ketamine   Click here for help

GtoPdb Ligand ID: 4233

Synonyms: Ketalar | ketamine HCl
Approved drug
ketamine is an approved drug (FDA (1970))
Compound class: Synthetic organic
Comment: Ketamine is a rapidly acting ionotropic glutamate channel blocker with broad therapeutic application, approved in 1970. The structure shown is the racemate that is also used as the hydrochloride PubChem CID 15851. Of the two ketamine enantiomers, esketamine (S enantiomer) is being developed as a drug in its own right, but the less active arketamine (R enantiomer) is not. A recent report (Nature April 2016) implicated certain ketamine metabolites and their stereoisomers in different mechanisms of action [3]. In particular, (2R,6R) 6-hydroxynorketamine seems to be responsible for NMDAR-independent antidepressant effects. The Nature paper authors filed a patent including some of the data [2].
Ketamine is on the World Health Organisation's List of Essential Medicines. Click here to access the pdf version of the WHO's 21st Essential Medicines list (2019).
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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

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View more information in the IUPHAR Pharmacology Education Project: ketamine

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 2
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 29.1
Molecular weight 237.09
XLogP 2.88
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 CNC1(CCCCC1=O)c1ccccc1Cl
Isomeric SMILES CNC1(CCCCC1=O)c1ccccc1Cl
InChI InChI=1S/C13H16ClNO/c1-15-13(9-5-4-8-12(13)16)10-6-2-3-7-11(10)14/h2-3,6-7,15H,4-5,8-9H2,1H3
InChI Key YQEZLKZALYSWHR-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/)
References
1. Dravid SM, Erreger K, Yuan H, Nicholson K, Le P, Lyuboslavsky P, Almonte A, Murray E, Mosely C, Barber J et al.. (2007)
Subunit-specific mechanisms and proton sensitivity of NMDA receptor channel block.
J Physiol (Lond.), 581 (Pt 1): 107-28. [PMID:17303642]
2. Wainer, IW et al.. (2013)
The use of (2r, 6r)-hydroxynorketamine, (s)-dehydronorketamine and other stereoisomeric dehydro and hydroxylated metabolites of (r,s)- ketamine in the treatment of depression and neuropathic pain.
Patent number: WO2013056229. Assignee: US Government. Priority date: 14/10/2011. Publication date: 18/04/2013.
3. Zanos P, Moaddel R, Morris PJ, Georgiou P, Fischell J, Elmer GI, Alkondon M, Yuan P, Pribut HJ, Singh NS et al.. (2016)
NMDAR inhibition-independent antidepressant actions of ketamine metabolites.
Nature, 533 (7604): 481-6. [PMID:27144355]