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Esketamine

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7 API Suppliers, 6 USDMF, 4 CEP/COS, 1 EU WC, 7 NDC API, 7 Listed Suppliers

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Synopsis

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Chemistry

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Also known as: (s)-ketamine, L-ketamine, (-)-ketamine, S-ketamine, 33643-46-8, (s)-(-)-ketamine

Molecular Formula

C₁₃H₁₆ClNO

Molecular Weight

237.72 g/mol

InChI Key

YQEZLKZALYSWHR-ZDUSSCGKSA-N

FDA UNII

50LFG02TXD

Esketamine is a cyclohexanone derivative and S-enantiomer of racemic ketamine, with analgesic, anesthetic and antidepressant activities. Although the mechanism of action is not fully understood, upon administration, esketamine targets, non-competitively binds to, and blocks N-methyl D-aspartate (NMDA) receptors. This reduces pain perception, induces sedation, and produce dissociative anesthesia.

1 2D Structure

Esketamine Hydrochloride

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one

2.1.2 InChI

InChI=1S/C13H16ClNO/c1-15-13(9-5-4-8-12(13)16)10-6-2-3-7-11(10)14/h2-3,6-7,15H,4-5,8-9H2,1H3/t13-/m0/s1

2.1.3 InChI Key

YQEZLKZALYSWHR-ZDUSSCGKSA-N

2.1.4 Canonical SMILES

CNC1(CCCCC1=O)C2=CC=CC=C2Cl

2.1.5 Isomeric SMILES

CN[C@@]1(CCCCC1=O)C2=CC=CC=C2Cl

2.2 Other Identifiers

2.2.1 UNII

50LFG02TXD

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (-)-ketamine

2. (s)-2-(o-chlorophenyl)-2-(methylamino)cyclohexanone

3. Kataved

4. L-ketamine

5. S-ketamine

6. Spravato

2.3.2 Depositor-Supplied Synonyms

1. (s)-ketamine

2. L-ketamine

3. (-)-ketamine

4. S-ketamine

5. 33643-46-8

6. (s)-(-)-ketamine

7. Spravato

8. S-(-)-ketamine

9. Ketaved

10. Keta-s

11. Ketamine, S-

12. Esketamine Free Base

13. Ketamine, (s)-

14. (s)-2-(o-chlorophenyl)-2-(methylamino)cyclohexanone

15. 50lfg02txd

16. Chebi:60799

17. Jnj-54135419

18. (+)-ketamine

19. (2s)-2-(2-chlorophenyl)-2-(methylamino)cyclohexanone

20. (2s)-2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one

21. Cyclohexanone, 2-(2-chlorophenyl)-2-(methylamino)-, (2s)-

22. (2~{s})-2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one

23. Cyclohexanone, 2-(2-chlorophenyl)-2-(methylamino)-, (s)-

24. Unii-50lfg02txd

25. Kataved

26. Esketamine [usan:inn:ban]

27. S-ketamin

28. Jc9

29. Esketamine [inn]

30. Esketamine (usan/inn)

31. Esketamine [usan]

32. Dsstox_cid_27787

33. Dsstox_rid_82562

34. Esketamine [who-dd]

35. Dsstox_gsid_47810

36. Chembl395091

37. Gtpl9152

38. Schembl5512024

39. Dtxsid6047810

40. 33643-46-8 (free Base)

41. Tox21_113206

42. Zinc35999642

43. Akos027321219

44. Db11823

45. Ncgc00185910-01

46. Cas-33643-46-8

47. D07283

48. Q2365493

49. (2s)-2-(2-chlorophenyl)-2-methylaminocyclohexan-1-one

50. (s)-2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one

51. Cyclohexanone, 2-(2-chlorophenyl)-2-(methylamino)-, (2s)- (9ci)

52. Cyclohexanone, 2-(o-chlorophenyl)-2-(methylamino)-, (-)-

53. Cyclohexanone, 2-(o-chlorophenyl)-2-(methylamino)-, (-)- (8ci)

2.4 Create Date

2005-06-08

3 Chemical and Physical Properties

Molecular Formula	C₁₃H₁₆ClNO
Molecular Weight	237.72 g/mol
XLogP3	2.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	2
Exact Mass	237.0920418 g/mol
Monoisotopic Mass	237.0920418 g/mol
Topological Polar Surface Area	29.1 Å²
Heavy Atom Count	16
Formal Charge	0
Complexity	269
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

This drug is indicated in conjunction with an oral antidepressant for the treatment of treatment-resistant depression (TRD) in adults. Note: Esketamine is not approved as an anesthetic agent. The safety and effectiveness of esketamine as an anesthetic agent have not been established to this date.

FDA Label

Spravato, in combination with a SSRI or SNRI, is indicated for adults with treatment-resistant Major Depressive Disorder, who have not responded to at least two different treatments with antidepressants in the current moderate to severe depressive episode.

5 Pharmacology and Biochemistry

5.1 Pharmacology

**General effects** Esketamine is considered a central nervous system (CNS) depressant agent. It may cause sedation, dizziness, and lethargy, among other symptoms. This drug has dissociative and antidepressant properties. Acutely, esketamine may impair attention, judgment, thinking, reaction speed, and motor skills. Two placebo-controlled studies were performed to evaluate the effects of ketamine on the ability to drive. The effects of esketamine 84 mg were comparable to placebo at 6 hours and 18 hours post ingestion. **Effects on cardiac electrophysiology** The effect of esketamine (84 mg nasal spray and 0.8 mg/kg esketamine intravenously infused over 40 minutes) on the QTc interval was studied in a randomized, double-blind, placebo-, and positive-controlled (moxifloxacin 400 mg), 4-period, crossover study in 60 healthy volunteers. A marked increase in heart rate (higher than 10 bpm) was measured in subjects receiving intranasal and intravenous esketamine. Summative evidence from both nonclinical and clinical data suggests a lack of clinically relevant QTc prolongation at the normal therapeutic dose of esketamine. **Effects on blood pressure** Eskestamine causes increases in systolic and/or diastolic blood pressure at all therapeutic doses. Peak blood pressure elevation after esketamine administration occurs about 40 minutes after administration and lasts approximately 4 hours. **Cognitive effects** In a study of healthy volunteers, one dose of this agent caused decline in cognitive performance 40 minutes after administration. Compared to subjects ingesting a placebo, esketamine-treated subjects required a higher level of effort to complete assigned cognitive tests at 40 minutes after administration. Cognitive performance and mental effort were found to be similar between esketamine and placebo at 2 hours after administration. Reports of long-term memory or cognitive impairment have been made following repeated ketamine misuse or abuse. No adverse effects of esketamine nasal spray on cognitive function were seen in a one-year open-label safety study. The long-term cognitive effects of esketamine have not been studied for more than a 1 year period, therefore, the risk of cognitive decline with long-term use is not yet confirmed.

5.2 MeSH Pharmacological Classification

Antidepressive Agents

Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems. (See all compounds classified as Antidepressive Agents.)

5.3 ATC Code

N06AX27

N - Nervous system

N01 - Anesthetics

N01A - Anesthetics, general

N01AX - Other general anesthetics

N01AX14 - Esketamine

N - Nervous system

N06 - Psychoanaleptics

N06A - Antidepressants

N06AX - Other antidepressants

N06AX27 - Esketamine

5.4 Absorption, Distribution and Excretion

Absorption

Due to the fact that this drug is administered via nasal spray, absorption is rapid. The mean absolute bioavailability is approximately 48% after esketamine nasal spray administration. The time to achieve peak esketamine plasma concentration is 20 to 40 minutes after the last nasal spray of esketamine. Inter-subject variability of esketamine ranges from 27% to 66% for Cmax (maximum concentration) and 18% to 45% for AUC (area under the curve). The intra-subject variability of esketamine is about 15% for Cmax and 10% for AUC.

Route of Elimination

Less than 1% of a dose of nasal esketamine is measured as unchanged drug, excreted in the urine. Following intravenous (IV) or oral (PO) administration, esketamine-derived metabolites were mainly recovered in urine ( 78% of a radiolabeled dose), and a smaller percentage was measured in the feces ( 2% of a radiolabeled dose).

Volume of Distribution

The average steady-state volume of distribution of esketamine administered by the intravenous route is 709 L.

Clearance

The average clearance of esketamine is approximately 89 L/hour following intravenous administration. Elimination of the major esketamine metabolite, _noresketamine_, from plasma is slower than esketamine. The decrease of noresketamine plasma concentrations occurs in a biphasic fashion, with a more rapid decline for the first 4 hours post-administration, and an average terminal t1/2 of approximately 8 hours.

5.5 Metabolism/Metabolites

Esketamine is mainly metabolized to the _noresketamine_ metabolite by cytochrome P450 (CYP) enzymes, CYP2B6 and CYP3A4, and to a lesser extent, CYP2C9 and CYP2C19. Noresketamine is metabolized by cytochrome-dependent metabolic pathways followed by subsequent glucuronidation of metabolites.

5.6 Biological Half-Life

The mean terminal half-life (t1/2) ranges from 7 to 12 hours.

5.7 Mechanism of Action

Esketamine, the S-enantiomer of racemic ketamine, is a non-selective, non-competitive antagonist of the N-methyl-D-aspartate (NMDA) receptor, an ionotropic glutamate receptor. The exact mechanism by which esketamine acts as an antidepressant is unknown. The primary circulating metabolite of esketamine (_noresketamine_) shows activity at the same receptor with a weaker affinity.

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