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Azathioprine

Azathioprine

Product ID A9803
Cas No. 446-86-6
Purity ≥98%
Product Unit SizeCostQuantityStock
1 g $112.60 In stock
5 g $422.50 In stock
10 g $704.10 In stock
Bulk Quote

Quicklinks

  • Description
  • Product Info
  • Shipping and Storage
  • Downloads
  • References
  • Description
  • Product Info
  • Shipping and Storage
  • Downloads
  • References
  • Custom Order

Description

Azathioprine is a purine analog that acts as a prodrug of mercaptopurine. Azathioprine exhibits anticancer chemotherapeutic, immunosuppressive, and antiviral activities. Azathioprine inhibits amidophosphoribosyl transferase, inhibiting the production of adenine and guanine purines and preventing DNA synthesis. Azathioprine is clinically used to suppress the immune response in organ transplant subjects and is currently in clinical trials exploring its chemotherapeutic benefit. Azathioprine suppresses experimental autoimmune myasthenia gravis in animal models. In vitro, azathioprine downregulates expression of ANF-related apoptosis-inducing ligand and, separately, inhibits Vav activity on Rac GTPases, preventing conjugation of antigen-presenting cells (APCs) and T cells. Azathioprine also exhibits antiviral activity against bovine viral diarrhea virus.

Product Info

Cas No.

446-86-6

Purity

≥98%

Formula

C9H7N7O2S

Formula Wt.

277.26

Chemical Name

6-((1-methyl-4-nitroimidazol-5-yl)thio)purine; 6-((1-Methyl-4-nitro-1H-imidazol-5-yl)thio)purine; Imuran; Imurek; Imurel; Methylnitroimidazolylmercaptopurine

IUPAC Name

6-(3-methyl-5-nitroimidazol-4-yl)sulfanyl-7H-purine

Synonym

AZA

Melting Point

243-244°C(dec)

Solubility

Insoluble in water, slightly soluble in ethanol, soluble in DMSO.

Appearance

Light-yellow crystalline powder

Shipping and Storage

Store Temp

Ambient

Ship Temp

Ambient

Downloads

MSDS

A9803 MSDS PDF

Info Sheet

A9803 Info Sheet PDF

References

Hernández-Breijo B, Monserrat J, Ramírez-Rubio S, et al. Preclinical evaluation of azathioprine plus buthionine sulfoximine in the treatment of human hepatocarcinoma and colon carcinoma. World J Gastroenterol. 2011 Sep 14;17(34):3899-911. PMID: 22025878.

Hoover S, Striker R. Thiopurines inhibit bovine viral diarrhea virus production in a thiopurine methyltransferase-dependent manner. J Gen Virol. 2008 Apr;89(Pt 4):1000-9. PMID: 18343842.

Poppe D, Tiede I, Fritz G, et al. Azathioprine suppresses ezrin-radixin-moesin-dependent T cell-APC conjugation through inhibition of Vav guanosine exchange activity on Rac proteins. J Immunol. 2006 Jan 1;176(1):640-51. PMID: 16365460.

Fuchs S, Bartfeld D, Eshhar Z, et al. Immune regulation of experimental myasthenia. J Neurol Neurosurg Psychiatry. 1980 Jul;43(7):634-43. PMID: 7400824.

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