pomalidomide   Click here for help

GtoPdb Ligand ID: 7348

Synonyms: CC-4047 | IMID-3 | Imnovid® | Pomalyst®
Approved drug Immunopharmacology Ligand
pomalidomide is an approved drug (FDA and EMA (2013))
Compound class: Synthetic organic
Comment: Pomalidomide is an analogue of thalidomide with similar immunomodulatory antineoplastic activity.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

pomalidomide 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 7
Hydrogen bond donors 2
Rotatable bonds 1
Topological polar surface area 109.57
Molecular weight 273.07
XLogP -0.56
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 O=C1CCC(C(=O)N1)N1C(=O)c2c(C1=O)c(N)ccc2
Isomeric SMILES O=C1CCC(C(=O)N1)N1C(=O)c2c(C1=O)c(N)ccc2
InChI InChI=1S/C13H11N3O4/c14-7-3-1-2-6-10(7)13(20)16(12(6)19)8-4-5-9(17)15-11(8)18/h1-3,8H,4-5,14H2,(H,15,17,18)
InChI Key UVSMNLNDYGZFPF-UHFFFAOYSA-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
Pomalidomide is approved to treat multiple myeloma. In May 2020, the FDA expanded approval to permit pomalidomide's use to treat Kaposi sarcoma (in HAART-resistant HIV+ve patients or HIV-ve patients).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The mechanism of action of this drug is complex. Its immunomodulatory action may involve inhibition of the production of pro-inflammatory cytokines and inhibition of COX2 transcription [6]. See the DrugBank link for more details. The primary target of pomalidomide (and thalidomide) may be the protein cereblon (CRBM, Q96SW2) [3,5], which has been linked to the teratogenic activity of these drugs [1]. Cereblon has multiple actions, including participation in protein ubiquitination complexes and regulation of potassium channels [2].
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com
European Medicines Agency (EMA)