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Baricitinib

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Chemistry

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Also known as: 1187594-09-7, Olumiant, Incb028050, Ly3009104, 2-(3-(4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl)-1-(ethylsulfonyl)azetidin-3-yl)acetonitrile, Incb 028050

Molecular Formula

C₁₆H₁₇N₇O₂S

Molecular Weight

371.4 g/mol

InChI Key

XUZMWHLSFXCVMG-UHFFFAOYSA-N

FDA UNII

ISP4442I3Y

Baricitinib is an orally bioavailable inhibitor of Janus kinases 1 and 2 (JAK1/2), with potential anti-inflammatory, immunomodulating and antineoplastic activities. Upon administration, baricitinib binds to JAK1/2, which inhibits JAK1/2 activation and leads to the inhibition of the JAK-signal transducers and activators of transcription (STAT) signaling pathway. This decreases the production of inflammatory cytokines and may prevent an inflammatory response. In addition, baricitinib may induce apoptosis and reduce proliferation of JAK1/2-expressing tumor cells. JAK kinases are intracellular enzymes involved in cytokine signaling, inflammation, immune function and hematopoiesis; they are also upregulated and/or mutated in various tumor cell types.

Baricitinib is a Janus Kinase Inhibitor. The mechanism of action of baricitinib is as a Janus Kinase Inhibitor.

1 2D Structure

Baricitinib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[1-ethylsulfonyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]azetidin-3-yl]acetonitrile

2.1.2 InChI

InChI=1S/C16H17N7O2S/c1-2-26(24,25)22-9-16(10-22,4-5-17)23-8-12(7-21-23)14-13-3-6-18-15(13)20-11-19-14/h3,6-8,11H,2,4,9-10H2,1H3,(H,18,19,20)

2.1.3 InChI Key

XUZMWHLSFXCVMG-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCS(=O)(=O)N1CC(C1)(CC#N)N2C=C(C=N2)C3=C4C=CNC4=NC=N3

2.2 Other Identifiers

2.2.1 UNII

ISP4442I3Y

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3-azetidineacetonitrile, 1-(ethylsulfonyl)-3-(4-(7h-pyrrolo(2,3-d)pyrimidin-4-yl)-1h-pyrazol-1-yl)-

2. 3-azetidineacetonitrile, 1-(ethylsulfonyl)-3-(4-(7h-pyrrolo(2,3-d)pyrimidin-4-yl)-1h-pyrazol-1-yl)-, Phosphate (1:1)

3. Baricitinib Phosphate

4. Baricitinib Phosphate Salt

5. Incb-028050

6. Incb-28050

7. Incb028050

8. Ly-3009104

9. Ly3009104

10. Olumiant

2.3.2 Depositor-Supplied Synonyms

1. 1187594-09-7

2. Olumiant

3. Incb028050

4. Ly3009104

5. 2-(3-(4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl)-1-(ethylsulfonyl)azetidin-3-yl)acetonitrile

6. Incb 028050

7. Incb-028050

8. Ly-3009104

9. 1-(ethylsulfonyl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl]-3-azetidineacetonitrile

10. Baricitinib (ly3009104, Incb028050)

11. 2-[1-ethylsulfonyl-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]azetidin-3-yl]acetonitrile

12. Isp4442i3y

13. Ly 3009104

14. 3-azetidineacetonitrile, 1-(ethylsulfonyl)-3-(4-(7h-pyrrolo(2,3-d)pyrimidin-4-yl)-1h-pyrazol-1-yl)-

15. Ly3009104 (phosphate);incb028050 (phosphate)

16. Incb28050

17. Baricitinib [usan]

18. Baricitinib [usan:inn]

19. Unii-isp4442i3y

20. Incb 28050

21. Olumiant (tn)

22. 3-azetidineacetonitrile, 1-(ethylsulfonyl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl]-

23. 3jw

24. Baricitinib [mi]

25. Baricitinib [inn]

26. Baricitinib [jan]

27. Baricitinib [who-dd]

28. Mls006011247

29. Schembl871150

30. Baricitinib (jan/usan/inn)

31. Baricitinib (ly3009104)

32. Baricitinib [ema Epar]

33. Baricitinib (incb028050)

34. Gtpl7792

35. Chembl2105759

36. Ammd00005

37. Chebi:95341

38. Baricitinib [orange Book]

39. Dtxsid30152228

40. Ex-a413

41. Hms3651l17

42. Hms3672m15

43. Hms3747g21

44. Bcp04686

45. Bdbm50021656

46. Mfcd21608464

47. Nsc799357

48. S2851

49. Zinc73069247

50. Akos022186127

51. Akos025401933

52. Am81232

53. Bcp9000380

54. Ccg-268312

55. Cs-0724

56. Db11817

57. Ds-7641

58. Nsc-799357

59. Pb27275

60. Sb10845

61. Ncgc00345839-01

62. Ncgc00345839-14

63. Ncgc00345839-16

64. 2-(3-(4-(3h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl)-1-(ethylsulfonyl)azetidin-3-yl)acetonitrile

65. Ac-27404

66. Hy-15315

67. Smr004703006

68. Bcp0726000031

69. Baricitinib (incb28050, Ly3009104)

70. Ft-0775037

71. Sw220096-1

72. D10308

73. A892931

74. J-503551

75. Q4860707

76. (1-(ethylsulfonyl)-3-(4-(7h-pyrrolo(2,3-d)pyrimidin-4-yl)-1h-pyrazol-1-yl)azetidin-3-yl)ethanenitrile

77. {1-(ethylsulfonyl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl]azetidin-3-yl}acetonitrile

78. Incb 28050; Incb28050; Ly-3009104;1-(ethylsulfonyl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl]-3-azetidineacetonitrile

2.4 Create Date

2009-09-28

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₁₇N₇O₂S
Molecular Weight	371.4 g/mol
XLogP3	-0.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	5
Exact Mass	371.11644398 g/mol
Monoisotopic Mass	371.11644398 g/mol
Topological Polar Surface Area	129 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	678
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Indicated for the treatment of moderate to severe active rheumatoid arthritis in adult patients who have responded inadequately to, or who are intolerant to one or more disease-modifying anti-rheumatic drugs as monotherapy or in combination with methotrexate.

FDA Label

Rheumatoid arthritis

Baricitinib is indicated for the treatment of moderate to severe active rheumatoid arthritis in adult patients who have responded inadequately to, or who are intolerant to one or more disease modifying anti rheumatic drugs. Olumiant may be used as monotherapy or in combination with methotrexate.

Atopic Dermatitis

Baricitinib is indicated for the treatment of moderate to severe atopic dermatitis in adult patients who are candidates for systemic therapy.

Alopecia areata

Baricitinib is indicated for the treatment of severe alopecia areata in adult patients (see section 5. 1).

Treatment of chronic idiopathic arthritis (including rheumatoid arthritis , ankylosing spondylarthritis , psoriatic arthritis and juvenile idiopathic arthritis )

Treatment of Systemic Lupus Erythematosus (SLE)

Treatment of Coronavirus disease 2019

Treatment of alopecia areata

Treatment of atopic dermatitis

5 Pharmacology and Biochemistry

5.1 FDA Pharmacological Classification

5.1.1 Active Moiety

BARICITINIB

5.1.2 FDA UNII

ISP4442I3Y

5.1.3 Pharmacological Classes

Janus Kinase Inhibitors [MoA]; Janus Kinase Inhibitor [EPC]

5.2 ATC Code

L04AA37

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

L - Antineoplastic and immunomodulating agents

L04 - Immunosuppressants

L04A - Immunosuppressants

L04AA - Selective immunosuppressants

L04AA37 - Baricitinib

5.3 Absorption, Distribution and Excretion

Absorption

Baricitinib diaplays a dose-proportional increase in systemic exposure in the therapeutic dose range with linear pharmacokinetics. When orally administered, baricitinb is rapidly absorbed with an oral bioavailability of approximately 79 % (CV = 3.94 %). It has a median time to reach peak plasma concentration (Tmax) of 1hour (range: 0.5-3hours). Food consumption affects the exposure by decreasing it by up to 14 %, and decreasing the peak plasma concentration (Cmax) by up to 18 % and Tmax by 0.5 hours.

Route of Elimination

In a clinical pharmacology study, baricitinib was excreted predominately as the unchanged active substance in urine (69 %) and feces (15 %) and only 4 minor oxidative metabolites were identified (3 in urine; 1 in feces) constituting approximately 5 % and 1 % of the dose, respectively.

Volume of Distribution

Mean volume of distribution following intravenous infusion administration is 76 L.

Clearance

Mean apparent clearance (CL/F) in patients with rheumatoid arthritis is approximately 9.42 L/hr (CV = 34.3 %).

5.4 Metabolism/Metabolites

Baricitinib undergoes oxidation by CYP3A4, although less than 10% of the total dose is prone to this biotransformation. There is no formation of quantifiable metabolites in the plasma.

5.5 Biological Half-Life

Mean half-life in patients with rheumatoid arthritis is approximately 12.5 hrs (CV = 27.4 %).

5.6 Mechanism of Action

JAK enzymes are part of the family of tyrosine kinases that constitutively bind to the intracellular domains of cytokine receptors and promote the signalling cascades of cytokines and growth factors involved in haematopoiesis, inflammation and immune function that are also implicated in the pathogenesis of rheumatoid arthritis. Circulating proinflammatory cytokines bind to these cell surface receptors. Upon binding of extracellular cytokines and growth factors, JAKs are phosphorylated and activate signal transducers and activators of transcription (STATs). Through the signalling cascades, inflammatory cytokine and chemokine transcription is induced to form inflammatory mediators including IL-2, IL-6, IL-12, IL-15, IL-23, IFN- and GM-CSF. Baricitinib selectively and reversibly inhibits JAK1 and JAK2 to modulates their signalling pathways, thereby reducing the phosphorylation and activation of STATs. In isolated enzyme assays, baricitinib also exhibited an inhibitory effect on other types of JAK enzymes,Tyrosine Kinase 2 and JAK3, at higher concentrations needed for JAK1/2 inhibition.

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