26631-90-3

Basic information

• Product Name: brobactam
• Synonyms: brobactam;6-bromopenicillanic acid;(2S,5R,6R)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;Sulbactam EP Impurity D
• CAS NO: 26631-90-3
• Molecular Formula: C₈H₁₀BrNO₃S
• Molecular Weight: 280.14
• EINECS: 247-856-3
• Product Categories: Heterocycles;Impurities;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;Heterocycles, Impurities, Inhibitors, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds
• Mol File: 26631-90-3.mol

Chemical Properties

• Boiling Point: 462.6°Cat760mmHg
• Flash Point: 233.6°C
• Appearance: /
• Density: 1.84
• Vapor Pressure: 7.66E-10mmHg at 25°C
• Refractive Index: 1.664
• PKA: 2.43±0.50(Predicted)
• CAS DataBase Reference: brobactam(CAS DataBase Reference)
• NIST Chemistry Reference: brobactam(26631-90-3)
• EPA Substance Registry System: brobactam(26631-90-3)

Safety Data

• Hazardous Substances Data: 26631-90-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Brobactam is used as a β-lactamase inhibitor for enhancing the effectiveness of β-lactam antibiotics by preventing the inactivation of these antibiotics by bacterial β-lactamase enzymes. This allows for a broader spectrum of activity and improved treatment outcomes in bacterial infections.

InChI:InChI=1/C8H10BrNO3S/c1-8(2)4(7(12)13)10-5(11)3(9)6(10)14-8/h3-4,6H,1-2H3,(H,12,13)/t3-,4+,6-/m1/s1

Upstream product

• 24138-28-1 6-bromopenicillanic acid 
• 24158-88-1 6,6-dibromopenicillanic acid 
• 551-16-6 6-aminopenicillanic acid 
• 157843-37-3 phenyldibutylstannane 
• 144-55-8 sodium hydrogencarbonate 
• 688-73-3 tri-n-butyl-tin hydride 
• 75527-85-4 benzhydryl 6β-bromopenicillanate 
• 24158-88-1 6,6-Dibromopenicillanic acid 
• 551-16-6 6-Aminopenicillanic Acid 

Downstream Products

• 87-53-6 penicillanic acid 
• 24138-27-0 methyl-6,6-dibromopenicillanate 

Relevant articles and documents

Method for preparing penam sulfoxide acid diphenyl methyl ester which is tazobactam precursor

The invention provides a method for preparing penam sulfoxide acid diphenyl methyl ester. The method includes steps of carrying out bromination reaction on 6-aminopenicillanic acid to obtain first reaction products; carrying out reaction on the first reac

Microwave-Induced Organic Reaction Enhancement Chemistry. 2. Simplified Techniques

A variety of organic reactions have been conducted efficiently in a few minutes in unsealed vessels at ambient pressure in unmodified microwave ovens by using selected organic solvents.

Method for preparing 6-β-halopenicillanic acids

The present invention relates to a new and improved method for the preparation of a compound of the formula I STR1 in which R stands for halogen, giving rise to high yields of substantially pure 6β-halopenicillanic acids, obtained in one step.

6-β-substituted penicillanic acid compound free of the 6-α-epimer

6-β-Substituted penicillanic acids and derivatives thereof as useful enhancers of the effectiveness of several β-lactam antibiotics against many β-lactamase producing bacteria, and 6-β-substituted penicillanic acid derivatives wherein the carboxy group is protected by a conventional penicillin carboxy protecting group as useful intermediates leading to said synergistic agents. A process for converting 6,6-disubstituted penicillanic acid derivatives to the corresponding 6-β-substituted penicillanic acid congeners.

6-beta-Halopenicillanic acid 1,1-dioxides as beta-lactamase inhibitors

6-beta-Halopenicillanic acid 1,1-dioxides, physiologically acceptable salts thereof and esters thereof readily hydrolyzable; pharmaceutical compositions containing a 6-beta-halopenicillanic acid 1,1-dioxide, a physiologically acceptable salt thereof or an ester thereof readily hydrolyzable; and a method for enhancing the effectiveness of a beta-lactam antibiotic, using a 6-beta-halopenicillanic acid 1,1-dioxide, a physiologically acceptable salt thereof or an ester thereof readily hydrolyzable.

Derivatives of penicillanic acid

This invention relates to penicillanic acid derivatives of the formula I STR1 in which X stands for chlorine, bromine or iodine, to pharmaceutically acceptable, non-toxic salts of the compounds of formula I, to pharmaceutically acceptable, easily hydrolyz

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.

Process for converting 6,6-disubstituted penicillanic acid derivatives to the 6-β-congeners

6-β-Substituted penicillanic acids and derivatives thereof as useful enhancers of the effectiveness of several β-lactam antibiotics against many β-lactamase producing bacteria, and 6-β-substituted penicillanic acid derivatives wherein the carboxy group is protected by a conventional penicillin carboxy protecting group as useful intermediates leading to said synergistic agents. A process for converting 6,6-disubstituted penicillanic acid derivatives to the corresponding 6-β-substituted penicillanic acid congeners.

6-Perhaloalkylsulfonyloxy-penicillanic acids and derivatives thereof

6-Alpha and 6-beta-substituted penicillanic acid derivatives of the formula: STR1 wherein R is H or a conventional penicillin carboxy protecting group or an ester forming residue readily hydrolyzable in vivo and R1 is a perhaloalkyl group of from 1 to 4 carbon atoms wherein the halogen atoms are fluoro or chloro, undergo SN2 nucleophilic displacement with halide or azide ions with inversion of configuration at C-6 to yield the corresponding 6-beta or 6-alpha-halo- or azido-substituted product.