tipiracil   Click here for help

GtoPdb Ligand ID: 8696

Synonyms: MA-1 | TAS-1-462
Approved drug
tipiracil is an approved drug (Japan only)
Compound class: Synthetic organic
Comment: Tipracil is a a uracil derivative that inhibits thymidine phosphorylase (TYMP, P19971; a.k.a. platelet-derived endothelial cell growth factor), an enzyme which metabolises trifluridine.
TAS-102 contains tipracil as the hydrochloride salt (PubChem CID 9903778).

SARS-CoV-2: Tipracil has been shown to bind to the uridine-specific endoribonuclease Nsp15 of SARS-CoV-2, and this interaction inhibits the enzyme's uridine-degrading catalytic activity [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 3
Rotatable bonds 2
Topological polar surface area 92.81
Molecular weight 242.06
XLogP 1.26
No. Lipinski's rules broken 0
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Canonical SMILES O=c1[nH]c(CN2CCCC2=N)c(c(=O)[nH]1)Cl
Isomeric SMILES O=c1[nH]c(CN2CCCC2=N)c(c(=O)[nH]1)Cl
InChI InChI=1S/C9H11ClN4O2/c10-7-5(12-9(16)13-8(7)15)4-14-3-1-2-6(14)11/h11H,1-4H2,(H2,12,13,15,16)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (Japan only)
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
9500 tipiracil
Synonyms Click here for help
MA-1 | TAS-1-462
Database Links Click here for help
CAS Registry No. 183204-74-2 (source: PubChem)
ChEMBL Ligand CHEMBL235668
DrugBank Ligand DB02631
DrugCentral Ligand 4893
GtoPdb PubChem SID 252166896
PubChem CID 6323266
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UniChem Compound Search for chemical match using the InChIKey QQHMKNYGKVVGCZ-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey QQHMKNYGKVVGCZ-UHFFFAOYSA-N
Wikipedia Tipiracil