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Cefotetan

Cefotetan Structure
CAS No.
69712-56-7
Chemical Name:
Cefotetan
Synonyms
CEFOTETAN SODIUM;Apatef;Apacef;Ceftenon;YM 09330;CEFOTETAN;Yamatetan;Cefotetan>Cepan Darvilen;Cefotetan acid
CBNumber:
CB1152489
Molecular Formula:
C17H17N7O8S4
Molecular Weight:
575.62
MOL File:
69712-56-7.mol
Modify Date:
2024/5/10 14:18:40

Cefotetan Properties

Melting point 173-178°C (dec.)
Density 1.5157 (rough estimate)
refractive index 1.7400 (estimate)
storage temp. Store at 0-5°C
solubility DMSO (Slightly), Methanol (Very Slightly)
form Solid
pka 1.69±0.41(Predicted)
color White to Off-White
Merck 14,1934
Stability Hygroscopic
InChIKey SRZNHPXWXCNNDU-IXOPCIAXSA-N
CAS DataBase Reference 69712-56-7(CAS DataBase Reference)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P280-P305+P351+P338
RTECS  XI0330800
HS Code  2941906000

Cefotetan price More Price(2)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
TCI Chemicals (India) C2936 Cefotetan 69712-56-7 25MG ₹3000 2022-05-26 Buy
TCI Chemicals (India) C2936 Cefotetan 69712-56-7 250MG ₹9800 2022-05-26 Buy
Product number Packaging Price Buy
C2936 25MG ₹3000 Buy
C2936 250MG ₹9800 Buy

Cefotetan Chemical Properties,Uses,Production

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

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

Definition

ChEBI: Cefotetan is a semi-synthetic second-generation cephamycin 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 7beta 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. It has a role as an antibacterial drug. It is a conjugate acid of a cefotetan(2-).

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.

General Description

Cefotetan was synthesized by Yamanouchi Pharmaceutical Co. in 1979 starting with oganomycin, a cephamycin, produced by Streptomyces oganoensis YG19Z. Its 7β side chain, 1,3-dithietan, is unique and contributes greatly to its strong activity against gramnegative bacteria, including Serratia, Citrobacter, Enterobacter, indole-positive Proteus, and anaerobes. Its half-life in the serum is as long as three hours, and about 90 % of it is excreted in the urine.

Pharmacokinetics

Cefotetan is a semisynthetic cephamycin antibiotic that is administered intravenously or intramuscularly. The drug is highly resistant to a broad spectrum of beta-lactamases and is active against a wide range of both aerobic and anaerobic gram-positive and gram-negative microorganisms.

Mode of action

Cefotetan is a semi-synthetic, broad-spectrum, beta-lactamase-resistant, second-generation cephalosporin antibiotic derived from cephalosporium. The bactericidal activity of cefotetan disodium is caused by an inhibition of bacterial cell wall synthesis via inhibition of cross-linking of peptidoglycans. This results in a reduction of cell wall stability and causes cell lysis. Cefotetan disodium is more active against gram-negative organisms and less active against gram-positive organisms compared to first-generation cephalosporins.

Cefotetan Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 184)Suppliers
Supplier Tel Country ProdList Advantage Inquiry
OCEAN TRADING CORPORATION +91(22) 24921669 New Delhi, India 6211 58 Inquiry
TCI Chemicals (India) Pvt. Ltd. 1800 425 7889 New Delhi, India 6778 58 Inquiry
Pharmaffiliates Analytics and Synthetics P. Ltd +91-172-5066494 Haryana, India 6773 58 Inquiry
Pharma Affiliates 172-5066494 Haryana, India 6761 58 Inquiry
Clearsynth Labs 91-22-45045900 Maharashtra, India 3889 58 Inquiry
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Shanghai Daken Advanced Materials Co.,Ltd +86-371-66670886 China 16220 58 Inquiry
Henan Tianfu Chemical Co.,Ltd. +86-0371-55170693 +86-19937530512 China 21676 55 Inquiry

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CEFOTETAN CEFOTETAN DISODIUM SALT 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 Cepan Darvilen Yamatetan YM 09330 (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 Cefotetan free acid (6R,7S)-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-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (6R,7S)-7α-[4-(Carbamoylcarboxymethylene)-1,3-dithietan-2-ylcarbonylamino]-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 Cefotetan (500 mg) Cefotetan, Antibiotic for Culture Media Use Only Cefotetan acid [6R-(6ALPHA,7ALPHA)]-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-5-THIA-1-AZABICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACID (6r-(6-alpha,7-alpha))--1h-tetrazol-5-yl)thio)methyl)-8-oxo 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylicacid,7-(((4-(2-amino-1-carbox y-2-oxoethylidene)-1,3-dithietan-2-yl)carbonyl)amino)-7-methoxy-3-(((1-methyl 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-(6alpha,7alpha)]- CefotetanDisodiumC17H15N7Na2O8S4 Cefotetansodiumsalt 1,3-Dithietane, 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid deriv. 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-, (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-, [6R-(6α,7α)]- Apacef Cefotetan (1097975) Cefotetan USP/EP/BP Cefotetan> disodium 7-[[[4-(2-amino-1-carboxylato-2-oxoethylidene)-1,3-dithietan-2-yl]-oxomethyl]amino]-7-methoxy-3-[[(1-methyl-5-tetrazolyl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate CEFOTETAN SODIUM 69712-56-7 74365-00-6 C17H15N7O8S42Na C17H17N7O8S4 C17H15N7Na2O8S4 CEFOTAN Intermediates & Fine Chemicals Pharmaceuticals Sulfur & Selenium Compounds