esketamine : The S- (more active) enantiomer of ketamine. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
ID Source | ID |
---|---|
PubMed CID | 182137 |
CHEMBL ID | 395091 |
CHEBI ID | 60799 |
SCHEMBL ID | 5512024 |
Synonym |
---|
(s)-2-(o-chlorophenyl)-2-(methylamino)cyclohexanone |
(2s)-2-(2-chlorophenyl)-2-(methylamino)cyclohexanone |
D07283 |
esketamine (usan/inn) |
(s)-(-)-ketamine |
cyclohexanone, 2-(2-chlorophenyl)-2-(methylamino)-, (s)- |
l-ketamine |
(s)-ketamine |
esketamine |
cyclohexanone, 2-(o-chlorophenyl)-2-(methylamino)-, (-)- (8ci) |
33643-46-8 |
cyclohexanone, 2-(2-chlorophenyl)-2-(methylamino)-, (2s)- |
(-)-ketamine |
cyclohexanone, 2-(2-chlorophenyl)-2-(methylamino)-, (2s)- (9ci) |
s-ketamine |
ketaved |
CHEMBL395091 |
ketamine, (s)- |
keta-s |
chebi:60799 , |
jnj-54135419 |
ketamine, s- |
s-(-)-ketamine |
(2s)-2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one |
unii-50lfg02txd |
spravato |
kataved |
esketamine [usan:inn:ban] |
50lfg02txd , |
cas-33643-46-8 |
dtxcid4027787 |
tox21_113206 |
NCGC00185910-01 |
dtxsid6047810 , |
esketamine [usan] |
cyclohexanone, 2-(o-chlorophenyl)-2-(methylamino)-, (-)- |
esketamine [who-dd] |
esketamine [inn] |
SCHEMBL5512024 |
gtpl9152 |
(2s)-2-(2-chlorophenyl)-2-methylaminocyclohexan-1-one |
AKOS027321219 |
YQEZLKZALYSWHR-ZDUSSCGKSA-N |
s-ketamin |
DB11823 |
Q2365493 |
33643-46-8 (free base) |
esketamine free base |
(s)-2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one |
JC9 , |
(2~{s})-2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one |
esketaminum |
n06ax27 |
n01ax14 |
esketamina |
Esketamine is a novel treatment for treatment resistant depression (TRD) and was approved by the FDA in early 2019. Esketamine, which is an S-enantiomer of ketamine, is better than conventional antidepressants and even better than R-ketamine.
Esketamine has been approved as a rapid-acting intranasal treatment for treatment-resistant depression (TRD) Esketamine and ketamine have been shown to decrease inflammation in numerous ways principally through reducing pro-inflammatory cytokines.
Excerpt | Reference | Relevance |
---|---|---|
"Esketamine has a favorable risk-to-benefit profile, with demonstrated efficacy in reducing depressive symptoms more rapidly than monotherapy with traditional oral antidepressants." | ( Intranasal esketamine: A novel drug for treatment-resistant depression. Khorassani, F; Talreja, O, 2020) | 1.67 |
"Esketamine (ESK) has been approved as a rapid-acting intranasal treatment for treatment-resistant depression (TRD). " | ( Long-Term Efficacy of Intranasal Esketamine in Treatment-Resistant Major Depression: A Systematic Review. Buoli, M; Caldiroli, A; Capellazzi, M; Capuzzi, E; Clerici, M; Colmegna, F; Dakanalis, A; Marcatili, M; Tagliabue, I, 2021) | 2.35 |
"Esketamine has recently emerged as a new treatment for TRD due to its rapid antidepressant effects." | ( Cost-utility analysis of esketamine and electroconvulsive therapy in adults with treatment-resistant depression. Asellus, P; Degerlund Maldi, K; Myléus, A; Norström, F, 2021) | 1.65 |
"Esketamine and ketamine have been shown to decrease inflammation in numerous ways principally through reducing pro-inflammatory cytokines (e.g., TNF-α, IL-6) (Loix et al., Acta Anaesthesiol Belg 62(1):47-58, 2011; Chen et al., Psychiatry Res 269:207-11, 2018; Kopra et al., J Psychopharmacol 35(8):934-45, 2021)." | ( The Glutamatergic System in Treatment-Resistant Depression and Comparative Effectiveness of Ketamine and Esketamine: Role of Inflammation? Cook, J; Halaris, A, 2023) | 1.85 |
"Esketamine has higher potency, stronger receptor affinity, a stronger analgesic effect, a higher in vivo clearance rate, and a lower incidence of adverse reactions when compared to ketamine. " | ( Intraoperative intravenous low-dose esketamine improves quality of early recovery after laparoscopic radical resection of colorectal cancer: A prospective, randomized controlled trial. Ai, Y; He, L; Liu, S; Xu, Y; Zhang, C, 2023) | 2.63 |
"Esketamine has been licensed for 'treatment-resistant depression' in the USA, UK and Europe. " | ( Are we repeating mistakes of the past? A review of the evidence for esketamine. Horowitz, MA; Moncrieff, J, 2021) | 2.3 |
"Esketamine has a favorable risk-to-benefit profile, with demonstrated efficacy in reducing depressive symptoms more rapidly than monotherapy with traditional oral antidepressants." | ( Intranasal esketamine: A novel drug for treatment-resistant depression. Khorassani, F; Talreja, O, 2020) | 1.67 |
Esketamine is a novel treatment for treatment resistant depression (TRD) and was approved by the FDA in early 2019. Treatment with esketamine may lead to an increased risk of lower urinary tract symptoms, such as dysuria or urgency.
All esketamine doses were safe and tolerated. Propofol was effective and safe in painless gastrointestinal endoscopy as evidenced by less propofol consumption per minute, shorter induction time, and lower incidence of cough and body movement. Intravenous, subcutaneous, and possibly oral esketamines may offer an effective andsafe addition to the depression treatment armamentarium.
Esketamine showed high bioavailability (62%) and relatively low maximum concentration peaks. A population pharmacokinetic (popPK) model of esketamine and its metabolite (noresketamine) was previously developed.
Remimazolam combined with esketamine anesthesia has the sa. A subanesthetic dose of esketamines combined with hip capsule PNB for elderly patients undergoing THA has better postoperative analgesic effects.
Excerpt | Reference | Relevance |
---|---|---|
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs." | ( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019) | 0.51 |
" Esketamine showed a clinically relevant pharmacokinetic profile, with high bioavailability (62%) and relatively low maximum concentration peaks." | ( Esketamine inhaled as dry powder: Pharmacokinetic, pharmacodynamic and safety assessment in a preclinical study. Abramski, K; Dera, P; Gajos-Draus, A; Janicka, M; Janowska, S; Kamil, K; Mach, M; Matłoka, M; Moszczyński-Pętkowski, R; Pankiewicz, P; Perko, P; Pieczykolan, J; Teska-Kamińska, M; Tratkiewicz, E; Wieczorek, M; Ziółkowski, H, 2022) | 3.07 |
Esketamine is cheap, requires less frequent dosing (once a week), and is a simpler procedure compared to intravenous infusions. This study compared the efficacy and safety of switching patients with treatment-resistant depression from an ineffective antidepressant to flexibly dosed esketamine nasal spray plus a newly initiated antidepressant.
Role | Description |
---|---|
analgesic | An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms. |
NMDA receptor antagonist | Any substance that inhibits the action of N-methyl-D-aspartate (NMDA) receptors. They tend to induce a state known as dissociative anesthesia, marked by catalepsy, amnesia, and analgesia, while side effects can include hallucinations, nightmares, and confusion. Due to their psychotomimetic effects, many NMDA receptor antagonists are used as recreational drugs. |
intravenous anaesthetic | null |
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] |
Class | Description |
---|---|
ketamine | A member of the class of cyclohexanones in which one of the hydrogens at position 2 is substituted by a 2-chlorophenyl group, while the other is substituted by a methylamino group. |
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] |
Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
Glutamate receptor ionotropic, NMDA 1 | Rattus norvegicus (Norway rat) | Ki | 0.4950 | 0.0003 | 0.8666 | 6.6900 | AID1692782; AID1692783 |
Glutamate receptor ionotropic, NMDA 2A | Rattus norvegicus (Norway rat) | Ki | 0.4950 | 0.0003 | 0.6805 | 6.6900 | AID1692782; AID1692783 |
Glutamate receptor ionotropic, NMDA 2B | Rattus norvegicus (Norway rat) | Ki | 0.4950 | 0.0003 | 0.7071 | 6.6900 | AID1692782; AID1692783 |
Glutamate receptor ionotropic, NMDA 2C | Rattus norvegicus (Norway rat) | Ki | 0.4950 | 0.0003 | 0.8196 | 6.6900 | AID1692782; AID1692783 |
Glutamate receptor ionotropic, NMDA 1 | Homo sapiens (human) | IC50 (µMol) | 0.0114 | 0.0010 | 1.8877 | 9.8000 | AID1255979 |
Glutamate receptor ionotropic, NMDA 2A | Homo sapiens (human) | IC50 (µMol) | 0.0114 | 0.0010 | 1.9958 | 9.8000 | AID1255979 |
Glutamate receptor ionotropic, NMDA 2D | Rattus norvegicus (Norway rat) | Ki | 0.4950 | 0.0003 | 0.7072 | 6.6900 | AID1692782; AID1692783 |
Glutamate receptor ionotropic, NMDA 3B | Rattus norvegicus (Norway rat) | Ki | 0.4950 | 0.0003 | 0.7072 | 6.6900 | AID1692782; AID1692783 |
Glutamate receptor ionotropic, NMDA 3A | Rattus norvegicus (Norway rat) | Ki | 0.4950 | 0.0003 | 0.7072 | 6.6900 | AID1692782; AID1692783 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID1296008 | Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening | 2020 | SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1 | Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening. |
AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
AID1346987 | P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
AID1346986 | P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
AID704017 | Displacement of [3H]-(+)-MK-801 from PCP binding site of NMDA receptor in pig brain cortex | 2012 | Journal of medicinal chemistry, Oct-25, Volume: 55, Issue:20 | Enantiomerically pure 1,3-dioxanes as highly selective NMDA and σ₁ receptor ligands. |
AID1247113 | Ratio of IC50 for NMDA receptor in Wistar rat brain membranes in presence of 20 mM NH4+ to IC50 for NMDA receptor in Wistar rat brain membranes in absence of 20 mM NH4+ | 2015 | Bioorganic & medicinal chemistry letters, Oct-01, Volume: 25, Issue:19 | Differential influence of 7 cations on 16 non-competitive NMDA receptor blockers. |
AID1247108 | Ratio of IC50 for NMDA receptor in Wistar rat brain membranes in presence of 30 uM spermine to IC50 for NMDA receptor in Wistar rat brain membranes in absence of 30 uM spermine | 2015 | Bioorganic & medicinal chemistry letters, Oct-01, Volume: 25, Issue:19 | Differential influence of 7 cations on 16 non-competitive NMDA receptor blockers. |
AID1255979 | Antagonist activity against NR1-1a/NR2A NMDA receptor (unknown origin) expressed in mouse recombinant L(tk-) cells assessed as inhibition of glycine and glutamate induced excitotoxicity incubated for 12 hrs by LDH assay | 2015 | Journal of medicinal chemistry, Nov-12, Volume: 58, Issue:21 | Novel Potent N-Methyl-d-aspartate (NMDA) Receptor Antagonists or σ1 Receptor Ligands Based on Properly Substituted 1,4-Dioxane Ring. |
AID1247112 | Ratio of IC50 for NMDA receptor in Wistar rat brain membranes in presence of 50 mM K+ to IC50 for NMDA receptor in Wistar rat brain membranes in absence of 50 mM K+ | 2015 | Bioorganic & medicinal chemistry letters, Oct-01, Volume: 25, Issue:19 | Differential influence of 7 cations on 16 non-competitive NMDA receptor blockers. |
AID1692782 | Displacement of [3H]-MK801 from NMDA receptor in rat brain homogenate | 2020 | Journal of medicinal chemistry, 11-25, Volume: 63, Issue:22 | Repurposing of Drugs-The Ketamine Story. |
AID1247111 | Ratio of IC50 for NMDA receptor in Wistar rat brain membranes in presence of 3 to 50 mM Na+ to IC50 for NMDA receptor in Wistar rat brain membranes in absence of 3 to 50 mM Na+ | 2015 | Bioorganic & medicinal chemistry letters, Oct-01, Volume: 25, Issue:19 | Differential influence of 7 cations on 16 non-competitive NMDA receptor blockers. |
AID1672601 | Cytotoxicity against human MCF7 cells assessed as reduction in cell viability after 48 hrs by SRB assay | 2019 | ACS medicinal chemistry letters, Apr-11, Volume: 10, Issue:4 | Role of the NMDA Receptor in the Antitumor Activity of Chiral 1,4-Dioxane Ligands in MCF-7 and SKBR3 Breast Cancer Cells. |
AID1672602 | Cytotoxicity against human SK-BR-3 cells assessed as reduction in cell viability incubated for 48 hrs by SRB assay | 2019 | ACS medicinal chemistry letters, Apr-11, Volume: 10, Issue:4 | Role of the NMDA Receptor in the Antitumor Activity of Chiral 1,4-Dioxane Ligands in MCF-7 and SKBR3 Breast Cancer Cells. |
AID1247110 | Ratio of IC50 for NMDA receptor in Wistar rat brain membranes in presence of H+ at pH 6.4 to 8.2 to IC50 for NMDA receptor in Wistar rat brain membranes in absence of H+ at pH 6.4 to 8.2 | 2015 | Bioorganic & medicinal chemistry letters, Oct-01, Volume: 25, Issue:19 | Differential influence of 7 cations on 16 non-competitive NMDA receptor blockers. |
AID353104 | Ratio of Ki for rat brain NMDA receptor in presence of 100 uM spermine to Ki for rat brain NMDA receptor in absence of spermine | 2009 | Bioorganic & medicinal chemistry, May-01, Volume: 17, Issue:9 | NMDA receptor affinities of 1,2-diphenylethylamine and 1-(1,2-diphenylethyl)piperidine enantiomers and of related compounds. |
AID1247114 | Ratio of IC50 for NMDA receptor in Wistar rat brain membranes in presence of 1.3 mM Mg2+ to IC50 for NMDA receptor in Wistar rat brain membranes in absence of 1.3 mM Mg2+ | 2015 | Bioorganic & medicinal chemistry letters, Oct-01, Volume: 25, Issue:19 | Differential influence of 7 cations on 16 non-competitive NMDA receptor blockers. |
AID1247109 | Ratio of IC50 for NMDA receptor in Wistar rat brain membranes in presence of 10 to 50 mM Tris to IC50 for NMDA receptor in Wistar rat brain membranes in absence of 10 to 50 mM Tris | 2015 | Bioorganic & medicinal chemistry letters, Oct-01, Volume: 25, Issue:19 | Differential influence of 7 cations on 16 non-competitive NMDA receptor blockers. |
AID1255978 | Displacement of [3H]MK801 from NMDA receptor PCP binding site in guinea pig brain cortex membranes incubated for 120 mins by scintillation counting method | 2015 | Journal of medicinal chemistry, Nov-12, Volume: 58, Issue:21 | Novel Potent N-Methyl-d-aspartate (NMDA) Receptor Antagonists or σ1 Receptor Ligands Based on Properly Substituted 1,4-Dioxane Ring. |
AID353103 | Displacement of [3H]MK801 from NMDA receptor in rat brain neuronal membrane | 2009 | Bioorganic & medicinal chemistry, May-01, Volume: 17, Issue:9 | NMDA receptor affinities of 1,2-diphenylethylamine and 1-(1,2-diphenylethyl)piperidine enantiomers and of related compounds. |
AID1247107 | Displacement of [3H]MK-801 from NMDA receptor in Wistar rat brain membranes by scintillation counting analysis | 2015 | Bioorganic & medicinal chemistry letters, Oct-01, Volume: 25, Issue:19 | Differential influence of 7 cations on 16 non-competitive NMDA receptor blockers. |
AID295934 | Displacement of [3H]MK-801 from NMDA receptor in guinea pig brain membrane | 2007 | European journal of medicinal chemistry, Oct, Volume: 42, Issue:10 | Synthesis of bridged piperazines with sigma receptor affinity. |
AID1692776 | Cmax in mouse brain at 10 mg/kg, ip measured after 10 mins | 2020 | Journal of medicinal chemistry, 11-25, Volume: 63, Issue:22 | Repurposing of Drugs-The Ketamine Story. |
AID1692783 | Displacement of [3H]-MK801 from NMDA receptor in rat brain membranes | 2020 | Journal of medicinal chemistry, 11-25, Volume: 63, Issue:22 | Repurposing of Drugs-The Ketamine Story. |
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 0 (0.00) | 18.7374 |
1990's | 0 (0.00) | 18.2507 |
2000's | 2 (0.48) | 29.6817 |
2010's | 47 (11.27) | 24.3611 |
2020's | 368 (88.25) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.
| This Compound (86.41) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 131 (30.25%) | 5.53% |
Reviews | 79 (18.24%) | 6.00% |
Case Studies | 16 (3.70%) | 4.05% |
Observational | 10 (2.31%) | 0.25% |
Other | 197 (45.50%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |