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Record Information
Version1.0
Creation Date2014-09-11 05:15:51 UTC
Update Date2016-11-09 01:09:12 UTC
Accession NumberCHEM003727
Identification
Common NameTioguanine
ClassSmall Molecule
DescriptionAn antineoplastic compound which also has antimetabolite action. The drug is used in the therapy of acute leukemia.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Antimetabolite, Antineoplastic
  • Drug
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
2-Amino 6MPChEBI
2-Amino-1,7-dihydro-6H-purine-6-thioneChEBI
2-Amino-1,9-dihydropurine-6-thioneChEBI
2-Amino-6-mercaptopurineChEBI
2-Amino-6-merkaptopurinChEBI
2-Amino-6-purinethiolChEBI
2-Aminopurin-6-thiolChEBI
2-Aminopurine-6(1H)-thioneChEBI
2-Aminopurine-6-thiolChEBI
6-Mercapto-2-aminopurineChEBI
6-MercaptoguanineChEBI
6-TGChEBI
6-ThioguanineChEBI
TGChEBI
ThGChEBI
TioguaninChEBI
TioguaninaChEBI
TioguaninumChEBI
LanvisKegg
6 ThioguanineHMDB
Glaxo wellcome brand OF thioguanineHMDB
GlaxoSmithKline brand OF thioguanineHMDB
ThioguaninGSKHMDB
Thioguanine hemihydrateHMDB
Tioguanina wellcomeHMDB
Wellcome brand OF thioguanineHMDB
2 Amino 6 purinethiolHMDB
GlaxoSmithKline brand OF tioguanineHMDB
Thioguanine tabloidHMDB
Glaxo wellcome brand OF tioguanineHMDB
TabloidHMDB
Thioguanine anhydrousHMDB
Anhydrous, thioguanineHMDB
Thioguanin GSKHMDB
Thioguanin-GSKHMDB
Thioguanine monosodium saltHMDB
Tioguanine glaxosmithkline brandHMDB
ThioguanineChEBI
Chemical FormulaC5H5N5S
Average Molecular Mass167.192 g/mol
Monoisotopic Mass167.027 g/mol
CAS Registry Number154-42-7
IUPAC Name2-amino-6,7-dihydro-3H-purine-6-thione
Traditional Namethioguanine
SMILESNC1=NC(=S)C2=C(N1)N=CN2
InChI IdentifierInChI=1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
InChI KeyWYWHKKSPHMUBEB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as purinethiones. These are purines in which the purine moiety bears a thioketone.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentPurinethiones
Alternative Parents
Substituents
  • Purinethione
  • Aminopyrimidine
  • Pyrimidinethione
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Azacycle
  • Organopnictogen compound
  • Primary amine
  • Organosulfur compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Kidney
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Thioguanine PathwayNot AvailableNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point>360°C
Boiling PointNot Available
Solubility36.3 mg/mL
Predicted Properties
PropertyValueSource
Water Solubility0.83 g/LALOGPS
logP-0.36ALOGPS
logP-0.35ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)10.53ChemAxon
pKa (Strongest Basic)3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area79.09 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity46.89 m³·mol⁻¹ChemAxon
Polarizability15.65 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-014i-4900000000-d9b2da47228aaa85556aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-c1b1c192793adf5933a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-379c32e68ff490bc5f5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-9700000000-757c534cc2a9d57cf055View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-f711c8fa62d6eed053b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0159-2900000000-afd9900ecc0fd78faf88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9300000000-2ef0a5c247f78f7847a3View in MoNA
Toxicity Profile
Route of ExposureAbsorption of an oral dose is incomplete and variable, averaging approximately 30% of the administered dose (range: 14% to 46%)
Mechanism of ToxicityThioguanine competes with hypoxanthine and guanine for the enzyme hypoxanthine-guanine phosphoribosyltransferase (HGPRTase) and is itself converted to 6-thioguanilyic acid (TGMP), which reaches high intracellular concentrations at therapeutic doses. TGMP interferes with the synthesis of guanine nucleotides by its inhibition of purine biosynthesis by pseudofeedback inhibition of glutamine-5-phosphoribosylpyrophosphate amidotransferase, the first enzyme unique to the de novo pathway of purine ribonucleotide synthesis. TGMP also inhibits the conversion of inosinic acid (IMP) to xanthylic acid (XMP) by competition for the enzyme IMP dehydrogenase. Thioguanine nucleotides are incorporated into both the DNA and the RNA by phosphodiester linkages, and some studies have shown that incorporation of such false bases contributes to the cytotoxicity of thioguanine. Its tumor inhibitory properties may be due to one or more of its effects on feedback inhibition of de novo purine synthesis; inhibition of purine nucleotide interconversions; or incorporation into the DNA and RNA. The overall result of its action is a sequential blockade of the utilization and synthesis of the purine nucleotides.
MetabolismHepatic. First converted to 6-thioguanilyic acid (TGMP). TGMP is further converted to the di- and tri-phosphates, thioguanosine diphosphate (TGDP) and thioguanosine triphosphate (TGTP) by the same enzymes that metabolize guanine nucleotides. Half Life: When the compound was given in singles doses of 65 to 300 mg/m^2, the median plasma half-disappearance time was 80 minutes (range 25-240 minutes)
Toxicity ValuesOral, mouse: LD50 = 160 mg/kg.
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor remission induction and remission consolidation treatment of acute nonlymphocytic leukemias.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms of overdose include nausea, vomiting, malaise, hypotension, and diaphoresis.
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00352
HMDB IDHMDB0014496
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00018807
BiGG IDNot Available
BioCyc IDCPD-5721
METLIN IDNot Available
PDB IDDX4
Wikipedia LinkThioguanine
Chemspider ID2005804
ChEBI ID9555
PubChem Compound ID2723601
Kegg Compound IDC07648
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. FDA label
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21803983
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22178190
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22245861
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22261533
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22280519
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22563779
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22646133
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22822082
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22983983
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=23259153
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=23261807
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23377192
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=23377281
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=23393198
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=28166217