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.
In the Vinony graph
Within Vinony's link graph, cefazolin is referenced by 219 other articles, and connects out to antibiotic, urinary tract infection and intravenous infusion and defusion.
It is catalogued under topics including 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 Ų
- 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
Sources (8)
via Wikidata · CC0
~9 min read
Encyclopedic overview
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
Excerpted from Wikipedia’s “cefazolin” article, available under the CC BY-SA 4.0 licence.