Esketamine: Difference between revisions
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| verifiedrevid = 461095357 | | verifiedrevid = 461095357 | ||
| IUPAC_name = (''S'')-2-(2-chlorophenyl)-2-(methylamino)cyclohexanone | | IUPAC_name = (''S'')-2-(2-chlorophenyl)-2-(methylamino)cyclohexanone | ||
| image = | | image = 800px-S-ketamine-3D-balls.png | ||
| width = 180 | | width = 180 | ||
| image2 = | | image2 =Esketamine2DCSD.png | ||
| drug_name = Esketamine | | drug_name = Esketamine | ||
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| StdInChIKey = YQEZLKZALYSWHR-ZDUSSCGKSA-N | | StdInChIKey = YQEZLKZALYSWHR-ZDUSSCGKSA-N | ||
}} | }} | ||
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==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 [[Receptor antagonist#Non-competitive|non-competitive]] [[NMDA receptor antagonist]], but is also a [[dopamine reuptake inhibitor]]. As of July 2014, it is in [[Phases of clinical research#Phase_II|phase II]] [[clinical trial]]s for [[treatment-resistant depression]] (TRD).<ref name="issn2168-9709">{{cite journal | author = Wijesinghe, R | year = 2014 | title = Emerging Therapies for Treatment Resistant Depression | url = http://cpnp.org/resource/mhc/2014/09/emerging-therapies-treatment-resistant-depression | journal = Ment Health Clin | publisher = | volume = 4 | issue = 5 | page = 56 | issn = 2168-9709}}</ref> | '''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 [[Receptor antagonist#Non-competitive|non-competitive]] [[NMDA receptor antagonist]], but is also a [[dopamine reuptake inhibitor]]. As of July 2014, it is in [[Phases of clinical research#Phase_II|phase II]] [[clinical trial]]s for [[treatment-resistant depression]] (TRD).<ref name="issn2168-9709">{{cite journal | author = Wijesinghe, R | year = 2014 | title = Emerging Therapies for Treatment Resistant Depression | url = http://cpnp.org/resource/mhc/2014/09/emerging-therapies-treatment-resistant-depression | journal = Ment Health Clin | publisher = | volume = 4 | issue = 5 | page = 56 | issn = 2168-9709}}</ref> | ||
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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.<ref>{{cite pmid|24316345}}</ref> | 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.<ref>{{cite pmid|24316345}}</ref> | ||
==References== | ==References== | ||
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{{Hallucinogens}} | {{Hallucinogens}} | ||
{{Antidepressants}} | {{Antidepressants}} | ||
[[Category: | [[Category:Drug]] | ||
[[Category:Dopamine reuptake inhibitors]] | [[Category:Dopamine reuptake inhibitors]] | ||
[[Category:NMDA receptor antagonists]] | [[Category:NMDA receptor antagonists]] | ||
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[[Category:Organochlorides]] | [[Category:Organochlorides]] | ||
[[Category:Amines]] | [[Category:Amines]] | ||
[[Category:Antidepressants]] | [[Category:Antidepressants]] | ||
Latest revision as of 15:47, 8 April 2015
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| Trade names | Ketanest S |
| AHFS/Drugs.com | Consumer Drug Information |
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| E number | {{#property:P628}} |
| ECHA InfoCard | {{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value). |
| Chemical and physical data | |
| Formula | C13H16ClNO |
| Molar mass | 237.725 g/mol |
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WikiDoc Resources for Esketamine |
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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
- ↑ 1.0 1.1 1.2 1.3 Wijesinghe, R (2014). "Emerging Therapies for Treatment Resistant Depression". Ment Health Clin. 4 (5): 56. ISSN 2168-9709.
- ↑ 2.0 2.1 PMID 9893910 (PMID 9893910)
Citation will be completed automatically in a few minutes. Jump the queue or expand by hand - ↑ PMID 11719729 (PMID 11719729)
Citation will be completed automatically in a few minutes. Jump the queue or expand by hand - ↑ PMID 10553955 (PMID 10553955)
Citation will be completed automatically in a few minutes. Jump the queue or expand by hand - ↑ 5.0 5.1 PMID 1443509 (PMID 1443509)
Citation will be completed automatically in a few minutes. Jump the queue or expand by hand - ↑ PMID 7840417 (PMID 7840417)
Citation will be completed automatically in a few minutes. Jump the queue or expand by hand - ↑ 7.0 7.1 PMID 9088882 (PMID 9088882)
Citation will be completed automatically in a few minutes. Jump the queue or expand by hand - ↑ http://clinicaltrials.gov/show/NCT01998958
- ↑ PMID 24316345 (PMID 24316345)
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