thioguanine 🐶 Veterinary Use | 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 286.31 47.05 94 820 97573 50506637
Haematotoxicity 238.61 47.05 49 865 7846 50596364
Venoocclusive disease 70.33 47.05 14 900 1882 50602328
Staphylococcal sepsis 56.81 47.05 15 899 7021 50597189
Toxic neuropathy 55.61 47.05 9 905 373 50603837

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 512.77 41.05 207 1634 112033 29460653
Haematotoxicity 305.92 41.05 73 1768 6626 29566060
Febrile bone marrow aplasia 83.75 41.05 27 1814 7324 29565362
Venoocclusive liver disease 77.13 41.05 25 1816 6892 29565794
Osteonecrosis 60.79 41.05 25 1816 13494 29559192

FDA Adverse Event Reporting System (Geriatric)

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 732.45 35.95 276 2382 187381 64308693
Haematotoxicity 539.09 35.95 121 2537 12775 64483299
Venoocclusive liver disease 94.88 35.95 29 2629 9986 64486088
Venoocclusive disease 90.93 35.95 23 2635 3962 64492112
Osteonecrosis 68.82 35.95 30 2628 28199 64467875
Pancytopenia 65.24 35.95 51 2607 143258 64352816
Glioma 51.12 35.95 10 2648 530 64495544
Cerebral venous sinus thrombosis 43.76 35.95 11 2647 1844 64494230
Staphylococcal sepsis 42.49 35.95 17 2641 12882 64483192
Toxic neuropathy 41.58 35.95 9 2649 787 64495287
Neutropenia 41.28 35.95 50 2608 239574 64256500
Febrile bone marrow aplasia 41.16 35.95 16 2642 11239 64484835
Sepsis 37.94 35.95 47 2611 230294 64265780
Thymus enlargement 36.47 35.95 6 2652 117 64495957
Second primary malignancy 36.32 35.95 15 2643 12322 64483752

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC L01BB03 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
ANTIMETABOLITES
Purine analogues
MeSH PA D000963 Antimetabolites
MeSH PA D000964 Antimetabolites, Antineoplastic
MeSH PA D000970 Antineoplastic Agents
MeSH PA D009676 Noxae
CHEBI has role CHEBI:35221 antimetabolite
CHEBI has role CHEBI:35610 antineoplastic agents
CHEBI has role CHEBI:149553 anticoronaviral drug

Drug Use | Suggest Off label Use Form| |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




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

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
Adenosine receptor A3 GPCR Ki 4.91 DRUG MATRIX
Multidrug resistance-associated protein 5 Transporter WOMBAT-PK
Multidrug resistance-associated protein 4 Transporter WOMBAT-PK
Xanthine dehydrogenase/oxidase Enzyme IC50 4.03 CHEMBL
Mitogen-activated protein kinase 3 Kinase IC50 5.26 DRUG MATRIX
Hypoxanthine-guanine phosphoribosyltransferase Enzyme WOMBAT-PK
Prostaglandin G/H synthase 1 Enzyme IC50 6.22 DRUG MATRIX
Arachidonate 15-lipoxygenase Enzyme IC50 4.79 DRUG MATRIX
2-amino-4-hydroxy-6-hydroxymethyldihydropteridine pyrophosphokinase Kinase Kd 4.75 CHEMBL

External reference:

IDSource
4018777 VUID
N0000147080 NUI
D06109 KEGG_DRUG
4018777 VANDF
C0039902 UMLSCUI
CHEBI:9555 CHEBI
CHEMBL727 ChEMBL_ID
DB00352 DRUGBANK_ID
D013866 MESH_DESCRIPTOR_UI
2723601 PUBCHEM_CID
6845 IUPHAR_LIGAND_ID
FTK8U1GZNX UNII
10485 RXNORM
2109 MMSL
5569 MMSL
d01345 MMSL
002652 NDDF
387407006 SNOMEDCT_US
72623000 SNOMEDCT_US
DX4 PDB_CHEM_ID
5580-03-0 SECONDARY_CAS_RN

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
TABLOID HUMAN PRESCRIPTION DRUG LABEL 1 76388-880 TABLET 40 mg ORAL NDA 23 sections