voclosporin   Click here for help

GtoPdb Ligand ID: 11388

Synonyms: 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] | E-ISA247 | ISA(TX)247 | ISA-247 | ISA247 | ISATX247 | Lupkynis® | R 1524 | R-1524 | R1524
Approved drug Immunopharmacology Ligand
voclosporin is an approved drug (FDA (2021))
Comment: Voclosporin (ISA247, ISATX247) is a cyclic peptide that is a semi-synthetic cyclosporine analogue [1-3,6], but with distinct clinical efficacy and safety profiles [5]. Like cyclosporine, it has immunosuppressive action, and it binds cyclophilin A [4]. Functionally, it acts as a calcineurin inhibitor. Prior to voclosporin, clinically used calcineurin inhibitors were cyclosporine (cyclosporin A), tacrolimus, and pimecrolimus.
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2D Structure
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SMILES / InChI / InChIKey
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Canonical SMILES C=C/C=C/C[C@H]([C@H]([C@H]1C(=O)N[C@@H](CC)C(=O)N(C)CC(=O)N(C)[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N(C)[C@@H](CC(C)C)C(=O)N[C@H](C(=O)N[C@@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N1C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)O)C
Isomeric SMILES C=C/C=C/C[C@H]([C@H]([C@H]1C(=O)N[C@@H](CC)C(=O)N(C)CC(=O)N(C)[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N(C)[C@@H](CC(C)C)C(=O)N[C@H](C(=O)N[C@@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N1C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)O)C
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
InChI Key BICRTLVBTLFLRD-PTWUADNWSA-N
Classification Click here for help
Compound class Peptide or derivative
Approved drug? Yes (FDA (2021))
IUPAC Name Click here for help
(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
International Nonproprietary Names Click here for help
INN number INN
8889 voclosporin
Synonyms Click here for help
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] | E-ISA247 | ISA(TX)247 | ISA-247 | ISA247 | ISATX247 | Lupkynis® | R 1524 | R-1524 | R1524
Database Links Click here for help
CAS Registry No. 515814-01-4 (source: WHO INN record)
DrugBank Ligand DB11693
GtoPdb PubChem SID 440816757
PubChem CID 6918486
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