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/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
N-[2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-3-oxo-1H-isoindol-4-yl]cyclopropanecarboxamide
International Nonproprietary Names Click here for help
INN number INN
12150 dovramilast
Synonyms Click here for help
AMG-634 | CC-11050
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo CC-11050
Other databases
CAS Registry No. 340019-69-4 (source: Scifinder)
ChEMBL Ligand CHEMBL4297460
DrugBank Ligand DB16242
GtoPdb PubChem SID 504705400
PubChem CID 10322579
Search Google for chemical match using the InChIKey QDZOBXFRIVOQBR-LJQANCHMSA-N
Search Google for chemicals with the same backbone QDZOBXFRIVOQBR
Search PubMed clinical trials dovramilast
Search PubMed titles dovramilast
Search PubMed titles/abstracts dovramilast
UniChem Compound Search for chemical match using the InChIKey QDZOBXFRIVOQBR-LJQANCHMSA-N
UniChem Connectivity Search for chemical match using the InChIKey QDZOBXFRIVOQBR-LJQANCHMSA-N

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MedChemExpress
Dovramilast (links to external site)
Cat. No. HY-147263