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Substance Name: Mercaptopurine [USAN:USP:INN]
RN: 50-44-2
UNII: PKK6MUZ20G
InChIKey: GLVAUDGFNGKCSF-UHFFFAOYSA-N

Note

  • An antimetabolite antineoplastic agent with immunosuppressant properties. It interferes with nucleic acid synthesis by inhibiting purine metabolism and is used, usually in combination with other drugs, in the treatment of or in remission maintenance programs for leukemia.

Molecular Formula

  • C5-H4-N4-S

Molecular Weight

  • 152.181
 

Classification Codes

Classification Codes

  • Antimetabolites
  • Antimetabolites, Antineoplastic
  • Antineoplastic Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Immunologic Factors
  • Immunosuppressive Agents
  • Mutation Data
  • Noxae
  • Nucleic Acid Synthesis Inhibitors
  • Reproductive Effect
  • Tumor Data

Superlist Classification Code

  • Overall Carcinogenic Evaluation: Group 3

Names and Synonyms

Name of Substance

  • 6-Mercaptopurine
  • Mercaptopurine
  • Mercaptopurine [USAN:USP:INN]

MeSH Heading

  • 6-Mercaptopurine

Synonyms

  • 1,7-Dihydro-6H-purine-6-thione
  • 1H-Purine, 6-mercapto-
  • 3H-Purine-6-thiol
  • 6 MP
  • 6-Mercaptopurin
  • 6-Mercaptopurine
  • 6-Merkaptopurin
  • 6-Merkaptopurin [Czech]
  • 6-MP
  • 6-Purinethiol
  • 6-Thiohypoxanthine
  • 6-Thiopurine
  • 6-Thioxopurine
  • 6H-Purine-6-thione, 1,7-dihydro-
  • 7-Mercapto-1,3,4,6-tetrazaindene
  • 9H-Purine-6(1H)-thione
  • BW 57323H
  • CCRIS 2761
  • EINECS 200-037-4
  • HSDB 3235
  • Hypoxanthine, thio-
  • Ismipur
  • Leukerin
  • Leupurin
  • Mercaleukin
  • Mercaptopurin
  • Mercaptopurin [German]
  • Mercaptopurina
  • Mercaptopurina [INN-Spanish]
  • Mercaptopurine
  • Mercaptopurine (anhydrous)
  • Mercaptopurine (VAN)
  • Mercaptopurinum
  • Mercaptopurinum [INN-Latin]
  • Mercapurin
  • Merkaptopuryna
  • Merkaptopuryna [Polish]
  • Mern
  • NCI-C04886
  • NSC 755
  • NSC-755
  • Puri-Nethol
  • Purine, 6-mercapto-
  • Purine-6-thione
  • Purinethol
  • Purixan
  • U-4748
  • UNII-PKK6MUZ20G
  • Xaluprine

Systematic Names

  • 6-Mercaptopurine
  • 6H-Purine-6-thione, 1,7-dihydro-
  • Mercaptopurine
  • Purine-6(1H)-thione
  • Purine-6-thiol

Superlist Name

  • 6-Mercaptopurine

Registry Numbers

CAS Registry Number

  • 50-44-2

FDA UNII

  • PKK6MUZ20G

Other Registry Numbers

  • 39454-94-9
  • 5759-99-9
  • 5818-33-7
  • 5818-60-0

Related Registry Number

  • 6112-76-1 (monohydrate)

System Generated Number

  • 0000050442

Structure Descriptors

InChI

1S/C5H4N4S/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)

InChIKey

GLVAUDGFNGKCSF-UHFFFAOYSA-N

Smiles

c12c(nc[nH]c1=S)nc[nH]2

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
hamster LD50 intraperitoneal 364mg/kg (364mg/kg)   Archives of Toxicology. Vol. 32, Pg. 1, 1974.
man TDLo oral 40mg/kg/1W-I (40mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Archives of Dermatology. Vol. 122, Pg. 1413, 1986.
mouse LD50 intraperitoneal 80mg/kg (80mg/kg)   Cancer Research. Vol. 42, Pg. 122, 1982.
mouse LD50 intravenous 80mg/kg (80mg/kg)   Cancer Research. Vol. 42, Pg. 122, 1982.
mouse LD50 oral 260mg/kg (260mg/kg)   Cesko-Slovenska Farmacie. Vol. 14, Pg. 389, 1965.
mouse LD50 subcutaneous 100mg/kg (100mg/kg) IMMUNOLOGICAL INCLUDING ALLERGIC: DECREASE IN HUMORAL IMMUNE RESPONSE Journal of Medicinal Chemistry. Vol. 18, Pg. 320, 1975.
rat LD50 intraperitoneal 159mg/kg (159mg/kg)   Acta Poloniae Pharmaceutica. For English translation, see APPFAR. Vol. 41, Pg. 571, 1984.
rat LD50 intravenous 250mg/kg (250mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 1467, 1970.
rat LD50 oral 277mg/kg (277mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 15, Pg. 1037, 1973.
rat LD50 parenteral 250mg/kg (250mg/kg)   Recent Results in Cancer Research. Vol. 52, Pg. 76, 1975.
rat LD50 subcutaneous 90mg/kg (90mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 15, Pg. 1037, 1973.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 313 dec deg C   EXP
log P (octanol-water) 0.01 (none)   EXP
Water Solubility 6.85E+04 mg/L   EXP
Vapor Pressure 1.43E-06 mm Hg 25 EST
Henry's Law Constant 7.49E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.00E-10 cm3/molecule-sec 25 EST

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