thioguanine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
2632 154-42-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • 6-Thioguanine
  • thioguanine
  • tioguanine
An antineoplastic compound which also has antimetabolite action. The drug is used in the therapy of acute leukemia.
  • Molecular weight: 167.19
  • Formula: C5H5N5S
  • CLOGP: -1.70
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 3
  • TPSA: 79.09
  • ALOGS: -2.31
  • ROTB: 0

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.20 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.50 % Benet LZ, Broccatelli F, Oprea TI
BA (Bioavailability) 30 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 2.89 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 15.40 mL/min/kg Lombardo F, Berellini G, Obach RS
t_half (Half-life) 24.35 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Jan. 18, 1966 FDA ASPEN GLOBAL INC

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Febrile neutropenia 410.13 89.75 83 303 10799 2346900
Haematotoxicity 377.37 89.75 56 330 1111 2356588
Venoocclusive liver disease 233.27 89.75 34 352 574 2357125
Febrile bone marrow aplasia 133.46 89.75 22 364 835 2356864
Perineal necrosis 102.72 89.75 11 375 5 2357694
Venoocclusive disease 102.54 89.75 15 371 253 2357446
Perineal infection 95.45 89.75 11 375 20 2357679

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Febrile neutropenia 830.03 124.07 175 439 10925 1735242
Haematotoxicity 580.01 124.07 90 524 868 1745299
Venoocclusive liver disease 285.54 124.07 49 565 884 1745283
Febrile bone marrow aplasia 167.88 124.07 31 583 847 1745320

Pharmacologic Action:

SourceCodeDescription
ATC L01BB03 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
ANTIMETABOLITES
Purine analogues
CHEBI has role CHEBI:35610 antineoplastic agent
MeSH PA D000963 Antimetabolites
MeSH PA D000964 Antimetabolites, Antineoplastic
MeSH PA D000970 Antineoplastic Agents
MeSH PA D009676 Noxae

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Acute myeloid leukemia, disease indication 91861009
Acute lymphoid leukemia off-label use 91857003 DOID:9952
Hyperbilirubinemia contraindication 14783006 DOID:2741
Obstruction of bile duct contraindication 30144000
Hyperuricemia contraindication 35885006 DOID:1920
Portal vein obstruction contraindication 57348003
Acute infectious disease contraindication 63171007
Leukopenia contraindication 84828003 DOID:615
Bleeding contraindication 131148009
Liver function tests abnormal contraindication 166603001
Disease of liver contraindication 235856003 DOID:409
Drug-induced hepatitis contraindication 235876009
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Bone marrow depression contraindication 307762000
Breastfeeding (mother) contraindication 413712001
Chemotherapy-Induced Hyperuricemia contraindication
Thiopurine S-Methyltransferase Deficiency contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.96 acidic
pKa2 10.93 acidic
pKa3 1.72 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Inosine-5'-monophosphate dehydrogenase 2 Enzyme INHIBITOR WOMBAT-PK CHEMBL
Inosine-5'-monophosphate dehydrogenase 1 Enzyme INHIBITOR WOMBAT-PK CHEMBL
Xanthine dehydrogenase/oxidase Enzyme IC50 4.03 CHEMBL
Prostaglandin G/H synthase 1 Enzyme IC50 6.22 DRUG MATRIX
Adenosine receptor A3 GPCR Ki 4.91 DRUG MATRIX
Mitogen-activated protein kinase 3 Kinase IC50 5.26 DRUG MATRIX
Hypoxanthine-guanine phosphoribosyltransferase Enzyme WOMBAT-PK
Multidrug resistance-associated protein 4 Transporter WOMBAT-PK
Multidrug resistance-associated protein 5 Transporter WOMBAT-PK
Arachidonate 15-lipoxygenase Enzyme IC50 4.79 DRUG MATRIX

External reference:

IDSource
4018777 VUID
N0000147080 NUI
C0039902 UMLSCUI
D06109 KEGG_DRUG
72623000 SNOMEDCT_US
387407006 SNOMEDCT_US
4018777 VANDF
2109 MMSL
10485 RXNORM
5569 MMSL
d01345 MMSL
002652 NDDF
2723601 PUBCHEM_CID
CHEBI:9555 CHEBI
CHEMBL727 ChEMBL_ID
DB00352 DRUGBANK_ID
FTK8U1GZNX UNII
5580-03-0 SECONDARY_CAS_RN
D013866 MESH_DESCRIPTOR_UI
6845 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
TABLOID HUMAN PRESCRIPTION DRUG LABEL 1 76388-880 TABLET 40 mg ORAL NDA 13 sections