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69712-56-7

Basic Information
CAS No.: 69712-56-7
Name: Cefotetan disodium
Article Data: 7
Molecular Structure:
Molecular Structure of 69712-56-7 (Cefotetan disodium)
Formula: C17H17N7O8S4
Molecular Weight: 575.628
Synonyms: 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,7-[[[4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietan-2-yl]carbonyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-,[6R-(6a,7a)]-;Apacef;
EINECS: 274-093-3
Density: 2.07 g/cm3
Melting Point: 173-178°C (dec.)
Appearance: Off-white solid
PSA: 321.13000
LogP: -0.36840
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    Cefotetan Acid

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Chemistry

Molecular Structure of Cefotetan disodium (CAS NO.69712-56-7):

IUPAC Name: (6R,7S)-7-[[4-(1-amino-3-hydroxy-1,3-dioxopropan-2-ylidene)-1,3-Dithietane-2-carbonyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
CAS: 69712-56-7
Empirical Formula: C17H17N7O8S4
Molecular Weight: 575.62
EINECS: 277-834-9
H bond acceptors: 15
H bond donors: 5
Freely Rotating Bonds: 9
Polar Surface Area: 321.13Å2
Index of Refraction: 1.921
Molar Refractivity: 131.49 cm3
Molar Volume: 278 cm3
Surface Tension: 111 dyne/cm
Density: 2.07 g/cm3
Mol File: 69712-56-7.mol
Density: 2.07 g/cm3 
Storage temp:  Store at 0-5°C
Synonyms: (6R,7S)-4-((2-Carboxy-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-7-yl)carbamoyl)-1,3-dithietane-delta(sup 2,alpha)-malonamic acid ; (6R,7S)-7-(4-(Carbamoylcarboxymethylene)-1,3-dithiethane-2-carboxamido)-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid

Uses

 Cefotetan disodium (CAS NO.69712-56-7) is an injectable antibiotic of the cephamycin type for prophylaxis and treatment of bacterial infections. It is often grouped together with second-generation cephalosporins and has a similar antibacterial spectrum, but with additional anti-anaerobe converage.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous > 6gm/kg (6000mg/kg)   Yakkyoku. Pharmacy. Vol. 35, Pg. 2033, 1984.
mouse LD50 intraperitoneal 8120mg/kg (8120mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LIVER: OTHER CHANGES
Chemotherapy Vol. 30(Suppl,
mouse LD50 intravenous 4990mg/kg (4990mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BLOOD: CHANGES IN SPLEEN
Chemotherapy Vol. 30(Suppl,
mouse LD50 oral > 10gm/kg (10000mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Chemotherapy Vol. 30(Suppl,
mouse LD50 subcutaneous > 10gm/kg (10000mg/kg) BEHAVIORAL: TREMOR

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Chemotherapy Vol. 30(Suppl,
rat LD50 intraperitoneal 8250mg/kg (8250mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BLOOD: CHANGES IN SPLEEN
Chemotherapy Vol. 30(Suppl,
rat LD50 intravenous 5gm/kg (5000mg/kg)   "Current Chemotherapy and Infectious Diseases, Proceedings of the 11th International Congress of Chemotherapy and the 19th Interscience Conference on Antimicrobial Agents and Chemotherapy, Boston, MA, 1979," Washington, DC, American Soc. for Microbiology, 1980Vol. 1, Pg. 273, 1980.
rat LD50 oral > 10gm/kg (10000mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Chemotherapy Vol. 30(Suppl,
rat LD50 subcutaneous > 10gm/kg (10000mg/kg) BEHAVIORAL: TREMOR

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Chemotherapy Vol. 30(Suppl,

Specification

 Cefotetan disodium (CAS NO.69712-56-7) is a white to pale yellow powder which is very soluble in water. Reconstituted solutions of Cefotetan disodium (Cefotetan disodium disodium for injection) are intended for intravenous and intramuscular administration. The solution varies from colorless to yellow depending on the concentration. The pH of freshly reconstituted solutions is usually between 4.5 to 6.5.

 Cefotetan disodium in the ADD-Vantage Vial† is intended for intravenous use only after dilution with the appropriate volume of ADD-Vantage diluent solution. Cefotetan disodium (CAS NO.69712-56-7) is a parenteral, semisynthetic cephalosporin antibiotic. Reproduction studies in rats and monkeys found no evidence of impaired fertility or fetal harm at doses up to 20 times the human dose. Cephalosporins are usually considered safe to use during pregnancy.

 The chemical structure of Cefotetan disodium , like that of several other cephalosporins, contains an N-methylthiotetrazole (NMTT or 1-MTT) side chain. As the antibiotic is broken down in the body, it releases free NMTT, which can cause hypoprothrombinemia (likely due to inhibition of the enzyme vitamin K epoxide reductase) and a reaction with ethanol similar to that produced by disulfiram (Antabuse), due to inhibition of aldehyde dehydrogenase. Cefotetan disodium disodium is a semisynthetic, beta-lactamase resistant, cephalosporin (cephamycin) antibiotic.