Azathioprine

CAS 446-86-6C9H7N7O2SMW 277.27

Azathioprine (CAS 446-86-6) — formula C9H7N7O2S, molecular weight 277.27.

Product Overview

CAS Number	446-86-6
Molecular Formula	C9H7N7O2S
Molecular Weight	277.27
Melting Point	243.5
LogP	0.1
Applications	Uses: Used as an immunosuppressant and anticancer drug, [Kanerva, p. 1753], MEDICATION, Use (kg, approx.) in Germany (2009): >2500, exact) in Germany (2009): 3323, Use (kg) in USA (2002): 715, Consumption (g per capita, approx.) in Germany (2009): 0.0305, exact) in Germany (2009): 0.0406, Consumption (g per capita) in the USA (2002): 0.00253, Excretion rate: 0.17, Calculated removal (%): 22, Azathioprine is used alone or in combination with other immunosuppressive therapy to prevent rejection following organ transplantation, and to treat an array of autoimmune diseases, including rheumatoid arthritis, pemphigus, systemic lupus erythematosus, Behcet's disease and other forms of vasculitis, autoimmune hepatitis, atopic dermatitis, myasthenia gravis, neuromyelitis optica (Devic's disease), restrictive lung disease, and others. It is also an important therapy and steroid-sparing agent for inflammatory bowel disease (such as Crohn's disease and ulcerative colitis) and for multiple sclerosis. In the United States it is currently approved by the Food and Drug Administration (FDA) for use in kidney transplantation from human donors, and for rheumatoid arthritis. Other uses are off-label. (Wikipedia), Use Classification: Pharmaceuticals, Methods of Manufacturing: Prepn: G.H. Hitchings, G.B. Elion, US 3056785 (1962 to Burroughs Wellcome)., Formulations, Preparations: Imuran (Azathioprine sodium)

Applications

Documented applications: Uses: Used as an immunosuppressant and anticancer drug, [Kanerva, p. 1753], MEDICATION, Use (kg, approx.) in Germany (2009): >2500, exact) in Germany (2009): 3323, Use (kg) in USA (2002): 715, Consumption (g per capita, approx.) in Germany (2009): 0.0305, exact) in Germany (2009): 0.0406, Consumption (g per capita) in the USA (2002): 0.00253, Excretion rate: 0.17, Calculated removal (%): 22, Azathioprine is used alone or in combination with other immunosuppressive therapy to prevent rejection following organ transplantation, and to treat an array of autoimmune diseases, including rheumatoid arthritis, pemphigus, systemic lupus erythematosus, Behcet's disease and other forms of vasculitis, autoimmune hepatitis, atopic dermatitis, myasthenia gravis, neuromyelitis optica (Devic's disease), restrictive lung disease, and others. It is also an important therapy and steroid-sparing agent for inflammatory bowel disease (such as Crohn's disease and ulcerative colitis) and for multiple sclerosis. In the United States it is currently approved by the Food and Drug Administration (FDA) for use in kidney transplantation from human donors, and for rheumatoid arthritis. Other uses are off-label. (Wikipedia), Use Classification: Pharmaceuticals, Methods of Manufacturing: Prepn: G.H. Hitchings, G.B. Elion, US 3056785 (1962 to Burroughs Wellcome)., Formulations, Preparations: Imuran (Azathioprine sodium).

Technical Profile

What this product is

Azathioprine is a chemical compound with CAS registry number 446-86-6 and molecular formula C9H7N7O2S (molecular weight 277.27).

Identification

CAS number: 446-86-6

Its molecular formula C9H7N7O2S comprises 9 C, 7 H, 7 N, 2 O, 1 S atoms.

Also known as: Azathioprine · azathioprine usp

Frequently Asked Questions

What is the CAS number of Azathioprine?

The CAS registry number of Azathioprine is 446-86-6.

What is the molecular formula and molecular weight of Azathioprine?

Molecular formula C9H7N7O2S, molecular weight 277.27.

What other names is Azathioprine known by?

It is also registered under: Azathioprine, azathioprine usp.

What are the documented applications of Azathioprine?

Recorded applications: Uses: Used as an immunosuppressant and anticancer drug, [Kanerva, p. 1753], MEDICATION, Use (kg, approx.) in Germany (2009): >2500, exact) in Germany (2009): 3323, Use (kg) in USA (2002): 715, Consumption (g per capita, approx.) in Germany (2009): 0.0305, exact) in Germany (2009): 0.0406, Consumption (g per capita) in the USA (2002): 0.00253, Excretion rate: 0.17, Calculated removal (%): 22, Azathioprine is used alone or in combination with other immunosuppressive therapy to prevent rejection following organ transplantation, and to treat an array of autoimmune diseases, including rheumatoid arthritis, pemphigus, systemic lupus erythematosus, Behcet's disease and other forms of vasculitis, autoimmune hepatitis, atopic dermatitis, myasthenia gravis, neuromyelitis optica (Devic's disease), restrictive lung disease, and others. It is also an important therapy and steroid-sparing agent for inflammatory bowel disease (such as Crohn's disease and ulcerative colitis) and for multiple sclerosis. In the United States it is currently approved by the Food and Drug Administration (FDA) for use in kidney transplantation from human donors, and for rheumatoid arthritis. Other uses are off-label. (Wikipedia), Use Classification: Pharmaceuticals, Methods of Manufacturing: Prepn: G.H. Hitchings, G.B. Elion, US 3056785 (1962 to Burroughs Wellcome)., Formulations, Preparations: Imuran (Azathioprine sodium).

PubChem Public Data

Independent reference data for Azathioprine (CAS 446-86-6), compiled from public chemistry databases.

Registry identifiers across databases

CAS Registry Number	446-86-6
PubChem CID	2265
Molecular formula	C9H7N7O2S
IUPAC name	6-(3-methyl-5-nitroimidazol-4-yl)sulfanyl-7H-purine
UNII (FDA)	MRK240IY2L

Computed descriptors

Molecular Weight	277.27
XLogP3	0.1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	2
Exact Mass	277.03819367
Monoisotopic Mass	277.03819367
Topological Polar Surface Area	143
Heavy Atom Count	19

Physicochemical values on record

Melting Point	243.5
Melting Point	dec 243-244 °C
Melting Point	243.5 °C
Solubility	1.07e+00 g/L
LogP	0.1
LogP	log Kow = 0.10
LogP	0.7
LogP	0.89
Dissociation Constants	7.87 (at 25 °C)
Dissociation Constants	pKa = 8.2

Documented uses on record

Synonyms and trade names

azathioprine; 446-86-6; Azothioprine; Azanin; Azathioprin; Azatioprin; Azamun; Azasan; Ccucol; Imurek; Muran; NSC-39084; Azathioprinum; Azatioprina; BW 57-322; BW-57-322

GHS hazard classification

Reported hazard statements	H302 (100%), H315 (88.8%), H319 (88.8%), H335 (87.9%), H340 (62.6%), H350 (100%), H360 (58.9%), H317

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

H315 (88.8%): Causes skin irritation [Warning Skin corrosion/irritation]

What the public record says

Azathioprine · CAS 446-86-6 · C9H7N7O2S. UNII MRK240IY2L. Melting Point: 243.5; Melting Point: dec 243-244 °C; Melting Point: 243.5 °C.

Physical description and handling notes

Source: PubChem / Wikidata; the batch COA governs where values differ.