thioguanine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,ALK,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK1,CDK5,CDK9,CSF1R,CSNK2A1,CSNK2A3,DDR1,DYRK1B,EIF2AK3,ERBB2,FLT3,GRK2,GRK3,GSK3B,IRAK1,ITK,JAK1,JAK2,MAP3K21,MAP3K7,MAP4K1,MAP4K3,MAPK10,MAPK12,MAPK7,MAPK9,MARK4,MTOR,NTRK2,PDK1,PDK2,PIK3CD,PIK3CG,PIM2,PRKCD,PRKDC,SGK1,SIK2,SIK3,STK33,SYK,TEK,TTK,ULK1 53
kinase-selectivity-class GRK2,MAP2K3,MAP3K21,MAPK7 4
pfas-class PFAS structural alert (1 = True, 0 = False) 0

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 411.81 44.13 136 1343 158213 90468755
Haematotoxicity 226.00 44.13 50 1429 12485 90614483
Venoocclusive disease 68.10 44.13 14 1465 2441 90624527
Staphylococcal sepsis 68.07 44.13 18 1461 9365 90617603
Toxic neuropathy 67.31 44.13 11 1468 537 90626431
Pancytopenia 56.80 44.13 31 1448 120232 90506736
Venoocclusive liver disease 55.66 44.13 14 1465 5979 90620989
Glioma 55.22 44.13 9 1470 432 90626536
Enterococcal infection 53.06 44.13 15 1464 9976 90616992
Neutropenia 50.22 44.13 36 1443 224868 90402100
Glioblastoma multiforme 48.43 44.13 9 1470 929 90626039
Congestive cardiomyopathy 48.08 44.13 13 1466 7341 90619627
Second primary malignancy 48.04 44.13 14 1465 10364 90616604
Acute myeloid leukaemia 46.19 44.13 16 1463 20624 90606344
Cerebral venous sinus thrombosis 45.60 44.13 10 1469 2366 90624602

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 607.57 34.92 273 2454 185430 42433178
Haematotoxicity 300.64 34.92 80 2647 10905 42607703
Venoocclusive liver disease 85.36 34.92 30 2697 10272 42608336
Febrile bone marrow aplasia 78.09 34.92 28 2699 10153 42608455
Osteonecrosis 72.76 34.92 30 2697 15835 42602773
Hypertriglyceridaemia 63.44 34.92 24 2703 10102 42608506
Glioblastoma multiforme 52.40 34.92 12 2715 870 42617738
Facial paresis 49.43 34.92 15 2712 3235 42615373
Glioma 47.38 34.92 10 2717 496 42618112
Neutropenia 46.06 34.92 60 2667 199371 42419237
Mucosal inflammation 45.41 34.92 32 2695 49342 42569266
Parainfluenzae virus infection 43.60 34.92 14 2713 3629 42614979
Pancytopenia 39.67 34.92 43 2684 117700 42500908
Venoocclusive disease 38.62 34.92 13 2714 3902 42614706
Pneumonia viral 37.50 34.92 13 2714 4261 42614347
Periorbital infection 37.19 34.92 7 2720 192 42618416

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 976.09 33.41 381 3693 316386 110268839
Haematotoxicity 533.34 33.41 129 3945 20953 110564272
Venoocclusive liver disease 127.22 33.41 39 4035 15168 110570057
Glioma 102.00 33.41 19 4055 869 110584356
Glioblastoma multiforme 98.07 33.41 20 4054 1470 110583755
Neutropenia 89.51 33.41 88 3986 374532 110210693
Pancytopenia 88.10 33.41 68 4006 209545 110375680
Venoocclusive disease 87.44 33.41 24 4050 6326 110578899
Osteonecrosis 83.21 33.41 35 4039 33706 110551519
Staphylococcal sepsis 70.92 33.41 26 4048 17428 110567797
Mucosal inflammation 68.09 33.41 43 4031 96098 110489127
Hypertriglyceridaemia 65.39 33.41 24 4050 16130 110569095
Second primary malignancy 62.78 33.41 24 4050 18044 110567181
Thrombocytopenia 58.51 33.41 68 4006 348817 110236408
Parainfluenzae virus infection 54.56 33.41 17 4057 6957 110578268
Facial paresis 52.47 33.41 16 4058 6097 110579128
Toxic neuropathy 50.47 33.41 11 4063 1112 110584113
Hepatotoxicity 49.02 33.41 30 4044 63370 110521855
Aspergillus infection 48.28 33.41 22 4052 25594 110559631
Enterococcal infection 46.46 33.41 20 4054 20346 110564879
Sepsis 45.42 33.41 58 4016 327288 110257937
Cerebral venous sinus thrombosis 44.80 33.41 12 4062 2883 110582342
Stenotrophomonas infection 40.51 33.41 13 4061 5845 110579380
Klebsiella infection 40.29 33.41 18 4056 19991 110565234
Hepatic fibrosis 40.26 33.41 14 4060 8052 110577173
Febrile bone marrow aplasia 39.34 33.41 17 4057 17448 110567777
Leukoencephalopathy 38.46 33.41 14 4060 9181 110576044
Pneumonia fungal 35.34 33.41 15 4059 14739 110570486
Thymus enlargement 35.06 33.41 6 4068 168 110585057
Myelodysplastic syndrome 34.88 33.41 20 4054 37464 110547761
Acute myeloid leukaemia 34.58 33.41 20 4054 38090 110547135

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
CHEBI has role CHEBI:35221 antimetabolite
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:75835 anti-anaemic agent
CHEBI has role CHEBI:149553 anticoronaviral agent

Related Drugs by ATC class:

L01BB Purine analogues 5 drugs
cladribineclofarabinefludarabine phosphatemercaptopurinenelarabine

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 1 Enzyme INHIBITOR WOMBAT-PK CHEMBL
Inosine-5'-monophosphate dehydrogenase 2 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
Polyphenol oxidase 2 Enzyme Ki 4.28 CHEMBL
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 80725-630 TABLET 40 mg ORAL NDA 23 sections