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2 Drugs in Development

2 Drugs in Development

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Also known as: Amdizalisib [inn], F3ymy7783p, 1894229-03-8, 4-amino-6-[[(1s)-1-(3-chloro-6-phenylimidazo[1,2-b]pyridazin-7-yl)ethyl]amino]pyrimidine-5-carbonitrile, 4-amino-6-{[(1s)-1-(3-chloro-6-phenylimidazo[1,2-b]pyridazin-7-yl)ethyl]amino}pyrimidine-5-carbonitrile, 5-pyrimidinecarbonitrile, 4-amino-6-(((1s)-1-(3-chloro-6-phenylimidazo(1,2-b)pyridazin-7-yl)ethyl)amino)-

Molecular Formula

C₁₉H₁₅ClN₈

Molecular Weight

390.8 g/mol

InChI Key

WKDBRCUUDXLTIM-NSHDSACASA-N

FDA UNII

F3YMY7783P

Amdizalisib is an orally bioavailable selective inhibitor of the delta isoform of phosphatidylinositide 3-kinase (phosphoinositide 3'-kinase delta; PI3Kd; PI3K-d), with potential antineoplastic activity. Upon oral administration, amdizalisib selectively binds to and inhibits PI3Kd, and prevents the activation of the PI3Kd/AKT signaling pathway, and B-cell activation. This both decreases proliferation and induces cell death in PI3Kd-overexpressing tumor cells. PI3Kd plays a key role in the B-cell receptor (BCR) signaling pathway and the proliferation of hematologic cancer cells. The targeted inhibition of PI3Kd is designed to preserve PI3K signaling in normal, non-neoplastic cells and thereby to minimize serious side effects. PI3Kd, an enzyme often overexpressed in cancer cells, plays a crucial role in tumor cell regulation and survival.

1 2D Structure

Amdizalisib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-amino-6-[[(1S)-1-(3-chloro-6-phenylimidazo[1,2-b]pyridazin-7-yl)ethyl]amino]pyrimidine-5-carbonitrile

2.1.2 InChI

InChI=1S/C19H15ClN8/c1-11(26-19-14(8-21)18(22)24-10-25-19)13-7-16-23-9-15(20)28(16)27-17(13)12-5-3-2-4-6-12/h2-7,9-11H,1H3,(H3,22,24,25,26)/t11-/m0/s1

2.1.3 InChI Key

WKDBRCUUDXLTIM-NSHDSACASA-N

2.1.4 Canonical SMILES

CC(C1=CC2=NC=C(N2N=C1C3=CC=CC=C3)Cl)NC4=NC=NC(=C4C#N)N

2.1.5 Isomeric SMILES

C[C@@H](C1=CC2=NC=C(N2N=C1C3=CC=CC=C3)Cl)NC4=NC=NC(=C4C#N)N

2.2 Other Identifiers

2.2.1 UNII

F3YMY7783P

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Amdizalisib [inn]

2. F3ymy7783p

3. 1894229-03-8

4. 4-amino-6-[[(1s)-1-(3-chloro-6-phenylimidazo[1,2-b]pyridazin-7-yl)ethyl]amino]pyrimidine-5-carbonitrile

5. 4-amino-6-{[(1s)-1-(3-chloro-6-phenylimidazo[1,2-b]pyridazin-7-yl)ethyl]amino}pyrimidine-5-carbonitrile

6. 5-pyrimidinecarbonitrile, 4-amino-6-(((1s)-1-(3-chloro-6-phenylimidazo(1,2-b)pyridazin-7-yl)ethyl)amino)-

7. 5-pyrimidinecarbonitrile, 4-amino-6-[[(1s)-1-(3-chloro-6-phenylimidazo[1,2-b]pyridazin-7-yl)ethyl]amino]-

8. Amdizalisib [who-dd]

9. Amdizalisib [usan]

10. Unii-f3ymy7783p

11. Hmpl-689

12. Chembl4438249

13. Schembl17633481

14. Gtpl11699

15. Us10208066, Compound 4

16. Bdbm350391

17. Zinc584641354

18. Compound 4 [wo2016045591a1]

19. Compound 28 [pmid: 30582813]

20. Hy-132807

21. Cs-0204054

22. (s)-4-amino-6-((1-(3-chloro-6-phenylimidazo[1,2-b]pyridazin-7-yl)ethyl)amino)pyrimidine-5-carbonitrile

23. 4-amino-6-(((1s)-1-(3-chloro-6-phenylimidazo(1,2-b)pyridazin-7-yl)ethyl)amino)-5-pyrimidinecarbonitrile

2.4 Create Date

2016-04-09

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₁₅ClN₈
Molecular Weight	390.8 g/mol
XLogP3	3.4
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	4
Exact Mass	g/mol
Monoisotopic Mass	g/mol
Topological Polar Surface Area	118
Heavy Atom Count	28
Formal Charge	0
Complexity	576
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