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Compound Detail

CHEMBL681

ETOMIDATE
💊 Approved Drug
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💊 Approved Drug
CCOC(=O)c1cncn1[C@H](C)c1ccccc1

Basic Information

ChEMBL ID CHEMBL681
Name ETOMIDATE
Phase Approved
Structure Type MOL
InChI Key NPUKDXXFDDZOKR-LLVKDONJSA-N
Therapeutic ✓ Yes

Known Names

Amidate Etomidate Etomidato Hypnomidate NSC-759160
11
Targets
27
Activities
3
Assay Types
5
PK Parameters
20
Publications
5
Known Names
3
Indications
1
Mechanisms

Molecular Properties

244.3
MW (Da)
2.67
ALogP
4
HBA
0
HBD
44.1
PSA (Ų)
0.78
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1982
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Natural Product
USAN Year 1975

Extended Properties

Molecular Formula C14H16N2O2
MW 244.29
Aromatic Rings 2
Heavy Atoms 18
NP-Likeness -0.96

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
GABA-A receptor; anion channel positive modulator POSITIVE MODULATOR GABA-A receptor; anion channel

Indications

Hypertension Stroke Respiratory Insufficiency

ATC Classification

N01AX07
etomidate
Level 1: NERVOUS SYSTEM
Level 2: ANESTHETICS

Activity Summary

IC50 16 meas. best 10.0
EC50 10 meas. best 5.92
Kd 1 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cytochrome P450 11B2, mitochondrial
CHEMBL2722
IC50 10.0 9.385 0.1 4
Cytochrome P450 11B1, mitochondrial
CHEMBL1908
IC50 9.3 9.3 0.5 4
Unchecked
CHEMBL612545
IC50 8.97 6.855 1.1 4
GABA-A receptor; alpha-1/beta-2/gamma-2
CHEMBL2095172
EC50 5.92 5.2367 1200.0 3
Unchecked
CHEMBL612545
EC50 5.64 5.5833 2300.0 3
Xenopus sp.
CHEMBL612667
EC50 5.64 5.64 2300.0 1
GABA A receptor alpha-2/beta-2/gamma-2
CHEMBL2111413
EC50 5.46 5.46 3500.0 1
Gamma-aminobutyric acid receptor subunit alpha-1
CHEMBL1962
EC50 4.96 4.96 11000.0 1
Rana temporaria
CHEMBL613031
EC50 4.96 4.96 11000.0 1
Acetylcholine receptor
CHEMBL2096975
IC50 4.39 4.39 41000.0 1
Nicotinic acetylcholine receptor alpha1/beta1/gamma/delta
CHEMBL3038460
IC50 4.3 4.3 50000.0 1
Bile salt export pump
CHEMBL6020
IC50 4.21 4.21 61610.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 13.0 mL.min-1.kg-1 Homo sapiens
CL 253.7 mL.min-1.g-1 Homo sapiens
Fu 0.23 - Homo sapiens
MRT 2.9 hr Homo sapiens
T1/2 3.5 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cytochrome P450 11B2, mitochondrial IC50 = 0.1 nM 10.0 Inhibition of human CYP11B2 expressed in hamster V79MZ cells using 11-deoxycorti... 24900247
Cytochrome P450 11B2, mitochondrial IC50 = 0.1 nM 10.0 Inhibition of human CYP11B2 expressed in hamster V79 MZ cells using [3H] 11 deox... 24900349
Cytochrome P450 11B1, mitochondrial IC50 = 0.5 nM 9.3 Inhibition of human CYP11B1 expressed in V79 MZ cells pretreated with compound f... 24422519
Cytochrome P450 11B1, mitochondrial IC50 = 0.5 nM 9.3 Inhibition of human CYP11B1 expressed in hamster V79 MZ cells using [3H] 11 deox... 24900349
Cytochrome P450 11B1, mitochondrial IC50 = 0.5 nM 9.3 Inhibition of human CYP11B1 expressed in hamster V79MZ cells using 11-deoxycorti... 24900247
Cytochrome P450 11B1, mitochondrial IC50 = 0.5 nM 9.3 Inhibition of human CYP11B1 expressed in chinese hamster V79 cells 20121113
Unchecked IC50 = 1.08 nM 8.97 Displacement of [131I]IMTO from CYP450c 11 in Wistar rat adrenal membrane 18348518
Cytochrome P450 11B2, mitochondrial IC50 = 1.7 nM 8.77 Inhibition of human aldosterone synthase expressed in V79 MZ cells pretreated wi... 24422519
Cytochrome P450 11B2, mitochondrial IC50 = 1.7 nM 8.77 Inhibition of human CYP11B2 expressed in chinese hamster V79 cells 20121113
Unchecked IC50 = 4.57 nM 8.34 Inhibition on cortisol secretion in human NCI-H295 cells after 48 hrs 18348518
GABA-A receptor; alpha-1/beta-2/gamma-2 EC50 = 1200.0 nM 5.92 Ability to enhance currents from alpha-1-beta-2-gamma-2L-subunit of GABA recepto... 12646036
Unchecked IC50 = 2050.0 nM 5.69 Displacement of [3H]ethynylpropylbicycloorthobenzoate from GABAA receptor from r... 19497738
Unchecked EC50 = 2300.0 nM 5.64 Anesthetic potency, Concentration for loss of righting reflexes (LORR) in Xenopu... 12646036
Xenopus sp. EC50 = 2300.0 nM 5.64 Anesthetic activity in Xenopus tadpole measured as loss of righting reflex 16884293
Unchecked EC50 = 2300.0 nM 5.64 Effective concentration required for reversible loss of righting reflex in Xenop... 15801854
GABA-A receptor; alpha-1/beta-2/gamma-2 EC50 = 2500.0 nM 5.6 Enhancement of currents elicited by GABA at EC5 (6-12 uM) 12646036
Unchecked EC50 = 3400.0 nM 5.47 Anesthetic potency, Concentration for loss of righting reflexes (LORR) in Rana t... 12646036
GABA A receptor alpha-2/beta-2/gamma-2 EC50 = 3500.0 nM 5.46 Effective concentration against GABA-evoked chloride currents mediated by human ... 15801854
Rana temporaria EC50 = 11000.0 nM 4.96 Anesthetic potency in Rana temporaria tadpoles assessed as loss of righting refl... 17311911
Gamma-aminobutyric acid receptor subunit alpha-1 EC50 = 11000.0 nM 4.96 Activity at human GABAA alpha-1-beta-2-gamma-2s receptor expressed in HEK293 cel... 17311911

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
12646036 10.1021/jm020465v GABA-A receptor; alpha-1/beta-2/gamma-2 8
- 10.6019/CHEMBL5303304 U2OS 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
32247113 10.1016/j.ejmech.2020.112261 Unchecked 5
7452689 10.1021/jm00186a013 Mus musculus 4
20704351 10.1021/jm100498u GABA-A receptor; alpha-1/beta-2/gamma-2 4
- 10.6019/CHEMBL5303304 Fibroblast 4
18426954 10.1124/dmd.108.020479 ADMET 4
18348518 10.1021/jm800012w Unchecked 4
19497738 10.1016/j.bmcl.2009.05.065 Unchecked 3
17311911 10.1074/jbc.m700479200 Gamma-aminobutyric acid receptor subunit alpha-1 3
20014752 10.1021/tx900326k Hepatotoxicity 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 3
18027916 10.1021/jm070524a No relevant target 2
15801854 10.1021/jm049120y GABA A receptor alpha-2/beta-2/gamma-2 2

Data from ChEMBL 36 via Core Engine