Structure via PubChem · Public domain (PubChem)
esketamine
Sign in to saveAlso known as (-)-ketamine, (S)-(-)-ketamine, (S)-2-(o-chlorophenyl)-2-(methylamino)cyclohexanone, (S)-ketamine
Key facts
- Drug.UNII
- 50LFG02TXD
- Drug.UNII2
- L8P1H35P2Z
- Drug.Verifiedfields
- verified
- Drug.Watchedfields
- verified
- Drug.verifiedrevid
- 461095357
- Drug.image
- Esketamine2DCSD.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 150
- Drug.image2
- S-ketamine-from-HCl-xtal-3D-balls.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 175
- Drug.tradename
- Spravato, Ketanest, Spravado, others
- Drug.MedlinePlus
- a619017
- Drug.licence_EU
- yes
- Drug.DailyMedID
- Esketamine
- Drug.licence_US
- Esketamine
- Drug.pregnancy_AU
- B3
- Drug.addiction_liability
- Moderate
via Wikipedia infobox
Chemical data
- Formula
- C13H16ClNO
- Molecular weight
- 237.72 g/mol
- IUPAC name
- (2S)-2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one
- SMILES
- CN[C@@]1(CCCCC1=O)C2=CC=CC=C2Cl
- InChIKey
- YQEZLKZALYSWHR-ZDUSSCGKSA-N
- XLogP
- 2.2
- Polar surface area
- 29.1 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 237.092042
Show 5 more facts
- chemical formula
- C₁₃H₁₆ClNO
- canonical SMILES
- CNC1(CCCCC1=O)C2=CC=CC=C2Cl
- isomeric SMILES
- CN[C@@]1(CCCCC1=O)C2=CC=CC=C2Cl
- World Health Organisation international non-proprietary name
- esketamine
- Commons category
- Esketamine
via Wikidata · CC0
~15 min read
Article
14 sectionsContents
- Medical uses
- Anesthesia
- Depression
- Adverse effects
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- History
- Society and culture
- Names
- Controversy
- Legal status
- References
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 medication used as a general anesthetic and as an antidepressant. Esketamine is the active enantiomer of ketamine in terms of NMDA receptor antagonism and is more potent than racemic ketamine. However, racemic ketamine produces larger and more sustained antidepressant effects than esketamine.
As an anesthetic, esketamine is indicated for high-risk patients or as a supplement to incomplete regional anesthesia. As an antidepressant, it is specifically used as both a monotherapy and combination therapy for treatment-resistant depression (TRD) as well as major depressive disorder (MDD) with co-occurring suicidal ideation or behavior. Its efficacy as combination therapy for TRD is modest and similar to that of atypical antipsychotics; evidence for its efficacy as a monotherapy is very limited. Antisuicidal efficacy remains unproven. Esketamine is not used by infusion into a vein for depression as it is only FDA-approved in the form of a nasal spray under direct medical supervision for this indication (the parent compound ketamine is most often administered intravenously).