Voclosporin
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
- 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.
Learn More- Pharmacodynamics
- Not Available
- Mechanism of action
Voclosporin inhibits calcineurin. As a consequence, it inhibits T cell activation by blocking the transcription of early cytokines.
Target Actions Organism UCalcineurin subunit B type 1 Not Available Humans UCalcineurin subunit B type 2 Not Available Humans - 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.
Learn More- 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.
Drug Interaction Unlock Additional DataAbatacept The risk or severity of adverse effects can be increased when Abatacept is combined with Voclosporin. Adalimumab The risk or severity of adverse effects can be increased when Adalimumab is combined with Voclosporin. Adenovirus type 7 vaccine live The risk or severity of infection can be increased when Adenovirus type 7 vaccine live is combined with Voclosporin. Aldesleukin The risk or severity of adverse effects can be increased when Aldesleukin is combined with Voclosporin. Alefacept The risk or severity of adverse effects can be increased when Alefacept is combined with Voclosporin. Alemtuzumab The risk or severity of adverse effects can be increased when Alemtuzumab is combined with Voclosporin. Altretamine The risk or severity of adverse effects can be increased when Altretamine is combined with Voclosporin. Amsacrine The risk or severity of adverse effects can be increased when Amsacrine is combined with Voclosporin. Anakinra The risk or severity of adverse effects can be increased when Anakinra is combined with Voclosporin. Anthrax immune globulin human The therapeutic efficacy of Anthrax immune globulin human can be decreased when used in combination with Voclosporin. Additional Data Available- Extended DescriptionExtended DescriptionAvailable for Purchase
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - SeveritySeverityAvailable for Purchase
A severity rating for each drug interaction, from minor to major.
Learn more - Evidence LevelEvidence LevelAvailable for Purchase
A rating for the strength of the evidence supporting each drug interaction.
Learn more - ActionActionAvailable for Purchase
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- 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
- 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]
- 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
- PubChem Compound
- 6918486
- PubChem Substance
- 347828058
- ChemSpider
- 5293683
- ChEBI
- 135957
- Wikipedia
- Voclosporin
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Active Not Recruiting Treatment Nephritis, Lupus 1 3 Completed Treatment Anterior Uveitis (AU) / Panuveitis 1 3 Completed Treatment Chorioretinitis / Panuveitis / Uveitis, Intermediate 2 3 Completed Treatment Nephritis, Lupus 1 3 Completed Treatment Noninfectious Uveitis 1 3 Completed Treatment Psoriasis 3 3 Withdrawn Prevention Transplantation, Renal 1 2 Completed Treatment Dry Eyes 1 2 Completed Treatment Kidney Diseases 1 2 Completed Treatment Nephritis, Lupus 2
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
Property Value Source Water Solubility 0.00401 mg/mL ALOGPS logP 4.2 ALOGPS logP 3.78 ChemAxon logS -5.5 ALOGPS pKa (Strongest Acidic) 11.83 ChemAxon pKa (Strongest Basic) -2.4 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 12 ChemAxon Hydrogen Donor Count 5 ChemAxon Polar Surface Area 278.8 Å2 ChemAxon Rotatable Bond Count 16 ChemAxon Refractivity 331.79 m3·mol-1 ChemAxon Polarizability 133.16 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 0 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - 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