Azlocillin
- CAS NO.:37091-66-0
- Empirical Formula: C20H23N5O6S
- Molecular Weight: 461.49
- MDL number: MFCD00864967
- EINECS: 2533482
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-04 20:04:50
What is Azlocillin?
Absorption
Not significantly absorbed from the gastrointestinal tract.
Originator
Securopen,Bayer,W. Germany,1977
The Uses of Azlocillin
Azlocillin is an antibiotic.
The Uses of Azlocillin
Antibacterial.
Indications
For the treatment of infections caused by Pseudomonas aeruginosa, Escherichia coli, and Haemophilus influenzae.
Background
Azlocillin is a semisynthetic ampicillin-derived acylureido penicillin.
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.
Pharmacokinetics
Similar to mezlocillin and piperacillin, azlocillin is an acylampicillin that exhibits an extended-spectrum of activity and in vitro potency that is greater than that of the carboxy penicillins. Azlocillin is shown to be effective against a broad spectrum of bacteria, including Pseudomonas aeruginosa and enterococci.
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).
Metabolism
Eliminated predominantly by renal mechanisms, but also undergoes biotransformation within body tissues and intraintestinal degradation by bowel bacteria, with high concentrations found in bile.
Properties of Azlocillin
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) |
form | Solid |
pka | pKa 2.8 (Uncertain) |
color | White to Off-White |
Safety information for Azlocillin
Computed Descriptors for Azlocillin
New Products
4-AMINO-TETRAHYDRO-PYRAN-4-CARBOXYLIC ACID HCL 4-(Dimethylamino)tetrahydro-2H-pyran-4-carbonitrile 4-Aminotetrahydropyran-4-carbonitrile Hydrochloride (R)-3-Aminobutanenitrile Hydrochloride 3-((Dimethylamino)methyl)-5-methylhexan-2-one oxalate 1,4-Dioxa-8-azaspiro[4.5]decane 5-Bromo-2-nitropyridine Nimesulide BP Aceclofenac IP/BP/EP Diclofenac Sodium IP/BP/EP/USP Mefenamic Acid IP/BP/EP/USP Ornidazole IP Diclofenac Potassium THOMAIND PAPER PH 2.0 TO 4.5 1 BOX BUFFER CAPSULE PH 9.2 - 10 CAP SODIUM CHLORIDE 0.1N CVS ALLOXAN MONOHYDRATE 98% PLATINUM 0.5% ON 3 MM ALUMINA PELLETS (TYPE 73) LITHIUM AAS SOLUTION 2-Bromo-1-(bromomethyl)-3-chloro-5-nitrobenzene 2-Bromo-3-nitroaniline N-(3-Hydroxypropyl)-N-methylacetamide 3-Bromo-6-chloropyridazine 4-ethyl-3-nitrobenzoic acidRelated products of tetrahydrofuran
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