mifepristone ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
steroidal compounds acting on progesterone receptors 1805 84371-65-3

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • mifepristone
  • mifegyne
  • mifeprex
  • mifestone
A progestational and glucocorticoid hormone antagonist. Its inhibition of progesterone induces bleeding during the luteal phase and in early pregnancy by releasing endogenous prostaglandins from the endometrium or decidua. As a glucocorticoid receptor antagonist, the drug has been used to treat hypercortisolism in patients with nonpituitary CUSHING SYNDROME.
  • Molecular weight: 429.60
  • Formula: C29H35NO2
  • CLOGP: 4.47
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 1
  • TPSA: 40.54
  • ALOGS: -5.11
  • ROTB: 3

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
0.20 g O
0.20 g O

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 23.28 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Hosey CM, Chan R, Benet LZ
BA (Bioavailability) 69 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.45 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 0.50 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.02 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 16.60 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Sept. 28, 2000 FDA DANCO LABS LLC

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
Abortion incomplete 4575.57 56.41 665 3743 2461 50598255
Haemorrhage 2407.35 56.41 609 3799 52832 50547884
Pregnancy 784.46 56.41 224 4184 29353 50571363
Endometritis 441.29 56.41 76 4332 899 50599817
Anaemia 264.95 56.41 199 4209 252257 50348459
Drug ineffective for unapproved indication 193.90 56.41 72 4336 21209 50579507
Muscle spasms 153.66 56.41 109 4299 125444 50475272
Induced abortion failed 152.78 56.41 25 4383 210 50600506
Retained products of conception 123.18 56.41 19 4389 104 50600612
Intermenstrual bleeding 116.65 56.41 37 4371 6777 50593939
Abortion induced incomplete 98.58 56.41 13 4395 15 50600701
Product use in unapproved indication 94.22 56.41 79 4329 115740 50484976
Vaginal haemorrhage 82.40 56.41 41 4367 24510 50576206
Uterine haemorrhage 73.03 56.41 22 4386 3393 50597323
Ectopic pregnancy 72.08 56.41 20 4388 2307 50598409
Pelvic inflammatory disease 70.57 56.41 18 4390 1504 50599212
Pain 63.98 56.41 149 4259 578754 50021962
Ruptured ectopic pregnancy 57.51 56.41 12 4396 410 50600306

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
Abortion incomplete 4752.08 57.39 661 3542 2400 64492129
Haemorrhage 2326.35 57.39 605 3598 78746 64415783
Pregnancy 926.76 57.39 224 3979 20641 64473888
Endometritis 437.85 57.39 70 4133 696 64493833
Anaemia 240.52 57.39 197 4006 378483 64116046
Muscle spasms 166.00 57.39 107 4096 140916 64353613
Induced abortion failed 157.63 57.39 24 4179 167 64494362
Retained products of conception 137.33 57.39 20 4183 98 64494431
Drug ineffective for unapproved indication 119.01 57.39 52 4151 31081 64463448
Intermenstrual bleeding 100.89 57.39 29 4174 5096 64489433
Pain 98.53 57.39 148 4055 553363 63941166
Abortion induced incomplete 86.46 57.39 11 4192 13 64494516
Ectopic pregnancy 85.74 57.39 20 4183 1544 64492985
Uterine haemorrhage 85.46 57.39 22 4181 2557 64491972
Pelvic inflammatory disease 79.17 57.39 18 4185 1240 64493289
Vaginal haemorrhage 76.13 57.39 33 4170 19311 64475218
Ruptured ectopic pregnancy 62.12 57.39 12 4191 372 64494157
Product use in unapproved indication 61.14 57.39 66 4137 176552 64317977
Uterine rupture 60.31 57.39 13 4190 700 64493829
Pelvic pain 57.73 57.39 23 4180 10887 64483642

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC G03XB01 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
OTHER SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
Progesterone receptor modulators
ATC G03XB51 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
OTHER SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
Progesterone receptor modulators
FDA MoA N0000000115 Progestational Hormone Receptor Antagonists
FDA EPC N0000175841 Progestin Antagonist
CHEBI has role CHEBI:49020 hormone antagonists
CHEBI has role CHEBI:49323 contraceptive drugs
CHEBI has role CHEBI:49326 synthetic oral contraceptives
CHEBI has role CHEBI:50691 abortifacient drug
MeSH PA D000019 Abortifacient Agents
MeSH PA D000021 Abortifacient Agents, Steroidal
MeSH PA D003270 Contraceptive Agents
MeSH PA D003271 Contraceptive Agents, Female
MeSH PA D000080066 Contraceptive Agents, Hormonal
MeSH PA D003280 Contraceptives, Oral, Synthetic
MeSH PA D003283 Contraceptives, Postcoital, Synthetic
MeSH PA D006727 Hormone Antagonists
MeSH PA D008186 Luteolytic Agents
MeSH PA D008600 Menstruation-Inducing Agents
MeSH PA D012102 Reproductive Control Agents

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Pregnancy with abortive outcome indication 363681007
Severe adrenal insufficiency contraindication 24867002
Ectopic pregnancy contraindication 34801009 DOID:0060329
Erythropoietic protoporphyria contraindication 51022005 DOID:13270
Hepatic porphyria contraindication 55056006 DOID:3133
Variegate porphyria contraindication 58275005 DOID:4346
Porphyria cutanea tarda contraindication 61860000 DOID:3132
Blood coagulation disorder contraindication 64779008 DOID:1247
Intermenstrual bleeding - irregular contraindication 64996003
Miscarriage with sepsis contraindication 67465009
Bacterial infectious disease contraindication 87628006
Leukocytosis contraindication 111583006
Incomplete miscarriage contraindication 156072005
Acute intermittent porphyria contraindication 234422006 DOID:3890
Adrenal cortical hypofunction contraindication 386584007 DOID:10493
Postabortal Hemorrhage contraindication
Uterine Adnexal Mass contraindication




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.08 acidic
pKa2 3.7 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
300MG KORLYM CORCEPT THERAP N202107 Feb. 17, 2012 RX TABLET ORAL 8921348 Aug. 27, 2028 TREATING CUSHINGS SYNDROME
300MG KORLYM CORCEPT THERAP N202107 Feb. 17, 2012 RX TABLET ORAL 10842801 Nov. 15, 2032 TREATING CUSHINGS SYNDROME
300MG KORLYM CORCEPT THERAP N202107 Feb. 17, 2012 RX TABLET ORAL 10500216 March 5, 2033 TREATING CUSHINGS SYNDROME
300MG KORLYM CORCEPT THERAP N202107 Feb. 17, 2012 RX TABLET ORAL 10166242 April 20, 2036 TREATING CUSHINGS SYNDROME
300MG KORLYM CORCEPT THERAP N202107 Feb. 17, 2012 RX TABLET ORAL 10166243 April 20, 2036 TREATING CUSHINGS SYNDROME
300MG KORLYM CORCEPT THERAP N202107 Feb. 17, 2012 RX TABLET ORAL 10660904 April 20, 2036 TREATING CUSHINGS SYNDROME
300MG KORLYM CORCEPT THERAP N202107 Feb. 17, 2012 RX TABLET ORAL 9943526 April 20, 2036 TREATING CUSHINGS SYNDROME
300MG KORLYM CORCEPT THERAP N202107 Feb. 17, 2012 RX TABLET ORAL 10006924 Aug. 12, 2036 TREATING CUSHINGS SYNDROME
300MG KORLYM CORCEPT THERAP N202107 Feb. 17, 2012 RX TABLET ORAL 10495650 Aug. 12, 2036 TREATING CUSHINGS SYNDROME
300MG KORLYM CORCEPT THERAP N202107 Feb. 17, 2012 RX TABLET ORAL 9829495 Aug. 15, 2036 TREATING CUSHINGS SYNDROME
300MG KORLYM CORCEPT THERAP N202107 Feb. 17, 2012 RX TABLET ORAL 10151763 Jan. 18, 2037 TREATING CUSHINGS SYNDROME
300MG KORLYM CORCEPT THERAP N202107 Feb. 17, 2012 RX TABLET ORAL 10195214 June 19, 2037 TREATING CUSHINGS SYNDROME
300MG KORLYM CORCEPT THERAP N202107 Feb. 17, 2012 RX TABLET ORAL 10842800 June 19, 2037 TREATING CUSHINGS SYNDROME
300MG KORLYM CORCEPT THERAP N202107 Feb. 17, 2012 RX TABLET ORAL 10231983 Aug. 22, 2038 TREATING CUSHINGS SYNDROME
300MG KORLYM CORCEPT THERAP N202107 Feb. 17, 2012 RX TABLET ORAL 10314850 Aug. 22, 2038 TREATING CUSHINGS SYNDROME
300MG KORLYM CORCEPT THERAP N202107 Feb. 17, 2012 RX TABLET ORAL 10780097 Aug. 22, 2038 TREATING CUSHINGS SYNDROME

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Progesterone receptor Nuclear hormone receptor ANTAGONIST Ki 8.74 WOMBAT-PK CHEMBL
Glucocorticoid receptor Nuclear hormone receptor ANTAGONIST IC50 9 WOMBAT-PK CHEMBL
Cytochrome P450 3A4 Enzyme Ki 6.64 WOMBAT-PK
Alpha-2B adrenergic receptor GPCR Ki 4.92 DRUG MATRIX
Nuclear receptor subfamily 1 group I member 2 Nuclear hormone receptor AGONIST EC50 5 IUPHAR
Kappa-type opioid receptor GPCR Ki 5.10 DRUG MATRIX
Mineralocorticoid receptor Nuclear hormone receptor IC50 5.68 WOMBAT-PK
Estrogen receptor Nuclear hormone receptor IC50 5.30 CHEMBL
Androgen receptor Nuclear hormone receptor Ki 8.33 WOMBAT-PK
Estrogen receptor beta Nuclear hormone receptor Ki 5.54 CHEMBL
Tyrosine-protein kinase Fyn Kinase IC50 4.67 DRUG MATRIX
Mitogen-activated protein kinase 14 Kinase IC50 4.08 DRUG MATRIX
Mu-type opioid receptor GPCR Ki 6.00 DRUG MATRIX
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 4.96 DRUG MATRIX
Androgen receptor Transcription factor Ki 8.26 DRUG MATRIX
Arachidonate 15-lipoxygenase Enzyme IC50 6.26 DRUG MATRIX
Progesterone receptor Transcription factor Ki 9.37 DRUG MATRIX
Glucocorticoid receptor Transcription factor IC50 8.85 CHEMBL
Progesterone receptor Transcription factor IC50 8.46 CHEMBL
P-glycoprotein 3 Transporter Kd 4.70 CHEMBL
Glucocorticoid receptor Nuclear hormone receptor IC50 7.70 CHEMBL
Glucocorticoid receptor Nuclear hormone receptor IC50 7.96 CHEMBL

External reference:

IDSource
4021235 VUID
N0000148679 NUI
D00585 KEGG_DRUG
4021235 VANDF
C0026088 UMLSCUI
CHEBI:50692 CHEBI
486 PDB_CHEM_ID
CHEMBL1276308 ChEMBL_ID
D015735 MESH_DESCRIPTOR_UI
DB00834 DRUGBANK_ID
55245 PUBCHEM_CID
2805 IUPHAR_LIGAND_ID
5752 INN_ID
320T6RNW1F UNII
284781 RXNORM
15775 MMSL
231857 MMSL
40538 MMSL
d04718 MMSL
004008 NDDF
129483007 SNOMEDCT_US
395796009 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Mifepristone HUMAN PRESCRIPTION DRUG LABEL 1 43393-001 TABLET 200 mg ORAL ANDA 21 sections
Korlym HUMAN PRESCRIPTION DRUG LABEL 1 76346-073 TABLET 300 mg ORAL NDA 28 sections
Korlym HUMAN PRESCRIPTION DRUG LABEL 1 76346-073 TABLET 300 mg ORAL NDA 28 sections