ChemicalBook > CAS DataBase List > Azlocillin

Azlocillin

Product Name: Azlocillin
CAS No.: 37091-66-0
Chemical Name: Azlocillin
Synonyms: (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-((R)-2-(2-oxoimidazolidine-1-carboxamido)-2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;Azlocillin;Aloxicillin;AZLOCILLIN ACID;Aloxicillin acid;Azlocillin USP/EP/BP;Abamectin Impurity 11;Azlocillin solution,100ppm;6α-[[(R)-[[(2-Oxo-1-imidazolidinyl)carbonyl]amino]phenylacetyl]amino]penicillanic 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
CBNumber: CB6511850
Molecular Formula: C20H23N5O6S
Formula Weight: 461.49
MOL File: 37091-66-0.mol

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Azlocillin Property

Melting point:: 157 - 160oC
Density: 1.55±0.1 g/cm3(Predicted)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
solubility: DMSO (Slightly), Methanol (Slightly)
pka: pKa 2.8 (Uncertain)
form: Solid
color: White to Off-White

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

TRC

Product number: A930003
Product name: Azlocillin
Packaging: 5g
Price: $465
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FA36822
Product name: Azlocillin
Packaging: 250mg
Price: $100
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FA36822
Product name: Azlocillin
Packaging: 1g
Price: $250
Updated: 2021/12/16

AK Scientific

Product number: E867
Product name: Azlocillin
Packaging: 25g
Price: $516
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FA36822
Product name: Azlocillin
Packaging: 5G
Price: $550
Updated: 2021/12/16

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Azlocillin Chemical Properties,Usage,Production

Originator

Securopen,Bayer,W. Germany,1977

Uses

Antibacterial.

Uses

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.

Manufacturing Process

3.8 parts by weight of D-(-)-α-[(imidazolidin-2-on-1-yl)carbonylamino]phenylacetic acid were dissolved in 65 parts by volume of dichloromethane. 2.7 parts by weight of 1-methyl-2-chloro-δ1-pyrrolinium chloride were added, and after cooling to -10°C 2.0 parts by volume of triethylamine were added gradually. This reaction mixture was then stirred for one hour at -5°C (mixture A). 4.0 parts by weight of 6-aminopenicillanic acid in 80 parts by volume of dichloromethane were treated with 4.4 parts by volume of triethylamine and 4.0 parts by weight of anhydrous sodium sulfate and then stirred for two hours at room temperature. After filtration, the solution was cooled to -20°C and combined with the mixture A. The reaction mixture was left to reach 0°C of its own accord, and was then stirred for a further hour at 0°C. The solvent was removed in a rotary evaporator, the residue was dissolved in water, and the solution was covered with a layer of ethyl acetate and acidified with dilute hydrochloric acid at 0° to 5°C, while stirring, until pH 1.5 was reached. The organic phase was then separated off, washed with water, dried over magnesium sulfate while cooling, and filtered, and after dilution with an equal amount of ether the sodium salt of the penicillin was precipitated from the filtrate by adding a solution of sodium 2-ethylcaproate dissolved in ether containing methanol. Yield: 1.3 parts by weight.

brand name

Azlin (Bayer).

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(?)-|á-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).

References

[1] Patent: CN105753886, 2016, A. Location in patent: Paragraph 0032; 0033; 0034; 0035; 0036; 0037
[2] European Journal of Medicinal Chemistry, 1982, vol. 17, # 1, p. 59 - 63
[3] Patent: CN105777778, 2016, A. Location in patent: Paragraph 0031; 0032; 0033; 0034; 0035; 0036; 0037

Azlocillin Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Azlocillin manufacturers

Shaanxi Xianhe Biotech Co., Ltd

Product: Azlocillin 37091-66-0
Price: US $0.00/kg
Min. Order: 1kg
Purity: 0.99
Supply Ability: 1000kg
Release date: 2025-04-23

Hebei Chuanghai Biotechnology Co., Ltd

Product: Azlocillin 37091-66-0
Price: US $0.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 500000kg
Release date: 2024-11-04

Henan Aochuang Chemical Co.,Ltd.

Product: Azlocillin 37091-66-0
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: 1Ton
Release date: 2022-09-27

37091-66-0, AzlocillinRelated Search:

Ampicillin sodium Acetylacetone ETHANE Dimethyl sulfide Dimethyl ether Dimethyl fumarate Dimethyl phthalate N-ACETYL-L-TYROSINE ETHYL ESTER Imidazolidinyl urea Acetylferrocene Dimethyl sulfoxide Amoxicillin N,N-Dimethylformamide Ampicillin Glycine Ampicillin Alkylimidazole tributyl acetocitrate

(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[[(2S)-1-oxo-2-[[oxo-(2-oxo-1-imidazolidinyl)methyl]amino]-2-phenylethyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

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

4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[[(2R)-2-[[(2-oxo-1-imidazolidinyl)carbonyl]amino]-2-phenylacetyl]amino]-, (2S,5R,6R)-

Azlocillin USP/EP/BP

(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-((R)-2-(2-oxoimidazolidine-1-carboxamido)-2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Aloxicillin acid

Aloxicillin

Abamectin Impurity 11

37091-66-0

7091-66-0

C20H23N5O6S

37091-66-0