Voclosporin

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

Voclosporin
Names
	Preferred IUPAC name (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-di(propan-2-yl)-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)
Routes of; administration	By mouth
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, sold under the brand name Lupkynis, is a calcineurin inhibitor used as an immunosuppressant medication.^[2] It was approved by the U.S. Food and Drug Administration (FDA) for the treatment of lupus nephritis (LN) in January 2021.^[3]^[4]^[5]

It is an analog of ciclosporin that has enhanced action against calcineurin and greater metabolic stability.^[6] Voclosporin was discovered by Robert T. Foster and his team at Isotechnika in the mid 1990s.^[7] Isotechnika was founded in 1993 and merged with Aurinia Pharmaceuticals in 2013. In January 2021, Aurinia Pharmaceuticals received approval from the Food & Drug Administration to sell the drug Lupkynis.^[5]^[8]

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.^{[medical citation needed]}

References[]

^ "Lupkynis- voclosporin capsule". DailyMed. Retrieved 13 September 2021.
^ Sin FE, Isenberg D (October 2018). "An evaluation of voclosporin for the treatment of lupus nephritis" (PDF). Expert Opinion on Pharmacotherapy. 19 (14): 1613–1621. doi:10.1080/14656566.2018.1516751. PMID 30207816. S2CID 52196375.
^ "Voclosporin: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 25 January 2021.
^ "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.
^ ^a ^b "Drug Trials Snapshot: Lupkynis". U.S. Food and Drug Administration (FDA). 22 January 2021. Retrieved 12 February 2021.
^ "What is voclosporin?". Isotechnika. Retrieved 19 October 2012.
^ U.S. Patent 6,605,593
^ "Drug Approval Package: Lupkynis". U.S. Food and Drug Administration (FDA). 24 February 2021. Retrieved 14 September 2021.

External links[]

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

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[Lupkynis_FDA_label-1] "Lupkynis- voclosporin capsule". DailyMed. Retrieved 13 September 2021.

[pmid30207816-2] Sin FE, Isenberg D (October 2018). "An evaluation of voclosporin for the treatment of lupus nephritis" (PDF). Expert Opinion on Pharmacotherapy. 19 (14): 1613–1621. doi:10.1080/14656566.2018.1516751. PMID 30207816. S2CID 52196375.

[3] "Voclosporin: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 25 January 2021.

[4] "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.

[FDA_snapshot-5] "Drug Trials Snapshot: Lupkynis". U.S. Food and Drug Administration (FDA). 22 January 2021. Retrieved 12 February 2021.

[6] "What is voclosporin?". Isotechnika. Retrieved 19 October 2012.

[7] U.S. Patent 6,605,593

[8] "Drug Approval Package: Lupkynis". U.S. Food and Drug Administration (FDA). 24 February 2021. Retrieved 14 September 2021.

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