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Compound Detail

CHEMBL934

METYRAPONE
💊 Approved Drug
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💊 Approved Drug
CC(C)(C(=O)c1cccnc1)c1cccnc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL934
Name METYRAPONE
Phase Approved
Structure Type MOL
InChI Key FJLBFSROUSIWMA-UHFFFAOYSA-N

Known Names

Metirapona Metopiron Metopirone Metyrapone NSC-25265
6
Targets
36
Activities
2
Assay Types
3
PK Parameters
20
Publications
5
Known Names
5
Indications
1
Mechanisms

Molecular Properties

226.3
MW (Da)
2.64
ALogP
3
HBA
0
HBD
42.9
PSA (Ų)
0.76
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1961
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product
USAN Year 1963

Extended Properties

Molecular Formula C14H14N2O
MW 226.28
Aromatic Rings 2
Heavy Atoms 17
NP-Likeness -0.36

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Cytochrome P450 11B1, mitochondrial inhibitor INHIBITOR Cytochrome P450 11B1, mitochondrial ✓ ✓

Indications

Cushing Syndrome Depressive Disorder Depressive Disorder, Major Cocaine-Related Disorders Tobacco Use Disorder

ATC Classification

V04CD01
metyrapone
Level 1: VARIOUS
Level 2: DIAGNOSTIC AGENTS

Activity Summary

IC50 35 meas. best 8.94
Ki 1 meas. best 6.24

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 8.94 8.94 1.2 1
Cytochrome P450 11B1, mitochondrial
CHEMBL1908
 IC50 7.84 7.7833 14.6 12
Cytochrome P450 11B2, mitochondrial
CHEMBL2722
 IC50 7.38 7.1217 42.0 12
Cytochrome P450 11B1, mitochondrial
CHEMBL2927
 Ki 6.24 6.24 580.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 6.1 5.6125 800.0 4
Cytochrome P450 11B1, mitochondrial
CHEMBL4970
 IC50 5.34 5.3267 4600.0 3
Cytochrome P450 11B1, mitochondrial
CHEMBL2927
 IC50 5.11 5.11 7830.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.8167 hr Homo sapiens
T1/2 0.2 hr Rattus norvegicus
T1/2 0.8167 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 1.16 nM 8.94 Displacement of [131I]IMTO from CYP450c 11 in Wistar rat adrenal membrane 18348518
Cytochrome P450 11B1, mitochondrial IC50 = 14.6 nM 7.84 Inhibition of human steroid-11beta-hydroxylase expressed in chinese hamster V79 ... 21129965
Cytochrome P450 11B1, mitochondrial IC50 = 14.6 nM 7.84 Inhibition of CYP11B1 (unknown origin) expressed in Chinese hamster V79MZ cells ... -
Cytochrome P450 11B1, mitochondrial IC50 = 15.0 nM 7.82 Cellular Inhibition Assay: V79MZ cells expressing human CYP11B1 and human CYP11B... -
Cytochrome P450 11B1, mitochondrial IC50 = 15.0 nM 7.82 Inhibition of human CYP11B1 expressed in hamster V79MZ cells using [1,2-3H]-11-d... 29207342
Cytochrome P450 11B1, mitochondrial IC50 = 15.0 nM 7.82 Inhibition of human CYP11B1 expressed in hamster V79MZ cells using [1,2-3H]-11-d... 28570067
Cytochrome P450 11B1, mitochondrial IC50 = 15.0 nM 7.82 Inhibition of human CYP11B1 expressed in hamster fibroblast using 100 nM [3H]-11... 25874338
Cytochrome P450 11B1, mitochondrial IC50 = 15.0 nM 7.82 Inhibition of human CYP11B1 expressed in hamster V79MZh cells using [1,2-3H]-11-... 25176013
Cytochrome P450 11B1, mitochondrial IC50 = 15.0 nM 7.82 Inhibition of human CYP11B1 expressed in hamster V79MZh11B1 cells using [1,2-3H]... 25462231
Cytochrome P450 11B1, mitochondrial IC50 = 15.0 nM 7.82 Inhibition of human CYP11B1 expressed in hamster V79MZh cells using [1,2-3H]-11-... 23869452
Cytochrome P450 11B1, mitochondrial IC50 = 15.0 nM 7.82 Inhibition of human CYP11B1 expressed in hamster V79 MZ cells using [3H] 11 deox... 24900349
Cytochrome P450 11B1, mitochondrial IC50 = 15.0 nM 7.82 Inhibition of human CYP11B1 expressed in hamster V79MZ cells using 11-deoxycorti... 24900247
Cytochrome P450 11B2, mitochondrial IC50 = 42.0 nM 7.38 Inhibition of human CYP11B2 expressed in hamster V79MZh cells using [1,2-3H]-11-... 23869452
Cytochrome P450 11B1, mitochondrial IC50 = 46.0 nM 7.34 Inhibition of human CYP11B1 expressed in V79 MZ cells pretreated with compound f... 24422519
Cytochrome P450 11B2, mitochondrial IC50 = 71.8 nM 7.14 Inhibition of CYP11B2 (unknown origin) expressed in Chinese hamster V79MZ cells ... -
Cytochrome P450 11B2, mitochondrial IC50 = 72.0 nM 7.14 Cellular Inhibition Assay: V79MZ cells expressing human CYP11B1 and human CYP11B... -
Cytochrome P450 11B2, mitochondrial IC50 = 72.0 nM 7.14 Inhibition of human CYP11B2 expressed in hamster V79MZ cells using [1,2-3H]-11-d... 28570067
Cytochrome P450 11B2, mitochondrial IC50 = 72.0 nM 7.14 Cellular Inhibition Assay: V79MZ cells expressing human CYP11B1 and human CYP11B... -
Cytochrome P450 11B2, mitochondrial IC50 = 72.0 nM 7.14 Inhibition of human CYP11B2 expressed in hamster fibroblast using 100 nM [3H]-11... 25874338
Cytochrome P450 11B2, mitochondrial IC50 = 72.0 nM 7.14 Inhibition of human CYP11B2 expressed in hamster V79MZh cells using [1,2-3H]-11-... 25176013

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
874952 10.1021/jm00216a005 Cytochrome P450 11B1, mitochondrial 7
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
28570067 10.1021/acs.jmedchem.7b00437 Cytochrome P450 11B1, mitochondrial 3
20014752 10.1021/tx900326k Hepatotoxicity 3
- 10.1039/C2MD20072D Cytochrome P450 11B1, mitochondrial 2
- 10.1039/C2MD20072D Cytochrome P450 11B2, mitochondrial 2
- 10.1039/C2MD20072D Aromatase 2
25462231 10.1016/j.ejmech.2014.10.021 Unchecked 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
25874338 10.1016/j.ejmech.2015.04.013 Cytochrome P450 11B1, mitochondrial 2
21129965 10.1016/j.bmcl.2010.11.040 Cytochrome P450 11B2, mitochondrial 2
21129965 10.1016/j.bmcl.2010.11.040 Cytochrome P450 11B1, mitochondrial 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
19497738 10.1016/j.bmcl.2009.05.065 Unchecked 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
29207342 10.1016/j.ejmech.2017.11.018 11-beta-hydroxysteroid dehydrogenase 1 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2

Data from ChEMBL 36 via Core Engine