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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
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
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
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Regulatory Agencies (Superlist Locators)
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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-NSmiles
Cn1cnc(c1Sc2ncnc3nc[nH]c23)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.