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Also known as: Ns-018, 1239358-86-1, 56r994wx4l, 6-n-[(1s)-1-(4-fluorophenyl)ethyl]-4-(1-methylpyrazol-4-yl)-2-n-pyrazin-2-ylpyridine-2,6-diamine, (s)-n-(1-(4-fluorophenyl)ethyl)-4-(1-methyl-1h-pyrazol-4-yl)-n'-(pyrazin-2-yl)pyridine-2,6-diamine, 2,6-pyridinediamine, n2-((1s)-1-(4-fluorophenyl)ethyl)-4-(1-methyl-1h-pyrazol-4-yl)-n6-2-pyrazinyl-

Molecular Formula

C₂₁H₂₀FN₇

Molecular Weight

389.4 g/mol

InChI Key

UQTPDWDAYHAZNT-AWEZNQCLSA-N

FDA UNII

56R994WX4L

Ilginatinib is an orally bioavailable, small molecule inhibitor of Janus-associated kinase 2 (JAK2) and Src-family kinases, with potential antineoplastic activity. Ilginatinib competes with ATP for binding to JAK2 as well as the mutated form JAK2V617F, thereby inhibiting the activation of JAK2 and downstream molecules in the JAK2/STAT3 (signal transducer and activator of transcription 3) signaling pathway that plays an important role in normal development, particularly hematopoiesis. In addition, ilginatinib inhibits the Src family tyrosine kinases. This eventually leads to the induction of tumor cell apoptosis. JAK2 is the most common mutated gene in bcr-abl-negative myeloproliferative disorders (MPDs); JAK2V617F is a constitutively activated kinase that activates the JAK/STAT signaling pathway and dysregulates cell growth and function, and its expression transforms hematopoietic cells to cytokine-independent growth.

1 2D Structure

Ilginatinib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

6-N-[(1S)-1-(4-fluorophenyl)ethyl]-4-(1-methylpyrazol-4-yl)-2-N-pyrazin-2-ylpyridine-2,6-diamine

2.1.2 InChI

InChI=1S/C21H20FN7/c1-14(15-3-5-18(22)6-4-15)26-19-9-16(17-11-25-29(2)13-17)10-20(27-19)28-21-12-23-7-8-24-21/h3-14H,1-2H3,(H2,24,26,27,28)/t14-/m0/s1

2.1.3 InChI Key

UQTPDWDAYHAZNT-AWEZNQCLSA-N

2.1.4 Canonical SMILES

CC(C1=CC=C(C=C1)F)NC2=CC(=CC(=N2)NC3=NC=CN=C3)C4=CN(N=C4)C

2.1.5 Isomeric SMILES

C[C@@H](C1=CC=C(C=C1)F)NC2=CC(=CC(=N2)NC3=NC=CN=C3)C4=CN(N=C4)C

2.2 Other Identifiers

2.2.1 UNII

56R994WX4L

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Ns-018

2. 1239358-86-1

3. 56r994wx4l

4. 6-n-[(1s)-1-(4-fluorophenyl)ethyl]-4-(1-methylpyrazol-4-yl)-2-n-pyrazin-2-ylpyridine-2,6-diamine

5. (s)-n-(1-(4-fluorophenyl)ethyl)-4-(1-methyl-1h-pyrazol-4-yl)-n'-(pyrazin-2-yl)pyridine-2,6-diamine

6. 2,6-pyridinediamine, N2-((1s)-1-(4-fluorophenyl)ethyl)-4-(1-methyl-1h-pyrazol-4-yl)-n6-2-pyrazinyl-

7. (s)-n2-(1-(4-fluorophenyl)ethyl)-4-(1-methyl-1h-pyrazol-4-yl)-n6-(pyrazin-2-yl)pyridine-2,6-diamine

8. (s)-n2-[1-(4-fluorophenyl)ethyl]-4-(1-methyl-1h-pyrazol-4-yl)-n6-(pyrazin-2-yl)pyridine-2,6-diamine

9. Ilginatinib [inn]

10. Unii-56r994wx4l

11. Gtpl7839

12. Chembl4303389

13. Schembl14954406

14. Dtxsid201115696

15. Ns018

16. Hy-19631a

17. Ns-018ns-018

18. Zinc68245917

19. Cs-5358

20. Db12784

21. A922051

22. Q27088043

23. (s)-n2-[1-(4-fluorophenyl)ethyl]-4-(1-methyl-1h-pyrazol-4-yl)-n6-(pyrazin-2yl)pyridine-2,6-diamine

24. 1526932-96-6

25. N2-[(1s)-1-(4-fluorophenyl)ethyl]-4-(1-methyl-1h-pyrazol-4-yl)-n6-(pyrazin-2-yl)pyridine-2,6-diamine

26. N2-[(1s)-1-(4-fluorophenyl)ethyl]-4-(1-methyl-1h-pyrazol-4-yl)-n6-2-pyrazinyl-2,6-pyridinediamine

2.4 Create Date

2010-09-13

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₀FN₇
Molecular Weight	389.4 g/mol
XLogP3	3.2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	6
Exact Mass	389.17642183 g/mol
Monoisotopic Mass	389.17642183 g/mol
Topological Polar Surface Area	80.6 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	501
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