69388-79-0

Basic information

• Product Name: Sulbactam pivoxil
• Synonyms: 3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (2,2-dimethyl-1-oxopropoxy)methyl ester 4,4-dioxide;PIVOXIL SULBACTAM;SULBACTAM PIVOXIL;SULBACTAM SODIUM STERILE;SULBACTAM PIVOXYL;Pivsulbactam;CP-47904;Penicillanic acid 4,4-dioxide (2,2-dimethyl-1-oxopropoxy)methyl ester
• CAS NO: 69388-79-0
• Molecular Formula: C₁₄H₂₁NO₇S
• Molecular Weight: 347.38
• EINECS: 1312995-182-4
• Product Categories: Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 69388-79-0.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 537.534 °C at 760 mmHg
• Flash Point: 278.891 °C
• Appearance: /
• Density: 1.371 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.538
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: -3.75±0.60(Predicted)
• CAS DataBase Reference: Sulbactam pivoxil(CAS DataBase Reference)
• NIST Chemistry Reference: Sulbactam pivoxil(69388-79-0)
• EPA Substance Registry System: Sulbactam pivoxil(69388-79-0)

Safety Data

• Hazardous Substances Data: 69388-79-0(Hazardous Substances Data)

Usage

Description

Sulbactam pivoxil is a prodrug of the semi-synthetic β-lactamase inhibitor Sulbactam (S699195), which is a white to pale white solid. It is used in the pharmaceutical industry as an antibiotic agent to enhance the effectiveness of other antibiotics by inhibiting bacterial β-lactamase enzymes.

Uses

Used in Pharmaceutical Industry:
Sulbactam pivoxil is used as an antibiotic agent for the inhibition of bacterial β-lactamase enzymes. This application helps to prevent the degradation of other antibiotics, allowing them to function more effectively against bacterial infections.
Used in Combination Therapy:
Sulbactam pivoxil is used in combination with other antibiotics, such as ampicillin or amoxicillin, to enhance their efficacy against a broader range of bacteria. This combination therapy is particularly useful in treating infections caused by β-lactamase producing bacteria, which can render certain antibiotics ineffective.

InChI:InChI=1/C14H21NO7S/c1-13(2,3)12(18)22-7-21-11(17)10-14(4,5)23(19,20)9-6-8(16)15(9)10/h9-10H,6-7H2,1-5H3/t9-,10+/m1/s1

Upstream product

• 18997-19-8 Chloromethyl pivalate 
• 69388-84-7 sodium sulbactam 
• 688-73-3 tri-n-butyl-tin hydride 
• 76454-57-4 (pivaloyloxy)methyl 6,6-dibromopenicillanate S,S-dioxide 
• 76454-58-5 (2S,6S)-6-Bromo-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester 
• 69388-92-7 pivaloyloxymethyl penicillanate 1-oxide 
• 68373-14-8 sulbactum 
• 75527-88-7 (2S,5R,6S)-6β-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,S,S-dioxide 
• 7440-66-6 zinc 
• 76468-87-6 6α-bromopenicillanic acid pivalolyloxymethyl ester 

Relevant articles and documents

An efficient method for the synthesis of sulbactam pivoxil

Sulbactam pivoxil, a prodrug of the β-lactamase inhibitor sulbactam, was prepared in high yield by reacting the sodium salt of sulbactam with chloromethyl pivalate in a polar solvent, then diluting the reaction mixture with water and isolating the product by filtration. Dimethyl sulfoxide was found to be the solvent of choice among several aprotic organic solvents. Copyright (C) 2000 Elsevier Science S.A.

A novel synthetic method for penicillanic acid derivatives by electroreduction

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6,6-dihalopenicillanic acid 1,1-dioxides and process

A process for the preparation of penicillanic acid 1,1-dioxide and esters thereof readily hydrolyzable in vivo, which comprises oxidation of a 6,6-dihalopenicillanic acid, or an ester thereof readily hydrolyzable in vivo, to the corresponding 6,6-dihalopenicillanic acid 1,1-dioxide or ester thereof, followed by dehalogenation (e.g. by hydrogenolysis). The 6,6-dihalopenicillanic acid 1,1-dioxides and esters thereof readily hydrolyzable in vivo are novel intermediates. Penicillanic acid 1,1-dioxide, and esters thereof readily hydrolyzable in vivo, are known compounds which are useful as beta-lactamase inhibitors and for enhancing the effectiveness of certain beta-lactam antibiotics (e.g. the penicillins) in the treatment of bacterial infections in mammals, particularly humans.