Azathioprine
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MedKoo CAT#: 100073

CAS#: 446-86-6

Description: Azathioprine sodium is the sodium salt form of azathioprine, a pro-drug of purine analogue with immunosuppressive activity. Azathioprine is converted in vivo to its active metabolite 6-mercaptopurine (6-MP), which substitutes for the normal nucleoside and mistakenly gets incorporated into DNA sequences. This leads to inhibition of DNA, RNA, and protein synthesis. As a result, cell proliferation may be inhibited, particularly in lymphocytes and leukocytes.


Chemical Structure

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Azathioprine
CAS# 446-86-6

Theoretical Analysis

MedKoo Cat#: 100073
Name: Azathioprine
CAS#: 446-86-6
Chemical Formula: C9H7N7O2S
Exact Mass: 277.0382
Molecular Weight: 277.262
Elemental Analysis: C, 38.99; H, 2.54; N, 35.36; O, 11.54; S, 11.56

Price and Availability

Size Price Availability Quantity
1.0g USD 90.0 Same Day
2.0g USD 160.0 Same Day
5.0g USD 340.0 2 Weeks
10.0g USD 550.0 2 Weeks
25.0g USD 950.0 2 Weeks
50.0g USD 1650.0 2 Weeks
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Related CAS #: 55774-33-9 (sodium)  

Synonym: Azathioprine, US brand name: Imuran. Foreign brand name: Imurel. Abbreviations: AZA. AZTP.

IUPAC/Chemical Name: 6-((1-methyl-4-nitro-1H-imidazol-5-yl)thio)-7H-purine

InChi Key: LMEKQMALGUDUQG-UHFFFAOYSA-N

InChi Code: InChI=1S/C9H7N7O2S/c1-15-4-14-7(16(17)18)9(15)19-8-5-6(11-2-10-5)12-3-13-8/h2-4H,1H3,(H,10,11,12,13)

SMILES Code: O=[N+](C1=C(SC2=C3NC=NC3=NC=N2)N(C)C=N1)[O-]

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Certificate of Analysis:

Safety Data Sheet (SDS):

Preparing Stock Solutions

The following data is based on the product molecular weight 277.262 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Gordon M, Taylor K, Akobeng AK, Thomas AG. Azathioprine and 6-mercaptopurine for maintenance of surgically-induced remission in Crohn's disease. Cochrane Database Syst Rev. 2014 Aug 1;8:CD010233. doi: 10.1002/14651858.CD010233.pub2. Review. PubMed PMID: 25081347.

2: Henkenberens C, Franzke A, Raab P, Oschlies I, Klapper W, Christiansen H. Primary EBV-positive Hodgkin's lymphoma of the CNS under azathioprine treatment: case report and review of the literature. Strahlenther Onkol. 2014 Sep;190(9):847-52. doi: 10.1007/s00066-014-0670-9. Epub 2014 May 14. Review. PubMed PMID: 24823896.

3: Maneiro JR, Lopez-Canoa N, Salgado E, Gomez-Reino JJ. Maintenance therapy of lupus nephritis with mycophenolate or azathioprine: systematic review and meta-analysis. Rheumatology (Oxford). 2014 May;53(5):834-8. doi: 10.1093/rheumatology/ket429. Epub 2013 Dec 24. Review. PubMed PMID: 24369416.

4: Dooremont D, Decaestecker J, De Wulf D, Ghillebert G, Van Vlierberghe H, Van Dorpe J, Baert F. Azathioprine induced serious portal hypertension: a case series of three IBD patients and review of the literature. Acta Gastroenterol Belg. 2013 Sep;76(3):342-6. Review. PubMed PMID: 24261031.

5: Mahmood K, Khan AM, Ramanan AV, Martin K. Intentional overdose of azathioprine in a patient with systemic lupus erythematosus. Scott Med J. 2013 Nov;58(4):e3-4. doi: 10.1177/0036933013508040. Review. PubMed PMID: 24215056.

6: Kennedy NA, Rhatigan E, Arnott ID, Noble CL, Shand AG, Satsangi J, Lees CW. A trial of mercaptopurine is a safe strategy in patients with inflammatory bowel disease intolerant to azathioprine: an observational study, systematic review and meta-analysis. Aliment Pharmacol Ther. 2013 Nov;38(10):1255-66. doi: 10.1111/apt.12511. Epub 2013 Oct 5. Review. PubMed PMID: 24117596.

7: Yeter KC, Afkhami M, Brynes RK, Quismorio FP Jr. Aplastic anemia secondary to azathioprine in systemic lupus erythematosus: report of a case with normal thiopurine S-methyltransferase enzyme activity and review of the literature. Lupus. 2013 Dec;22(14):1526-8. doi: 10.1177/0961203313504636. Epub 2013 Sep 12. Review. PubMed PMID: 24029750.

8: Kim MJ, Choe YH. Monitoring and safety of azathioprine therapy in inflammatory bowel disease. Pediatr Gastroenterol Hepatol Nutr. 2013 Jun;16(2):65-70. doi: 10.5223/pghn.2013.16.2.65. Epub 2013 Jun 30. Review. PubMed PMID: 24010109; PubMed Central PMCID: PMC3760698.

9: Koduri PR, Vanajakshi S, Anuradha R. Azathioprine-associated pure red cell aplasia in renal transplant recipients: a report of two cases. Ann Hematol. 2014 Feb;93(2):329-30. doi: 10.1007/s00277-013-1779-0. Epub 2013 May 17. Review. PubMed PMID: 23680868.

10: Chande N, Tsoulis DJ, MacDonald JK. Azathioprine or 6-mercaptopurine for induction of remission in Crohn's disease. Cochrane Database Syst Rev. 2013 Apr 30;4:CD000545. doi: 10.1002/14651858.CD000545.pub4. Review. PubMed PMID: 23633304.



Additional Information

Azathioprine is used in organ transplantation and autoimmune disease. Some of the autoimmune diseases are rheumatoid arthritis, pemphigus, Inflammatory Bowel Disease (such as Crohn's disease and Ulcerative Colitis), multiple sclerosis, autoimmune hepatitis, atopic dermatitis, Myasthenia Gravis and restrictive lung disease. Azathioprine interferes with the synthesis of purines (adenine and guanine), which is required for DNA synthesis. Fast-growing cells, including T-cells and B-cells, are particularly affected by the inhibition of purine synthesis. It is a pro-drug, converted in the body to the active metabolites 6-mercaptopurine (6-MP) and 6-thioinosinic acid. Azathioprine is produced by a number of generic manufacturers and as branded names (Azasan by Salix in the U.S., Imuran by GlaxoSmithKline in Canada and the U.S., Australia and UK, Azamun in Finland and Imurel in Scandinavia and France).
 
According to http://en.wikipedia.org/wiki/Azathioprine, Azathioprine was first introduced into clinical practice by Sir Roy Calne, the British pioneer in transplantation. Following the work done by Sir Peter Medawar in discovering the immunological basis of rejection of transplanted tissues and organs, Calne introduced 6-mercaptopurine as an experimental immunosuppressant for kidney transplants cardiac transplantation. When azathioprine was discovered, he then introduced it as a less toxic replacement for 6-mercaptopurine. For many years, dual therapy with azathioprine and steroids was the standard anti-rejection regime, until cyclosporine was introduced into clinical practice (also by Calne) in 1978.
 
DRUG DESCRIPTION
AZASAN®, an immunosuppressive antimetabolite, is available in tablet form for oral administration. Each scored tablet contains 75 mg or 100 mg azathioprine and the inactive ingredients lactose monohydrate, pregelatinized starch, povidone, corn starch, magnesium stearate, and stearic acid. It is an imidazolyl derivative of 6-mercaptopurine and many of its biological effects are similar to those of the parent compound. Azathioprine is insoluble in water, but may be dissolved with addition of one molar equivalent of alkali. The sodium salt of azathioprine is sufficiently soluble to make a 10 mg/mL water solution which is stable for 24 hours at 59° to 77°F (15° to 25°C). Azathioprine is stable in solution at neutral or acid pH but hydrolysis to mercaptopurine occurs in excess sodium hydroxide (0.1N), especially on warming. Conversion to mercaptopurine also occurs in the presence of sulfhydryl compounds such as cysteine, glutathione, and hydrogen sulfide.