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6-Mercaptopurine

CAS No.50-44-2
Chemical Name:6-Mercaptopurine
CBNumber:CB1425059
Molecular Formula:C5H4N4S
Formula Weight:152.18
MOL File:50-44-2.mol

6-Mercaptopurine Property

Melting point 241-244°C
Boiling point 498.6±37.0 °C(Predicted)
Density 1.463 (estimate)
refractive index 1.5605 (estimate)
storage temp. Inert atmosphere,2-8°C
solubility DMSO : 35.71 mg/mL (234.66 mM; Need ultrasonic)
form solid
pka 7.77, 11.17(at 25℃)
color Light yellow to yellow
Water Solubility 124mg/L(25 ºC)
CAS DataBase Reference 50-44-2(CAS DataBase Reference)
EWG's Food Scores 1
NCI Dictionary of Cancer Terms Purinethol
FDA UNII PKK6MUZ20G
NCI Drug Dictionary Purinethol
IARC 3 (Vol. 26, Sup 7) 1987
EPA Substance Registry System Mercaptopurine (50-44-2)

Safety

RIDADR :3249
HazardClass :6.1(b)
PackingGroup :III
HS Code :2933599590
Hazardous Substances Data :50-44-2(Hazardous Substances Data)
Toxicity :LD50 oral in rat: 277mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H302-H315-H319-H335
Precautionary statements P261-P280-P301+P312-P302+P352-P305+P351+P338

6-Mercaptopurine Chemical Properties,Usage,Production

Chemical Properties Yellowish-Greenish Solid
Originator Purinethol,Sandoz,France,1950
Uses 6-Mercaptopurine (6-MP) is a antineoplastic, immonusupressant; inhibits purine nucleotide synthesis and metabolism. 6-MP have been used for several decades in the treatment of leukemia and certain other neoplastic diseases. 6-Mercaptopurine is used for maintenance therapy of acute lymphocytic and acute myelogenous leukemia.
Uses Has a cytotoxicity effect
Definition A sulfurcontaining purine base not found in animal nucleoproteins.
Manufacturing Process 7.5 g of 4-amino-6-chloro-5-nitropyrimidine was suspended in 200 ml of 1 N potassium hydrosulfide and heated on the steam bath for 2 hours while passing hydrogen sulfide through the reaction mixture. The reaction mixture was allowed to cool slowly, acidified with 10 N sulfuric acid and chilled. The precipitate consisted of 4,5-diamino-6-mercaptopyrimidine and sulfur. It was boiled with 300 ml of water, filtered hot and then chilled. The product precipitated as pale yellow needles (4.2 g); an additional 0.95 g was obtained by concentration of the mother liquors to 100 ml.
A mixture of 2 g of 4,5-diamino-6-mercaptopyrimidine and 10 ml of 98% formic acid was heated at 70°C for two hours and then evaporated to dryness on the steam bath to give as a residue, 7-amino-thiazolo (5,4-d) pyrimidine.
To 820 mg of 7-amino-thiazolo[5,4-d]pyrimidine was added 2.5 cc of 2 N sodium hydroxide. The water was removed under reduced pressure. The sodium salt was then heated at 240°C for one hour, during which time it melted, gave off water and resolidified. The sodium salt of 6-mercaptopurine was dissolved in 15 ml of water and acidified to pH 5 with acetic acid. Yellow crystals of 6-mercaptopurine hydrate precipitated, according to US Patent 2,933,498.
brand name Purinethol (Teva).
Therapeutic Function Cancer chemotherapy
Hazard Questionable carcinogen.
Safety Profile Poison by ingestion, intraperitoneal, subcutaneous, parenteral, and intravenous routes. Human systemic effects by ingestion: dermatitis. Experimental teratogenic and reproductive effects. Questionable human carcinogen producing Hodgkin's disease and leukemia. Human mutation data reported. When heated to decomposition it emits very toxic fumes of SOx and NOx. See also MERCAPTANS.
Veterinary Drugs and Treatments Veterinary uses of mercaptopurine include adjunctive therapy of lymphosarcoma, acute leukemias, and severe rheumatoid arthritis. It may have potential benefit in treating other autoimmune conditions (e.g., unresponsive ulcerative colitis) as well.