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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2D Structure
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Physico-chemical Properties
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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
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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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1970))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
2156 ketamine
Synonyms Click here for help
Ketalar | ketamine HCl
Database Links Click here for help
CAS Registry No. 6740-88-1 (source: Scifinder)
DrugBank Ligand DB01221
DrugCentral Ligand 1523
GtoPdb PubChem SID 178101050
PubChem CID 3821
Search Google for chemical match using the InChIKey YQEZLKZALYSWHR-UHFFFAOYSA-N
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UniChem Compound Search for chemical match using the InChIKey YQEZLKZALYSWHR-UHFFFAOYSA-N
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Wikipedia Ketamine