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Compound Detail

CHEMBL742

KETAMINE
💊 Approved Drug
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💊 Approved Drug
CNC1(c2ccccc2Cl)CCCCC1=O

Basic Information

ChEMBL ID CHEMBL742
Name KETAMINE
Phase Approved
Structure Type MOL
InChI Key YQEZLKZALYSWHR-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Anaket v Calypsol Clorketam 1000 Dl-ketamine Imalgene 1000 Ketalar Ketamina Ketamine Ketamine component of ketafol Ketasol 100 Narketan NSC-70151 +4 more
9
Targets
45
Activities
2
Assay Types
16
PK Parameters
20
Publications
16
Known Names
20
Indications

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 1970
Availability Prescription
Chirality Racemic

Routes of Administration

Parenteral

Flags

Natural Product
USAN Year 1966

Extended Properties

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

Indications

Alcoholism Anemia, Sickle Cell Bipolar Disorder Chronic Pain Delirium Depression, Postpartum Depressive Disorder Depressive Disorder, Major Epilepsy Fractures, Bone Headache Lung Diseases Mucositis Neoplasms Neuralgia Obesity, Morbid Pain Pharyngitis Postoperative Complications Renal Colic

ATC Classification

N01AX03
ketamine
Level 1: NERVOUS SYSTEM
Level 2: ANESTHETICS

Activity Summary

Ki 25 meas. best 6.75
IC50 20 meas. best 6.21

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Glutamate NMDA receptor; GRIN1/GRIN2A
CHEMBL1907604
Ki 6.75 6.75 180.0 1
Glutamate NMDA receptor
CHEMBL1907608
Ki 6.75 6.75 180.0 13
Glutamate [NMDA] receptor
CHEMBL2094124
Ki 6.75 6.4 180.0 4
Glutamate NMDA receptor; Grin1/Grin2b
CHEMBL2096666
Ki 6.75 6.75 180.0 1
Glutamate NMDA receptor; Grin1/Grin2a
CHEMBL2096680
Ki 6.75 6.75 180.0 1
Unchecked
CHEMBL612545
Ki 6.75 6.634 180.0 5
Glutamate NMDA receptor
CHEMBL1907608
IC50 6.21 5.7833 610.0 6
Glutamate NMDA receptor; Grin1/Grin2a
CHEMBL2096680
IC50 6.0 6.0 1000.0 1
Unchecked
CHEMBL612545
IC50 6.0 5.04 1010.0 2
Glutamate NMDA receptor; GRIN1/GRIN2A
CHEMBL1907604
IC50 5.9 5.53 1258.9 3
Voltage-dependent L-type calcium channel subunit alpha-1C
CHEMBL1940
IC50 5.75 5.75 1800.0 1
Glutamate NMDA receptor; GRIN1/GRIN2B
CHEMBL1907603
IC50 5.5 5.4 3200.0 2
Acetylcholine receptor subunit alpha
CHEMBL3097
IC50 5.3 5.13 4950.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 136.0 mL.min-1.g-1 Homo sapiens
CL 19.0 mL.min-1.kg-1 Homo sapiens
Cmax 7600.0 nM Homo sapiens
F 20.0 % Homo sapiens
F 93.0 % Homo sapiens
F 17.0 % Homo sapiens
F 100.0 % Homo sapiens
F 8.0 % Homo sapiens
F 11.0 % Homo sapiens
F 24.0 % Homo sapiens
Fu 0.47 - Homo sapiens
MRT 2.5 hr Homo sapiens
T1/2 2.8 hr Homo sapiens
T1/2 2.0 hr Homo sapiens
T1/2 8.0 hr Rattus norvegicus
T1/2 0.1167 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 180.0 nM 6.75 Displacement of [3H]-MK801 from NMDA receptor in Dunkin-Hartley guinea pig brain... 32915563
Glutamate NMDA receptor Ki = 180.0 nM 6.75 Displacement of [3H]-MK801 from NMDA receptor in Sprague-Dawley rat cerebellum b... 32915563
Glutamate NMDA receptor; Grin1/Grin2a Ki = 180.0 nM 6.75 Displacement of [3H]-MK801 from rat brain GluN1/GluN2A expressed in HEK293 cells 32915563
Glutamate NMDA receptor Ki = 180.0 nM 6.75 Displacement of [3H]-MK801 from NMDA receptor in rat striatum incubated for 2 hr... 32915563
Glutamate NMDA receptor Ki = 180.0 nM 6.75 Displacement of [3H]-MK801 from NMDA receptor in Sprague-Dawley rat cortex incub... 32915563
Glutamate [NMDA] receptor Ki = 180.0 nM 6.75 Displacement of [3H]-MK801 from NMDA receptor in human cortex incubated for 2 hr... 32915563
Glutamate NMDA receptor; GRIN1/GRIN2A Ki = 180.0 nM 6.75 Displacement of [3H]-MK801 from human forebrain GluN1/GluN2B expressed in HEK293... 32915563
Glutamate NMDA receptor Ki = 180.0 nM 6.75 Displacement of [3H]-MK801 from NMDA receptor in rat forebrain homogenate incuba... 32915563
Glutamate NMDA receptor Ki = 180.0 nM 6.75 Displacement of [3H]-MK801 from NMDA receptor in rat spinal cord incubated for 4... 32915563
Unchecked Ki = 180.0 nM 6.75 Displacement of [3H]-MK801 from NMDA receptor in dog brain homogenate incubated ... 32915563
Unchecked Ki = 180.0 nM 6.75 Displacement of [3H]-MK801 from NMDA receptor in dog cerebral cortex incubated f... 32915563
Unchecked Ki = 180.0 nM 6.75 Displacement of [3H]-MK801 from NMDA receptor in ICR Harlan mouse brain homogena... 32915563
Glutamate NMDA receptor Ki = 180.0 nM 6.75 Displacement of [3H]-MK801 from NMDA receptor in rat brain membranes incubated f... 32915563
Glutamate NMDA receptor Ki = 180.0 nM 6.75 Displacement of [3H]-MK801 from NMDA receptor in rat whole brain homogenate incu... 32915563
Glutamate NMDA receptor Ki = 180.0 nM 6.75 Displacement of [3H]-MK801 from NMDA receptor in rat brain membranes incubated f... 32915563
Glutamate NMDA receptor Ki = 180.0 nM 6.75 Displacement of [3H]-MK801 from NMDA receptor in rat brain membranes incubated f... 32915563
Glutamate NMDA receptor Ki = 180.0 nM 6.75 Displacement of [3H]-MK801 from NMDA receptor in Sprague-Dawley rat cerebral cor... 32915563
Glutamate NMDA receptor Ki = 180.0 nM 6.75 Displacement of [3H]-MK801 from NMDA receptor in rat brain membranes incubated f... 32915563
Glutamate NMDA receptor Ki = 180.0 nM 6.75 Displacement of [3H]-TCP from NMDA receptor in rat brain membranes incubated for... 32915563
Glutamate [NMDA] receptor Ki = 180.0 nM 6.75 Displacement of [3H]-MK801 from NMDA receptor in human frontal cortex in presenc... 32915563

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 332
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
32915563 10.1021/acs.jmedchem.0c01193 Glutamate NMDA receptor 14
32915563 10.1021/acs.jmedchem.0c01193 ADMET 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
38593423 10.1021/acs.jmedchem.3c01961 Mus musculus 10
38593423 10.1021/acs.jmedchem.3c01961 Hippocampus 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
23876339 10.1016/j.bmc.2013.06.047 Rattus norvegicus 6
32915563 10.1021/acs.jmedchem.0c01193 Homo sapiens 6
32915563 10.1021/acs.jmedchem.0c01193 Unchecked 4
- 10.1584/jpestics.20.49 Acetylcholine receptor subunit alpha 4
18426954 10.1124/dmd.108.020479 ADMET 4
35453065 10.1016/j.ejmech.2022.114354 Glutamate NMDA receptor; Grin1/Grin2a 3
3783598 10.1021/jm00161a043 ADMET 3
32915563 10.1021/acs.jmedchem.0c01193 No relevant target 3
20361801 10.1021/jm1000024 Glutamate NMDA receptor; GRIN1/GRIN2A 3
8336337 10.1021/jm00066a007 Glutamate NMDA receptor 3
32915563 10.1021/acs.jmedchem.0c01193 Glutamate [NMDA] receptor 3
30792105 10.1016/j.bmc.2019.02.010 Rattus norvegicus 3

Data from ChEMBL 36 via Core Engine