28002-18-8

Basic information

• Product Name: Sulbenicillin sodium
• Synonyms: alpha-sulfobenzylpenicillindisodium;disodiumalpha-sulfobenzylpenicillin;disodiumsulbenicillin;disodiumsulfobenzylpenicillin;kedacillin;lilacillin;sulbenicillindisodium;sulfobenzylpenicillin
• CAS NO: 28002-18-8
• Molecular Formula: C₁₆H₁₆N₂O₇S₂*2Na
• Molecular Weight: 458.42
• EINECS: 248-769-3
• Product Categories: API;antibiotic
• Mol File: 28002-18-8.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: Sulbenicillin sodium(CAS DataBase Reference)
• NIST Chemistry Reference: Sulbenicillin sodium(28002-18-8)
• EPA Substance Registry System: Sulbenicillin sodium(28002-18-8)

Safety Data

• Hazardous Substances Data: 28002-18-8(Hazardous Substances Data)

Usage

Originator

Lillacillin,Takeda,Japan,1973

Manufacturing Process

To a suspension of 1.08 parts by weight of 6-aminopenicillanic acid in 8 parts by volume of water is added 1.48 parts by weight of sodium bicarbonate. After the mixture is dissolved, a solution of 1.18 parts by weight of α-sulfophenylacetyl chloride in 10 parts by volume of diethylether is gradually added thereto. The mixture is stirred at a temperature in the neighborhood of 0°C for 1 hour. The aqueous layer is washed twice with 10 parts by volume of portions of ether and adjusted to pH 1.2 with cation exchange resin of polystyrene sulfonic acid type under constant cooling. Then the solution is washed twice with 15 parts by volume of portions of ethyl acetate, followed by extraction twice with 15 parts by volume of portions of n-butanol. The extracts are combined and washed twice with 15 parts by volume of portions of water and, then, extracted with an aqueous solution of sodium bicarbonate. The extract is adjusted to pH 6.5, washed with ether and lyophilized to give the sodium salt of α-sulfobenzylpenicillin. Yield is 1.2 parts by weight.

Therapeutic Function

Antibacterial

InChI:InChI=1/C16H18N2O7S2.2Na/c1-16(2)11(15(21)22)18-13(20)9(14(18)26-16)17-12(19)10(27(23,24)25)8-6-4-3-5-7-8;;/h3-7,9-11,14H,1-2H3,(H,17,19)(H,21,22)(H,23,24,25);;/q;2*+1/p-2/t9-,10?,11+,14-;;/m1../s1

Upstream product

• 551-16-6 6-Aminopenicillanic Acid 
• 39925-38-7 2-phenyl-2-sulfoacetic acid 
• 41360-32-1 racemic α-sulfophenylacetic acid 
• 39925-35-4 2-sulfo-2-phenylacetyl chloride 
• 19460-36-7 triethylammonium 6β-penicillanate 
• 58569-36-1 Sulbenicillin 
• 103-82-2 phenylacetic acid 
• 40125-73-3 2-sulpho-2-phenylacetyl chloride 

Relevant articles and documents

Sulbenicillin sodium intermediate and method for preparing sulbenicillin sodium therefrom

The invention belongs to the field of drug synthesis and in particular relates to a sulbenicillin sodium intermediate and a method for preparing sulbenicillin sodium thereform. The method specificallycomprises the following steps: reacting phenyl-2-sulfoacetic acid and isopropenyl acetate to produce an intermediate Z1; reacting the intermediate Z1 and a solution 6-APA, and further crystallizing out sulbenicillin sodium with sodium iso-octoate. Compared with the traditional acyl chloride method for preparing the intermediate, the method for producing the intermediate Z1 in the invention has the advantages that the problem that the raw materials and intermediate are damaged due to moisture absorption is solved, emission of acid gases such as sulfur dioxide and hydrogen chloride produced during acyl chloride preparation is reduced, the process is simple and easy to operate, and the solvent is convenient to recycle. The method for preparing sulbenicillin sodium from the intermediate Z1 inthe invention has the advantages of being low in cost, high in yield and excellent in quality, the prepared sulbenicillin sodium has the purity of 99%, and the method is mild in reaction condition, easy to operate and suitable for industrial production.

Method for preparing D-sulbenicillin sodium

The invention discloses a method for preparing D-sulbenicillin sodium. The method includes steps of removing L-amino acid from L-amino acid salt of D-sulfophenylacetic acid in solvents and carrying out salt forming to obtain D-sulfophenylacetic acid salt; carrying out reaction on the D-sulfophenylacetic acid salt and acylating agents to obtain mixed acid anhydride; dissolving 6-APA in organic solvents under the effect of organic alkali; dropwise adding mixed acid anhydride solution into 6-APA solution, and carrying out sufficient reaction and after-treatment to obtain the D-sulbenicillin sodium. The D-sulfophenylacetic acid is an intermediate. The 6-APA is a matrix. The method has the advantages that the D-sulbenicillin sodium is prepared by the aid of novel synthetic routes, conditions are mild, the method includes stable process and is easy to implement, and the problems of instable processes of existing methods or insufficient optical purity of products and the like can be solved bythe aid of the method.

To facilitate the industrial production of synthesis method of sulbenicillin sodium (by machine translation)

The invention discloses a method of easy industrial production sulbenicillin sodium synthetic method, comprises the following steps: (1) sulfonation reaction; (2) alkalization reaction; (3) ion exchange; (4) chloro acylation reaction; (5) extracting sulphur benzene acetyl chloride; (6) preparation of (-) - α - D - sulbenicillin; (7) the preparation of (-) - α - D - sulbenicillin sodium. The invention relates to a convenient industrial production of synthetic method of sulbenicillin sodium, through reasonable synthetic route design, simplifies the sulphur benzene acetic acid disodium salt of the tedious operation, improves the yield; direct the synthetic process for preparing optically pure (-) - α - D - of sulbenicillin, saves the cost, more favorable to the industrialized production, market prospect. (by machine translation)