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) 0.83 mg/mL Bocci G, Oprea TI, Benet LZ
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 305.87 50.73 102 970 118347 63369603
Haematotoxicity 233.30 50.73 49 1023 9327 63478623
Venoocclusive disease 70.11 50.73 14 1058 2044 63485906
Staphylococcal sepsis 65.20 50.73 17 1055 8111 63479839
Toxic neuropathy 62.38 50.73 10 1062 418 63487532

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 602.34 36.70 244 1881 136605 34818201
Haematotoxicity 292.83 36.70 73 2052 8121 34946685
Venoocclusive liver disease 94.48 36.70 30 2095 7936 34946870
Febrile bone marrow aplasia 81.42 36.70 27 2098 8182 34946624
Osteonecrosis 76.13 36.70 30 2095 14860 34939946
Venoocclusive disease 43.27 36.70 13 2112 2854 34951952
Facial paresis 42.48 36.70 13 2112 3036 34951770
Pancytopenia 41.47 36.70 39 2086 95118 34859688
Periorbital infection 39.21 36.70 7 2118 150 34954656

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 850.99 36.13 320 2758 230679 79510631
Haematotoxicity 524.29 36.13 121 2957 15398 79725912
Venoocclusive liver disease 117.70 36.13 35 3043 11736 79729574
Venoocclusive disease 94.17 36.13 24 3054 4549 79736761
Osteonecrosis 84.44 36.13 35 3043 31060 79710250
Pancytopenia 74.48 36.13 57 3021 165688 79575622
Glioma 56.44 36.13 11 3067 611 79740699
Staphylococcal sepsis 51.84 36.13 20 3058 14706 79726604
Toxic neuropathy 45.83 36.13 10 3068 970 79740340
Facial paresis 44.82 36.13 14 3064 5512 79735798
Thrombocytopenia 44.68 36.13 53 3025 265206 79476104
Neutropenia 42.81 36.13 54 3024 287656 79453654
Cerebral venous sinus thrombosis 42.17 36.13 11 3067 2280 79739030
Febrile bone marrow aplasia 39.91 36.13 16 3062 13004 79728306
Sepsis 39.17 36.13 50 3028 269378 79471932
Aspergillus infection 37.08 36.13 17 3061 19144 79722166
Thymus enlargement 36.39 36.13 6 3072 127 79741183

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
Multidrug resistance-associated protein 5 Transporter WOMBAT-PK
Multidrug resistance-associated protein 4 Transporter WOMBAT-PK
Xanthine dehydrogenase/oxidase Enzyme IC50 4.03 CHEMBL
Hypoxanthine-guanine phosphoribosyltransferase Enzyme WOMBAT-PK
Mitogen-activated protein kinase 3 Kinase IC50 5.26 DRUG MATRIX
Prostaglandin G/H synthase 1 Enzyme IC50 6.22 DRUG MATRIX
Adenosine receptor A3 GPCR Ki 4.91 DRUG MATRIX
Arachidonate 15-lipoxygenase Enzyme IC50 4.79 DRUG MATRIX
2-amino-4-hydroxy-6-hydroxymethyldihydropteridine pyrophosphokinase Kinase Kd 4.75 CHEMBL
Replicase polyprotein 1ab Enzyme IC50 7 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 69784-630 TABLET 40 mg ORAL NDA 23 sections
TABLOID HUMAN PRESCRIPTION DRUG LABEL 1 69784-630 TABLET 40 mg ORAL NDA 23 sections
TABLOID HUMAN PRESCRIPTION DRUG LABEL 1 76388-880 TABLET 40 mg ORAL NDA 23 sections
TABLOID HUMAN PRESCRIPTION DRUG LABEL 1 76388-880 TABLET 40 mg ORAL NDA 23 sections
TABLOID HUMAN PRESCRIPTION DRUG LABEL 1 80725-630 TABLET 40 mg ORAL NDA 23 sections