dexmedetomidine   Click here for help

GtoPdb Ligand ID: 521

Synonyms: Dexdor® | Igalmi® (dexmedetomidine sublingual film) | MPV 1440 | Precedex®
Approved drug PDB Ligand
dexmedetomidine is an approved drug (FDA (1999), EMA (2011))
Compound class: Synthetic organic
Comment: Dexmedetomidine is a somewhat selective α2-adrenoceptor agonist with sedative properties.
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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

dexmedetomidine 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 1
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 28.68
Molecular weight 200.13
XLogP 3.13
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 Cc1cccc(c1C)C(c1c[nH]cn1)C
Isomeric SMILES Cc1cccc(c1C)[C@@H](c1c[nH]cn1)C
InChI InChI=1S/C13H16N2/c1-9-5-4-6-12(10(9)2)11(3)13-7-14-8-15-13/h4-8,11H,1-3H3,(H,14,15)/t11-/m0/s1
InChI Key CUHVIMMYOGQXCV-NSHDSACASA-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. Jasper JR, Lesnick JD, Chang LK, Yamanishi SS, Chang TK, Hsu SA, Daunt DA, Bonhaus DW, Eglen RM. (1998)
Ligand efficacy and potency at recombinant alpha2 adrenergic receptors: agonist-mediated [35S]GTPgammaS binding.
Biochem Pharmacol, 55 (7): 1035-43. [PMID:9605427]
2. MacDonald E, Kobilka BK, Scheinin M. (1997)
Gene targeting--homing in on alpha 2-adrenoceptor-subtype function.
Trends Pharmacol Sci, 18 (6): 211-9. [PMID:9227000]
3. Peltonen JM, Pihlavisto M, Scheinin M. (1998)
Subtype-specific stimulation of [35S]GTPgammaS binding by recombinant alpha2-adrenoceptors.
Eur J Pharmacol, 355 (2-3): 275-9. [PMID:9760042]
4. Pihlavisto M, Sjöholm B, Scheinin M, Wurster S. (1998)
Modulation of agonist binding to recombinant human alpha2-adrenoceptors by sodium ions.
Biochim Biophys Acta, 1448 (1): 135-46. [PMID:9824686]
5. Proudman RGW, Akinaga J, Baker JG. (2022)
The signaling and selectivity of α-adrenoceptor agonists for the human α2A, α2B and α2C-adrenoceptors and comparison with human α1 and β-adrenoceptors.
Pharmacol Res Perspect, 10 (5): e01003. [PMID:36101495]