Aztreonam E-Isomer

Base Information

• Chemical Name: Aztreonam E-Isomer
• CAS No.: 99341-02-3
• Molecular Formula: C₁₃H₁₇N₅O₈S₂
• Molecular Weight: 435.439
• European Community (EC) Number: 278-839-9
• NSC Number: 758913
• UNII: 5Q55M3D9UA
• DSSTox Substance ID: DTXSID20244045
• Nikkaji Number: J20.598B,J306.677K
• Wikipedia: Aztreonam
• Wikidata: Q418546
• NCI Thesaurus Code: C28845
• RXCUI: 1272
• ChEMBL ID: CHEMBL410081
• Mol file: 99341-02-3.mol

Synonyms:Az threonam;Az-threonam;Azactam;Azthreonam;Aztreonam;SQ 26,776;SQ-26,776;SQ26,776;Urobactam

Chemical Property of Aztreonam E-Isomer

Chemical Property:

• PSA: 238.20000
• Density: 1.83±0.1 g/cm3 (20 °C, 760 mmHg)
• LogP: 0.81830
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 7
• Exact Mass: 435.05185486
• Heavy Atom Count: 28
• Complexity: 808

Purity/Quality:

NLT 98% ^*data from raw suppliers

(E)-Aztreonam ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiinfective Agents
• Canonical SMILES: CC1C(C(=O)N1S(=O)(=O)O)NC(=O)C(=NOC(C)(C)C(=O)O)C2=CSC(=N2)N
• Isomeric SMILES: C[C@H]1[C@@H](C(=O)N1S(=O)(=O)O)NC(=O)/C(=N/OC(C)(C)C(=O)O)/C2=CSC(=N2)N
• Recent ClinicalTrials: Ceftobiprole in the Treatment of Patients With Acute Bacterial Skin and Skin Structure Infections
• Recent EU Clinical Trials: A Phase 3, Multi-Center, Randomized, Single-Blind Study to Assess the Efficacy and Safety of Cefepime/Nacubactam and Aztreonam/Nacubactam Versus Best Available Therapy in Adults With Complicated Urinary Tract Infection, Acute Uncomplicated Pyelonephritis, Hospital-Acquired Bacterial Pneumonia, Ventilator-Associated Bacterial Pneumonia, and Complicated Intra-Abdominal Infection due to Carbapenem-Resistant Enterobacterales
• Uses: (E)-Aztreonam is the (E)-isomer of Aztreonam (A965200), an synthetic monocyclic β-lactam antibiotic.

Technology Process of Aztreonam E-Isomer

There total 36 articles about Aztreonam E-Isomer which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.9%

(3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1) + (Z)-2-<<<1-(2-amino-4-thiazolyl)-2-<(2-benzothiazolyl)thio>-2-oxoethylidene>amino>oxy>-2-methyl propanoic acid 1,1-dimethylethyl ester (89604-92-2,158183-05-2) → azthreonam (78110-38-0,80951-91-3,149496-40-2,99341-02-3,85506-30-5)

Guidance literature:

(3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid; (Z)-2-<<<1-(2-amino-4-thiazolyl)-2-<(2-benzothiazolyl)thio>-2-oxoethylidene>amino>oxy>-2-methyl propanoic acid 1,1-dimethylethyl ester; With pyridine; In acetonitrile; at -5 ℃; for 4h;

With nitric acid; at 35 ℃; for 2h; pH=1; Solvent; Reagent/catalyst; Temperature;

Reference yield: 81.0%

(Z)-2-[[[1-(2-amino-4-thiazolyl)-2-(3-oxido-1H-benzotriazol-1-yl)-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid methanesulfonate (1:1) salt (139714-28-6) + (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1) → azthreonam (78110-38-0,80951-91-3,149496-40-2,99341-02-3,85506-30-5)

Guidance literature:

(Z)-2-[[[1-(2-amino-4-thiazolyl)-2-(3-oxido-1H-benzotriazol-1-yl)-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid methanesulfonate (1:1) salt; (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid; With triethylamine; In ethanol; water; at -6 - -3 ℃; for 3h;

With hydrogenchloride; In ethanol; water; at -3 - 0 ℃;

DOI:10.1021/op025572d

Reference yield: 72.0%

[3S-[3α(Z),4β]]-3-[[(2-amino-4-thiazolyl)[(1-t-butoxycarbonyl-1-methylethoxy)imino]acetyl]amino]-4-methyl-2-oxo-1-azetidinesulfonic acid (330944-50-8) → azthreonam (78110-38-0,80951-91-3,149496-40-2,99341-02-3,85506-30-5)

Guidance literature:

With hydrogenchloride; water; at 0 - 65 ℃; for 4.75h;

upstream raw materials:

3-<<(2-amino-4-thiazolyl)-<<1-(diphenylmethoxycarbonyl)-1-methyl ethoxy>-imino>-acetyl>-amino>-4-methyl-2-oxoazetidi-ne-1-sulfonic acid

[3S-[3α(Z),4β]]-3-[[(2-amino-4-thiazolyl)[(1-t-butoxycarbonyl-1-methylethoxy)imino]acetyl]amino]-4-methyl-2-oxo-1-azetidinesulfonic acid

aztreonam

water

Refernces

• 1、 Ding, Pingyu,Duncton, Matthew A. J.,Fan, Dazhong,Gordon, Eric M.,Grygorash, Ruslan,Li, Xianfeng,Low, Eddy,Ni, Zhi-Jie,Qi, Longwu,Sun, Jiawei,Wang, Brian J.,Yu, Guijun. "Toward Orally Absorbed Prodrugs of the Antibiotic Aztreonam. Design of Novel Prodrugs of Sulfate Containing Drugs. Part 2". . p. 162 - 165. Retrieved 2020/01/31.
• 2、 -. "AN IMPROVED PROCESS FOR THE PREPARATION OF MONOBACTAM ANTIBIOTIC". Page/Page column 8-9. . Retrieved 2008/06/13.