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Ruxolitinib

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Also known as: 1092939-17-7, Jakafi, (r)-3-(4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl)-3-cyclopentylpropanenitrile phosphate, Jakavi, Ruxolitinib (phosphate), Ruxolitinib monophosphate

Molecular Formula

C₁₇H₂₁N₆O₄P

Molecular Weight

404.4 g/mol

InChI Key

JFMWPOCYMYGEDM-XFULWGLBSA-N

FDA UNII

436LRU32H5

Ruxolitinib Phosphate is the phosphate salt form of ruxolitinib, an orally bioavailable Janus-associated kinase (JAK) inhibitor with potential antineoplastic and immunomodulating activities. Ruxolitinib specifically binds to and inhibits protein tyrosine kinases JAK 1 and 2, which may lead to a reduction in inflammation and an inhibition of cellular proliferation. The JAK-STAT (signal transducer and activator of transcription) pathway plays a key role in the signaling of many cytokines and growth factors and is involved in cellular proliferation, growth, hematopoiesis, and the immune response; JAK kinases may be upregulated in inflammatory diseases, myeloproliferative disorders, and various malignancies.

1 2D Structure

Ruxolitinib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3R)-3-cyclopentyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile;phosphoric acid

2.1.2 InChI

InChI=1S/C17H18N6.H3O4P/c18-7-5-15(12-3-1-2-4-12)23-10-13(9-22-23)16-14-6-8-19-17(14)21-11-20-16;1-5(2,3)4/h6,8-12,15H,1-5H2,(H,19,20,21);(H3,1,2,3,4)/t15-;/m1./s1

2.1.3 InChI Key

JFMWPOCYMYGEDM-XFULWGLBSA-N

2.1.4 Canonical SMILES

C1CCC(C1)C(CC#N)N2C=C(C=N2)C3=C4C=CNC4=NC=N3.OP(=O)(O)O

2.1.5 Isomeric SMILES

C1CCC(C1)[C@@H](CC#N)N2C=C(C=N2)C3=C4C=CNC4=NC=N3.OP(=O)(O)O

2.2 Other Identifiers

2.2.1 UNII

436LRU32H5

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3r)-3-cyclopentyl-3-(4-(7h-pyrrolo(2,3-d)pyrimidin-4-yl)pyrazol-1-yl)propanenitrile

2. Inc-424

3. Inc424

4. Inca24

5. Incb-018424

6. Incb-018424 Phosphate

7. Incb-018424 Salt

8. Incb-18424

9. Incb-18424 Phosphate

10. Incb018424

11. Incb018424 Phosphate

12. Jakafi

13. Jakavi

14. Opzelura

15. Ruxolitinib

16. Ruxolitinib (as Phosphate)

17. Ruxolitinib Monophosphate

2.3.2 Depositor-Supplied Synonyms

1. 1092939-17-7

2. Jakafi

3. (r)-3-(4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl)-3-cyclopentylpropanenitrile Phosphate

4. Jakavi

5. Ruxolitinib (phosphate)

6. Ruxolitinib Monophosphate

7. Incb018424 Phosphate

8. Ruxolitinib (as Phosphate)

9. Incb-018424 Phosphate

10. Incb-018424 Salt

11. Ruxolitinib Phosphate [usan]

12. Incb-18424 Phosphate

13. Incb018424 Salt

14. Chebi:66917

15. 436lru32h5

16. 1092939-17-7 (phosphate)

17. (betar)-beta-cyclopentyl-4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazole-1-propanenitrile Phosphate

18. Incb-18424

19. Ruxolitinib Phosphate Salt

20. (3r)-3-cyclopentyl-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl]propanenitrile Phosphate

21. (3r)-3-cyclopentyl-3-(4-(7h-pyrrolo(2,3-d)pyrimidin-4-yl)-1h-pyrazol-1-yl)propanenitrile Phosphate (1:1)

22. Phosphenoperoxoic Acid Compound With (r)-3-(4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)- 1h-pyrazol-1-yl)-3-cyclopentylpropanenitrile And Dihydrogen (1:1:1)

23. Opzelura

24. Unii-436lru32h5

25. (3r)-3-cyclopentyl-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl]propanenitrilephosphoricacid

26. Jakafi (tn)

27. Jakavi (tn)

28. Ruxolitinib Phosphate(incb018424)

29. Inc 424 Phosphate

30. Incb 018424 Phosphate

31. Incb-424

32. Schembl1369365

33. Chembl1795071

34. Amy5620

35. Dtxsid00911086

36. Ruxolitinib Phosphate (jan/usan)

37. Ruxolitinib Phosphate [mi]

38. Ruxolitinib Phosphate [jan]

39. Ex-a2660

40. Cs1956

41. Mfcd18452860

42. S5243

43. Akos024464417

44. Ruxolitinib (incb-18424) Phosphate

45. Ruxolitinib Phosphate [who-dd]

46. Bcp9000783

47. Ccg-268687

48. Cs-0326

49. 1h-pyrazole-1-propanenitrile, Beta-cyclopentyl-4-(7h-pyrrolo(2,3-d)pyrimidin-4-yl)-,(betar)-, Phosphate (1:1)

50. Ac-30901

51. As-74723

52. Hy-50858

53. Ruxolitinib Phosphate [orange Book]

54. Ruxolitinib (as Phosphate) [ema Epar]

55. D09960

56. J-501793

57. Q27135517

58. (3r)-3-cyclopentyl-3-(4-{7h-pyrrolo[2,3-d]pyrimidin-4-yl}-1h-pyrazol-1-yl)propanenitrile; Phosphoric Acid

59. (3r)-3-cyclopentyl-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile;phosphoric Acid

60. (r)-3-(4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl)-3-cyclopentylpropanenitrilephosphate

61. 1h-pyrazole-1-propanenitrile,.beta.-cyclopentyl-4-(7h-pyrrolo(2,3-d)pyrimidin-4-yl)-,(.beta.r)-,phosphate (1:1)

62. Phosphoric Acid--3-cyclopentyl-3-[4-(1h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl]propanenitrile (1/1)

2.4 Create Date

2009-01-19

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₂₁N₆O₄P
Molecular Weight	404.4 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	4
Exact Mass	404.13619017 g/mol
Monoisotopic Mass	404.13619017 g/mol
Topological Polar Surface Area	161 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	503
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	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Jakafi
PubMed Health	Ruxolitinib (By mouth)
Drug Classes	Antineoplastic Agent
Active Ingredient	Ruxolitinib phosphate
Dosage Form	Tablet
Route	Oral
Strength	eq 5mg base; eq 20mg base; eq 15mg base; eq 10mg base; eq 25mg base
Market Status	Prescription
Company	Incyte

2 of 2
Drug Name	Jakafi
PubMed Health	Ruxolitinib (By mouth)
Drug Classes	Antineoplastic Agent
Active Ingredient	Ruxolitinib phosphate
Dosage Form	Tablet
Route	Oral
Strength	eq 5mg base; eq 20mg base; eq 15mg base; eq 10mg base; eq 25mg base
Market Status	Prescription
Company	Incyte

4.2 Drug Indication

* Myelofibrosis (MF):

Jakavi is indicated for the treatment of disease related splenomegaly or symptoms in adult patients with primary myelofibrosis (also known as chronic idiopathic myelofibrosis), post polycythaemia vera myelofibrosis or post essential thrombocythaemia myelofibrosis.

* Polycythaemia vera (PV):

Jakavi is indicated for the treatment of adult patients with polycythaemia vera who are resistant to or intolerant of hydroxyurea.

* Graft versus host disease (GvHD):

Jakavi is indicated for the treatment of patients aged 12 years and older with acute graft versus host disease or chronic graft versus host disease who have inadequate response to corticosteroids or other systemic therapies (see section 5. 1).

Treatment of chronic Graft versus Host Disease (cGvHD)

Treatment of acute graft-versus-host disease (aGvHD)

Treatment of vitiligo

5 Pharmacology and Biochemistry

5.1 ATC Code

L01EJ01