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Cefotetan

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
MDL Number:
MFCD00864983
MOL File:
69712-56-7.mol
Last updated:2023-05-18 11:31:13

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)
FDA UNII 48SPP0PA9Q
ATC code J01DC05

SAFETY

Risk and Safety Statements

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

Cefotetan price More Price(13)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
TCI Chemical C2936 Cefotetan >98.0%(HPLC) 69712-56-7 25mg $34 2023-06-20 Buy
TCI Chemical C2936 Cefotetan >98.0%(HPLC) 69712-56-7 250mg $191 2024-03-01 Buy
TRC C242970 Cefotetan 69712-56-7 250mg $250 2021-12-16 Buy
TRC C242970 Cefotetan 69712-56-7 100mg $120 2021-12-16 Buy
Chem-Impex 14300 Cefotetanfreeacid,≥99%(HPLC)Antibiotic ≥99%(HPLC) 69712-56-7 1G $151.42 2021-12-16 Buy
Product number Packaging Price Buy
C2936 25mg $34 Buy
C2936 250mg $191 Buy
C242970 250mg $250 Buy
C242970 100mg $120 Buy
14300 1G $151.42 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-).

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.

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.

Synthesis

Cefotetan, 7|?-[(-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 7|?-bromoacetamido-7|á-methoxycephalosporanic acid, which is synthesized by a scheme described previously (32.1.2.31) ?ú (32.1.2.37), the only difference being that the acylation in the stage (32.1.2.35) ?ú (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).

Synthesis_69712-56-7

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( 179)Suppliers
Supplier Tel Email Country ProdList Advantage
Finetech Industry Limited
+86-27-87465837 +8618971612321 info@finetechnology-ind.com China 9589 58
Shanghai Daken Advanced Materials Co.,Ltd
+86-371-66670886 info@dakenam.com China 14764 58
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21700 55
Alchem Pharmtech,Inc.
8485655694 sales@alchempharmtech.com United States 63711 58
CONIER CHEM AND PHARMA LIMITED
+8618523575427 sales@conier.com China 47465 58
career henan chemical co
+86-0371-86658258 15093356674; factory@coreychem.com China 29826 58
ANHUI WITOP BIOTECH CO., LTD
+8615255079626 eric@witopchemical.com China 23556 58
Shaanxi Dideu Medichem Co. Ltd
+86-029-89586680 +86-18192503167 1026@dideu.com China 9802 58
Dideu Industries Group Limited
+86-29-89586680 +86-15129568250 1026@dideu.com China 29831 58
AFINE CHEMICALS LIMITED
0571-85134551 info@afinechem.com CHINA 15377 58

View Lastest Price from Cefotetan manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Cefotetan pictures 2021-11-06 Cefotetan
69712-56-7
US $0.00 / Kg/Drum 1KG 98%min 1000kg WUHAN FORTUNA CHEMICAL CO., LTD
Cefotetan disodium pictures 2021-08-12 Cefotetan disodium
69712-56-7
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd
Cefotetan USP/EP/BP pictures 2021-07-01 Cefotetan USP/EP/BP
69712-56-7
US $1.10 / g 1g 99.9% 100 Tons Min Dideu Industries Group Limited
  • Cefotetan pictures
  • Cefotetan
    69712-56-7
  • US $0.00 / Kg/Drum
  • 98%min
  • WUHAN FORTUNA CHEMICAL CO., LTD
  • Cefotetan disodium pictures
  • Cefotetan disodium
    69712-56-7
  • US $15.00-10.00 / KG
  • 99%+ HPLC
  • Zhuozhou Wenxi import and Export Co., Ltd
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