ketamine

Ligand id: 4233

Name: ketamine

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 2.97
No. Lipinski's rules broken 0

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
Approved drug? Yes (source: FDA (1970))
IUPAC Name
2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one
International Nonproprietary Names
INN number INN
2156 ketamine
Synonyms
Ketalar
ketamine HCl
Database Links
CAS Registry No. 6740-88-1 (source: Scifinder)
ChEMBL Ligand CHEMBL742
DrugBank Ligand DB01221
PubChem CID 3821
Search Google for chemical match using the InChIKey YQEZLKZALYSWHR-UHFFFAOYSA-N
Search Google for chemicals with the same backbone YQEZLKZALYSWHR
Search PubMed clinical trials ketamine
Search PubMed titles ketamine
Search PubMed titles/abstracts ketamine
Wikipedia Ketamine
Comments
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].