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Metyrapone

drug
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Also known as MetiraponaMetopironMetopironeNSC-25265SID11112126SID124881925SID56323421SID170465268C0164989

Summary

Metyrapone (CHEMBL934) is an approved small-molecule diagnostic agent (ATC V04CD01) targeting CYP11B1 and CYP11B2; indicated across 5 conditions including cushing syndrome and depressive disorder.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: V04CD01
  • Targets: 2 (CYP11B1, CYP11B2)
  • Indications: 5 conditions
  • Clinical trials: 15
  • Chemistry: 226.27 Da · C14H14N2O

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL934
NameMetyrapone
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID4174
ChEBICHEBI:44241
ATCV04CD01
Molecular formulaC14H14N2O
Molecular weight226.27
InChIKeyFJLBFSROUSIWMA-UHFFFAOYSA-N

SMILES: CC(C)(C1=CN=CC=C1)C(=O)C2=CN=CC=C2

IUPAC name: 2-methyl-1,2-dipyridin-3-ylpropan-1-one

ChEBI definition: An aromatic ketone that is 3,3-dimethylbutan-2-one in which the methyl groups at positions 1 and 4 are replaced by pyridin-3-yl groups. A steroid 11β-monooxygenase (EC 1.14.15.4) inhibitor, it is used in the diagnosis of adrenal insufficiency.

Pharmacological roles (ChEBI): diagnostic agent, EC 1.14.15.4 (steroid 11β-monooxygenase) inhibitor.

Other ChEBI roles (chemical / environmental): antimetabolite.

Also known as: Metirapona, Metopiron, Metopirone, Metyrapone, NSC-25265, metyrapone, SID11112126, METYRAPONE, SID124881925, SID56323421, SID170465268, C0164989

Parent form; salt/anhydrous children: CHEMBL3989720

Patent coverage: 844 distinct patent families (2,893 SureChEMBL compound mentions), from 3 matched compound structure(s). One matched structure accounts for 2,880 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
CYP11B1CYP11B1Inhibition7.840.1%P15538
CYP11B2CYP11B2Inhibition7.10.7%P19099

Broader ChEMBL bioactivity targets: 8 (assay-derived). Sample: Tyrosyl-DNA phosphodiesterase 1, Prelamin-A/C, Cytochrome P450 11B1, mitochondrial, Cytochrome P450 11B2, mitochondrial, Cytochrome P450 11B1, mitochondrial, Cytochrome P450 1A2, Cytochrome P450 3A4, Cytochrome P450 11B1, mitochondrial.

Bioactivity

ChEMBL activities: 37 potent at pChembl ≥ 5 of 39 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
CYP11B17.84IC5014.6nMCHEMBL_ACT_14531437
CYP11B17.84IC5014.6nMCHEMBL_ACT_5128095
CYP11B17.82IC5015nMCHEMBL_ACT_10835520
CYP11B17.82IC5015nMCHEMBL_ACT_13435483
CYP11B17.82IC5015nMCHEMBL_ACT_14970318
CYP11B17.82IC5015nMCHEMBL_ACT_15137441
CYP11B17.82IC5015nMCHEMBL_ACT_15235522
CYP11B17.82IC5015nMCHEMBL_ACT_17778868
CYP11B17.82IC5015nMCHEMBL_ACT_18078674
CYP11B17.82IC5015nMCHEMBL_ACT_18690412
CYP11B17.82IC5015nMCHEMBL_ACT_5152240
CYP11B27.38IC5042nMCHEMBL_ACT_13435451
CYP11B17.34IC5046nMCHEMBL_ACT_15030787
CYP11B27.14IC5072nMCHEMBL_ACT_10835565
CYP11B27.14IC5071.8nMCHEMBL_ACT_14531445
CYP11B27.14IC5072nMCHEMBL_ACT_14970346
CYP11B27.14IC5072nMCHEMBL_ACT_15137386
CYP11B27.14IC5072nMCHEMBL_ACT_15235541
CYP11B27.14IC5072nMCHEMBL_ACT_17778913
CYP11B27.14IC5072nMCHEMBL_ACT_18078752
CYP11B27.14IC5072nMCHEMBL_ACT_26636413
CYP11B27.14IC5072nMCHEMBL_ACT_5128103
CYP11B27.14IC5072nMCHEMBL_ACT_5152270
CYP11B26.68IC50208nMCHEMBL_ACT_15030794
P151506.24Ki580nMCHEMBL_ACT_14640718
CYP3A46.1IC50800nMCHEMBL_ACT_7768948
CYP3A45.9Potency1259nMCHEMBL_ACT_4949283
CYP3A45.9Potency1259nMCHEMBL_ACT_5018162
CYP3A45.9AC501259nMCHEMBL_ACT_6053415
CYP3A45.52IC503000nMCHEMBL_ACT_17706608

Target pathways

Aggregated over 2 target gene(s): CYP11B1, CYP11B2.

Top Reactome pathways

15 total, by targets touching each:

PathwayTargetsGenes
Metabolism2CYP11B1, CYP11B2
Disease2CYP11B1, CYP11B2
Glucocorticoid biosynthesis2CYP11B1, CYP11B2
Metabolism of steroid hormones2CYP11B1, CYP11B2
Biological oxidations2CYP11B1, CYP11B2
Cytochrome P450 - arranged by substrate type2CYP11B1, CYP11B2
Phase I - Functionalization of compounds2CYP11B1, CYP11B2
Endogenous sterols2CYP11B1, CYP11B2
Metabolism of lipids2CYP11B1, CYP11B2
Metabolic disorders of biological oxidation enzymes2CYP11B1, CYP11B2
Diseases of metabolism2CYP11B1, CYP11B2
Metabolism of steroids2CYP11B1, CYP11B2
Mineralocorticoid biosynthesis1CYP11B2
Defective CYP11B2 causes CMO-1 deficiency1CYP11B2
Defective CYP11B1 causes AH41CYP11B1

Dominant GO biological processes

GO termTargets
C21-steroid hormone biosynthetic process2
glucocorticoid biosynthetic process2
cholesterol metabolic process2
sterol metabolic process2
aldosterone biosynthetic process2
cellular response to hormone stimulus2
cortisol metabolic process2
cortisol biosynthetic process2
cellular response to potassium ion2
cellular response to peptide hormone stimulus2
alcohol metabolic process2
lipid metabolic process2
steroid biosynthetic process2
immune response1
regulation of blood pressure1

Indications & clinical

Indications

5 indications (0 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
Cushing syndrome3MONDO:0018912EFO:0003099
depressive disorder3MONDO:0002050MONDO:0002050
major depressive disorder2MONDO:0002009MONDO:0002009
cocaine dependence1MONDO:0005186EFO:0002610
nicotine dependence1MONDO:0008575EFO:0003768

Clinical trials

Total trials: 15.

Phase distribution

PhaseTrials
PHASE14
Not specified4
PHASE43
PHASE32
PHASE22

Top trials by phase / activity

NCTPhaseStatusTitle
NCT07494084PHASE4NOT_YET_RECRUITINGSleep Loss and Circadian Misalignment - Mechanisms of Insulin Resistance
NCT01620684PHASE4UNKNOWNCortisol and Nutritional Sympathetic Responsiveness
NCT03491696PHASE4UNKNOWNEffects of the Addition of Metyrapone to Antidepressant Therapy in Depression With Dexamethasone Suppression Test Non-suppression.
NCT01375920PHASE3COMPLETEDAntiglucocorticoid Augmentation of antiDepressants in Depression
NCT02297945PHASE3COMPLETEDEffects of Metyrapone in Patients With Endogenous Cushing’s Syndrome
NCT06106295PHASE2ACTIVE_NOT_RECRUITINGMetyrapone for Mild Autonomous Cortisol Secretion (MACS)
NCT00125554PHASE2COMPLETEDMetyrapone as Additive Treatment in Major Depression
NCT00033098PHASE1UNKNOWNCocaine-Metyrapone Interaction Study - 1
NCT00426608PHASE1COMPLETEDTo Investigate Effects GSK561679 on Part of the Body’s System That Controls the Balance of Many of the Hormones.
NCT01673087PHASE1COMPLETEDStress Biomarkers:Attaching Biological Meaning to Field Friendly Salivary Measures
NCT02406066PHASE1COMPLETEDSingle and Multiple Rising Dose Study of Safety and PK of Metyrapone/Oxazepam Combination (EMB-001)
NCT00006270Not specifiedUNKNOWNStudy of the Approximate Entropy of Adrenocorticotropic Hormone and Cortisol Secretion in Patients With Head Injury
NCT00567814Not specifiedCOMPLETEDA Placebo-Controlled Study of a Combination of Metyrapone and Oxazepam in Cocaine Addiction
NCT05255900Not specifiedCOMPLETEDEffects of Metyrapone in Patients With Hypercortisolism
NCT06556277Not specifiedCOMPLETEDAcute Consequences of Glucocorticoid Secretion in Overweight and Obese Individuals During Maximum Calorie Intake

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

13 molecules share ≥1 primary target. Top 13 by shared-target count:

MoleculeSourceStatusShared targets
ABIRATERONEChEMBL + PubChemPhase 4 (approved)CYP11B1, CYP11B2
ETOMIDATEChEMBLPhase 4 (approved)CYP11B1, CYP11B2
FLUCONAZOLEChEMBLPhase 4 (approved)CYP11B1, CYP11B2
KETOCONAZOLEChEMBLPhase 4 (approved)CYP11B1, CYP11B2
LETROZOLEChEMBLPhase 4 (approved)CYP11B1, CYP11B2
OSILODROSTATChEMBLPhase 4 (approved)CYP11B1, CYP11B2
POSACONAZOLEChEMBLPhase 4 (approved)CYP11B1, CYP11B2
BAXDROSTATChEMBLPhase 3CYP11B1, CYP11B2
DEXFADROSTATChEMBLPhase 2CYP11B1, CYP11B2
FADROZOLEChEMBLPhase 2CYP11B1, CYP11B2
LORUNDROSTATChEMBLPhase 3CYP11B2
AZALANSTATChEMBLPhase 2CYP11B1
VOROZOLEChEMBLPhase 2CYP11B1

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot