mitapivat   Click here for help

GtoPdb Ligand ID: 10473

Synonyms: AG-348 | AG348 | compound 80a [WO2011002817A1] | PKM2 activator 1020 | PKR-IN-1 | Pyrukynd®
Approved drug
mitapivat is an approved drug (FDA (2022))
Compound class: Synthetic organic
Comment: Mitapivat (AG-348) is a first-in-class, small molecule allosteric activator of the pyruvate kinases. It activates the PK isoform that is found in erythrocytes (PKR protein that is expressed from the PKLR gene) and the embryonic PKM2 isoform (expressed from the PKM gene) that is only expressed by cancer cells in adult tissues. Mitapivat was developed by Agios Pharmaceuticals as a novel therapy for diseases of red blood cells that are associated with inherited PKR deficiency [2], and for potential in cancer therapy via activation of PKM2. Activation of PK in red cells increases hemoglobin levels [4-5]. The active drug is the sulfate hydrate (PubChem CID 134693700). We show the structure for the parent molecule as described by its INN.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 7
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 90.99
Molecular weight 450.17
XLogP 2.75
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES O=C(c1ccc(cc1)NS(=O)(=O)c1cccc2c1nccc2)N1CCN(CC1)CC1CC1
Isomeric SMILES O=C(c1ccc(cc1)NS(=O)(=O)c1cccc2c1nccc2)N1CCN(CC1)CC1CC1
InChI InChI=1S/C24H26N4O3S/c29-24(28-15-13-27(14-16-28)17-18-6-7-18)20-8-10-21(11-9-20)26-32(30,31)22-5-1-3-19-4-2-12-25-23(19)22/h1-5,8-12,18,26H,6-7,13-17H2
InChI Key XAYGBKHKBBXDAK-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2022))
International Nonproprietary Names Click here for help
INN number INN
10226 mitapivat
Synonyms Click here for help
AG-348 | AG348 | compound 80a [WO2011002817A1] | PKM2 activator 1020 | PKR-IN-1 | Pyrukynd®
Database Links Click here for help
CAS Registry No. 1260075-17-9 (source: WHO INN record)
GtoPdb PubChem SID 385612232
PubChem CID 59634741
Search Google for chemical match using the InChIKey XAYGBKHKBBXDAK-UHFFFAOYSA-N
Search Google for chemicals with the same backbone XAYGBKHKBBXDAK
Search PubMed clinical trials mitapivat
Search PubMed titles mitapivat
Search PubMed titles/abstracts mitapivat
UniChem Compound Search for chemical match using the InChIKey XAYGBKHKBBXDAK-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey XAYGBKHKBBXDAK-UHFFFAOYSA-N