Esketamine

Esketamine
Clinical data
Trade names	Spravato, Ketanest, others
Other names	(S)-Ketamine; S(+)-Ketamine; JNJ-54135419
AHFS/Drugs.com	Monograph
MedlinePlus	a619017
License data	EU EMA: by INN; US DailyMed: Esketamine; US FDA: Esketamine;
Pregnancy; category	AU: B3;
Addiction; liability	Moderate
Routes of; administration	Intranasal, Intravenous infusion
Drug class	NMDA receptor antagonists; Antidepressants; General anesthetics; Dissociative hallucinogens; Analgesics
ATC code	N01AX14 (WHO) N06AX27 (WHO);
Legal status
Legal status	AU: S8 (Controlled drug); BR: Class B1 (Psychoactive drugs); CA: ℞-only; UK: POM (Prescription only); US: Schedule III; EU: Rx-only; In general: ℞ (Prescription only);
Identifiers
	IUPAC name (S)-2-(2-chlorophenyl)-2-(methylamino)cyclohexanone;
CAS Number	33643-46-8 ; HCl: 33643-47-9 ;
PubChem CID	182137;
IUPHAR/BPS	9152;
DrugBank	DB01221 ; HCl: DBSALT002086 ;
ChemSpider	158414 ; HCl: 26332012 ;
UNII	50LFG02TXD; HCl: L8P1H35P2Z ;
KEGG	D07283 ; HCl: D10627 ;
ChEBI	CHEBI:60799 ; HCl: CHEBI:60800 ;
ChEMBL	ChEMBL395091 ; HCl: ChEMBL2364609 ;
PDB ligand	JC9 (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID6047810 ;
ECHA InfoCard	100.242.065
Chemical and physical data
Formula	C13H16ClNO
Molar mass	237.73 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN[C@]1(c2ccccc2Cl)CCCCC1=O;
	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/t13-/m0/s1 ; Key:YQEZLKZALYSWHR-ZDUSSCGKSA-N ;
	(verify)

Esketamine, sold under the brand names Spravato (for depression) and Ketanest (for anesthesia) among others, is the S(+) enantiomer of ketamine. It is a dissociative hallucinogen drug used as a general anesthetic and as an antidepressant for treatment of depression. Esketamine is the active enantiomer of ketamine in terms of NMDA receptor antagonism and is more potent than racemic ketamine.

It is specifically used as a therapy for treatment-resistant depression (TRD) and for major depressive disorder (MDD) with co-occurring suicidal ideation or behavior. Its efficacy for depression is modest and similar to that of other antidepressants. Esketamine is not used by infusion into a vein for anesthesia as it is only FDA approved for depression in the form of an intranasal spray (the parent compound Ketamine is most often administered intravenously) and under direct medical supervision as a nasal spray.

Adverse effects of esketamine include dissociation, dizziness, sedation, nausea, vomiting, vertigo, numbness, anxiety, lethargy, increased blood pressure, and feelings of drunkenness. Less often, esketamine can cause bladder problems. Esketamine acts primarily as a N-methyl-D-aspartate (NMDA) receptor antagonist but also has other actions.

In the form of racemic ketamine, esketamine was first synthesized in 1962 and introduced for medical use as an anesthetic in 1970. Enantiopure esketamine was introduced for medical use as an anesthetic in 1997 and as an antidepressant in 2019. It is used as an anesthetic in the European Union and as an antidepressant in the United States and Canada. Due to misuse liability as a dissociative hallucinogen, esketamine is a controlled substance.

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