443508421 | drug_name = | IUPAC_name = (6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl}-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | image = Cefazolin.svg | image_class = skin-invert-image | image2 = Cefazolinate-from-xtal-3D-bs-17.png | image_class2 = bg-transparent
| pronounce = | tradename = Ancef, Cefacidal, other | Drugs.com = | class = First-generation cephalosporin | pregnancy_AU = B1 | pregnancy_US = B | legal_status = Rx-only | routes_of_administration = intravenous, intramuscular