Esketamine

Short-term antidepressant
efficacy of esketamine versus placebo
added to an existing oral antidepressant in people with depression.png

Short-term antidepressant efficacy of esketamine
versus placebo added to an existing oral antidepressant
in people with depression and suicidality.png

Medication used for treatment-resistant depression

Esketamine
Trade names	Spravato
Chemical nomenclature
IUPAC name	(2S)-2-(2-chlorophenyl)-2-(methylamino)cyclohexanone
Routes	Nasal spray
Metabolism	Liver (CYP2B6, CYP3A4)
Half-life	7-12 hours
Excretion	Urine
Identifiers
CAS Number	33643-46-8
PubChem	123631
DrugBank	DB01221
ChemSpider	110146
UNII	50LFG48P1T
KEGG	D09373
ChEMBL	1201208
Chemical data
Chemical formula	C13H16N1O1Cl1
SMILES	ClC1=CC=CC=C1[C@@H](C2(NC)CCCCC2)=O
InChI	1S/C13H16ClNO/c1-15-12(13(16)10-6-2-3-7-10)9-4-5-8-11(14)12/h4-5,8-10,15H,2-3,6-7H2,1H3/t12-/m0/s1
InChIKey	YQEZLKZALYSWHR-LBPRGKRZSA-N

Esketamine, sold under the brand name Spravato, is a medication used for the treatment of treatment-resistant depression (TRD). It is a stereoisomer of ketamine, specifically the S(+) enantiomer. Esketamine is administered as a nasal spray and works as a NMDA receptor antagonist.

Medical uses

Esketamine is primarily used for treatment-resistant depression in adults who have not responded adequately to at least two different antidepressant treatments. It is often used in conjunction with an oral antidepressant.

Mechanism of action

Esketamine acts as a NMDA receptor antagonist, which is believed to contribute to its rapid antidepressant effects. By blocking the NMDA receptor, esketamine increases the levels of glutamate in the brain, which in turn activates AMPA receptors and leads to the release of brain-derived neurotrophic factor (BDNF). This cascade of events is thought to contribute to the synaptic plasticity and antidepressant effects observed with esketamine.

Side effects

Common side effects of esketamine include dissociation, dizziness, nausea, sedation, vertigo, and increased blood pressure. Due to its potential for abuse and dissociative effects, esketamine is classified as a Schedule III controlled substance in the United States.

History

Esketamine was approved by the U.S. Food and Drug Administration (FDA) in March 2019 for the treatment of treatment-resistant depression. It was developed by Janssen Pharmaceuticals, a subsidiary of Johnson & Johnson.

Related pages

• Ketamine
• Antidepressant
• NMDA receptor antagonist
• Treatment-resistant depression
• Brain-derived neurotrophic factor

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