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Cefotetan

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Cefotetan Basic information

Product Name:
Cefotetan
Synonyms:
  • CEFOTETAN
  • CEFOTETAN DISODIUM SALT
  • CEFOTETAN SODIUM
  • disodium (7r)-7-[[4-(carbamoyl-carboxylato-methylidene)-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-carboxylate
  • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 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-, disodium salt, (6R,7S)-
  • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 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-, disodium salt, [6R-(6α,7α)]-
  • Apatef
  • Ceftenon
CAS:
69712-56-7
MF:
C17H17N7O8S4
MW:
575.62
EINECS:
274-093-3
Product Categories:
  • CEFOTAN
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Sulfur & Selenium Compounds
Mol File:
69712-56-7.mol
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Cefotetan Chemical Properties

Melting point:
173-178°C (dec.)
Density 
1.5157 (rough estimate)
refractive index 
1.7400 (estimate)
storage temp. 
Store at 0-5°C
pka
1.69±0.41(Predicted)
Merck 
14,1934
InChIKey
SRZNHPXWXCNNDU-IXOPCIAXSA-N
CAS DataBase Reference
69712-56-7(CAS DataBase Reference)
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Safety Information

RTECS 
XI0330800
HS Code 
2941906000
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Cefotetan Usage And Synthesis

Description

Cefotetan is comparatively stable, lasting for approximately 24 hours at room temperature when reconstituted. Slight yellowing and slight darkening produce materials that are still acceptable for therapy. Cefotetan is chemically incompatible with tetracycline, aminoglycosides, and with heparin, often forming precipitates with them. With respect to its molecular mode of action, it has a special affinity for PBP-3 of Gram-negative bacteria, consequently producing filamentous forms. It also binds well with PBP-1A and -1B,therefore leading to cell lysis and death. Whereas it is stable to a wide range of β-lactamases, it also is a potent inducer in some bacteria.

Chemical Properties

Off-White Solid

Uses

antibacterial

Uses

Cefotetan disodium is an antibiotic related to Cephalosporin, used in the treatment of bacterial infections.

Definition

ChEBI: A semi-synthetic cephalosporin antibiotic with [(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl, methoxy and {[4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietan-2-yl]carbonyl}amino groups at the 3, 7alpha, and 7bet positions, respectively, of the cephem skeleton. It is resistant to a wide range of beta-lactamases and is active against a broad spectrum of aerobic and anaerobic Gram-positive and Gram-negative microorganisms.

brand name

Cefotan (Zeneca).

Antimicrobial activity

A semisynthetic cephamycin formulated as the disodium salt for intravenous administration. The activity is similar to that of cefoxitin, but cefotetan exhibits more potent activity against enterobacteria and more modest activity against Staph. aureus.
A 1 g intravenous dose achieves a serum concentration of 140–180 mg/L. There is no evidence of accumulation on a dosage of 1 g every 12 h. Tissue fluid concentrations are about 30% of the simultaneous serum level. The plasma half-life is about 3 h and protein binding is around 88%.
About 85% of the drug is eliminated in the urine over 24 h. Accumulation in renal failure is inversely related to the creatinine clearance, the plasma half-life rising to 20 h in patients requiring hemodialysis. During hemodialysis the half-life falls to around 7.5 h and on peritoneal dialysis it falls to 15.5 h, 5–10% of the dose being recovered in the dialysate over 24 h.
Side effects are those typical of the group. Anaphylaxis has been described. Because of the methylthiotetrazole side chain there is some risk of hypoprothrombinemia, and disulfiramlike reactions can occur. Marked changes in the bowel flora, with appearance of C. difficile, have been reported. Uses are similar to those of other cephamycins, but it is not widely available.

Chemical Synthesis

Cefotetan, 7β-[(-carbamoylcarboxylatomethylen)-1,3-dithietan-2-yl]-carboxamido-7-methoxy-3-(1-methyltetrazol-5-yl)-thiomethyl-3-cefem-4-carboxylic acid (32.1.2.43), is synthesized by the following scheme. First, trisodium salt of 4-carboxy-3-hydroxy-5-mercaptoisothiazole (32.1.2.41) undergoes S-alkylation by 7β-bromoacetamido-7α-methoxycephalosporanic acid, which is synthesized by a scheme described previously (32.1.2.31) → (32.1.2.37), the only difference being that the acylation in the stage (32.1.2.35) → (32.1.2.36) is accomplished not with 2-(2-thienyl)acetylchloride, but with bromoacetyl bromide. Next, upon reacting the resulting product (32.1.2.42) with 1-methyl-1,2,3,4-tetrazol-5-thiol in the presence of sodium bicarbonate with the expected replacement reaction, in the reaction conditions a ring rearrangement takes place in which the isothiazole ring is opened, and transformed into a derivative of carbamoylcarboxylatomethylen-1,3-dithiethane, namely cefotetan (32.1.2.43).

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