Ligand id: 4233

Name: ketamine

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Structure and Physico-chemical Properties

2D Structure
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

Compound class Synthetic organic
Approved drug? Yes (FDA (1970))
International Nonproprietary Names
INN number INN
2156 ketamine
Ketalar | ketamine HCl
Ketamine is a rapidly acting ionotropic glutamate channel blocker with broad therapeutic application, approved in 1970. It is on the World Health Organisation's List of Essential Medicines as a generic product. 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].
Database Links
CAS Registry No. 6740-88-1 (source: Scifinder)
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