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Aztreonam

pharmaceutical raw materials
Aztreonam structure

Aztreonam 

structure
  • CAS No:

    78110-38-0

  • Formula:

    C13H17N5O8S2

  • Chemical Name:

    Aztreonam

  • Synonyms:

    Propanoic acid,2-[[(Z)-[1-(2-amino-4-thiazolyl)-2-[[(2S,3S)-2-methyl-4-oxo-1-sulfo-3-azetidinyl]amino]-2-oxoethylidene]amino]oxy]-2-methyl-;Propanoic acid,2-[[[1-(2-amino-4-thiazolyl)-2-[(2-methyl-4-oxo-1-sulfo-3-azetidinyl)amino]-2-oxoethylidene]amino]oxy]-2-methyl-,[2S-[2α,3β(Z)]]-;2-[[(Z)-[1-(2-Amino-4-thiazolyl)-2-[[(2S,3S)-2-methyl-4-oxo-1-sulfo-3-azetidinyl]amino]-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid;SQ 26776;Azthreonam;Antibiotic Squibb 26,776;Squibb 26776;Aztreonam;Nebactam;Aztreon;Primbactam;Azonam

  • Categories:

    Active Pharmaceutical Ingredients  >  Antibiotics

Description

Aztreonam is a synthetic monocyclic beta-lactam antibiotic, which has a very high affinity for penicillin-binding protein 3 (PBP-3).Target: Penicillin-binding proteins 3 (PBP-3)Aztreonam is a synthetic monocyclic beta-lactam antibiotic (a monobactam), with the nucleus based on a simpler monobactam isolated from Chromobacterium violaceum. It was approved by the U.S. Food and Drug Administration in 1986. It is resistant to some beta-lactamases, but is inactivated by extended-spectrum beta-


Aztreonam is a parenterally administered, synthetic monobactam antibiotic that is specifically active against aerobic gram-negative bacilli is resistant to many beta-lactamases. Aztreonam therapy is often accompanied by mild, asymptomatic elevations in serum aminotransferase levels, but it has not been reported to cause clinically apparent liver injury.|A monocyclic beta-lactam antibiotic originally isolated from Chromobacterium violaceum. It is resistant to beta-lactamases and is used in gram-negative infections, especially of the meninges, bladder, and kidneys. It may cause a superinfection with gram-positive organisms.

Aztreonam Basic Attributes

435.43

435.43

278-839-9

DTXSID0022640

J01DF01|J - Antiinfectives for systemic use

29419000

Characteristics

238

0.81830

solid

1.83

227°C

1.74

soluble in DMF/water (1:1) at 50 mg/ml

Store at 0-5°C

Abdominal-rat LD50: 2549 mg/kg; Abdominal-mouse LD50: 2897 mg/kg

Flammable; burning produces toxic nitrogen oxides and sulfur oxide fumes

Safety Information

2811

2

20/21/22-36/37/38

22-24/25-36-26

UA2451400

Xn

Ventilated, low temperature and dry

|Danger|H317 (50%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P273, P280, P285, P302+P352, P304+P341, P321, P333+P313, P342+P311, P363, P391, and P501|Aggregated GHS information provided by 4 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

moderately toxic

Aztreonam has systemic toxicities that are similar to those of other beta lactam antibiotics, but it is unclear whether it can cause hepatic injury similar to that of the penicillins or cephalosporins. Asymptomatic serum aminotransferase elevations are common during high dose, intravenous aztreonam therapy (10% to 38%). The enzyme abnormalities are usually mild-to-moderate, asymptomatic, self-limited and not requiring drug discontinuation. Enzyme elevations occur slightly more commonly during aztreonam therapy than with other comparative antibiotics. Cases of frank liver injury and jaundice attributable to aztreonam must be extremely rare as no individual cases have been reported. For this reason, there is no data regarding the latency or pattern of the injury. Instances of marked aminotransferase elevations within 3 to 5 days of starting aztreonam have been reported, but these cases were without jaundice and resolved rapidly once the drug was stopped.

Drug Information

Cayston is indicated for the suppressive therapy of chronic pulmonary infections due to Pseudomonas aeruginosa in patients with cystic fibrosis (CF) aged 6 years and older.Consideration should be given to official guidance on the appropriate use of antibacterial agents.|Treatment of Gram-negative endobronchial infection in bronchiectasis patients|Treatment of infections caused by aerobic gram-negative bacteria|Treatment of Pseudomonas aeruginosa pulmonary infection / colonisation in patients with cystic fibrosis

Aztreonam is a parenterally administered, synthetic monobactam antibiotic that is specifically active against aerobic gram-negative bacilli is resistant to many beta-lactamases. Aztreonam therapy is often accompanied by mild, asymptomatic elevations in serum aminotransferase levels, but it has not been reported to cause clinically apparent liver injury.

Antiinfective Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

Az threonam

Aztreonam Use and Manufacturing

Methods of Manufacturing

Using threonine as the raw material, the acid chloride generated by chlorination is then subjected to aminolysis to form an amide, the α-amino group is protected with benzyl chloroformate, the β-hydroxyl group is esterified with methanesulfonyl chloride, and tetrabutylammonium sulfate is used Sulfonate the amide group, then cyclic synthesis of azetidine derivatives under the action of potassium bicarbonate, and then dehydrogenate to remove the protecting group to generate 3-amino-2-methyl-4-oxo-1-sulfonitrogen Heterocyclobutane. The azetidine derivative and the side chain thiazole derivative obtained above are dehydrated and amidated, and then hydrolyzed to remove the protective group to obtain aztreonam.

Uses

Aztreonam is a synthetic β-lactam antibiotic of the monobactam class. It is effective against Gram-negative bacteria but inactive against Gram-positive bacteria.Its mechanism of action involves the inhibition of mucopeptide synthesis in the bacterial cell wall, thereby blocking peptidoglycan crosslinking. Aztreonam is resistant to hydrolysis by some β-lactamases, but is inactivated by extended-spectrum β-lactamases.

Human drugs -> Cayston -> EMA Drug Category|Antibacterials for systemic use -> Human pharmacotherapeutic group|Human Drugs -> EU pediatric investigation plans|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:435.4
XLogP3:0.3
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:12
Rotatable Bond Count:7
Exact Mass:435.05185486
Monoisotopic Mass:435.05185486
Topological Polar Surface Area:238
Heavy Atom Count:28
Complexity:808
Undefined Atom Stereocenter Count:2
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

No specific description provided

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Registered Holders

  • GUANG'AN KINGDAY PHARMA AND CHEM CO LTD

    United States United States
    Active
  • APITORIA PHARMA PRIVATE LTD

    United States United States
    Active
  • TAPI NL B.V.

    France France
    Active

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