dovramilast   Click here for help

GtoPdb Ligand ID: 13581

Synonyms: AMG-634 | CC-11050
Compound class: Synthetic organic
Comment: Dovramilast is a phosphodiesterase 4 (PDE4) inhibitor with anti-inflammatory properties. It is in clinical development as an adjunctive host-directed therapy, to be used in the treatment of leprosy (Hansen's disease) and in combination with conventional antibacterial regimens as a strategy for shortening the duration of treatment for tuberculosis (TB).

dovramilast is commercially available from our sponsors

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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 8
Hydrogen bond donors 1
Rotatable bonds 10
Topological polar surface area 110.39
Molecular weight 472.56
XLogP 0.72
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCOC1=CC(=CC=C1OC)[C@@H](CS(=O)(=O)C)N2CC3=CC=CC(=C3C2=O)NC(=O)C4CC4
Isomeric SMILES CCOC1=C(C=CC(=C1)[C@@H](CS(=O)(=O)C)N2CC3=C(C2=O)C(=CC=C3)NC(=O)C4CC4)OC
InChI InChI=1S/C24H28N2O6S/c1-4-32-21-12-16(10-11-20(21)31-2)19(14-33(3,29)30)26-13-17-6-5-7-18(22(17)24(26)28)25-23(27)15-8-9-15/h5-7,10-12,15,19H,4,8-9,13-14H2,1-3H3,(H,25,27)/t19-/m1/s1
InChI Key QDZOBXFRIVOQBR-LJQANCHMSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
In November 2023, the US FDA issued Orphan Drug Designation for dovramilast as a treatment for leprosy type 2 reactions (also known as erythema nodosum leprosum), a severe complication of leprosy that is immune-mediated.
Dovramilast has completed a Phase 2 clinical trial (NCT01300208) to evaluate safety and efficacy in subjects with leprosy type 2 reactions, with a second trial now recruiting (NCT03807362). It has also completed a Phase 2 study, as an adjunctive host-directed TB therapy (NCT02968927) and found to be safe, reasonably well tolerated, and with potential to enhance recovery [3].
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT01300208 To Evaluate the Preliminary Safety, Tolerability, Pharmacokinetics, Pharmacodynamics and Efficacy of CC-11050 in Subjects With Discoid Lupus Erythematosus and Subacute Cutaneous Lupus Erythematosus Phase 2 Interventional Amgen
NCT03807362 CC-11050 Trial in Nepalese Patients With Erythema Nodosum Leprosum Phase 2 Interventional The Leprosy Mission Nepal
NCT02968927 TB Host Directed Therapy Phase 2 Interventional The Aurum Institute NPC 3