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Substance Name: Cefazolin sodium [USAN:USP:JAN]
RN: 27164-46-1
UNII: P380M0454Z
InChIKey: FLKYBGKDCCEQQM-WYUVZMMLSA-M

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 Formulas

  • C14-H13-N8-Na-O4-S3
  • C14-H13-N8-O4-S3.Na
  • C14-H14-N8-O4-S3.Na

Molecular Weight

  • 476.4967
 

Classification Codes

  • Antibacterial (Systemic)
  • Antibiotics
  • Drug / Therapeutic Agent
  • Human Data
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Cefazolin sodium [USAN:USP:JAN]

MeSH Heading

  • Cefazolin

Synonyms

  • 46083
  • Ancef
  • Ancef in dextrose 5% in plastic container
  • Ancef in plastic container
  • Ancef in sodium chloride 0.9% in plastic container
  • Atirin
  • Biazolina
  • Bor-Cefazol
  • Cefabiozim
  • Cefacidal
  • Cefalomicina
  • Cefamedin
  • Cefazil
  • Cefazina
  • Cefazolin
  • Cefazolin and dextrose
  • Cefazolin sodium
  • Cefazolin sodium salt
  • Cefazoline sodium
  • CEZ sodium
  • EINECS 248-278-4
  • Firmacef
  • Gramaxin
  • Kefzol
  • Lampocef
  • Lilly 46083
  • Liviclina
  • Monosodium (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-carboxylate
  • Monosodium cefazolin
  • Neofazol
  • NSC 291561
  • Recef
  • SK&F 41558
  • SKF 41558
  • Sodium (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-carboxylate
  • Sodium cefazolin
  • Sodium cephazolin
  • Sodium CEZ
  • Totacef
  • UNII-P380M0454Z
  • Zolicef
  • Zolin
  • Zolisint

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)-, sodium salt
  • 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)-, monosodium salt (6R-trans)-
  • Sodium (6R-trans)-3-(((5-methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-7-(1H-tetrazol-1-ylacetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

Registry Numbers

CAS Registry Number

  • 27164-46-1

FDA UNII

  • P380M0454Z

System Generated Number

  • 0027164461

Molecular Formulas

Molecular Formulas

  • C14-H13-N8-Na-O4-S3
  • C14-H13-N8-O4-S3.Na
  • C14-H14-N8-O4-S3.Na

Molecular Formula Fragments

  • C14-H13-N8-O4-S3
  • C14-H14-N8-O4-S3
  • COMPONENT
  • Na

Structure Descriptors

InChI

1S/C14H14N8O4S3.Na/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);/q;+1/p-1/t9-,12-;/m1./s1

InChIKey

FLKYBGKDCCEQQM-WYUVZMMLSA-M

Smiles

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 2200mg/kg (2200mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 29, Pg. 424, 1979.
dog LD50 subcutaneous 4gm/kg (4000mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Chemotherapy Vol. 18, Pg. 528, 1970.
human TDLo intramuscular 14mg/kg/D (14mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE"

GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
Japan Medical Gazette. Vol. 8(8), Pg. 10, 1971.
mouse LD50 intraperitoneal 6200mg/kg (6200mg/kg)   Drugs in Japan Vol. 6, Pg. 404, 1982.
mouse LD50 intravenous 3900mg/kg (3900mg/kg)   Journal of Infectious Diseases. Vol. 128, Pg. S379, 1973.
mouse LD50 oral > 11gm/kg (11000mg/kg)   Chemotherapy Vol. 18, Pg. 528, 1970.
mouse LD50 subcutaneous 7600mg/kg (7600mg/kg)   Journal of Infectious Diseases. Vol. 128, Pg. S379, 1973.
rabbit LD50 intravenous 2500mg/kg (2500mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 29, Pg. 424, 1979.
rabbit LD50 subcutaneous > 6gm/kg (6000mg/kg)   Chemotherapy Vol. 18, Pg. 528, 1970.
rat LD50 intraperitoneal 7400mg/kg (7400mg/kg)   Drugs in Japan Vol. 6, Pg. 404, 1982.
rat LD50 intravenous 2760mg/kg (2760mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Chemotherapy Vol. 35(Suppl,
rat LD50 oral > 11gm/kg (11000mg/kg)   Chemotherapy Vol. 18, Pg. 528, 1970.
rat LD50 subcutaneous 10gm/kg (10000mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Japan Medical Gazette. Vol. 8(8), Pg. 10, 1971.
women TDLo intravenous 660mg/kg/11D- (660mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Nephron. Vol. 45, Pg. 72, 1987.