mocravimod   Click here for help

GtoPdb Ligand ID: 9727

Synonyms: compound 2 [PMID: 23124563] | KRP-203 | KRP203
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Mocravimod (KRP-203) is a sphingosine 1-phosphate receptor type 1 (S1P1R) agonist with immunomodulatory potential [2]. It is a highly modified analogue of the approved MS drug fingolimod.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 3
Rotatable bonds 10
Topological polar surface area 101.01
Molecular weight 443.13
XLogP 4.71
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES OCC(CCc1ccc(cc1Cl)Sc1cccc(c1)OCc1ccccc1)(CO)N
Isomeric SMILES OCC(CCc1ccc(cc1Cl)Sc1cccc(c1)OCc1ccccc1)(CO)N
InChI InChI=1S/C24H26ClNO3S/c25-23-14-22(10-9-19(23)11-12-24(26,16-27)17-28)30-21-8-4-7-20(13-21)29-15-18-5-2-1-3-6-18/h1-10,13-14,27-28H,11-12,15-17,26H2
InChI Key IINUNQPYJGJCJI-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Preclinical evidence suggests efficacy in preventing graft rejection [1-3].A Phase 1 trial in patients undergoing stem cell transplant for hematological malignancies has been initiated to evaluate translatability to humans (NCT01830010). Mocravimod has completed a Phase 2 clinical trial in SLE patients (NCT01294774), and a separate Phase 2 trial in ulcerative colitis patients with refractory disease has been terminated (NCT01375179).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The structural similarity of mocravimod to that of fingolimod suggests that this compound may act via a similar mechanism to effectively sequester peripheral lymphocytes and accelerate lymphocyte homing into the secondary lymphoid organ.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT01294774 Safety and Efficacy of KRP203 in Subacute Cutaneous Lupus Erythematosus Phase 2 Interventional Novartis
NCT01375179 Efficacy & Safety in Moderately Active Refractory Ulcerative Colitis Patients Phase 2 Interventional Novartis
NCT01830010 A Two-part Study to Evaluate the Safety, Tolerability, Pharmacokinetics, and Efficacy of KRP203 in Patients Undergoing Stem Cell Transplant for Hematological Malignancies Phase 1 Interventional Novartis