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Chemistry

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Also known as: 1887014-12-1, Ft-2102, Olutasidenib [usan], Olutasidenib (ft-2102), 0t4imt8s5z, 5-[[(1s)-1-(6-chloro-2-oxo-1h-quinolin-3-yl)ethyl]amino]-1-methyl-6-oxopyridine-2-carbonitrile

Molecular Formula

C₁₈H₁₅ClN₄O₂

Molecular Weight

354.8 g/mol

InChI Key

NEQYWYXGTJDAKR-JTQLQIEISA-N

FDA UNII

0T4IMT8S5Z

Olutasidenib is an orally available inhibitor of isocitrate dehydrogenase type 1 (IDH1; IDH-1; IDH1 [NADP+] soluble) with a mutation at arginine (R) 132, IDH1(R132), with potential antineoplastic activity. Upon administration, olutasidenib specifically inhibits IDH1(R132), thereby inhibiting the formation of the oncometabolite 2-hydroxyglutarate (2HG) from alpha-ketoglutarate (a-KG). This prevents 2HG-mediated signaling and leads to both an induction of cellular differentiation and an inhibition of cellular proliferation in tumor cells expressing IDH(R132). IDH1(R132) mutations are highly expressed in certain malignancies, including gliomas; they initiate and drive cancer growth by both blocking cell differentiation and catalyzing the formation of 2HG.

1 2D Structure

Olutasidenib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-[[(1S)-1-(6-chloro-2-oxo-1H-quinolin-3-yl)ethyl]amino]-1-methyl-6-oxopyridine-2-carbonitrile

2.1.2 InChI

InChI=1S/C18H15ClN4O2/c1-10(21-16-6-4-13(9-20)23(2)18(16)25)14-8-11-7-12(19)3-5-15(11)22-17(14)24/h3-8,10,21H,1-2H3,(H,22,24)/t10-/m0/s1

2.1.3 InChI Key

NEQYWYXGTJDAKR-JTQLQIEISA-N

2.1.4 Canonical SMILES

CC(C1=CC2=C(C=CC(=C2)Cl)NC1=O)NC3=CC=C(N(C3=O)C)C#N

2.1.5 Isomeric SMILES

C[C@@H](C1=CC2=C(C=CC(=C2)Cl)NC1=O)NC3=CC=C(N(C3=O)C)C#N

2.2 Other Identifiers

2.2.1 UNII

0T4IMT8S5Z

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 5-((1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl)amino)-1-methyl-6-oxo-1,6-dihydropyridine-2-carbonitrile

2. Ft-2102

2.3.2 Depositor-Supplied Synonyms

1. 1887014-12-1

2. Ft-2102

3. Olutasidenib [usan]

4. Olutasidenib (ft-2102)

5. 0t4imt8s5z

6. 5-[[(1s)-1-(6-chloro-2-oxo-1h-quinolin-3-yl)ethyl]amino]-1-methyl-6-oxopyridine-2-carbonitrile

7. (s)-5-((1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl)amino)-1-methyl-6-oxo-1,6-dihydropyridine-2-carbonitrile

8. Ft2102

9. 2-pyridinecarbonitrile, 5-(((1s)-1-(6-chloro-1,2-dihydro-2-oxo-3-quinolinyl)ethyl)amino)-1,6-dihydro-1-methyl-6-oxo-

10. 5-(((1s)-1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl)amino)-1-methyl-6-oxo-1,6-dihydropyridine-2-carbonitrile

11. 5-{[(1s)-1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1-methyl-6-oxo-1,6-dihydropyridine-2-carbonitrile

12. 5-[[(1s)-1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino]-1-methyl-6-oxo-1,6-dihydropyridine-2-carbonitrile

13. Olutasidenib [inn]

14. Unii-0t4imt8s5z

15. Olutasidenib [who-dd]

16. Chembl4297610

17. Schembl17603134

18. Gtpl10319

19. Amy16919

20. Ex-a4523

21. Bdbm50506474

22. Example 26 [us9834539b2]

23. Nsc818621

24. S8949

25. Ft-2102ft-2102

26. Nsc-818621

27. Ac-36556

28. Hy-114226

29. Cs-0080183

30. D87221

31. 5-((1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl)amino)-1-methyl-6-oxo-1,6-dihydropyridine-2-carbonitrile

32. Pwv

2.4 Create Date

2016-04-09

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₁₅ClN₄O₂
Molecular Weight	354.8 g/mol
XLogP3	2.5
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Exact Mass	354.0883534 g/mol
Monoisotopic Mass	354.0883534 g/mol
Topological Polar Surface Area	85.2 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	745
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1