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Compound Detail

CHEMBL395091

ESKETAMINE
💊 Approved Drug
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💊 Approved Drug
CN[C@]1(c2ccccc2Cl)CCCCC1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL395091
Name ESKETAMINE
Phase Approved
Structure Type MOL
InChI Key YQEZLKZALYSWHR-ZDUSSCGKSA-N
Therapeutic ✓ Yes

Known Names

(-)-ketamine Esketamina Esketamine Jnj-54135419 Keta-s Ketamine s-isomer Ketamine, (s)- Ketamine, s- Ketaved L-ketamine S-(-)-ketamine S-ketamine
3
Targets
8
Activities
2
Assay Types
1
PK Parameters
20
Publications
12
Known Names
11
Indications
1
Mechanisms

Molecular Properties

237.7
MW (Da)
2.90
ALogP
2
HBA
1
HBD
29.1
PSA (Ų)
0.86
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2019
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Topical

Flags

Black Box Warning Natural Product
USAN Year 2013

Extended Properties

Molecular Formula C13H16ClNO
MW 237.73
Aromatic Rings 1
Heavy Atoms 16
NP-Likeness 0.02

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Glutamate [NMDA] receptor negative allosteric modulator NEGATIVE ALLOSTERIC MODULATOR Glutamate [NMDA] receptor ✓ ✓

Indications

Depressive Disorder Depressive Disorder Depressive Disorder, Treatment-Resistant Pain Shock, Septic Cancer Pain Kidney Diseases Liver Diseases Rhinitis, Allergic, Seasonal Substance-Related Disorders Delirium

ATC Classification

N01AX14
esketamine
Level 1: NERVOUS SYSTEM
Level 2: ANESTHETICS
N06AX27
esketamine
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Activity Summary

Ki 6 meas. best 6.97
IC50 2 meas. best 7.94

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Glutamate NMDA receptor; GRIN1/GRIN2A
CHEMBL1907604
 IC50 7.94 7.94 11.4 1
Unchecked
CHEMBL612545
 Ki 6.97 6.59 108.0 3
Glutamate NMDA receptor
CHEMBL1907608
 Ki 6.52 6.2333 300.0 3
Glutamate NMDA receptor
CHEMBL1907608
 IC50 6.19 6.19 640.0 1

Pharmacokinetic Data

Parameter Value Units Species
Cmax 7.33 umol/Kg Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Glutamate NMDA receptor; GRIN1/GRIN2A IC50 = 11.4 nM 7.94 Antagonist activity against NR1-1a/NR2A NMDA receptor (unknown origin) expressed... 26430967
Unchecked Ki = 108.0 nM 6.97 Displacement of [3H]MK-801 from NMDA receptor in guinea pig brain membrane 17420073
Glutamate NMDA receptor Ki = 300.0 nM 6.52 Displacement of [3H]-MK801 from NMDA receptor in rat brain homogenate 32915563
Unchecked Ki = 383.0 nM 6.42 Displacement of [3H]-(+)-MK-801 from PCP binding site of NMDA receptor in pig br... 23013229
Unchecked Ki = 419.0 nM 6.38 Displacement of [3H]MK801 from NMDA receptor PCP binding site in guinea pig brai... 26430967
Glutamate NMDA receptor IC50 = 640.0 nM 6.19 Displacement of [3H]MK-801 from NMDA receptor in Wistar rat brain membranes by s... 26296478
Glutamate NMDA receptor Ki = 690.0 nM 6.16 Displacement of [3H]-MK801 from NMDA receptor in rat brain membranes 32915563
Glutamate NMDA receptor Ki = 960.0 nM 6.02 Displacement of [3H]MK801 from NMDA receptor in rat brain neuronal membrane 19345586

Literature References

PubMed DOI Target Context # Activities
26296478 10.1016/j.bmcl.2015.08.017 Glutamate NMDA receptor 15
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
30996788 10.1021/acsmedchemlett.8b00536 MCF7 3
30996788 10.1021/acsmedchemlett.8b00536 SK-BR-3 3
19345586 10.1016/j.bmc.2009.03.025 Glutamate NMDA receptor 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
37468498 10.1038/s41467-023-40064-9 Androgen receptor 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 2
32915563 10.1021/acs.jmedchem.0c01193 Glutamate NMDA receptor 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 2
37468498 10.1038/s41467-023-40064-9 Voltage-dependent L-type calcium channel subunit alpha-1C 1
37468498 10.1038/s41467-023-40064-9 Glutamate receptor ionotropic, NMDA 1 1
37468498 10.1038/s41467-023-40064-9 Beta-1 adrenergic receptor 1
37468498 10.1038/s41467-023-40064-9 Voltage-gated inwardly rectifying potassium channel KCNH2 1
26430967 10.1021/acs.jmedchem.5b01214 Glutamate NMDA receptor; GRIN1/GRIN2A 1
26430967 10.1021/acs.jmedchem.5b01214 Unchecked 1

Data from ChEMBL 36 via Core Engine