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446-86-6

Basic Information
CAS No.: 446-86-6
Name: Azathioprine
Article Data: 6
Molecular Structure:
Molecular Structure of 446-86-6 (Azathioprine)
Formula: C9H7N7O2S
Molecular Weight: 277.266
Synonyms: 1H-Purine,6-[(1-methyl-4-nitro-1H-imidazol-5-yl)thio]- (9CI);Purine,6-[(1-methyl-4-nitroimidazol-5-yl)thio]- (6CI,8CI);6-(1-Methyl-4-nitroimidazol-5-yl)thiopurine;6-(1-Methyl-4-nitromidazol-5-ylthio)purine;Azamune;Azanin;Azathioprin;Azoran;BW 57-322;Imuran;Imurek;Imurel;Muran;NSC 39084;
EINECS: 207-175-4
Density: 1.9 g/cm3
Melting Point: 243-244 °C
Boiling Point: 685.7 °C at 760 mmHg
Flash Point: 368.5 °C
Solubility: <0.1 g/100 mL at 23 °C in water
Appearance: Yellow solid
Hazard Symbols: HarmfulXn, ToxicT, IrritantXi
Risk Codes: 45-22-36/37/38-20/21/22
Safety: 53-22-26-36/37-45-36
PSA: 143.40000
LogP: 1.66900
Downstream Products
3324-79-6
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Chemistry

Product Name: Azathioprine (CAS NO.446-86-6)
Molecular Formula: C9H7N7SO2

Molecular Weight: 277.26
EINECS: 207-175-4
Melting point:  243-244°C
Storage temp.:  Freezer
Water Solubility:  <0.1 g/100 mL at 23 °C
Merck: 902
Index of Refraction: 1.923 
Molar Refractivity: 68.88 cm3 
Surface Tension: 98.3 dyne/cm 
Density: 1.9 g/cm3 
Flash Point: 368.5 °C 
Enthalpy of Vaporization: 96.93 kJ/mol 
Boiling Point: 685.7 °C at 760 mmHg 
Vapour Pressure: 7.1E-18 mmHg at 25°C
Structure Descriptors of Product Name: Azathioprine (CAS NO.446-86-6):
  IUPAC Name: 6-(3-methyl-5-nitroimidazol-4-yl)sulfanyl-7H-purine
  Canonical SMILES: CN1C=NC(=C1SC2=NC=NC3=C2NC=N3)[N+](=O)[O-]
  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-

Uses

Azathioprine (CAS NO.446-86-6) is an immunosuppressant which is commonly used in organ transplantation, autoimmune disease or Inflammatory Bowel Disease (IBD). It is also used in multiple sclerosis, autoimmune hepatitis and restrictive lung disease. It's also active as disease modifying antirheumatic drug (DMARD).

Toxicity Data With Reference

1.    

mma-sat 300 µmol/L

    EXPEAM    Experientia. 40 (1984),370.
2.    

cyt-hmn-unr 1074 mg/kg/4Y

    MUREAV    Mutation Research. 94 (1982),501.
3.    

orl-wmn TDLo:273 mg/kg/13 W-C:CAR,BLD

    BMJOAE    British Medical Journal. 4 (1972),235.
4.    

orl-wmn TD:3 g/kg/3.5Y-C:CAR,KID

    JAMAAP    JAMA, Journal of the American Medical Association. 237 (1977),152.
5.    

orl-wmn TD:5460 mg/kg/6Y-I:CAR,BLD

    AMSVAZ    Acta Medica Scandinavica. 207 (1980),315.
6.    

orl-man TD:728 mg/kg/43 W-C:CAR,BLD

    AJMSA9    American Journal of the Medical Sciences. 273 (1977),335.
7.    

orl-man TD:1565 mg/kg/4Y-C:CAR,BLD

    AJMEAZ    American Journal of Medicine. 57 (1974),885.
8.    

orl-man TD:3266 mg/kg/3Y-C:CAR,BLD

    AJMEAZ    American Journal of Medicine. 57 (1974),885.
9.    

orl-wmn TD:2 g/kg/3Y-C:CAR,BLD

    PGMJAO    Postgraduate Medical Journal. 53 (1977),173.
10.    

orl-man LDLo:395 mg/kg/56 W-I:SYS

    GASTAB    Gastroenterology. 90 (1986),446.
11.  

RTECS:  UO8925000

Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 1 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 (1987),p. 119.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 26 (1981),p. 47.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Limited Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 26 (1981),p. 47.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . NCI Carcinogenesis Studies (ipr); No Evidence: rat CANCAR    Cancer. 40 (1977),1935. ; Clear Evidence: mouse CANCAR    Cancer. 40 (1977),1935. . EPA Genetic Toxicology Program.

Safety Profile

Confirmed human carcinogen producing bladder tumors and leukemia. Poison by subcutaneous, intradermal, and intraperitoneal routes. Moderately toxic by ingestion. Human systemic effects: liver changes, hypermotility, diarrhea, nausea or vomiting, increased body temperature, BP lowering, decreased urine volume or anuria, normocytic anemia, bone marrow changes. An experimental teratogen. Other experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and SOx. An immunosuppressant.

Hazard Codes:  XiIrritant,TToxic,XnHarmful
Risk Statements:  45-22-36/37/38-20/21/22 
R45:May cause cancer. 
R22:Harmful if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements:  53-22-26-36/37-45-36 
S53:Avoid exposure - obtain special instructions before use. 
S22:Do not breathe dust. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37:Wear suitable protective clothing and gloves. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36:Wear suitable protective clothing.
Hazard Note:  Irritant

Specification

Azathioprine (CAS NO.446-86-6) is also named as 6-((1-Methyl-4-nitro-1h-imidazol-5-yl)thio)-1h-purin ; 6-((1-Methyl-4-nitroimidazol-5-yl)thio)-purin ; 6-(1'-Methyl-4'-nitro-5'-imidazolyl)-mercaptopurine ; 6-(1-Methyl-4-nitro-5-imidazolythio)-9H-pur-ine ; 6-(1-Methyl-4-nitroimidazol-5-ylthio)purin ; 6-(1-Methyl-p-nitro-5-imidazolyl)-thiopurine ; Azamun and so on.