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Substance Name: Cefoperazone sodium [USAN:USP:JAN]
RN: 62893-20-3
UNII: 5FQG9774WD
InChIKey: NCFTXMQPRQZFMZ-WERGMSTESA-M

Note

  • Semisynthetic broad-spectrum cephalosporin with a tetrazolyl moiety that is resistant to beta-lactamase. It has been proposed especially against Pseudomonas infections.

Molecular Formulas

  • C25-H26-N9-Na-O8-S2
  • C25-H26-N9-O8-S2.Na
  • C25-H27-N9-O8-S2.Na

Molecular Weight

  • 667.6574
 

Classification Codes

  • Antibacterial
  • Antibiotics
  • Drug / Therapeutic Agent
  • Human Data
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Cefoperazone sodium [USAN:USP:JAN]

Synonyms

  • Cefobid
  • Cefobid in plastic container
  • Cefoperazone sodium
  • CP 52640-2
  • CP-52,640-2
  • EINECS 263-751-5
  • Sodium (6R,7R)-7-((R)-2-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-2-(p-hydroxyphenyl)acetamido)-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate
  • Sodium cefoperazone
  • T 1551
  • T-1551
  • Tomabef
  • UNII-5FQG9774WD

Systematic Name

  • 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((((4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl)amino)(4-hydroxyphenyl)acetyl)amino)-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-, monosodium salt, (6R-(6alpha,7beta(R*)))-

Registry Numbers

CAS Registry Number

  • 62893-20-3

FDA UNII

  • 5FQG9774WD

Related Registry Number

  • 62893-19-0 (Parent)

System Generated Number

  • 0062893203

Molecular Formulas

Molecular Formulas

  • C25-H26-N9-Na-O8-S2
  • C25-H26-N9-O8-S2.Na
  • C25-H27-N9-O8-S2.Na

Molecular Formula Fragments

  • C25-H26-N9-O8-S2
  • C25-H27-N9-O8-S2
  • COMPONENT
  • Na

Structure Descriptors

InChI

1S/C25H27N9O8S2.Na/c1-3-32-8-9-33(21(39)20(32)38)24(42)27-15(12-4-6-14(35)7-5-12)18(36)26-16-19(37)34-17(23(40)41)13(10-43-22(16)34)11-44-25-28-29-30-31(25)2;/h4-7,15-16,22,35H,3,8-11H2,1-2H3,(H,26,36)(H,27,42)(H,40,41);/q;+1/p-1/t15-,16-,22-;/m1./s1

InChIKey

NCFTXMQPRQZFMZ-WERGMSTESA-M

Smiles

CCN1CCN(C(=O)C1=O)C(=O)N[C@H](c2ccc(cc2)O)C(=O)N[C@H]3[C@@H]4N(C3=O)C(=C(CS4)CSc5nnnn5C)C(=O)[O-].[Na+]

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 6gm/kg (6000mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE
Chemotherapy Vol. 28(Suppl,
human TDLo parenteral 622mg/kg/10D- (622mg/kg) BLOOD: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: HEMATURIA

GASTROINTESTINAL: OTHER CHANGES
Southern Medical Journal. Vol. 80, Pg. 1360, 1987.
man TDLo intravenous 57mg/kg/4D-I (57mg/kg) BLOOD: HEMORRHAGE

SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

KIDNEY, URETER, AND BLADDER: HEMATURIA
Drug Intelligence and Clinical Pharmacy. Vol. 18, Pg. 314, 1984.
man TDLo unreported 229mg/kg/4D-I (229mg/kg) BLOOD: CHANGE IN CLOTTING FACTORS Annals of Internal Medicine. Vol. 102, Pg. 721, 1985.
mouse LD50 intraperitoneal 8200mg/kg (8200mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA Chemotherapy Vol. 28(Suppl,
mouse LD50 intravenous 3840mg/kg (3840mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA Chemotherapy Vol. 28(Suppl,
mouse LD50 oral > 15gm/kg (15000mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Chemotherapy Vol. 28(Suppl,
mouse LD50 subcutaneous 13gm/kg (13000mg/kg)   Drugs in Japan Vol. -, Pg. 663, 1995.
rat LD50 intraperitoneal > 12gm/kg (12000mg/kg) GASTROINTESTINAL: OTHER CHANGES

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Chemotherapy Vol. 28(Suppl,
rat LD50 intravenous 4260mg/kg (4260mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA Chemotherapy Vol. 28(Suppl,
rat LD50 oral > 12gm/kg (12000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Chemotherapy Vol. 28(Suppl,
rat LD50 subcutaneous > 12gm/kg (12000mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Chemotherapy Vol. 28(Suppl,
rat LD50 unreported 3200mg/kg (3200mg/kg)   Yaoxue Tongbao. Bulletin of Pharmacology. Vol. 21, Pg. 356, 1986.
women TDLo intravenous 220mg/kg/5D-I (220mg/kg) BLOOD: HEMORRHAGE

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM LARGE INTESTINE
Drug Intelligence and Clinical Pharmacy. Vol. 20, Pg. 281, 1986.