Voclosporin

Voclosporin, sold under the brand name Lupkynis, is a calcineurin inhibitor used as an immunosuppressant medication. It was approved by the U.S. Food and Drug Administration (FDA) for the treatment of lupus nephritis (LN) on January 22, 2021.[1][2]

Voclosporin

Names
IUPAC name (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-Ethyl-33-[(1R,2R,4E)-1-hydroxy-2-methyl-4,6-heptadien-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-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
Other names VCS, ISA247, Luveniq
Identifiers
CAS Number	515814-01-4
3D model (JSmol)	Interactive image
ChemSpider	5293683
PubChem CID	6918486
UNII	2PN063X6B1
InChI InChI=1S/C63H111N11O12/c1-25-27-28-29-41(15)53(76)52-57(80)66-44(26-2)59(82)68(18)34-49(75)69(19)45(30-35(3)4)56(79)67-50(39(11)12)62(85)70(20)46(31-36(5)6)55(78)64-42(16)54(77)65-43(17)58(81)71(21)47(32-37(7)8)60(83)72(22)48(33-38(9)10)61(84)73(23)51(40(13)14)63(86)74(52)24/h25,27-28,35-48,50-53,76H,1,26,29-34H2,2-24H3,(H,64,78)(H,65,77)(H,66,80)(H,67,79)/b28-27+/t41-,42+,43-,44+,45+,46+,47+,48+,50+,51+,52+,53-/m1/s1 Key: BICRTLVBTLFLRD-PTWUADNWSA-N InChI=1/C63H111N11O12/c1-25-27-28-29-41(15)53(76)52-57(80)66-44(26-2)59(82)68(18)34-49(75)69(19)45(30-35(3)4)56(79)67-50(39(11)12)62(85)70(20)46(31-36(5)6)55(78)64-42(16)54(77)65-43(17)58(81)71(21)47(32-37(7)8)60(83)72(22)48(33-38(9)10)61(84)73(23)51(40(13)14)63(86)74(52)24/h25,27-28,35-48,50-53,76H,1,26,29-34H2,2-24H3,(H,64,78)(H,65,77)(H,66,80)(H,67,79)/b28-27+/t41-,42+,43-,44+,45+,46+,47+,48+,50+,51+,52+,53-/m1/s1 Key: BICRTLVBTLFLRD-PTWUADNWBK
SMILES O=C1N(C)[C@H](C(=O)N[C@H](C(=O)N(C)CC(=O)N(C)[C@H](C(=O)N[C@H](C(=O)N(C)[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N([C@H](C(=O)N(C)[C@H](C(=O)N(C)[C@H]1C(C)C)CC(C)C)CC(C)C)C)C)C)CC(C)C)C(C)C)CC(C)C)CC)[C@H](O)[C@H](C)C\C=C\C=C
Properties
Chemical formula	C63H111N11O12
Molar mass	1214.646 g·mol^−1
Pharmacology
ATC code	L04AD03 (WHO)
Legal status	US: ℞-only
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Voclosporin

Clinical data
Trade names	Lupkynis
License data	US DailyMed: Voclosporin
Identifiers
DrugBank	DB11693
KEGG	D09033

It is an analog of ciclosporin that has enhanced action against calcineurin and greater metabolic stability.[3] Voclosporin was discovered by Robert T. Foster and his team at Isotechnika in the mid 1990s.[4] Isotechnika was founded in 1993 and merged with Aurinia Pharmaceuticals in 2013. In Jan. 2021, Aurinia Pharmaceuticals received approval from the Food & Drug Administration to sell the drug Lupkynis.

Initially, voclosporin was a mixture of equal proporations of cis and trans geometric isomers of amino acid-1 modified cyclosporin. Later, in collaboration with Roche in Basel, Switzerland, voclosporin's manufacturing was changed to yield the predominantly trans isomer which possesses most of the beneficial effect of the drug (immunosuppression) in the treatment of organ transplantation and autoimmune diseases.

References

1. "Voclosporin: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 25 January 2021.
2. "FDA Approves Aurinia Pharmaceuticals' Lupkynis (voclosporin) for Adult Patients with Active Lupus Nephritis". Aurinia Pharmaceuticals Inc. (Press release). 22 January 2021. Retrieved 25 January 2021.
3. "What is voclosporin?". Isotechnika. Retrieved October 19, 2012.
4. U.S. Patent 6,605,593

External links

• "Voclosporin". Drug Information Portal. U.S. National Library of Medicine.