Esketamine

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Esketamine
800px-S-ketamine-3D-balls.png
Esketamine2DCSD.png
Clinical data
Trade namesKetanest S
AHFS/Drugs.comConsumer Drug Information
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PubChem CID
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UNII
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ChEMBL
E number{{#property:P628}}
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Chemical and physical data
FormulaC13H16ClNO
Molar mass237.725 g/mol
3D model (JSmol)
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Esketamine (also (S)-ketamine or S(+)-ketamine) (brand name Ketanest S) is a general anaesthetic and a dissociative. It is the S(+) enantiomer of the drug ketamine, a general anaesthetic. Esketamine acts primarily as a non-competitive NMDA receptor antagonist, but is also a dopamine reuptake inhibitor. As of July 2014, it is in phase II clinical trials for treatment-resistant depression (TRD).[1]

Pharmacology

Esketamine is approximately twice as potent as racemic ketamine.[2] It is eliminated from the human body more quickly than R(−)-ketamine or racemic ketamine, although R(−)-ketamine slows its elimination.[3]

A number of studies have suggested that esketamine has a more medically useful pharmacological action than R(−)-ketamine or racemic ketamine. Esketamine inhibits dopamine transporters eight times more than R(−)-ketamine.[4] This increases dopamine activity in the brain. At doses causing the same intensity of effects, esketamine is generally considered to be more pleasant by patients.[5][6] Patients also generally recover mental function more quickly after being treated with pure esketamine, which may be a result of the fact that it is cleared from their system more quickly.[2][7]

Esketamine has an affinity for the PCP binding site of the NMDA receptor 3-4 times higher than that of R(−)-ketamine. Unlike R(−)-ketamine, esketamine does not bind significantly to sigma receptors. Esketamine increases glucose metabolism in frontal cortex, while R(−)-ketamine decreases glucose metabolism in the brain. This difference may be responsible for the fact that esketamine generally has a more dissociative or hallucinogenic effect while R(−)-ketamine is reportedly more relaxing.[7] However, other studies have found no difference between the isomers in the patient's level of vigilance.[5]

Potential use as an antidepressant

Johnson & Johnson is developing a nasal spray formulation of esketamine as a treatment for depression in patients that have been unresponsive to other antidepressants in the United States.[1] As of July 2014, phase II clinical trials of intranasal esketamine sponsored by the Johnson & Johnson subsidiary Janssen Pharmaceutica are underway.[1][8] Other pharmaceutical companies are also developing new antidepressant drugs that act similarly to ketamine, including Naurex's rapastinel (GLYX-13) and NRX-1074, and Cerecor's CERC-301.[1]

Although most studies suggest that esketamine is preferable for medical uses, a 2013 study found that the antidepressant effect of R(−)-ketamine lasted longer than those of S(+)-ketamine in mice.[9]


References

  1. 1.0 1.1 1.2 1.3 Wijesinghe, R (2014). "Emerging Therapies for Treatment Resistant Depression". Ment Health Clin. 4 (5): 56. ISSN 2168-9709.
  2. 2.0 2.1 PMID 9893910 (PMID 9893910)
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  3. PMID 11719729 (PMID 11719729)
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  4. PMID 10553955 (PMID 10553955)
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  5. 5.0 5.1 PMID 1443509 (PMID 1443509)
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  6. PMID 7840417 (PMID 7840417)
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  7. 7.0 7.1 PMID 9088882 (PMID 9088882)
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  8. http://clinicaltrials.gov/show/NCT01998958
  9. PMID 24316345 (PMID 24316345)
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