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Details

Stereochemistry ABSOLUTE
Molecular Formula C63H111N11O12
Molecular Weight 1214.6244
Optical Activity UNSPECIFIED
Defined Stereocenters 12 / 12
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of VOCLOSPORIN

SMILES

C=C/C(/[H])=C(\[H])/C[C@@]([H])(C)[C@]([H])([C@@]1([H])C(=N[C@@]([H])(CC)C(=O)N(C)CC(=O)N(C)[C@@]([H])(CC(C)C)C(=N[C@@]([H])(C(C)C)C(=O)N(C)[C@@]([H])(CC(C)C)C(=N[C@@]([H])(C)C(=N[C@]([H])(C)C(=O)N(C)[C@@]([H])(CC(C)C)C(=O)N(C)[C@@]([H])(CC(C)C)C(=O)N(C)[C@@]([H])(C(C)C)C(=O)N1C)O)O)O)O)O

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

Molecular Formula C63H111N11O12
Molecular Weight 1214.6244
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 12 / 12
E/Z Centers 1
Optical Activity UNSPECIFIED

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
Substance Class Chemical
Created
by admin
on Sat Jun 26 15:42:25 UTC 2021
Edited
by admin
on Sat Jun 26 15:42:25 UTC 2021
Record UNII
2PN063X6B1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VOCLOSPORIN
DASH   INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
VOCLOSPORIN [MART.]
Common Name English
VOCLOSPORIN [WHO-DD]
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 [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
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 Sat Jun 26 15:42:26 UTC 2021 , Edited by admin on Sat Jun 26 15:42:26 UTC 2021
WHO-ATC L04AD03
Created by admin on Sat Jun 26 15:42:26 UTC 2021 , Edited by admin on Sat Jun 26 15:42:26 UTC 2021
NCI_THESAURUS C574
Created by admin on Sat Jun 26 15:42:26 UTC 2021 , Edited by admin on Sat Jun 26 15:42:26 UTC 2021
WHO-VATC QL04AD03
Created by admin on Sat Jun 26 15:42:26 UTC 2021 , Edited by admin on Sat Jun 26 15:42:26 UTC 2021
FDA ORPHAN DRUG 227806
Created by admin on Sat Jun 26 15:42:26 UTC 2021 , Edited by admin on Sat Jun 26 15:42:26 UTC 2021
Code System Code Type Description
MERCK INDEX
M11494
Created by admin on Sat Jun 26 15:42:26 UTC 2021 , Edited by admin on Sat Jun 26 15:42:26 UTC 2021
PRIMARY Merck Index
EVMPD
SUB31127
Created by admin on Sat Jun 26 15:42:26 UTC 2021 , Edited by admin on Sat Jun 26 15:42:26 UTC 2021
PRIMARY
CAS
515814-01-4
Created by admin on Sat Jun 26 15:42:26 UTC 2021 , Edited by admin on Sat Jun 26 15:42:26 UTC 2021
PRIMARY
DRUG CENTRAL
4366
Created by admin on Sat Jun 26 15:42:26 UTC 2021 , Edited by admin on Sat Jun 26 15:42:26 UTC 2021
PRIMARY
DRUG BANK
DB11693
Created by admin on Sat Jun 26 15:42:26 UTC 2021 , Edited by admin on Sat Jun 26 15:42:26 UTC 2021
PRIMARY
FDA UNII
2PN063X6B1
Created by admin on Sat Jun 26 15:42:26 UTC 2021 , Edited by admin on Sat Jun 26 15:42:26 UTC 2021
PRIMARY
NCI_THESAURUS
C152902
Created by admin on Sat Jun 26 15:42:26 UTC 2021 , Edited by admin on Sat Jun 26 15:42:26 UTC 2021
PRIMARY
WIKIPEDIA
VOCLOSPORIN
Created by admin on Sat Jun 26 15:42:26 UTC 2021 , Edited by admin on Sat Jun 26 15:42:26 UTC 2021
PRIMARY
INN
8889
Created by admin on Sat Jun 26 15:42:26 UTC 2021 , Edited by admin on Sat Jun 26 15:42:26 UTC 2021
PRIMARY
ChEMBL
CHEMBL2218919
Created by admin on Sat Jun 26 15:42:26 UTC 2021 , Edited by admin on Sat Jun 26 15:42:26 UTC 2021
PRIMARY
PUBCHEM
6918486
Created by admin on Sat Jun 26 15:42:26 UTC 2021 , Edited by admin on Sat Jun 26 15:42:26 UTC 2021
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
IN VITRO
TRANSPORTER -> INHIBITOR
clinical studies indicate that voclosporin is a weak inhibitor of P-gp
WEAK
EXCRETED UNCHANGED
Following single oral administration of radiolabeled voclosporin 70 mg
FECAL
BINDER->LIGAND
TRANSPORTER -> INHIBITOR
IN VITRO
EXCRETED UNCHANGED
Following single oral administration of radiolabeled voclosporin 70 mg
URINE
METABOLIC ENZYME -> SUBSTRATE
MAJOR
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
Tmax PHARMACOKINETIC WHEN ADMINISTERED ON AN EMPTY STOMACH
PHARMACOKINETIC