ketamine

Ligand id: 4233

Name: ketamine

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Structure and Physico-chemical Properties

2D Structure
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Calculated Physico-chemical Properties
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

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1970))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one
International Nonproprietary Names
INN number INN
2156 ketamine
Synonyms
Ketalar | ketamine HCl
Comments
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).
Database Links
CAS Registry No. 6740-88-1 (source: Scifinder)
ChEMBL Ligand CHEMBL742
DrugBank Ligand DB01221
GtoPdb PubChem SID 178101050
PubChem CID 3821
Search Google for chemical match using the InChIKey YQEZLKZALYSWHR-UHFFFAOYSA-N
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Wikipedia Ketamine