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Substance Name: Thioguanine [USAN:USP]
RN: 154-42-7
UNII: WIX31ZPX66
InChIKey: WYWHKKSPHMUBEB-UHFFFAOYSA-N

Note

  • An antineoplastic compound which also has antimetabolite action. The drug is used in the therapy of acute leukemia.

Molecular Formula

  • C5-H5-N5-S

Molecular Weight

  • 167.195
 

Classification Codes

  • Antimetabolites
  • Antimetabolites, Antineoplastic
  • Antineoplastic
  • Antineoplastic Agents
  • Drug / Therapeutic Agent
  • Mutation Data
  • Noxae
  • Reproductive Effect
  • Skin / Eye Irritant

Names and Synonyms

Name of Substance

  • Thioguanine
  • Thioguanine [USAN:USP]
  • Tioguanine [INN]

MeSH Heading

  • Thioguanine

Synonyms

  • 2-Amino 6MP
  • 2-Amino-1,7-dihydro-6H-purin-6-thion
  • 2-Amino-1,7-dihydro-6H-purin-6-thion [Czech]
  • 2-Amino-1,7-dihydro-6H-purine-6-thione
  • 2-Amino-6-mercaptopurine
  • 2-Amino-6-merkaptopurin
  • 2-Amino-6-merkaptopurin [Czech]
  • 2-Amino-6-MP
  • 2-Aminopurin-6-thiol
  • 2-Aminopurin-6-thiol [Czech]
  • 2-Aminopurine-6(1H)-thione
  • 2-Aminopurine-6-thiol
  • 2-Thioguanine
  • 6-Mercapto-2-aminopurine
  • 6-Mercaptoguanine
  • 6-TG
  • 6-Thioguanine
  • 6-Tioguanine
  • 6H-Purine-6-thione, 2-amino-1,7-dihydro-
  • AI3-26078
  • BW 5071
  • CCRIS 8997
  • EINECS 205-827-2
  • Guanine, thio-
  • Guanine, thio- (VAN)
  • HSDB 2504
  • Lanvis
  • NSC 752
  • NSC-752
  • Purine-6(1H)-thione, 2-amino-
  • Purine-6-thiol, 2-amino-
  • Tabloid
  • TG
  • THG
  • Thioguanine
  • Tioguanin
  • Tioguanina
  • Tioguanina [INN-Spanish]
  • Tioguanine
  • Tioguaninum
  • Tioguaninum [INN-Latin]
  • UNII-WIX31ZPX66
  • Wellcome U3B
  • X 27

Systematic Names

  • 6H-Purine-6-thione, 2-amino-1,7-dihydro-
  • Purine-6(1H)-thione, 2-amino-
  • Tioguanine

Superlist Name

  • Thioguanine

Registry Numbers

CAS Registry Number

  • 154-42-7

FDA UNII

  • WIX31ZPX66

Related Registry Numbers

  • 5580-03-0 (hemihydrate)
  • 76078-67-6 (mono-Na salt)

System Generated Number

  • 0000154427

Structure Descriptors

InChI

1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)

InChIKey

WYWHKKSPHMUBEB-UHFFFAOYSA-N

Smiles

n1c2c(nc[nH]2)c([nH]c1N)=S

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 23720ug/kg (23.72mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE
Cancer Vol. 9, Pg. 1092, 1956.
mouse LD10 unreported 1600mg/kg (1600mg/kg) BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE Progress in Medical Chemistry. Vol. 7, Pg. 69, 1970.
mouse LD50 intraperitoneal 54mg/kg (54mg/kg) BLOOD: HEMORRHAGE

GASTROINTESTINAL: OTHER CHANGES
Eksperimental'naya i Klinicheskaya Farmakoterapiya. Vol. 9, Pg. 56, 1980.
mouse LD50 oral 160mg/kg (160mg/kg)   Eksperimental'naya i Klinicheskaya Farmakoterapiya. Vol. 9, Pg. 56, 1980.
mouse LD50 oral 160mg/kg (160mg/kg) BLOOD: HEMORRHAGE

GASTROINTESTINAL: OTHER CHANGES
Eksperimental'naya i Klinicheskaya Farmakoterapiya. Vol. 9, Pg. 56, 1980.
rat LD50 intraperitoneal 300mg/kg (300mg/kg)   Journal of Reproduction and Fertility. Vol. 4, Pg. 291, 1962.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point >360 deg C   EXP
log P (octanol-water) -0.07 (none)   EXP
Water Solubility 3.63E+04 mg/L 25 EST
Vapor Pressure 1.01E-10 mm Hg 25 EST
Henry's Law Constant 4.64E-15 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.31E-10 cm3/molecule-sec 25 EST

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