Cefazolin

Title: Cefazolin
CAS Registry Number: 25953-19-9
CAS 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
Additional Names: 7-(1-(1H)-tetrazolylacetamido)-3-[2-(5-methyl-1,3,4-thiadiazolyl)thiomethyl]-D3-cephem-4-carboxylic acid; CEZ
Molecular Formula: C14H14N8O4S3
Molecular Weight: 454.51
Percent Composition: C 37.00%, H 3.10%, N 24.65%, O 14.08%, S 21.16%
Literature References: Semi-synthetic antibiotic derived from 7-aminocephalosporanic acid, q.v. Prepn: T. Takano et al., ZA 6804513; eidem, US 3516997 (1969, 1970 to Fujisawa). Synthesis and properties: Kariyone et al., J. Antibiot. 23, 131 (1970). Activity and clinical studies: Nishida et al., ibid. 137, 184; Shibata, Fujii, Antimicrob. Agents Chemother. 1970, 467. Metabolic studies: Kozatani et al., Chem. Pharm. Bull. 20, 1105 (1972). Toxicology: H. A. Birkhead et al., J. Infect. Dis. 128, Suppl., 379 (1973). Comprehensive description: A. E. Zappala et al., Anal. Profiles Drug Subs. 4, 1-20 (1975). Review: H. Nakano in Pharmacological and Biochemical Properties of Drug Substances vol. 1, M. E. Goldberg, Ed. (Am. Pharm. Assoc., Washington, DC, 1977) pp 155-182.
Properties: Needles from aq acetone, mp 198-200° (dec). uv max (buffer pH 6.4): 272 nm (e 13150). Easily sol in DMF, pyridine; sol in aq acetone, aq dioxane, aq ethanol; slightly sol in methanol. Practically insol in chloroform, benzene, ether.
Melting point: mp 198-200° (dec)
Absorption maximum: uv max (buffer pH 6.4): 272 nm (e 13150)
Derivative Type: Sodium salt
CAS Registry Number: 27164-46-1
Additional Names: Sodium CEZ
Manufacturers' Codes: SKF-41558
Trademarks: Acef (Tiber); Ancef (GSK); Atirin (Intersint); Biazolina (Panthox & Burck); Bor-Cefazol (Proter); Cefacidal (Allard); Cefamedin (Fujisawa); Cefamezin (Fujisawa); Cefazil (Giustini); Cefazina (Chemil); Elzogram (Lilly); Firmacef (Firma); Gramaxin (Boehringer, Mann.); Kefzol (Lilly); Lampocef (Lampugnani); Liviclina (Sierochimica); Totacef (BMS); Zolicef (BMS)
Molecular Formula: C14H13N8NaO4S3
Molecular Weight: 476.49
Percent Composition: C 35.29%, H 2.75%, N 23.52%, Na 4.82%, O 13.43%, S 20.19%
Properties: White to yellowish-white, odorless crystalline powder with a bitter, salty taste. Crystallizes in a, b, and g-forms (Kariyone). Easily sol in water, slightly sol in methanol, ethanol. Practically insol in benzene, acetone, chloroform. LD50 in mice, rats (mg/kg): 3.9, 3.18 i.v.; 6.2, 7.4 i.p. (Birkhead).
Toxicity data: LD50 in mice, rats (mg/kg): 3.9, 3.18 i.v.; 6.2, 7.4 i.p. (Birkhead)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Cephalosporins.
Cefbuperazone Cefcapene Pivoxil Cefclidin Cefdinir Cefditoren

Cefazolin
Cefazolin.svg
Cefazolin ball-and-stick.png
Systematic (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
Clinical data
Trade names Ancef, Kefzol
AHFS/Drugs.com monograph
Pregnancy cat. B1 (AU) B (US)
Legal status Prescription only
Routes Intravenous, intramuscular
Pharmacokinetic data
Bioavailability NA
Metabolism  ?
Half-life 1.8 hours (given IV)
2 hours (given IM)
Excretion Renal, unchanged
Identifiers
CAS number 25953-19-9 YesY
ATC code J01DB04 QJ51DB04
PubChem CID 33255
DrugBank DB01327
ChemSpider 30723 YesY
UNII IHS69L0Y4T YesY
KEGG D02299 YesY
ChEBI CHEBI:474053 YesY
ChEMBL CHEMBL1435 YesY
Chemical data
Formula C14H14N8O4S3 
Mol. mass 454.51 g/mol
 YesY (what is this?)  (verify)

Cefazolin (INN), also known as cefazoline or cephazolin, is a first-generation cephalosporin antibiotic.

The drug is usually administered by either intramuscular injection (injection into a large muscle) or intravenous infusion (intravenous fluid into a vein).