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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Click here for structure editor
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/)
References
1. Subbian S, Koo MS, Tsenova L, Khetani V, Zeldis JB, Fallows D, Kaplan G. (2016)
Pharmacologic Inhibition of Host Phosphodiesterase-4 Improves Isoniazid-Mediated Clearance of Mycobacterium tuberculosis.
Front Immunol, 7: 238. [PMID:27379099]
2. Subbian S, Tsenova L, Holloway J, Peixoto B, O'Brien P, Dartois V, Khetani V, Zeldis JB, Kaplan G. (2016)
Adjunctive Phosphodiesterase-4 Inhibitor Therapy Improves Antibiotic Response to Pulmonary Tuberculosis in a Rabbit Model.
EBioMedicine, 4: 104-14. [PMID:26981575]
3. Wallis RS, Ginindza S, Beattie T, Arjun N, Likoti M, Edward VA, Rassool M, Ahmed K, Fielding K, Ahidjo BA et al.. (2021)
Adjunctive host-directed therapies for pulmonary tuberculosis: a prospective, open-label, phase 2, randomised controlled trial.
Lancet Respir Med, 9 (8): 897-908. [PMID:33740465]