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Substance Name: Cefazolin [USP:INN:BAN]
RN: 25953-19-9
UNII: IHS69L0Y4T
InChIKey: MLYYVTUWGNIJIB-BXKDBHETSA-N

Note

  • 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.

Molecular Formula

  • C14-H14-N8-O4-S3

Molecular Weight

  • 454.5146
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial (Systemic)
  • Drug / Therapeutic Agent

Names and Synonyms

Name of Substance

  • Cefazolin
  • Cefazolin [USP:INN:BAN]

MeSH Heading

  • Cefazolin

Synonyms

  • (6R,7R)-3-(((5-Methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-7-(2-(1H-tetrazol-1-yl)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
  • (6R-trans)-3-(((5-Methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-7-(((1H-tetrazol-1-yl)acetyl)-amino)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
  • 7-(1-(1H-)-Tetrazolylacetamido)-3-(2-(5-methyl-1,3,4-thiadiazolyl)thiomethyl)delta3-cephem-4-carboxylic acid
  • Ancef
  • BRN 4169371
  • Cefamezin
  • Cefazolin
  • Cefazolina
  • Cefazolina [INN-Spanish]
  • Cefazoline
  • Cefazoline [INN-French]
  • Cefazolinum
  • Cefazolinum [INN-Latin]
  • Cephamezine
  • Cephazolidin
  • Cephazolin
  • Cephazoline
  • CEZ
  • EC 247-362-8
  • EINECS 247-362-8
  • Elzogram
  • HSDB 3213
  • UNII-IHS69L0Y4T

Systematic Names

  • 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-(((5-methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-7-(((1H-tetrazol-1-yl)acetyl)amino)-, (6R-trans)-
  • 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-(((5-methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-7-(2-(1H-tetrazol-1-yl)acetamido)-
  • Cefazolin

Registry Numbers

CAS Registry Number

  • 25953-19-9

FDA UNII

  • IHS69L0Y4T

System Generated Number

  • 0025953199

Structure Descriptors

InChI

1S/C14H14N8O4S3/c1-6-17-18-14(29-6)28-4-7-3-27-12-9(11(24)22(12)10(7)13(25)26)16-8(23)2-21-5-15-19-20-21/h5,9,12H,2-4H2,1H3,(H,16,23)(H,25,26)/t9-,12-/m1/s1

InChIKey

MLYYVTUWGNIJIB-BXKDBHETSA-N

Smiles

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intramuscular 4gm/kg (4000mg/kg)   Byoin Yakugaku. Hospital Pharmacology. Vol. 3, Pg. 220, 1978.
mouse LD50 intravenous 3gm/kg (3000mg/kg)   Byoin Yakugaku. Hospital Pharmacology. Vol. 3, Pg. 220, 1978.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -0.58 (none)   EXP
Water Solubility 214 mg/L 25 EST
Vapor Pressure 1.50E-18 mm Hg 25 EST
Henry's Law Constant 2.01E-23 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.23E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.