Voclosporin

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
3D model (JSmol)	Interactive image;
ChemSpider	5293683;
ECHA InfoCard	100.357.472
PubChem CID	6918486;
	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
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Voclosporin is an experimental immunosuppressant drug being developed by Isotechnika and Lux Biosciences.^[1] It is being studied for use in solid organ transplantation and autoimmune diseases such as psoriasis. It is an analog of ciclosporin that has enhanced action against calcineurin and greater metabolic stability.^[2] Voclosporin was discovered by Dr. Robert T. Foster and his team at Isotechnika in the mid 1990s (U.S. patent 6,605,593). Isotechnika was founded in 1993. Initially, voclosporin was a mixture of equal proporations of cis and trans geometric isomers of amino acid-1 modified cyclosporine A. Later, in collaboration with Roche, Basle, Switzerland, voclosporin's manufacturing was changed to yield the predominantly trans geometric isomer. The trans isomer possesses most of the beneficial effect of the drug (immunosuppression) in the treatment of organ transplantation and autoimmune disease(s).

References

^ "Voclosporin". Psoriasis Cure Now. Retrieved October 19, 2012.
^ "What is voclosporin?". Isotechnika. Retrieved October 19, 2012.

External links

Voclosporin, ClinicalTrials.gov

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[1] "Voclosporin". Psoriasis Cure Now. Retrieved October 19, 2012.

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

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