152186-43-1

Basic information

• Product Name: cefotaxime
• Synonyms: 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-[[(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-8-oxo-, [6R-[6α,7α(Z)]]-
• CAS NO: 152186-43-1
• Molecular Formula: C16H17 N5 O7 S2
• Molecular Weight: 455.47
• EINECS: 264-299-1
• Mol File: 152186-43-1.mol

Chemical Properties

• Appearance: /
• Density: 1.8g/cm³
• Refractive Index: 1.778
• CAS DataBase Reference: cefotaxime(CAS DataBase Reference)
• NIST Chemistry Reference: cefotaxime(152186-43-1)
• EPA Substance Registry System: cefotaxime(152186-43-1)

Safety Data

• Hazardous Substances Data: 152186-43-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H17N5O7S2/c1-6(22)28-3-7-4-29-14-10(13(24)21(14)11(7)15(25)26)19-12(23)9(20-27-2)8-5-30-16(17)18-8/h5,10,14H,3-4H2,1-2H3,(H2,17,18)(H,19,23)(H,25,26)/b20-9-/t10-,14-/m0/s1

Upstream product

• 121464-41-3 (6R,7R)-3-Acetoxymethyl-7-(acetyl-{2-(2-amino-thiazol-4-yl)-2-[(E)-methoxyimino]-acetyl}-amino)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 65243-53-0 pyvaloyloxymethyl 7β-<2-(2-aminothiazol-4-yl)-(Z)-methoxyiminoacetamido>-3-acetoxymethyl-3-cephem-4-carboxylate 
• 108260-00-0 7-aminocephalosporanic acid 
• 179258-53-8 4-(diethylphosphoryl)-2-(2-amino-4-thiazolyl)-2-syn-(2-methoxyimino)acetate 
• 957-68-6 7-Aminocephalosporanic acid 
• 207725-19-7 (2-Amino-thiazol-4-yl)-[(Z)-methoxyimino]-acetic acid 4,6-dimethoxy-[1,3,5]triazin-2-yl ester 
• 80756-85-0 (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate 
• 65872-39-1 (Z)-γ-bromo-β-oxo-α-methoxyiminobutyric acid ethyl ester 
• 65052-66-6 2-(2-aminothiazol-4-yl)-2-methoxyiminoacetic acid-S-ethyl ester 
• 65052-67-7 (E)-methoxyimino-(2-tritylamino-thiazol-4-yl)-acetic acid ethyl ester 
• 64485-89-8 ethyl (Z)-2-(methoxyimino)-2-[2-(triphenylmethyl)-aminothiazol-4-yl]acetate 
• 17356-08-0 thiourea 
• 71754-15-9 C₁₅H₁₆ClN₃O₈S 
• 7440-44-0 pyrographite 

Downstream Products

• 121020-94-8 desacetyl cefotaxime 
• 60846-23-3 cefotaxime sodium salt 
• 1374584-89-0 benzhydryl (6R,7R, Z)-3-(acetoxymethyl)-7-(2-(methoxyimino)-2-(2-(2-(tritylamino)acetamido)thiazol-4-yl)acetamido)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate 
• 121020-94-8 desacetylcefotaxime 

Relevant articles and documents

A rapid procedure to prepare cefotaxime

A rapid procedure is reported for the synthesis of cefotaxime, by acylation of the 7-amino cephalosporanic acid with the 2- mercaptobenzothiazolyl thioester of (Z)-2-[2-aminothiazol-4-yl]-2- methoxyimino acetic acid (MAEM) that is a commercial reagent. The reaction was carried out at room temperature for 1 h, obtaining 95% yield. 2- Mercaptobenzothiazole was recovered as a side-product with a high purity and yield. The proposed method differentiates from those reported previously for a shorter time and very mild reaction condition, as well as for a ready for use reagent. (C) 2000 Elsevier Science S.A.

Cefotaxime sodium pharmaceutical preparation, and application thereof in treatment of new salmonella infection indications including typhoid and paratyphoid

The invention provides a cefotaxime sodium, and a preparation method, a cefotaxime sodium preparation and application thereof. The mass content of the cefotaxime sodium is 98% or above, and the cefotaxime sodium also comprises impurities A, B and C. The preparation method comprises the following steps: firstly, reacting methoxyiminoacetic acid with an activating agent to obtain an active ester intermediate; reacting 7-ACA with the active ester intermediate under a temperature control condition, and performing acid regulation and crystallization to obtain cefotaxime acid; carrying out a salifying reaction on cefotaxime acid and a salifying agent in a salifying solvent, and separating out to obtain the cefotaxime sodium. The cefotaxime sodium is low in impurity content, beneficial to long-term storage and placement, good in quality stability and better in clinical curative effect and safety, and can be used for treating salmonella infections including typhoid and paratyphoid.

Preparation method for improving product quality of cefotaxime sodium

The invention provides a preparation method for improving the product quality of cefotaxime sodium. The preparation method is characterized in that after pure water and organic alcohol are added into a reaction solvent, 7-aminocephalosporanic acid is dissolved under a neutral/slightly alkaline condition; then an impurity layer is separated; then a condensation reaction is performed with 2-(2-amino-4-thiazolyl)-2-methoxyiminoacetic to generate cefotaxime; a cefotaxime water solution obtained through extraction is directly added into an alcoholic solution of sodium acetate or sodium iso-octoate for a salt forming reaction without crystallization; decarbonization and sterile filtration are performed; then crystallization is performed by utilizing the solvent to obtain the target product cefotaxime sodium. The cefotaxime sodium prepared by the method provided by the invention is high in purity and good in yield.

Cefotaxime sodium pharmaceutical preparation in the transabdominal or vaginal hysterectomy, gastrointestinal tract and genital tract such as the prevention of infection before the application (by machine translation)

The present invention provides a head spore sai wowo sodium or its composition, preparation method, preparation and use. The head spore sai wowo sodium or its composition of active ingredients in the Cefotaxime quality content is 98% or more, the impurity content is low, and the safety is high. The present invention provides the preparation method AE - active thioester and 7 - ACA reaction to obtain the spore saisai wo acid; with the spore saisai wo acid generating sodium salt, can get [...]. The preparation method is simple, stable and reliable, production process stability is strong. Therefore, the head spore sai wowo sodium or its composition can be used for pharmaceutical use, particularly for the treatment of transvaginal/abdominal hysterectomy, gastrointestinal, genitourinary tract before and postoperative infection prevention of infection. (by machine translation)

1/4 water cefotaxime sodium compound

The invention discloses a 1/4 water cefotaxime sodium compound and a preparation method thereof. The cefotaxime sodium per mole contains 1/4 mole of water. The 1/4 water cefotaxime sodium compound obtained has good particle size distribution, good fluidity, low impurity content, thermodynamic stability and wide application prospects.

Preparation method for cefotaxime acid

The invention discloses a preparation method for cefotaxime acid, and belongs to the technical field of medicine. The preparation method comprises the following steps: firstly mixing dichloromethane with ethanol, purified water and isopropyl alcohol, and then adding 7-ACA (aminocephalosporanic acid), AE-active ester and antioxygen to obtain mixed liquor; dropwise adding triethylamine into the mixed liquor in 2 to 3 hours for a reaction, and when HPLC (high performance liquid chromatography) is adopted to detect that 7-ACA residual amount is less than 1 percent, regarding as a complete reaction; adding sodium bicarbonate aqueous solution of which the mass concentration is 1 percent to 5 percent for extraction, after reduced pressure suction filtration on an aqueous phase, adding acetone and mixing, dropwise adding hydrochloric acid of which the mass concentration is 10 percent to 25 percent under temperature of 10 to 15 DEG C until a pH (potential of hydrogen)value is 2.5 to 3.0, and cultivating crystals for 1 to 3 hours; centrifuging, spin-drying, leaching, and drying after spin-drying to obtain the cefotaxime acid. The cefotaxime acid prepared by the invention has uniform particle size distribution and stable performance; mass yield reaches more than 170 percent, and product purity can reach more than 99 percent.

PROCESS FOR PREPARATION OF CEFOTAXIME ACID

Cefotaxime acid of formula (I) is prepared by using a kind of alcohol as the single solvent in presence of a base.

PROCESS FOR PREPARATION OF CEFOTAXIME ACID AND PHARMACEUTICALLY ACCEPTABLE SALT THEREOF

A process for the preparation of cefotaxime acid of formula (IV) and pharmaceutically acceptable salt thereof, such as cefotaxime sodium of formula (I) is provided, which comprises condensing the compound of formula (II) with the compound of formula (III) and using aqueous glyme or aqueous cellosolve as the solvent.

IMPROVED PROCESS FOR THE PREPARATION OF CEPHALOSPORIN ANTIBIOTICS

Abstract The present invention more particularly relates to a process for the preparation of cephalosporin antibiotics of the Formula (I) wherein R1 represents hydrogen, trityl, alkyl like CH3, CRaRbCOORc where Ra and Rb independently represent hydrogen or methyl and Rc represents hydrogen or (C1-C6) alkyl; R2 is carboxylate ion or COORd, where Rd represents hydrogen, ester or a counter ion which forms a salt; R3 represents hydrogen, CH3, CH2OCH3, CH2OCOCH3, CH=CH2, Formula (II).

Process for the production of cefotaxime sodium

A process for the production of 7-[2-(2-amino-4-thiazolyl)-2-syn-methoxyimino-acetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid (Cefotaxime) in aqueous isopropyl alcohol is provided. The synthesis provides the product in greater than 99 % HPLC purity.