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Also known as: 2230974-62-4, Absk011, Absk-011, X46b7jm4a8, N-[(3s,4s)-3-[[6-(2,6-difluoro-3,5-dimethoxyphenyl)-8-(3-methoxy-3-methylazetidin-1-yl)pyrido[3,4-d]pyrimidin-2-yl]amino]oxan-4-yl]prop-2-enamide, N-((3s,4s)-3-((6-(2,6-difluoro-3,5-dimethoxyphenyl)-8-(3-methoxy-3-methylazetidin-1-yl)pyrido(3,4-d)pyrimidin-2-yl)amino)oxan-4-yl)prop-2-enamide

Molecular Formula

C₂₈H₃₂F₂N₆O₅

Molecular Weight

570.6 g/mol

InChI Key

PGRHEHZIRYNZDV-FUHWJXTLSA-N

FDA UNII

X46B7JM4A8

Irpagratinib is an orally bioavailable, selective inhibitor of human fibroblast growth factor receptor 4 (FGFR4), with potential antineoplastic activity. Upon oral administration, irpagratinib is specifically and irreversibly binds to the cysteine residue at position 552 (Cys 552) that is within the active site of FGFR4. This blocks FGFR4 autophosphorylation and activation of receptor tyrosine kinase activity that would normally occur after binding to its ligand, fibroblast growth factor 19 (FGF19), which both inhibits FGFR4-mediated signaling and leads to the inhibition of tumor cell proliferation in FGF19- and FGFR4-overexpressing cells. FGFR4, a receptor tyrosine kinase, is involved in angiogenesis and in the proliferation, differentiation, and survival of tumor cells. FGFR4 expression is associated with poor prognosis. FGF19 is overexpressed by certain tumor cell types.

1 2D Structure

Irpagratinib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-[(3S,4S)-3-[[6-(2,6-difluoro-3,5-dimethoxyphenyl)-8-(3-methoxy-3-methylazetidin-1-yl)pyrido[3,4-d]pyrimidin-2-yl]amino]oxan-4-yl]prop-2-enamide

2.1.2 InChI

InChI=1S/C28H32F2N6O5/c1-6-21(37)32-16-7-8-41-12-18(16)34-27-31-11-15-9-17(22-23(29)19(38-3)10-20(39-4)24(22)30)33-26(25(15)35-27)36-13-28(2,14-36)40-5/h6,9-11,16,18H,1,7-8,12-14H2,2-5H3,(H,32,37)(H,31,34,35)/t16-,18+/m0/s1

2.1.3 InChI Key

PGRHEHZIRYNZDV-FUHWJXTLSA-N

2.2 Other Identifiers

2.2.1 UNII

X46B7JM4A8

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 2230974-62-4

2. Absk011

3. Absk-011

4. X46b7jm4a8

5. N-[(3s,4s)-3-[[6-(2,6-difluoro-3,5-dimethoxyphenyl)-8-(3-methoxy-3-methylazetidin-1-yl)pyrido[3,4-d]pyrimidin-2-yl]amino]oxan-4-yl]prop-2-enamide

6. N-((3s,4s)-3-((6-(2,6-difluoro-3,5-dimethoxyphenyl)-8-(3-methoxy-3-methylazetidin-1-yl)pyrido(3,4-d)pyrimidin-2-yl)amino)oxan-4-yl)prop-2-enamide

7. Refchem:1087493

8. Irpagratinib [inn]

9. Orb2277624

10. Chembl5314522

11. Schembl20332300

12. Gtpl12869

13. Ex-a8168

14. Example 790 [us10968220]

15. Da-54384

16. Hy-156618

17. Cs-0886364

18. H42845

19. 2-propenamide, N-[(3s,4s)-3-[[6-(2,6-difluoro-3,5-dimethoxyphenyl)-8-(3-methoxy-3-methyl-1-azetidinyl)pyrido[3,4-d]pyrimidin-2-yl]amino]tetrahydro-2h-pyran-4-yl]-

20. N-((3s,4s)-3-((6-(2,6-difluoro-3,5-dimethoxyphenyl)-8-(3-methoxy-3-methylazetidin-1-yl)pyrido[3,4-d]pyrimidin-2-yl)amino)tetrahydro-2h-pyran-4-yl)acrylamide

21. N-[(3s,4s)-3-[[6-(2,6-difluoro-3,5-dimethoxyphenyl)-8-(3-methoxy-3-methyl-1-azetidinyl)pyrido[3,4-d]pyrimidin-2-yl]amino]tetrahydro-2h-pyran-4-yl]-2-propenamide

2.4 Create Date

2018-12-15

3 Chemical and Physical Properties

Molecular Formula	C₂₈H₃₂F₂N₆O₅
Molecular Weight	570.6 g/mol
XLogP3	2.9
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	9
Exact Mass	Da
Monoisotopic Mass	Da
Topological Polar Surface Area	120
Heavy Atom Count	41
Formal Charge	0
Complexity	899
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

Drugs in Development

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