Esketamine hydrochlorideProduct ingredient for Esketamine

Name
Esketamine hydrochloride
Drug Entry
Esketamine

Major depressive disorder (MDD) is a significant cause of disability worldwide and the most common illness preceding suicide.5,3 On March 5, 2019, the nasal spray drug, esketamine, also known as Spravato (by Janssen Pharmaceuticals), was approved by the FDA for treatment-resistant major depression.

Esketamine is the s-enantiomer of Ketamine. Ketamine is a mixture of two enantiomers (mirror image molecules). This is the first time that the FDA has approved esketamine for any use. The FDA approved ketamine (Ketalar) in 1970.4

Esketamine may prove to be a promising treatment for patients diagnosed with major depressive disorder who have not experienced an improvement in symptoms despite treatment with various medications and therapies. The intranasal route of administration for this drug allows for easy administration and a fast onset of action, which sets it apart from many other antidepressant agents that may take several weeks to take effect.

Accession Number
DBSALT002086
Structure
Synonyms
(S)-(+)-ketamine hydrochloride / (S)-2-(o-chlorophenyl)-2-(methylamino)cyclohexanone HCl / (S)-2-(o-chlorophenyl)-2-(methylamino)cyclohexanone hydrochloride / (S)-ketamine HCl / (S)-ketamine hydrochloride / Esketamine HCl / Esketamine hydrochloride
UNII
L8P1H35P2Z
CAS Number
33643-47-9
Weight
Average: 274.19
Monoisotopic: 273.0687196
Chemical Formula
C13H17Cl2NO
InChI Key
VCMGMSHEPQENPE-ZOWNYOTGSA-N
InChI
InChI=1S/C13H16ClNO.ClH/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;1H/t13-;/m0./s1
IUPAC Name
(2S)-2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one hydrochloride
SMILES
Cl.CN[C@@]1(CCCCC1=O)C1=CC=CC=C1Cl
ChemSpider
26332012
ChEBI
60800
ChEMBL
CHEMBL2364609
Wikipedia
Esketamine
Predicted Properties
PropertyValueSource
Water Solubility0.0464 mg/mLALOGPS
logP2.69ALOGPS
logP3.35ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)19.77ChemAxon
pKa (Strongest Basic)7.16ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.1 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity65.55 m3·mol-1ChemAxon
Polarizability24.97 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon