69712-56-7 Usage
Description
Cefotetan disodium is a stable antibiotic belonging to the Cephalosporin class, with a duration of approximately 24 hours at room temperature when reconstituted. It exhibits slight yellowing and darkening, but remains acceptable for therapy. Chemically, it is incompatible with tetracycline, aminoglycosides, and heparin, often forming precipitates with them. Its molecular mode of action involves a special affinity for PBP-3 of Gram-negative bacteria, leading to filamentous forms, and also binds well with PBP-1A and -1B, resulting in cell lysis and death. It is stable to a wide range of β-lactamases but can be a potent inducer in some bacteria.
Uses
Used in Pharmaceutical Industry:
Cefotetan disodium is used as an antibiotic for the treatment of bacterial infections. Its stability, compatibility, and molecular mode of action make it a valuable asset in combating various bacterial infections.
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.
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).
Check Digit Verification of cas no
The CAS Registry Mumber 69712-56-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,9,7,1 and 2 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 69712-56:
(7*6)+(6*9)+(5*7)+(4*1)+(3*2)+(2*5)+(1*6)=157
157 % 10 = 7
So 69712-56-7 is a valid CAS Registry Number.
InChI:InChI=1/C17H17N7O8S4/c1-23-16(20-21-22-23)34-4-5-3-33-15-17(32-2,14(31)24(15)7(5)11(29)30)19-9(26)13-35-12(36-13)6(8(18)25)10(27)28/h13,15H,3-4H2,1-2H3,(H2,18,25)(H,19,26)(H,27,28)(H,29,30)/b12-6-/t13?,15-,17+/m1/s1
69712-56-7Relevant articles and documents
Process development and pilot-scale synthesis of cefotetan
Fujimoto, Masaharu,Maeda, Tetsuya,Okumura, Keisuke,Uda, Mitsuru,Nakamura, Makoto,Kashiwagi, Teruya,Tsunoda, Takashi
, p. 915 - 919 (2004)
Strategies that were adopted during the process development of Cefotetan in order to achieve a cost-effective commercial-scale synthesis are described herein. These included replacement of the trifluoroacetic acid used for cleavage of the benzhydryl ester and the development of an alternative synthetic route. This work led to improvement of both the impurity profile and the yield of the process. The pilot-scale synthesis of Cefotetan is described in detail in the Experimental Section. The scaled-up process has been successfully used for the commercial manufacture of Cefotetan since 1983.
PROCESS FOR OBTAINING CEFOTETAN WITH HIGH YIELD
-
Page/Page column 1, (2008/06/13)
The invention relates to a method for obtaining cefotetan acid substantially free of tautomer, by treating crude cefotetan with Al3+ ions which cause the tautomer to precipitate. The precipitate is eliminated by filtration to provide a solution from which practically tautomer-free cefotetan is obtained.
Acid cefotetan totally solvent-free and method for obtaining same
-
Page/Page column 1-2, (2008/06/13)
The invention relates to a method for obtaining cefotetan acid substantially free of tautomer, by initial isolation of the crude product with a limited tautomer content, followed by purification through a chromatographic column. The invention also concerns the acid cefotetan totally solvent-free thereby obtained.
