69712-56-7 Usage
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
Different sources of media describe the Uses of 69712-56-7 differently. You can refer to the following data:
1. antibacterial
2. 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.
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
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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
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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.
