U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C63H111N11O12
Molecular Weight 1214.6219
Optical Activity UNSPECIFIED
Defined Stereocenters 12 / 12
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of VOCLOSPORIN

SMILES

[H][C@@]1([C@H](O)[C@H](C)C\C=C\C=C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C(=O)[C@H](CC)NC1=O)C(C)C

InChI

InChIKey=BICRTLVBTLFLRD-PTWUADNWSA-N
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

HIDE SMILES / InChI
Voclosporin (trans-ISA247) is a Cyclosporin A derivative and immunosuppressive compound currently being investigated for the treatment of psoriasis, lupus nephritis and for the prevention of organ rejection in kidney transplant patients. An animal study showed that a lower blood level of Voclosporin was able to produce a greater or similar inhibition of lymphocyte proliferation, expression of T-cell activation surface antigens, and T-cell cytokine production compared to Cyclosporin A. Voclosporin has been shown to be an efficacious and safe immunosuppressant in phase IIb and phase III trials in renal transplant recipients and in plaque psoriasis patients. In clinical trials, Voclosporin added to standard-of-care induction therapy for lupus nephritis increases complete renal remission (CRR) rates, but higher rates of adverse events including death were observed.

Approval Year

PubMed

PubMed

TitleDatePubMed
Name Type Language
VOCLOSPORIN
DASH   INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
VOCLOSPORIN [MART.]
Common Name English
VOCLOSPORIN [MI]
Common Name English
ISA-247
Code English
LUPKYNIS
Brand Name English
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)
Common Name English
Voclosporin [WHO-DD]
Common Name English
voclosporin [INN]
Common Name English
LX211
Code English
CYCLOSPORIN A, 6-((2S,3R,4R,6E)-3-HYDROXY-4-METHYL-2-(METHYLAMINO)-6,8- NONADIENOIC ACID)-
Common Name English
VOCLOSPORIN [USAN]
Common Name English
LX-211
Code English
VOCLOSPORIN [ORANGE BOOK]
Common Name English
ISA247
Code English
ISATX247
Code English
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)
Common Name English
ISATX-247
Code English
Classification Tree Code System Code
EU-Orphan Drug EU/3/12/1085
Created by admin on Fri Dec 15 15:43:14 GMT 2023 , Edited by admin on Fri Dec 15 15:43:14 GMT 2023
WHO-ATC L04AD03
Created by admin on Fri Dec 15 15:43:14 GMT 2023 , Edited by admin on Fri Dec 15 15:43:14 GMT 2023
NCI_THESAURUS C574
Created by admin on Fri Dec 15 15:43:14 GMT 2023 , Edited by admin on Fri Dec 15 15:43:14 GMT 2023
WHO-VATC QL04AD03
Created by admin on Fri Dec 15 15:43:14 GMT 2023 , Edited by admin on Fri Dec 15 15:43:14 GMT 2023
FDA ORPHAN DRUG 227806
Created by admin on Fri Dec 15 15:43:14 GMT 2023 , Edited by admin on Fri Dec 15 15:43:14 GMT 2023
Code System Code Type Description
MERCK INDEX
m11494
Created by admin on Fri Dec 15 15:43:14 GMT 2023 , Edited by admin on Fri Dec 15 15:43:14 GMT 2023
PRIMARY Merck Index
EVMPD
SUB31127
Created by admin on Fri Dec 15 15:43:14 GMT 2023 , Edited by admin on Fri Dec 15 15:43:14 GMT 2023
PRIMARY
CAS
515814-01-4
Created by admin on Fri Dec 15 15:43:14 GMT 2023 , Edited by admin on Fri Dec 15 15:43:14 GMT 2023
PRIMARY
USAN
SS-03
Created by admin on Fri Dec 15 15:43:14 GMT 2023 , Edited by admin on Fri Dec 15 15:43:14 GMT 2023
PRIMARY
DRUG CENTRAL
4366
Created by admin on Fri Dec 15 15:43:14 GMT 2023 , Edited by admin on Fri Dec 15 15:43:14 GMT 2023
PRIMARY
DRUG BANK
DB11693
Created by admin on Fri Dec 15 15:43:14 GMT 2023 , Edited by admin on Fri Dec 15 15:43:14 GMT 2023
PRIMARY
FDA UNII
2PN063X6B1
Created by admin on Fri Dec 15 15:43:14 GMT 2023 , Edited by admin on Fri Dec 15 15:43:14 GMT 2023
PRIMARY
SMS_ID
100000115486
Created by admin on Fri Dec 15 15:43:14 GMT 2023 , Edited by admin on Fri Dec 15 15:43:14 GMT 2023
PRIMARY
NCI_THESAURUS
C152902
Created by admin on Fri Dec 15 15:43:14 GMT 2023 , Edited by admin on Fri Dec 15 15:43:14 GMT 2023
PRIMARY
WIKIPEDIA
VOCLOSPORIN
Created by admin on Fri Dec 15 15:43:14 GMT 2023 , Edited by admin on Fri Dec 15 15:43:14 GMT 2023
PRIMARY
INN
8889
Created by admin on Fri Dec 15 15:43:14 GMT 2023 , Edited by admin on Fri Dec 15 15:43:14 GMT 2023
PRIMARY
ChEMBL
CHEMBL2218919
Created by admin on Fri Dec 15 15:43:14 GMT 2023 , Edited by admin on Fri Dec 15 15:43:14 GMT 2023
PRIMARY
RXCUI
2475166
Created by admin on Fri Dec 15 15:43:14 GMT 2023 , Edited by admin on Fri Dec 15 15:43:14 GMT 2023
PRIMARY
DAILYMED
2PN063X6B1
Created by admin on Fri Dec 15 15:43:14 GMT 2023 , Edited by admin on Fri Dec 15 15:43:14 GMT 2023
PRIMARY
PUBCHEM
6918486
Created by admin on Fri Dec 15 15:43:14 GMT 2023 , Edited by admin on Fri Dec 15 15:43:14 GMT 2023
PRIMARY
EPA CompTox
DTXSID401030488
Created by admin on Fri Dec 15 15:43:14 GMT 2023 , Edited by admin on Fri Dec 15 15:43:14 GMT 2023
PRIMARY