69388-79-0

Usage

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 
• 76468-87-6 6α-bromopenicillanic acid pivalolyloxymethyl ester 
• 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 
• 68373-14-8 sulbactum 
• 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 

Relevant academic research and scientific papers

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.

Orally effective acid prodrugs of the β-lactamase inhibitor sulbactam

Sulbactam (1) is a β-lactamase inhibitor with limited oral bioavailability. Lipophilic double-ester prodrug sulbactam pivoxil (2) significantly improves the oral absorption of sulbactam, as does the mutual prodrug double ester sultamicillin (3). We have found that double-ester prodrugs of sulbactam terminating in a carboxyl group (8) also were effective oral-delivery vehicles in rats. Carboxyl-terminated double esters have several potential advantages over their nonionizable lipophilic counterparts, including water solubility, crystallinity, choice of salts for dosage forms, and formation of innocuous byproducts on hydrolysis.

Stereoselective Reduction of (Pivaloyloxy)methyl Mixed 6,6-Dihalogenopenicillanates and their (1R)-Sulphoxides and Sulphones by Tributyltin Hydride.

Treatment of (pivaloyloxy)methyl (Pom) 6,6-dihalogenopenicillanates (1-4) and their corresponding sulphones (9-12) with tributyltin hydride under free-radical conditions results in mixture of products in which the 6β-halogeno isomers predominate.In contrast, Pom 6,6-dihalogenopenicillanate (1R)-S-oxides (5-7) under the same conditions react to yield exclusively their corresponding 6α-halogenopenicillanate (1R)-S-oxides.The causative factors which appear to underlie the chemo- and diastereo-selectivity of the reaction are discussed.

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.

Process for the preparation of penicillanic acid 1,1-dioxides

A process for the preparation of penicillanic acid-1,1-dioxides of the formula STR1 wherein X is selected from the group consisting of hydrogen and substituent such as halogen or acetoxy and R is selected from the group consisting of hydrogen, a pharmaceutically acceptable metal ion and/or ester radical comprising debrominating a 6-α-bromo- and/or 6,6-dibromo-penicillanic 1,1-dioxide selected from the group consisting of the formula STR2 wherein X and R have the above definition in an aqueous containing medium with zinc in association with an acid having a pKa -value measured in water less than 3.5 and optionally if R is H converting the acid into a pharmaceutically acceptable salt or ester.

Ester of 1,1-dioxopenicillanic acid, and use thereof as β-lactamase inhibitor

A 1,1-dioxopenicillanic acid ester represented by formula (I) STR1 wherein R represents a methyl or phenyl group. The ester of formula (I) may be prepared by reacting 1,1-dioxopenicillanic acid or its salt with a compound represented by formula (III) STR2 wherein R is as defined above, and X represents a halogen atom, or by oxidizing a compound of formula (V) STR3 wherein R is as defined above. The ester of the formula (I) is useful as a β-lactamase inhibitor and may be used in association with a β-lactam antibiotic.

6-Alpha-halopenicillanic acid 1,1-dioxides

A process for the preparation of penicillanic acid 1,1-dioxide and esters thereof readily hydrolyzable in vivo, which comprises oxidation of a 6-halopenicillanic acid, or an ester thereof readily hydrolyzable in vivo, to the corresponding 6-halopenicillanic acid 1,1-dioxide or ester thereof, followed by dehalogenation (e.g. by hydrogenolysis). Certain of the 6-halopenicillanic 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 beta-lactamase inhibitors and which enhance the effectiveness of certain beta-lactam antibiotics (e.g. the penicillins) in the treatment of bacterial infections in mammals, particularly humans.

Penicillanic acid 1,1-dioxides as β-lactamase inhibitors

Penicillanic acid 1,1-dioxide, and esters thereof readily hydrolyzable in vivo, are useful as antibacterial agents, and also for enhancing the effectiveness of several β-lactam antibiotics against many β-lactamase producing bacteria. Derivatives of penicillanic acid 1,1-dioxide having the carboxy group protected by a conventional penicillin carboxy protecting group are useful intermediates to penicillanic acid 1,1-dioxide. Penicillanic acid 1-oxides and certain esters thereof are useful chemical intermediates to penicillanic acid 1,1-dioxide and its esters.