1. Isa 247
2. Isa(tx)247
3. Isa-247
4. Isatx247
5. Lupkynis
1. 515814-01-4
2. Lupkynis
3. Luveniq
4. Isatx-247
5. Voclosporin [usan]
6. Isatx247
7. Isa-247
8. Isa247
9. Lx211
10. Lx-211
11. R 1524
12. R-1524
13. Isa(tx)247
14. (3s,6s,9s,12r,15s,18s,21s,24s,30s,33s)-30-ethyl-33-[(1r,2r,4e)-1-hydroxy-2-methylhepta-4,6-dienyl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
15. 515814-00-3
16. 2pn063x6b1
17. Trans-isa 247
18. Voclera
19. Isa 247
20. (3s,6s,9s,12r,15s,18s,21s,24s,30s,33s)-30-ethyl-33-((1r,2r,e)-1-hydroxy-2-methylhepta-4,6-dien-1-yl)-6,9,18,24-tetraisobutyl-3,21-diisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2,5,8,11,14,17,20,23,26,29,32-undecaone
21. Trans-isa-247
22. Voclosporin (usan/inn)
23. Voclosporin [usan:inn]
24. Isatx 247
25. Unii-2pn063x6b1
26. 3odi
27. Lx-214
28. Isatx-247; Luveniq
29. Voclosporin [mi]
30. Voclosporin [inn]
31. Voclosporin [mart.]
32. Voclosporin [who-dd]
33. E-isa247
34. Schembl12632344
35. Gtpl11388
36. Voclosporin [orange Book]
37. Chebi:135957
38. Dtxsid401030488
39. (e)-isa-247
40. Ex-a5922
41. At27977
42. Db11693
43. Hy-106638
44. Cs-0026210
45. R1524
46. D09033
47. Q7939256
48. Cyclosporin A, 6-((2s,3r,4r)-3-hydroxy-4-methyl-2-(methylamino)-6,8-nonadienoic Acid)-
49. (3s,6s,9s,12r,15s,18s,21s,24s,30s,33s)-30-ethyl-33-[(1r,2r,4e)-1-hydroxy-2-methylhepta-4,6-dien-1-yl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-bis(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2,5,8,11,14,17,20,23,26,29,32-undecone
50. 1,11-anhydro[l-alanyl-d-alanyl-n-methyl-l-leucyl-n-methyl-l-leucyl- N-methyl-l-valyl-[(2s,3r,4r,6e)-3-hydroxy-4-methyl- 2-(methylamino)nona-6,8-dienoyl][(2s)-2-aminobutanoyl]- N-methylglycyl-n-methyl-l-leucyl-l-valyl-n-methyl-l-leucine]
51. Cyclo (((e,z)-(2s,3r,4r)-3-hydroxy-4-methyl-2-(methylamino)nona-6,8-dienoyl)-l-2-aminobytyrl-n-methyl-glycyl-n-methyl-l-leucyl-l-valyl-n-methyl-l-leucyl-l-alanyl-d-alanyl-n-methyl-l-leucyl-n-methyl-l-leucyl-n-methyl-l-valyl)
52. Cyclo(l-alanyl-d-alanyl-n-methyl-l-leucyl-n-methyl-l-leucyl-n-methyl-l-valyl- ((2s,3r,4r,6e)-3-hydroxy-4-methyl-2-(methylamino)nona-6,8-dienoyl)-(2s)-2- Aminobutanoyl-n-methylglycyl-n-methyl-l-leucyl-l-valyl-n-methyl-l-leucyl)
53. Cyclosporin A, 6-((2s,3r,4r,6e)-3-hydroxy-4-methyl-2-(methylamino)-6,8- Nonadienoic Acid)-
| Molecular Weight | 1214.6 g/mol |
|---|---|
| Molecular Formula | C63H111N11O12 |
| XLogP3 | 7.9 |
| Hydrogen Bond Donor Count | 5 |
| Hydrogen Bond Acceptor Count | 12 |
| Rotatable Bond Count | 16 |
| Exact Mass | 1213.84136802 g/mol |
| Monoisotopic Mass | 1213.84136802 g/mol |
| Topological Polar Surface Area | 279 Ų |
| Heavy Atom Count | 86 |
| Formal Charge | 0 |
| Complexity | 2380 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 12 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 1 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
Voclosporin is used in combination with a background immunosuppressive regimen for the treatment of lupus nephritis. Safety has not been established in combination with cyclophosphamide.
Treatment of Systemic Lupus Erythematosus (SLE)
Treatment of non-infectious uveitis
Lupkynis is indicated in combination with mycophenolate mofetil for the treatment of adult patients with active class III, IV or V (including mixed class III/V and IV/V) lupus nephritis (LN).
Voclosporin inhibits calcineurin, leading to the inhibition of T cell activation by blocking the transcription of early inflammatory cytokines. This reduces inflammation in the kidney, treating lupus nephritis and preventing permanent renal damage.
L04AD03
L - Antineoplastic and immunomodulating agents
L04 - Immunosuppressants
L04A - Immunosuppressants
L04AD - Calcineurin inhibitors
L04AD03 - Voclosporin
Absorption
When administered on an empty stomach, the median Tmax of voclosporin is 1.5 hours, but can range from 1-4 hours. The AUC is estimated at 7693.6 ng/mL*h and the Cmax is estimated at 955.5 ng/mL.
Route of Elimination
Voclosporin is eliminated in the urine and feces, with about 88% detected in the feces and about 2% detected in the urine.
Volume of Distribution
The apparent volume of distribution of voclosporin is 2,154 L. Voclosporin distributes extensively into red blood cells; distribution between whole blood and plasma is dependent on concentration and temperature.
Clearance
The mean apparent steady-state clearance of voclosporin is 63.6 L/h. Hepatic and renal impairment significantly reduce the clearance of voclosporin.
Voclosporin is mainly metabolized by the CYP3A4 hepatic cytochrome enzyme. Pharmacologic activity is mainly attributed to the parent molecule. A major metabolite has been detected in human whole blood, representing 16.7% of total exposure; this metabolite is about 8-fold less potent than the parent drug, voclosporin.
The average terminal half-life of voclosporin is about 30 hours (24.9 to 36.5 hours).
Through the inhibition of calcineurin, voclosporin blocks IL-2 expression and T-cell mediated immune responses, stabilizing podocytes in the kidneys. Voclospoprin is a cyclosporine A analog. It is structurally similar to cyclosporine A (CsA) with the exception of an amino acid modification in one region. This modification changes the binding of voclosporin to calcineurin. Cyclosporine inhibitors reversibly inhibit T-lymphocytes. They also inhibit lymphokine production and release. Cyclosporine A exerts its inhibitory effects on T-lymphocytes by binding to cyclophilin. A cyclophilin-cyclosporine complex is formed, leading to the inhibition of calcium- and calmodulin-dependent serine-threonine phosphatase activity of calcineurin. Along with calcineurin inhibition, the inhibition of many transcription factors necessary for the induction of various cytokine genes such as IL-2, IFN-, IL-4 and GM-CSF occurs. This, in turn, reduces inflammation, treating renal glomerulonephritis associated with systemic lupus erythematosus.
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