Ivosidenib
(2S)-N-[(1S)-1-(2-chlorophenyl)-2-[(3,3-difluorocyclobutyl)amino]-2-oxoethyl]-1-(4-cyano-2-pyridinyl)-N-(5-fluoro-3-pyridinyl)-5-oxopyrrolidine-2-carboxamide
Molecular Identity
Ivosidenib
(2S)-N-[(1S)-1-(2-chlorophenyl)-2-[(3,3-difluorocyclobutyl)amino]-2-oxoethyl]-1-(4-cyano-2-pyridinyl)-N-(5-fluoro-3-pyridinyl)-5-oxopyrrolidine-2-carboxamide
PubChem CID: 71657455
Ivosidenib is a tertiary carboxamide resulting from the formal condensation of the carboxy group of (2S)-1-(4-cyanopyridin-2-yl)-5-oxopyrrolidine-2-carboxylic acid with the secondary amino group of (2S)-2-(2-chlorophenyl)-N-(3,3-difluorocyclobutyl)-2-[(5-fluoropyridin-3-yl)amino]acetamide. It is approved by the FDA for the treatment of acute myeloid leukemia (AML) in patients with an isocitrate dehydrogenase-1 (IDH1) mutation. It has a role as an EC 1.1.1.42 (isocitrate dehydrogenase) inhibitor and an antineoplastic agent. It is a secondary carboxamide, a tertiary carboxamide, a cyanopyridine, an organofluorine compound, a member of pyrrolidin-2-ones and a member of monochlorobenzenes.
2D Structure
Properties
C28H22ClF3N6O3
Molecular Formula
583.00
Molecular Weight
g/mol
582.1394
Exact Mass
Da
3.4
XLogP
Drug-like (Lipinski: < 5)
119
TPSA
Good oral absorption (< 140 A²)
1
H-Bond Donors
9
H-Bond Acceptors
1050
Complexity
SMILES
Canonical SMILES
SMILES: C1CC(=O)N(C1C(=O)N(C2=CC(=CN=C2)F)C(C3=CC=CC=C3Cl)C(=O)NC4CC(C4)(F)F)C5=NC=CC(=C5)C#NIsomeric SMILES
SMILES: C1CC(=O)N([C@@H]1C(=O)N(C2=CC(=CN=C2)F)[C@@H](C3=CC=CC=C3Cl)C(=O)NC4CC(C4)(F)F)C5=NC=CC(=C5)C#NSynonyms(20)
Ivosidenib1448347-49-6TibsovoAG-120AG120Q2PCN8MAM6ivosidenibumCHEBI:145430DTXSID801027928(2S)-N-[(1S)-1-(2-chlorophenyl)-2-[(3,3-difluorocyclobutyl)amino]-2-oxoethyl]-1-(4-cyanopyridin-2-yl)-N-(5-fluoropyridin-3-yl)-5-oxopyrrolidine-2-carboxamideGlycinamide, 1-(4-cyano-2-pyridinyl)-5-oxo-L-prolyl-2-(2-chlorophenyl)-N-(3,3-difluorocyclobutyl)-N2-(5-fluoro-3-pyridinyl)-, (2S)-(2S)-N-{(1S)-1-(2-chlorophenyl)-2-[(3,3-difluorocyclobutyl)amino]-2-oxoethyl}-1-(4-cyanopyridin-2-yl)-N-(5-fluoropyridin-3-yl)-5-oxopyrrolidine-2-carboxamide(2S)-2-(2-CHLOROPHENYL)-2-{1-[(2S)-1-(4-CYANOPYRIDIN-2-YL)-5-OXOPYRROLIDIN-2-YL]-N-(5-FLUOROPYRIDIN-3-YL)FORMAMIDO}-N-(3,3-DIFLUOROCYCLOBUTYL)ACETAMIDE(2S)-2-(2-chlorophenyl)-2-(1-((2S)-1-(4-cyanopyridin-2-yl)-5-oxopyrrolidin-2-yl)-N-(5-fluoropyridin-3-yl)formamido)-N-(3,3-difluorocyclobutyl)acetamide(2S)-N-((1S)-1-(2-CHLOROPHENYL)-2-((3,3-DIFLUOROCYCLOBUTYL)AMINO)-2-OXOETHYL)-1-(4-CYANOPYRIDIN-2-YL)-N-(5-FLUOROPYRIDIN-3-YL)-5-OXOPYRROLIDINE-2-CARBOXAMIDE
Data from PubChem (NCBI)
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