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Aztreonam

Aztreonam Structure
CAS No.
78110-38-0
Chemical Name:
Aztreonam
Synonyms
AZACTAM;clobetasol propionate powder;monobactam;Aztreonam/arginine;[2S-[2A,3B(Z)]]-2-[[[1-(2-AMINO-4-THIAZOLYL)-2-[(2-METHYL-4-OXO-1-SULFO-3-AZETIDINYL)AMINO]-2-OXOETHYLIDENE]AMINO]OXY]-2-METHYLPROPANOIC ACID;Azonam;Aztreon;NSC1245;sq26,776;Nebactam
CBNumber:
CB0386184
Molecular Formula:
C13H17N5O8S2
Molecular Weight:
435.43
MOL File:
78110-38-0.mol
MSDS File:
SDS
Modify Date:
2024/6/13 17:03:25
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Aztreonam Properties

Melting point 227°C
Density 1.83
refractive index 1.6460 (estimate)
storage temp. room temp
solubility DMSO (Slightly), Water (Slightly, Heated, Sonicated)
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
SMILES C(O)(=O)C(O/N=C(/C1=CSC(N)=N1)\C(N[C@@H]1C(=O)N(S(O)(=O)=O)[C@H]1C)=O)(C)C
CAS DataBase Reference 78110-38-0(CAS DataBase Reference)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS08,GHS09
Signal word  Danger
Hazard statements  H400-H334
Precautionary statements  P273-P391-P501-P261-P285-P304+P341-P342+P311-P501
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
Toxicity TDLo ivn-rat: 1100 mg/kg (7-17D preg):TER NKRZAZ33(Suppl 1),203,85

Aztreonam price More Price(5)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) PZ0038 Aztreonam ≥98% (HPLC) 78110-38-0 5MG ₹10619.33 2022-06-14 Buy
Sigma-Aldrich(India) PZ0038 Aztreonam ≥98% (HPLC) 78110-38-0 25MG ₹42877.83 2022-06-14 Buy
Sigma-Aldrich(India) PHR1785 Aztreonam Pharmaceutical Secondary Standard; Certified Reference Material 78110-38-0 500MG ₹24312.95 2022-06-14 Buy
Sigma-Aldrich(India) A6848 Aztreonam analytical standard 78110-38-0 50MG ₹21888.15 2022-06-14 Buy
SRL 13741 Aztreonam (AZN), 96% 78110-38-0 100mg ₹7120 2022-05-26 Buy
Product number Packaging Price Buy
PZ0038 5MG ₹10619.33 Buy
PZ0038 25MG ₹42877.83 Buy
PHR1785 500MG ₹24312.95 Buy
A6848 50MG ₹21888.15 Buy
13741 100mg ₹7120 Buy

Aztreonam Chemical Properties,Uses,Production

Description

Aztreonam is the first member of the monobactam class of antibiotics to be introduced into the world market. It possesses high β-lactamase stability and moderately good activity against gram negative aerobes such as E. coli, S. marcescens, -9 Proteus Providencia, Salmonella, g. influenzae, E. gonorrhea, and &. pneumonia. While somewhat less potent against Pseudomonas aeruginosa, it is nonetheless one of the better β-lactams against this species. It has poor activity against gram positive organisms.

Chemical Properties

White Crystalline Powder

History

Aztreonam was synthesized by the Squibb Institute for Medical Research in 1981 starting with l-threonine. The synthesis was based on findings about bacterial β-lactam compounds of a monocyclic nature . The β-lactam compounds, called monobactams, were isolated from Chromobacterium violaceum, Agrobacterium radiobacter, etc. Such monocyclic βlactams of bacterial origin had previously been found independently in 1981 by Takeda Chemicals Industries in the culture broths of Pseudomonas acidophila and P. mesoacidophila and named sulfazecin and isosulfazecin, respectively. Aztreonam was selected from among hundreds of derivatives as a candidate for clinical trials because of its unique antibacterial spectrum and strong activity. This antibiotic shows excellent activity against a variety of gram-negative aerobic bacteria but no activity against gram-positive bacteria or anaerobes. Its efficacy and safety are now being clinically evaluated.

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.

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.

Safety Profile

Moderately toxic by severalroutes. An experimental teratogen. Other experimentalreproductive effects. When heated to decomposition itemits toxic fumes of NOx and SOx.

Aztreonam Preparation Products And Raw materials

Raw materials

Potassium bicarbonate Azetidine L-Threonine Methanesulfonyl chloride Thiazole
Benzyl chloroformate D-Glucose monohydrate CARBOHYDRATES (2S-trans)-3-Amino-2-methyl-4-oxoazetidine-1-sulphonic acid 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-, 1-(1,1-dimethylethyl) ester
2-Mercaptobenzothiazolyl-(Z)-(2-aminothiazol-4-yl)-2-(tert-butoxycarbonyl) isopropoxyiminoacetate Water
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Preparation Products

Aztreonam Suppliers

Global( 526)Suppliers
Supplier Tel Country ProdList Advantage Inquiry
DAVY CHEM LABS +91-9603460845 +91-9493444489 Hyderabad, India 109 58 Inquiry
PROTECH TELELINKS +91-8571891912 +91-9855060837 Himachal Pradesh, India 62 58 Inquiry
Unitrade Agencies 08048372548Ext 632 Mumbai, India 197 58 Inquiry
Globofarm International Private Limited 91-22-49716506 Maharashtra, India 188 58 Inquiry
Hemarsh Technologies 08068441092Ext 237 Vadodara, India 23 58 Inquiry
Anand Agencies 91-20-24454597 Maharashtra, India 2337 58 Inquiry
Dharmanandan Export Pvt., Ltd. 91-79-48402200 Gujarat, India 161 58 Inquiry
Maas Pharma Chemicals +91-9958666224 Delhi, India 1607 58 Inquiry
Nakshatra Chemicals 09819631316 Mumbai, India 162 58 Inquiry
Shivam Pharma Chemicals 91-22-26403900 Maharashtra, India 656 58 Inquiry
Supplier Advantage
DAVY CHEM LABS 58
PROTECH TELELINKS 58
Unitrade Agencies 58
Globofarm International Private Limited 58
Hemarsh Technologies 58
Anand Agencies 58
Dharmanandan Export Pvt., Ltd. 58
Maas Pharma Chemicals 58
Nakshatra Chemicals 58
Shivam Pharma Chemicals 58

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Aztreonam Spectrum

Aztreonam(78110-38-0)1HNMR

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Aztreonam L-Arginine (E)-2-(((1-(2-aminothiazol-4-yl)-2-((2-methyl-4-oxo-1-sulfoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid Aztreonam(β-form) Aztreonam94-103% (HPLC) Aztreonam and Sodium Carbonate (2s-(2-alpha,3-beta(z)))-dinyl)amino)-2-oxoethylidene)amino)oxy)-2-methyl antibioticsquibb26,776 propanoicacid,2-(((1-(2-amino-4-thiazolyl)-2-((2-methyl-4-oxo-1-sulfo-3-azeti sq26,776 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)]]- Squibb 26776 Aztreonam, Azactam, Ayactam [2S-[2a,3(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 [2S-[2S-[2α，3β(Z)]]-2-[[[1-(2-Amino-4-thiazolyl)-2-[(2-methyl-4-oxo-1-sulfo-3-azetidinyl)amino]-2-oxoethylidene]amino]oxy]-2-methylpmpanoic acid 2-[(2-Amino-Thiazol-4-Yl)-(2-Methyl-4-Oxo-1-Sulfo-Azetidin-3 Aztreonam,[2S-[2α,3β(Z)]]-2-[[[1-(2-Amino-4-thiazolyl)-2-[(2-methyl-4-oxo-1-sulfo-3-azetidinyl)amino]-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid Aztreonam (200 mg) AztreonaM(AzactaM) (2S,3S)-3-[(2E)-2-(2-azaniuMyl-1,3-thiazol-4-yl)-2-[(1-carboxy-1-Methylethoxy)iMino]acetaMido]-2-Methyl-4-oxoazetidine-1-sulfonate AztreonaM(AzactaM, Cayston) [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 2-[[(Z)-[1-(2-Amino-4-thiazolyl)-2-[[(2S,3S)-2-methyl-4-oxo-1-sulfo-3-azetidinyl]amino]-2-oxoethylidene]amino]oxy]-2-methylpropionic Acid 2-((Z)-1-(2-aMinothiazol-4-yl)-2-((2S,3S)-2-Methyl-4-oxo-1-sulfoazetidin-3-ylaMino)-2-oxoethylideneaMinooxy)-2-Methylpropanoic acid 2-[(2-AMINO-THIAZOL-4-YL)-(2-METHYL-4-OXO-1-SULFO-AZETIDIN-3-YLCARBAMOYL)-METHYLENEAMINOOXY]-2-METHYL-PROPIONIC 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-METHYLPROPANOIC ACID (2S-(2ALPHA,3BETA(Z)))-2-(((1-(2-AMINO-4-THIAZOLYL)-2-((2-METHYL-4-OXO-1-SULFO-3-AZETIDINYL)AMINO)-2-OXOETHYLIDENE)AMINO)OXY)-2-METHYL-PROPANOIC ACID AZTHREONAM AZTREONAM AZTREONAM, E-ISOMER USP STANDARD AZTREONAM, USP STANDARD Azteronam [2S-[2a,3b(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 Aztreon Nebactam Squibb 2677 [2s-[2α,3β(z)]]-2-[[[1-(2-amino-4-thiazolyl)-2-[(2-methyl-4-oxo-1-sulfo-3-azetidinyl)amino]-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid (Z)-2-[[[(2-AMINO-4-AZTREONAM {2S-[2a,3b(Z)]}-2-{[((2-amino-4-thiazolyl)-2-((2-methyl-4-oxo-1-sulfo-3-azetidinyl)amino)-2-oxoethyl Azonam Primbactam Aztreonam for injection 2S-[2a,3b(Z)]]-2-[[[1-(2-Amino-4-thiazolyl)-2-[(2-methyl-4-oxo-1-sulfo-3-azetidinyl)amino]-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid Aztreonam (Anhydrous) Aztreonam/arginine mixing powder Aztreonam Sterile powder a-Form aztreonam Aztrenom Aztreonam,97% (Z)-Anhydrous Aztreonam 2-[(Z)-[1-(2-amino-1,3-thiazol-4-yl)-2-[[(2S)-2-methyl-4-oxo-1-sulfoazetidin-3-yl]amino]-2-oxoethylidene]amino]oxy-2-methylpropanoic acid Aztreonam USP/EP/BP 2-({[(2-amino-1,3-thiazol-4-yl)({[(2S,3S)-2-methyl-4 -oxo-1-sulfoazetidin-3-yl]carbamoyl})methylidene] amino}oxy)-2-methylpropanoic acid treonam L-Arginine Aztreonam (SQ-26776) AztreonamQ: What is Aztreonam Q: What is the CAS Number of Aztreonam Q: What is the storage condition of Aztreonam Q: What are the applications of Aztreonam α-Aztreonam Sterile Grade Aztreonam API