Azathioprine

Base Information

• Chemical Name: Azathioprine
• CAS No.: 446-86-6
• Molecular Formula: C9H7N7O2S
• Molecular Weight: 277.266
• Hs Code.: 29339900
• European Community (EC) Number: 207-175-4
• NSC Number: 755900,39084
• UNII: MRK240IY2L
• DSSTox Substance ID: DTXSID4020119
• Nikkaji Number: J2.047H
• Wikipedia: Azathioprine
• Wikidata: Q18939
• NCI Thesaurus Code: C290
• RXCUI: 1256
• Metabolomics Workbench ID: 43242
• ChEMBL ID: CHEMBL1542
• Mol file: 446-86-6.mol

Synonyms:Azathioprine;Azathioprine Sodium;Azathioprine Sodium Salt;Azathioprine Sulfate;Azothioprine;Immuran;Imuran;Imurel;Sodium, Azathioprine

Chemical Property of Azathioprine

Chemical Property:

• Appearance/Colour: Yellow solid
• Vapor Pressure: 7.98E-12mmHg at 25°C
• Melting Point: 243-244 °C
• Refractive Index: 1.923
• Boiling Point: 685.7 °C at 760 mmHg
• PKA: 8.2(at 25℃)
• Flash Point: 368.5 °C
• PSA: 143.40000
• Density: 1.9 g/cm³
• LogP: 1.66900
• Storage Temp.: Freezer
• Solubility.: Soluble in Dichloromethane and dimethyl sulfoxide.
• Water Solubility.: <0.1 g/100 mL at 23℃
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 277.03819367
• Heavy Atom Count: 19
• Complexity: 354

Purity/Quality:

98.5%, ^*data from raw suppliers

Azathioprine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, T, Xi
• Hazard Codes: Xi,T,Xn
• Statements: 45-22-36/37/38-20/21/22
• Safety Statements: 53-22-26-36/37-45-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Pharmaceuticals
• Drug Classes: Antineoplastic Agents
• Canonical SMILES: CN1C=NC(=C1SC2=NC=NC3=C2NC=N3)[N+](=O)[O-]
• Recent ClinicalTrials: HLADQA1*05 Genotype and the Efficacy of Treatment With Infliximab in Chinese Population Crohn's Disease
• Recent EU Clinical Trials: Immediate versus delayed treatment with azathioprine or rituximab in anti-myelin oligodendrocytes glycoprotein (anti-MOG) antibodies associated acute demyelinating syndromes in children: a randomized controlled clinical trial
• Recent NIPH Clinical Trials: A Randomized Multicenter Study for Isolated Skin Vasculitis
• Description: This immunosuppressive and antineoplastic drug is derived from 6-mercaptopurine. It caused occupational dermatitis in a pharmaceutical worker, reconditioner of old tablet packaging machines and in a production mechanic, working in packaging for a pharmaceutical company.
• Uses: Azathioprine is an immunosuppressive purine antimetabolite. The mechanism of action of azathioprine is as a nucleic acid synthesis inhibitor. It has shown promise in treatment of alopecia areata (autoimmune hair loss), with no difference in effectiveness between genders. immunosuppressant, antineoplastic, antirheumatic An immunosuppressive antimetabolite. Also active as disease modifying antirheumatic drug (DMARD). Azathioprine is a purine analog with immunosuppressive effects.
• Indications: Azathioprine (Imuran) is a cytotoxic agent that preferentially destroys any rapidly dividing cell. Since immunologically competent cells are generally rapidly dividing cells, azathioprine is very effective as an immunosuppressive drug. Unfortunately, any cell that is replicating is a target for this action. This lack of specificity leads to serious side effects. Azathioprine, in combination with corticosteroids, has historically been used more widely than any other drug in immunosuppressive therapy. It is classified as a purine antimetabolite and is a derivative of 6-mercaptopurine.
• Clinical Use: Azathioprine is a relatively powerful antiinflammatory agent. Although its beneficial effect in various conditions is principally attributable to its direct immunosuppressive action, the antiinflammatory properties of the drug play an important role in its overall therapeutic effectiveness. Azathioprine has been used widely in combination with corticosteroids to inhibit rejection of organ transplants, particularly kidney and liver allografts. However, it is usually reserved for patients who do not respond to cyclosporine plus corticosteroids alone. Azathioprine also has applications in certain disorders with autoimmune components, most commonly rheumatoid arthritis. It is as effective as cyclophosphamide in the treatment of Wegener’s granulomatosis. It has largely been replaced by cyclosporine in immunosuppressive therapy. Relative to other cytotoxic agents, the better oral absorption of azathioprine is the reason for its more widespread clinical use.
• Drug interactions: Potentially hazardous interactions with other drugs Allopurinol: enhances effect with increased toxicity. Reduce azathioprine dose by 50-75% if administered concomitantly - ideally avoid. Antibacterials: increased risk of haematological toxicity with co-trimoxazole. Anticoagulants: possibly reduced anticoagulant effect of coumarins. Antipsychotics: avoid with clozapine. Antivirals: myelosuppressive effects enhanced by ribavirin. Ciclosporin: decreased ciclosporin absorption and bioavailability. Cytotoxics may be additive or synergistic in producing toxicity, particularly on the bone marrow. Febuxostat: avoid concomitant use. Vaccines: risk of generalised infections with live vaccines - avoid.

Technology Process of Azathioprine

There total 4 articles about Azathioprine 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: 85.0%

5-chloro-1-methyl-4-nitroimidazole (4897-25-0) + 6-Mercaptopurine (157930-09-1,157930-10-4,157930-11-5,157930-13-7,157930-14-8) → Azathioprin (446-86-6)

Guidance literature:

6-Mercaptopurine; With (1,3,5-triaza-7-phosphaadamantan-1-ium-1-yl)butane-1-sulfonate; palladium diacetate; In N,N-dimethyl-formamide; for 0.0833333h; Schlenk technique; Inert atmosphere;

5-chloro-1-methyl-4-nitroimidazole; With potassium phosphate; In N,N-dimethyl-formamide; at 50 ℃; for 2h; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.joc.9b00840

Reference yield:

→ Azathioprin (446-86-6)

Guidance literature:

6-Mercaptopurin (III) * H2O, 5-Chlor-4-nitro-1-methylimidazol;

Reference yield:

9-acetyl-6-[(1-methyl-4-nitro-5-imidazolyl)thio]purine (304441-05-2) → azathioprine (446-86-6)

Guidance literature:

In methanol; for 0.166667h; Heating;

DOI:10.1007/BF02256869

upstream raw materials:

5-chloro-1-methyl-4-nitroimidazole

6-Mercaptopurine

9-acetyl-6-[(1-methyl-4-nitro-5-imidazolyl)thio]purine

Downstream raw materials:

9-carboxymethylhypoxanthine

9-Ethyl-9H-purin-6(1H)-thion

7-Methyl-6-thiopurin

6-mercaptopurine

Refernces

• 1、 -. "Concatamers for Immunemodulation". . . Retrieved 2012/04/23.