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esketamine

Structure via PubChem · Public domain (PubChem)

EntityQ2365493· pop 22· linked from 1,932 articles

esketamine

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Also 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
Sources (3)

via Wikidata · CC0

~15 min read

Article

14 sections
Contents
  • 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).

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