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
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
N-Bromosuccinimide Price
- Product number
- A930003
- Product name
- Azlocillin
- Packaging
- 5g
- Price
- $465
- Updated
- 2021/12/16
- Product number
- FA36822
- Product name
- Azlocillin
- Packaging
- 1g
- Price
- $250
- Updated
- 2021/12/16
- Product number
- E867
- Product name
- Azlocillin
- Packaging
- 25g
- Price
- $516
- Updated
- 2021/12/16
- Product number
- FA36822
- Product name
- Azlocillin
- Packaging
- 5G
- Price
- $550
- Updated
- 2021/12/16
- Product number
- FA36822
- Product name
- Azlocillin
- Packaging
- 250mg
- Price
- $100
- Updated
- 2021/12/16
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).
Azlocillin Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Azlocillin manufacturers
- Product
- Azlocillin 37091-66-0
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 50000KG/month
- Release date
- 2023-11-13
- Product
- Azlocillin 37091-66-0
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 500000kg
- Release date
- 2023-03-28
- 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