metyrapone 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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) 2 Bocci G, Oprea TI, Benet LZ
S (Water solubility) 0.43 mg/mL Bocci G, Oprea TI, Benet LZ

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 0.941 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 0.300 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 89.125 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 134.276 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 82.950 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 78.830 % High 1
herg hERG pIC50 3.778 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 20.137 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 49.888 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 84.660 % High 1
kinase-safety-class ACVR2A,ACVR2B,AURKA,AXL,BRAF,CAMK2B,CAMK2D,CDK5,CDK9,DDR1,DYRK1B,EIF2AK3,ERBB2,FLT3,GRK2,GRK3,JAK1,MAP3K21,MAPK7,MAPK9,MARK4,NTRK2,PDK2,PIK3CB,PRKCD,PRKDC,SIK2,SIK3,STK33,SYK,TEK,TTK 32
kinase-selectivity-class AXL,BRAF,CDK9,EPHB4,ERBB2,GRK2,PRKDC,SIK2 8
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 0.579 High 1
mh-clint Mouse hepatocyte intrinsic clearance 137.088 High 1
mppb Mouse plasma protein binding (% unbound) 83.590 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 0.760 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 86.540 % High 1
rh-clint Rat hepatocyte intrinsic clearance 34.514 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 97.540 % High 1
rppb Rat plasma protein binding (% unbound) 79.060 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 442.588 uM High 1

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 91.77 49.22 27 772 38735 90588913
Pneumocystis jirovecii pneumonia 73.51 49.22 20 779 21596 90606052
Cortisol free urine increased 68.77 49.22 8 791 54 90627594
Cortisol increased 67.22 49.22 10 789 496 90627152
Adrenal insufficiency 54.26 49.22 17 782 29904 90597744
Premature rupture of membranes 54.15 49.22 12 787 5546 90622102

FDA Adverse Event Reporting System (Male)

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 50.92 50.78 17 531 25164 42595623

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 116.32 41.79 35 1199 42700 110545365
Premature delivery 87.23 41.79 26 1208 30606 110557459
Adrenal insufficiency 87.05 41.79 28 1206 42362 110545703
Cortisol free urine increased 84.62 41.79 10 1224 60 110588005
Off label use 71.80 41.79 85 1149 1500100 109087965
Cortisol increased 69.90 41.79 11 1223 623 110587442
Premature rupture of membranes 53.47 41.79 12 1222 4625 110583440
Pre-eclampsia 46.03 41.79 12 1222 8638 110579427

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
FDA MoA N0000175921 Adrenal Steroid Synthesis Inhibitors
FDA EPC N0000175928 Adrenal Steroid Synthesis Inhibitor
CHEBI has role CHEBI:33295 diagnostic agent
CHEBI has role CHEBI:35221 antimetabolite
CHEBI has role CHEBI:35469 antidepressant
CHEBI has role CHEBI:76798 EC 1.14.15.4 (steroid 11β-monooxygenase) inhibitor

Related Drugs by ATC class:

V04CD Tests for pituitary function 4 drugs
corticorelinmacimorelinsermorelinsomatorelin

Drug Use | Suggest Off label Use Form| |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
5224 IUPHAR_LIGAND_ID
1404 INN_ID
ZS9KD92H6V UNII
203002 RXNORM
10389 MMSL
5107 MMSL
d00592 MMSL
002120 NDDF
395794007 SNOMEDCT_US
53848009 SNOMEDCT_US
ZS9KD92H6V INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Metopirone HUMAN PRESCRIPTION DRUG LABEL 1 68118-455 CAPSULE, GELATIN COATED 250 mg ORAL NDA 27 sections
Metopirone HUMAN PRESCRIPTION DRUG LABEL 1 76336-455 CAPSULE, GELATIN COATED 250 mg ORAL NDA 27 sections