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Aztreonam

Outline indications Precautions Chemical properties Uses production method Category Toxicity grading Acute toxicity Flammability and hazard characteristics Storage Characteristics Extinguishing agent
Aztreonam
Aztreonam
CAS No.
78110-38-0
Chemical Name:
Aztreonam
Synonyms
Azonam;AZACTAM;Aztreon;sq26,776;Nebactam;AZTREONAM;Azteronam;monobactam;78110-38-0;AZTHREONAM
CBNumber:
CB0386184
Molecular Formula:
C13H17N5O8S2
Formula Weight:
435.43
MOL File:
78110-38-0.mol

Aztreonam Properties

Melting point:
227°C
Density 
1.83
refractive index 
1.6460 (estimate)
storage temp. 
Store at 0-5°C
form 
solid
pka
pKa -0.7(H2O t=RT Iunde?ned) (Uncertain);2.75(H3O t=RT Iunde?ned) (Uncertain);3.91(H4O t=RT Iunde?ned) (Uncertain)
color 
white to beige
Water Solubility 
Soluble in DMF/water (1:1) at 50 mg/ml
Merck 
14,925
InChIKey
WZPBZJONDBGPKJ-VEHQQRBSSA-N
CAS DataBase Reference
78110-38-0(CAS DataBase Reference)

SAFETY

Hazard Codes  Xn
Risk Statements  20/21/22-36/37/38
Safety Statements  22-24/25-36-26
WGK Germany  2
RTECS  UA2451400
HS Code  29419000

Aztreonam price More Price(11)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich A6848 Aztreonam analytical standard 78110-38-0 50mg $131 2018-11-20 Buy
Sigma-Aldrich 1046205 Aztreonam United States Pharmacopeia (USP) Reference Standard 78110-38-0 200mg $352.8 2018-11-20 Buy
Alfa Aesar J62887 Aztreonam 78110-38-0 1g $92.6 2018-11-13 Buy
Alfa Aesar J62887 Aztreonam 78110-38-0 5g $290 2018-11-13 Buy
Cayman Chemical 19784 Aztreonam ≥95% 78110-38-0 50mg $25 2018-11-13 Buy

Aztreonam Chemical Properties,Uses,Production

Outline

Aztreonam is a novel kind ofβ-lactam antibiotics belonging to monobactams. In 1978 it was first discovered from the culture brot of New Jersey soil purple bacterium Chromobacterium violaceum, it has been obtained with synthesis method.
Mechanism
Aztreonam belongs to bacteria fungicides. It can quickly go through the outer membrane of Gram-negative aerobic bacteria wall, while it has a high affinity with the penicillin-binding protein 3 (PBP-3) . By acting on the PBP-3 and inhibiting synthesis of bacterial cell wall , it leads to cell lysis and death.
Aztreonam has a narrow antimicrobial spectrum, it only has antibacterial effect on aerobic gram-negative bacilli , such as E. coli, Klebsiella, Serratia spp, Proteus mirabilis, indole-positive Proteus, Citrobacter, influenza addicted blood coli, Pseudomonas aeruginosa and other Pseudomonas, some Enterobacter, Neisseria gonorrhoeae. The product is highly stable to β-lactamase produced by many bacteria .it is inactive in Gram-positive bacteria and anaerobic bacteria . Aztreonam compared with ceftazidime, gentamicin, it effect on aerogenes, and Enterobacter cloacae is higher than ceftazidime, but lower than gentamicin; the effect on Pseudomonas aeruginosa is lower than ceftazidime , and similar to gentamicin .

indications

It is mainly used for the treatment of infections caused by susceptible strains which include the respiratory system, urinary, reproductive system infections (including acute gonorrhea), intra-abdominal infections, skin and soft tissue infections, before surgery preventing infections, other serious infections, such as sepsis.

Precautions

1.contraindication: patients allergic to the products or having a history of allergy on lidocaine and other local anesthetics or having anaphylactic shock on other β-lactam drugs are banned.
2. caution following:
It does not exist cross-allergic reactions between aztreonam and penicillins, but people having allergy body and allergic to penicillins, cephalosporins should take caution.
renal dysfunction patients should take caution.
aztreonam does not have toxicity for liver , but the patients having impaired liver function should observe the dynamic changes. It has been reported that in patients with alcoholic cirrhosis , the total clearance of the products can be reduced by 20-25%.
pregnant and lactating women, infants and young children should use with caution.
3. The impact of drugs on clinical outcomes:
direct anti-human globulin test (Coombs test) can be positive.
there may be a temporary increase of serum alanine aminotransferase (ALT), aspartate aminotransferase (AST), lactate dehydrogenase (LDH) and serum creatinine values after medication among a few patients, part thromboplastin time (PTT) and prothrombin time (PT) may be extended.
adverse reactions are skin symptoms such as skin rashes, purpura, pruritus (approximately 2%); gastrointestinal symptoms such as diarrhea, nausea, vomiting, taste changes, jaundice, and drug-induced hepatitis (approximately 2%); local irritation such as thrombophlebitis. Injection site swelling (approximately 2.4%); there are other neurological symptoms, vaginitis, oral lesions, fatigue, dizziness, and bleeding.
4. Long-term medication should pay attention to monitoring of liver, kidney and hematopoietic system.
The above information is edited by the chemicalbook of Tian Ye.

Chemical properties

white or colorless powder crystals, melting at 227 ℃ (decomposition). It is dissolved in dimethyl formamide, slightly soluble in methanol, very slightly soluble in ethanol, insoluble in toluene, chloroform or ethyl acetate.
Aztreonam disodium: C13 H15N5Na2O8 . Acute toxicity LD50 (mg/kg): 3300 intravenous injection in mice, 6600 in rats intraperitoneally.

Uses

It is Mainly used for the infections caused by sensitive gram-negative bacteria , including pneumonia, pleurisy, abdominal infections, biliary tract infections, bone and joint infections, skin and soft tissue inflammation, especially for urinary tract infections, but also for sepsis. Because this product has good resistance to enzyme performance, therefore, when a microorganism is not sensitive to penicillins, cephalosporins, aminoglycosides and other drugs ,the product should often be effective.

production method

Threonine for raw materials,chloride resulting from the chlorination forms an amide through ammonolysis, protect α-amino with benzyl chloroformate,esterifyβ-hydroxy with methanesulfonyl chloride , the amide group is sulfonated with sulfuric acid tetrabutylammonium , then it is cyclized to generate azetidine derivative in the potassium bicarbonate, then after hydrogen and Deprotection, produce 3-amino-2-methyl-4-oxo-1-sulfo-N oxetane.
Afetr dehydration amidation of side chains Azetidine derivative and thiazole derivatives obtained in the above, hydrolyse to deprotect and to obtain aztreonam.

Category

Toxic substances

Toxicity grading

Middle toxic

Acute toxicity

Intraperitoneal-rat LD50: 2549 mg/kg; intraperitoneal-Mouse LD50: 2897 mg/kg.

Flammability and hazard characteristics

Combustible; combustion produces toxic fumes of nitrogen oxides and sulfur oxides.

Storage Characteristics

Ventilated, low-temperature ,dry storeroom.

Extinguishing agent

Dry powder, foam, sand, carbon dioxide, water spray.

Chemical Properties

White Crystalline Powder

Uses

The first totally synthetic monocyclic β-lactam antibiotic.

Uses

antiserotonin

Uses

The first totally synthetic monocyclic ?lactam antibiotic

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.

brand name

Azactam (Bristol-Myers Squibb).

Antimicrobial activity

Concentrations (mg/L) inhibiting 50% of other organisms are: Aeromonas spp., 0.1;Acinetobacter spp., 16; Mor. catarrhalis, 0.1; Burkholderia cepacia, 2; and Yersinia spp., 0.1. Synergy has been shown with gentamicin, tobramycin and amikacin against 52–89% of strains of Ps. aeruginosa and gentamicin-resistant Gram-negative bacteria.

Pharmacokinetics

Cmax 1 g intravenous: 90 mg/L end infusion
1 g intramuscular: 46 mg/L after 1 h
Plasma half-life: 1.7 h
Volume of distribution: 0.18 L/kg
Plasma protein binding: 56%
Absorption and distribution
Oral bioavailability is less than 1%. Peak concentrations above the median MIC for most Gram-negative pathogens are achieved in most tissues and body fluids after 1 g intramuscular or intravenous doses.
Metabolism and excretion
It is not extensively metabolized, the most prominent product, resulting from opening the β-lactam ring, being scarcely detectable in the serum and accounting for about 6% of the dose in the urine and 3% in the feces.
It is predominantly eliminated in the urine, where 58–72% appears within 8 h. Less than 12% is eliminated unchanged in the feces, suggesting low biliary excretion.

Clinical Use

Urinary tract infections, including pyelonephritis and cystitis
Lower respiratory tract infections, including pneumonia and bronchitis
caused by Gram-negative bacilli
Septicemia
Skin and skin structure infections, including postoperative wounds, ulcers
and burns
Intra-abdominal infections, including peritonitis
Gynecological infections, including endometritis and pelvic cellulitis

Side effects

Local reactions occasionally occur at the injection site. Systemic reactions include diarrhea, nausea and/or vomiting and rash (1–1.3%). Neutropenia was seen in 11.3% of the pediatric patients younger than 2 years. Pseudomembranous colitis has been reported.
There are no reactions in patients with immunoglobulin E (IgE) antibodies to benzylpenicillin or penicillin moieties. It is rarely cross-reactive with other β-lactam antibiotics and is weakly immunogenic.

Aztreonam Preparation Products And Raw materials

Raw materials

Preparation Products


Aztreonam Suppliers

Global( 296)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Capot Chemical Co.,Ltd.
+86 (0)571-855 867 18
+86 (0)571-858 647 95 sales@capotchem.com China 19953 60
Shenzhen Sendi Biotechnology Co.Ltd.
0755-23311925 18102838259
0755-23311925 Abel@chembj.com CHINA 3217 55
Henan DaKen Chemical CO.,LTD.
+86-371-55531817
info@dakenchem.com CHINA 22049 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 20786 55
Mainchem Co., Ltd.
+86-0592-6210733
+86-0592-6210733 sales@mainchem.com CHINA 32651 55
Nanjing ChemLin Chemical Industry Co., Ltd.
025-83697070;product@chemlin.com.cn
product@chemlin.com.cn CHINA 3015 60
Hubei Jusheng Technology Co.,Ltd.
86-155-27864001
peter@hubeijusheng.com CHINA 18004 58
Chemwill Asia Co.,Ltd.
86-21-51086038
86-21-51861608 chemwill_asia@126.com;sales@chemwill.com;chemwill@hotmail.com;chemwill@gmail.com CHINA 10967 58
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 19990 58
Shanghai Zheyan Biotech Co., Ltd.
18017610038
zheyansh@163.com CHINA 3624 58

View Lastest Price from Aztreonam manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2018-08-20 Aztreonam
78110-38-0
US $1.00 / KG 1G 98% 100KG career henan chemical co
2018-08-01 Aztreonam
78110-38-0
US $100.00 / KG 1KG 99% Customized career henan chemical co

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