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Substance Name: Azathioprine [USAN:USP:INN:BAN:JAN]
RN: 446-86-6
UNII: MRK240IY2L
InChIKey: LMEKQMALGUDUQG-UHFFFAOYSA-N

Note

  • An immunosuppressive agent used in combination with cyclophosphamide and hydroxychloroquine in the treatment of rheumatoid arthritis. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance has been listed as a known carcinogen. (Merck Index, 11th ed)

Molecular Formula

  • C9-H7-N7-O2-S

Molecular Weight

  • 277.2673
 

Classification Codes

Classification Codes

  • Antimetabolites
  • Antimetabolites, Antineoplastic
  • Antineoplastic Agents
  • Antirheumatic Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Immunologic Factors
  • Immunosuppressant
  • Immunosuppressive Agents
  • Mutation Data
  • Noxae
  • Reproductive Effect
  • Tumor Data

Superlist Classification Codes

  • Known to be a Carcinogen
  • Overall Carcinogenic Evaluation: Group 1

Names and Synonyms

Name of Substance

  • Azathioprine
  • Azathioprine [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Azathioprine

Synonyms

  • 1H-Purine, 6-((1-methyl-4-nitro-1H-imidazol-5-yl)thio)-
  • 6-((1-Methyl-4-nitro-1H-imidazol-5-yl)thio)-1H-purine
  • 6-((1-Methyl-4-nitroimidazol-5-yl)thio)purine
  • 6-(1'-Methyl-4'-nitro-5'-imidazolyl)-mercaptopurine
  • 6-(1-Methyl-4-nitroimidazol-5-ylthio)purin
  • 6-(1-Methyl-4-nitroimidazol-5-ylthio)purin [Czech]
  • 6-(1-Methyl-p-nitro-5-imidazolyl)-thiopurine
  • 6-1'-Methyl,4'-nitro,5'-imidazolyl mercaptopurine
  • AI3-50290
  • Azamun
  • Azamun [Czech]
  • Azanin
  • Azasan
  • Azathioprin
  • Azathioprine
  • Azathioprinum
  • Azathioprinum [INN-Latin]
  • Azatioprin
  • Azatioprina
  • Azatioprina [INN-Spanish]
  • Azothioprine
  • BW 57-322
  • BW-57-322
  • CCRIS 62
  • Ccucol
  • EINECS 207-175-4
  • HSDB 7084
  • Imuran
  • Imurek
  • Imurel
  • Methylnitroimidazolylmercaptopurine
  • Muran
  • NCI-C03474
  • NSC 39084
  • NSC-39084
  • Purine, 6-(1-methyl-4-nitro-5-imidazolylthio)-
  • Rorasul
  • UNII-MRK240IY2L

Systematic Names

  • 1H-Purine, 6-((1-methyl-4-nitro-1H-imidazol-5-yl)thio)-
  • Azathioprine
  • Purine, 6-((1-methyl-4-nitroimidazol-5-yl)thio)-

Superlist Names

  • 1H-Purine, 6-((1-methyl-4-nitro-1H-imidazol-5-yl)thio)-
  • Azathioprine

Registry Numbers

CAS Registry Number

  • 446-86-6

FDA UNII

  • MRK240IY2L

Related Registry Number

  • 55774-33-9 (hydrochloride salt)

System Generated Number

  • 0000446866

Structure Descriptors

InChI

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)

InChIKey

LMEKQMALGUDUQG-UHFFFAOYSA-N

Smiles

Cn1cnc(c1Sc2ncnc3nc[nH]c23)[N+](=O)[O-]

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo unreported 2500ug/kg/D-I (2.5mg/kg) BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE

BLOOD: NORMOCYTIC ANEMIA		 American Journal of Diseases of Children. Vol. 134, Pg. 377, 1980.
man LDLo oral 395mg/kg/56W- (395mg/kg) LIVER: OTHER CHANGES Gastroenterology. Vol. 90, Pg. 446, 1986.
man TDLo oral 7500ug/kg/1W- (7.5mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED		 Arthritis and Rheumatism. Vol. 24, Pg. 1453, 1981.
man TDLo oral 15mg/kg/7D-I (15mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

MUSCULOSKELETAL: JOINTS		 American Journal of Kidney Diseases. Vol. 23, Pg. 874, 1994.
man TDLo oral 50mg/kg/3W-I (50mg/kg) BLOOD: LEUKOPENIA Lancet. Vol. 342, Pg. 1245, 1993.
mouse LD50 intraduodenal 2437mg/kg (2437mg/kg)   Russian Pharmacology and Toxicology Vol. 31, Pg. 223, 1968.
mouse LD50 intraperitoneal 273mg/kg (273mg/kg)   Russian Pharmacology and Toxicology Vol. 34, Pg. 284, 1971.
mouse LD50 oral 2500mg/kg (2500mg/kg)   Drugs in Japan Vol. -, Pg. 8, 1995.
mouse LD50 subcutaneous 350mg/kg (350mg/kg) IMMUNOLOGICAL INCLUDING ALLERGIC: DECREASE IN HUMORAL IMMUNE RESPONSE Journal of Medicinal Chemistry. Vol. 18, Pg. 320, 1975.
rabbit LDLo intraduodenal 100mg/kg (100mg/kg)   Russian Pharmacology and Toxicology Vol. 31, Pg. 223, 1968.
rat LD50 intraduodenal 630mg/kg (630mg/kg)   Russian Pharmacology and Toxicology Vol. 31, Pg. 223, 1968.
rat LD50 intraperitoneal 300mg/kg (300mg/kg)   Journal of Reproduction and Fertility. Vol. 4, Pg. 297, 1962.
rat LD50 oral 400mg/kg (400mg/kg)   Drugs in Japan Vol. -, Pg. 8, 1995.
rat LD50 subcutaneous > 1gm/kg (1000mg/kg)   Drugs in Japan Vol. 6, Pg. 3, 1982.
women TDLo oral 500ug/kg (0.5mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"		 Journal of Rheumatology. Vol. 13, Pg. 1117, 1986.
women TDLo oral 42mg/kg/3W-I (42mg/kg) BLOOD: THROMBOCYTOPENIA

BLOOD: CHANGES IN CELL COUNT (UNSPECIFIED)

BLOOD: LEUKOPENIA		 Annals of the Rheumatic Diseases. Vol. 47, Pg. 503, 1988.
women TDLo oral 56mg/kg/4W-I (56mg/kg) BEHAVIORAL: FOOD INTAKE (ANIMAL)

GASTROINTESTINAL: NAUSEA OR VOMITING		 Postgraduate Medical Journal. Vol. 56, Pg. 274, 1980.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 243.5 deg C   EXP
log P (octanol-water) 0.1 (none)   EXP
Water Solubility 272 mg/L 25 EST
Vapor Pressure 2.41E-12 mm Hg 25 EST
Henry's Law Constant 2.64E-15 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.03E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.