metyrapone 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
1791 54-36-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • metyrapone
  • mepyrapone
  • methapyrapone
  • methbipyranone
  • methopirapone
  • methopyrapone
  • methopyrinine
  • methopyrone
  • metopiron
  • metopirone
  • metopyrone
  • metroprione
  • metyrapon
An inhibitor of the enzyme STEROID 11-BETA-MONOOXYGENASE. It is used as a test of the feedback hypothalamic-pituitary mechanism in the diagnosis of CUSHING SYNDROME.
  • Molecular weight: 226.28
  • Formula: C14H14N2O
  • CLOGP: 1.46
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 0
  • TPSA: 42.85
  • ALOGS: -2.72
  • ROTB: 3

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Hosey CM, Chan R, Benet LZ

Approvals:

DateAgencyCompanyOrphan
Dec. 4, 1961 FDA HRA PHARMA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Premature delivery 79.10 38.98 23 576 23640 50580885
Cortisol increased 75.52 38.98 11 588 349 50604176
Cortisol free urine increased 60.08 38.98 7 592 34 50604491
Adrenal insufficiency 52.68 38.98 15 584 14228 50590297
Pneumocystis jirovecii pneumonia 52.25 38.98 15 584 14648 50589877
Blood corticotrophin decreased 47.45 38.98 7 592 242 50604283
Premature rupture of membranes 42.31 38.98 10 589 4570 50599955

FDA Adverse Event Reporting System (Male)

None

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Pneumocystis jirovecii pneumonia 95.18 42.82 28 799 27606 64470299
Adrenal insufficiency 78.32 42.82 23 804 22464 64475441
Premature delivery 78.08 42.82 22 805 18567 64479338
Cortisol free urine increased 76.64 42.82 9 818 43 64497862
Cortisol increased 64.85 42.82 10 817 431 64497474
Premature rupture of membranes 43.50 42.82 10 817 3734 64494171

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC V04CD01 VARIOUS
DIAGNOSTIC AGENTS
OTHER DIAGNOSTIC AGENTS
Tests for pituitary function
MeSH PA D000963 Antimetabolites
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D009676 Noxae
FDA MoA N0000175921 Adrenal Steroid Synthesis Inhibitors
FDA EPC N0000175928 Adrenal Steroid Synthesis Inhibitor
CHEBI has role CHEBI:33295 diagnostic aid
CHEBI has role CHEBI:35221 antimetabolite
CHEBI has role CHEBI:76798 cytochrome p450 XIB1 inhibitor

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Diagnostic Test for Secondary Adrenocortical Insufficiency indication
Hypercortisolism off-label use 47270006
Primary adrenocortical insufficiency contraindication 373662000




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 4.64 Basic
pKa2 1.71 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Cytochrome P450 11B1, mitochondrial Enzyme INHIBITOR IC50 7.84 CHEMBL DRUG LABEL
Cytochrome P450 3A4 Enzyme IC50 6.10 DRUG MATRIX
Cytochrome P450 11B2, mitochondrial Enzyme IC50 7.38 CHEMBL
Cytochrome P450 11B1 Enzyme Ki 6.24 CHEMBL
Cytochrome P450 11B1, mitochondrial Enzyme IC50 5.34 CHEMBL

External reference:

IDSource
4018788 VUID
N0000147091 NUI
D00410 KEGG_DRUG
4018788 VANDF
C0025876 UMLSCUI
CHEBI:44241 CHEBI
MYT PDB_CHEM_ID
CHEMBL934 ChEMBL_ID
DB01011 DRUGBANK_ID
D008797 MESH_DESCRIPTOR_UI
4174 PUBCHEM_CID
1404 INN_ID
5224 IUPHAR_LIGAND_ID
ZS9KD92H6V UNII
203002 RXNORM
10389 MMSL
5107 MMSL
d00592 MMSL
002120 NDDF
395794007 SNOMEDCT_US
53848009 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Metopirone HUMAN PRESCRIPTION DRUG LABEL 1 76336-455 CAPSULE, GELATIN COATED 250 mg ORAL NDA 23 sections