37091-66-0

Basic information

• Product Name: Azlocillin
• Synonyms: AZLOCILLIN ACID;3,3-Dimethyl-6-oxo-7-[2-(2-oxoimidazolidin-1-yl)carbonylamino-2-phenyl-acetyl]amino-2-thia-5-azabicyclo[3.2.0]heptane-4-carboxylic acid;3,3-Dimethyl-7-oxo-6-[[[[(2-oxoimidazolidin-1-yl)carbonyl]amino]phenylacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;Azlocillin;[2S-[2a,5a,6(s*)]]3,3-dimethyl-7-oxo-6{[[[[(2-oxoimideazolidine-1-yl)carbonyl]amino]phenylacethyl]-amino]-4-thia-1-azabicyclo[3,2,0]-heptane-2-carboxylic acid;6α-[[(R)-[[(2-Oxo-1-imidazolidinyl)carbonyl]amino]phenylacetyl]amino]penicillanic acid;Azlocillin solution,100ppm
• CAS NO: 37091-66-0
• Molecular Formula: C₂₀H₂₃N₅O₆S
• Molecular Weight: 461.49152
• EINECS: 253-348-2
• Mol File: 37091-66-0.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Density: 1.55 g/cm³
• Refractive Index: 1.696
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: pKa 2.8 (Uncertain)
• CAS DataBase Reference: Azlocillin(CAS DataBase Reference)
• NIST Chemistry Reference: Azlocillin(37091-66-0)
• EPA Substance Registry System: Azlocillin(37091-66-0)

Safety Data

• Hazardous Substances Data: 37091-66-0(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 37091-66-0 differently. You can refer to the following data:
1. Antibacterial.
2. Azlocillin is an antibiotic.

Definition

ChEBI: A semisynthetic penicillin antibiotic used in treating infections caused by Pseudomonas aeruginosa, Escherichia coli, and Haemophilus influenzae.

Indications

Azlocillin is active with respect to Gram-positive and Gram-negative aerobic and anaerobic microorganisms. It is highly effective with respect to bacillus pyocyaneus, including strains that are resistant to carbenicillin and aminoglycosides. It is destroyed by betalactamases. It is used for bacterial infections such as pyelonephritis, uretritis, cystitis, endometritis, cholecystitis, sepsis, peritonitis, endocarditis, meningitis, pneumonia, infections of the skin and soft tissues, infected burns, and so on. Synonyms of this drug are securopen and azlin.

Therapeutic Function

Antibacterial

Antimicrobial activity

A semisynthetic acylureidopenicillin supplied as the sodium salt for parenteral administration. It is active against a wide range of other Gram-negative bacteria, but is distinguished mainly by its activity against Ps. aeruginosa. B. fragilis and other anaerobes are moderately susceptible. Like other ureidopenicillins, azlocillin is active against Grampositive cocci, H. influenzae and N. gonorrhoeae. Because it can be hydrolyzed by most β-lactamases, β-lactamase-producing isolates are resistant. It attains peak concentrations of 250 mg/L after a 3 g intravenous infusion, with a plasma half-life of approximately 1 h. Protein binding is 20–30%. It distributes into multiple tissues and human body fluids at therapeutically useful concentrations. Up to 60% of the dose is recoverable from the urine, mostly unchanged, although some hydrolysis of the β-lactam ring takes place in the body. Toxicity and side effects are similar to those associated with carboxypenicillins. Its clinical use is for serious infections with susceptible organisms, including lower respiratory tract, intra-abdominal, urinary tract and gynecological infections. Commercial availability is quite limited.

Synthesis

Azlocillin, (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(R)-2-(2-oxoimidazolidin-1-carboxamido)-2-phenylacetamido]-4-thia-1-azabicyclo[3.2.0]-heptan-2-carboxylic acid (32.1.1.24), is synthesized by the following scheme. 2-Imidazolidinone is acylated with phosgene, forming 1-chlorocarbonyl-2-imidazolidinone (32.1.1.22). The resulting 1-chlorocarbonyl-2-imidazolidinone (32.1.1.22) is reacted with D(?)-α-phenylglycine, forming N-(2-oxoimidazolidin- 1-carboxamido)-phenylglycine (32.1.1.23). Reacting this with 6-APA in the presence of triethylamine gives the desired azlocillin (32.1.1.24).

InChI:InChI=1/C20H23N5O6S/c1-20(2)13(17(28)29)25-15(27)12(16(25)32-20)22-14(26)11(10-6-4-3-5-7-10)23-19(31)24-9-8-21-18(24)30/h3-7,11-13,16H,8-9H2,1-2H3,(H,21,30)(H,22,26)(H,23,31)(H,28,29)/t11-,12-,13+,16-/m1/s1

Upstream product

• 69-53-4 ampicillin 
• 13214-53-4 2-oxoimidazolidine-1-carbonyl chloride 
• 551-16-6 6-Aminopenicillanic Acid 
• 37091-70-6 D-α-(2-Oxo-imidazolidinon-1-carboxamido)-α-phenylessigsaeure 

Downstream Products

• 37091-65-9 azlocillin sodium 

Relevant articles and documents

Preparation method of azlocillin and preparation method of azlocillin sodium freeze-dried powder for injection

The invention discloses a preparation method of azlocillin and a preparation method of azlocillin sodium freeze-dried powder for injection. The preparation method of the azlocillin comprises the steps that 25-35 parts of an ampicillin thihydrate, 55-65 parts of acetone, 240-260 parts of water and 4-6 parts of dioxane and tetrahydrofuran are added into a reaction container by weight under the room temperature condition and stirred to be uniform, wherein the weight part ratio of dioxane to tetrahydrofuran is (6-8):1; 6-12 parts by weight of triethylamine is dropwise added into the reaction container when the temperature of the materials in the reaction container is lowered to 10 DEG C-15 DEG C, and stirring is performed to enable the solution in the reaction container to be completely clear; 9.10-12.74 parts by weight of 1-chloroformyl-2-imidazolidinone is slowly added into the reaction container when the temperature of the materials is lowered to 5 DEG C-10 DEG C, the temperature is kept at 15 DEG C-20 DEG C, and reacting under stirring is performed for 2.5-3.5 h; the pH is regulated to be 3-4 by adding hydrochloric acid, crystallization of the azlocillin is performed under the 3 DEG C-5 DEG C condition, and a precipitate is separated out; filtering is performed, and a precipitate is taken, leached by acetone and then subjected to vacuum drying. The preparation method of the azocillin is high in yield, the prepared azocillin is high in purity, and no solvent is retained.

Azlocillin. Ein neues Penicillin aus der Acylureidoreihe. Synthese und chemische Eigenschaften

Azlocillin, 6--penicillanic acid is a new semi synthetic acylureido-penicillin presenting a broad antibacterial spectrum, especially against Pseudomonas.Synthesis from ampicillin and 6-aminopenicillanic acid as well as physicochemical properties of free acid and sodium salt are described.Azlocillin is cleaved by penicillinase to penicilloate which is further degraded by acid to peniollate.Keywords: Azlocillin. - Acylureidopenicillin. - Antibacterial activity.