This drug entry is a stub and has not been fully annotated. It was added on October 20, 2016 and is scheduled to be annotated soon.

Identification
NameVoclosporin
Accession NumberDB11693  (DB04906)
TypeSmall Molecule
GroupsInvestigational
Description

Voclosporin is a novel cyclosporine analog and immunosuppressive compound currently being investigated for the treatment of psoriasis and for the prevention of organ rejection in kidney transplant patients. All studies to date suggest that Voclosporin is more potent and less toxic than currently available treatments within the drug class of calcineurin inhibitors.

Structure
Thumb
SynonymsNot Available
External IDs ISA-247 / ISA247 / ISATX-247 / ISATX247 / LX-211 / LX211
Product Ingredients Not Available
ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNII2PN063X6B1
CAS number515814-01-4
WeightAverage: 1214.646
Monoisotopic: 1213.841368058
Chemical FormulaC63H111N11O12
InChI KeyBICRTLVBTLFLRD-PTWUADNWSA-N
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
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-bis(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2,5,8,11,14,17,20,23,26,29,32-undecone
SMILES
CC[C@@H]1NC(=O)[[email protected]]([[email protected]](O)[[email protected]](C)C\C=C\C=C)N(C)C(=O)[[email protected]](C(C)C)N(C)C(=O)[[email protected]](CC(C)C)N(C)C(=O)[[email protected]](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[[email protected]](C)NC(=O)[[email protected]](CC(C)C)N(C)C(=O)[C@@H](NC(=O)[[email protected]](CC(C)C)N(C)C(=O)CN(C)C1=O)C(C)C
Pharmacology
IndicationNot yet annotated
PharmacodynamicsNot yet annotated
Mechanism of actionVoclosporin inhibits calcineurin. As a consequence, it inhibits T cell activation by blocking the transcription of early cytokines.
TargetKindPharmacological actionActionsOrganismUniProt ID
Calcineurin subunit B type 1ProteinunknownNot AvailableHumanP63098 details
Calcineurin subunit B type 2ProteinunknownNot AvailableHumanQ96LZ3 details
Related Articles
Interactions
Drug Interactions
DrugInteractionDrug group
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Lx211.Approved
FingolimodLx211 may increase the immunosuppressive activities of Fingolimod.Approved, Investigational
G17DTThe risk or severity of adverse effects can be increased when Lx211 is combined with G17DT.Investigational
INGN 201The risk or severity of adverse effects can be increased when Lx211 is combined with INGN 201.Investigational
INGN 225The risk or severity of adverse effects can be increased when Lx211 is combined with INGN 225.Investigational
LeflunomideThe risk or severity of adverse effects can be increased when Lx211 is combined with Leflunomide.Approved, Investigational
NatalizumabThe risk or severity of adverse effects can be increased when Lx211 is combined with Natalizumab.Approved, Investigational
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Lx211.Approved, Investigational
RindopepimutThe risk or severity of adverse effects can be increased when Lx211 is combined with CDX-110.Investigational
RoflumilastRoflumilast may increase the immunosuppressive activities of Lx211.Approved
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Lx211.Approved
SRP 299The risk or severity of adverse effects can be increased when Lx211 is combined with SRP 299.Investigational
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Lx211.Approved, Investigational
TofacitinibLx211 may increase the immunosuppressive activities of Tofacitinib.Approved, Investigational
TrastuzumabTrastuzumab may increase the neutropenic activities of Lx211.Approved, Investigational
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General References
  1. Birsan T, Dambrin C, Freitag DG, Yatscoff RW, Morris RE: The novel calcineurin inhibitor ISA247: a more potent immunosuppressant than cyclosporine in vitro. Transpl Int. 2005 May;17(12):767-71. Epub 2005 Apr 13. [PubMed:15827754 ]
  2. Bissonnette R, Papp K, Poulin Y, Lauzon G, Aspeslet L, Huizinga R, Mayo P, Foster RT, Yatscoff RW, Maksymowych WP: A randomized, multicenter, double-blind, placebo-controlled phase 2 trial of ISA247 in patients with chronic plaque psoriasis. J Am Acad Dermatol. 2006 Mar;54(3):472-8. Epub 2006 Jan 23. [PubMed:16488299 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentKeratoconjunctivitis Sicca1
1RecruitingTreatmentVolunteers1
2Active Not RecruitingTreatmentNephritis, Lupus2
2CompletedTreatmentKidney Diseases1
3CompletedTreatmentAnterior Uveitis (AU) / Panuveitis1
3CompletedTreatmentNoninfectious Uveitis1
3CompletedTreatmentDiffuse posterior uveitis / Panuveitis / Uveitis, Intermediate2
3CompletedTreatmentPsoriasis3
3RecruitingTreatmentNephritis, Lupus1
3WithdrawnPreventionTransplantation, Renal1
Not AvailableAvailableNot AvailableImmunosuppression / Transplantation, Kidney1
Properties
StateNot Available
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00401 mg/mLALOGPS
logP4.2ALOGPS
logP3.78ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)11.83ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area278.8 Å2ChemAxon
Rotatable Bond Count16ChemAxon
Refractivity331.79 m3·mol-1ChemAxon
Polarizability133.16 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET featuresNot Available
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
ClassificationNot classified

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Protein domain specific binding
Specific Function:
Regulatory subunit of calcineurin, a calcium-dependent, calmodulin stimulated protein phosphatase. Confers calcium sensitivity.
Gene Name:
PPP3R1
Uniprot ID:
P63098
Molecular Weight:
19299.785 Da
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Calcium ion binding
Specific Function:
Regulatory subunit of calcineurin, a calcium-dependent, calmodulin stimulated protein phosphatase. Confers calcium sensitivity (By similarity).
Gene Name:
PPP3R2
Uniprot ID:
Q96LZ3
Molecular Weight:
19533.065 Da
Drug created on October 20, 2016 14:40 / Updated on June 24, 2017 13:34