Voclosporin

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Voclosporin
Accession Number
DB11693
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.

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 1214.646
Monoisotopic: 1213.841368058
Chemical Formula
C63H111N11O12
Synonyms
Not Available
External IDs
  • ISA-247
  • ISA247
  • ISATX-247
  • ISATX247
  • LX-211
  • LX211

Pharmacology

Indication
Not Available
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics
Not Available
Mechanism of action

Voclosporin inhibits calcineurin. As a consequence, it inhibits T cell activation by blocking the transcription of early cytokines.

TargetActionsOrganism
UCalcineurin subunit B type 1Not AvailableHumans
UCalcineurin subunit B type 2Not AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half-life
Not Available
Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbataceptThe risk or severity of adverse effects can be increased when Abatacept is combined with Voclosporin.
AdalimumabThe risk or severity of adverse effects can be increased when Adalimumab is combined with Voclosporin.
Adenovirus type 7 vaccine liveThe risk or severity of infection can be increased when Adenovirus type 7 vaccine live is combined with Voclosporin.
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Voclosporin.
AlefaceptThe risk or severity of adverse effects can be increased when Alefacept is combined with Voclosporin.
AlemtuzumabThe risk or severity of adverse effects can be increased when Alemtuzumab is combined with Voclosporin.
AltretamineThe risk or severity of adverse effects can be increased when Altretamine is combined with Voclosporin.
AmsacrineThe risk or severity of adverse effects can be increased when Amsacrine is combined with Voclosporin.
AnakinraThe risk or severity of adverse effects can be increased when Anakinra is combined with Voclosporin.
Anthrax immune globulin humanThe therapeutic efficacy of Anthrax immune globulin human can be decreased when used in combination with Voclosporin.
Additional Data Available
  • Extended Description
    Extended Description
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    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity
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  • Evidence Level
    Evidence Level
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  • Action
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Food Interactions
Not Available

Categories

ATC Codes
L04AD03 — Voclosporin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as cyclosporins. These are cyclic depsipeptides containing the cyclosporin backbone.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Peptidomimetics
Sub Class
Peptoid-peptide hybrids
Direct Parent
Cyclosporins
Alternative Parents
Oligopeptides / Macrolactams / Alpha amino acids and derivatives / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Secondary alcohols / Lactams / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds
show 3 more
Substituents
Alcohol / Aliphatic heteromonocyclic compound / Alpha-amino acid or derivatives / Alpha-oligopeptide / Azacycle / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Cyclosporin-backbone / Hydrocarbon derivative
show 12 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available

Chemical Identifiers

UNII
2PN063X6B1
CAS number
515814-01-4
InChI Key
BICRTLVBTLFLRD-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)[C@H]([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)C1=O)C(C)C

References

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]
PubChem Compound
6918486
PubChem Substance
347828058
ChemSpider
5293683
ChEBI
135957
Wikipedia
Voclosporin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3Active Not RecruitingTreatmentNephritis, Lupus1
3CompletedTreatmentAnterior Uveitis (AU) / Panuveitis1
3CompletedTreatmentChorioretinitis / Panuveitis / Uveitis, Intermediate2
3CompletedTreatmentNephritis, Lupus1
3CompletedTreatmentNoninfectious Uveitis1
3CompletedTreatmentPsoriasis3
3WithdrawnPreventionTransplantation, Renal1
2CompletedTreatmentDry Eyes1
2CompletedTreatmentKidney Diseases1
2CompletedTreatmentNephritis, Lupus2

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not 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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

Kind
Protein
Organism
Humans
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
Uniprot Name
Calcineurin subunit B type 1
Molecular Weight
19299.785 Da
Kind
Protein
Organism
Humans
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
Uniprot Name
Calcineurin subunit B type 2
Molecular Weight
19533.065 Da

Drug created on October 20, 2016 14:40 / Updated on June 12, 2020 10:53