mifepristone 🐶 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 µM/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
S (Water solubility) 0.00 mg/mL Bocci G, Oprea TI, Benet LZ

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 4663.45 50.32 666 4193 2465 63481698
Haemorrhage 2421.19 50.32 613 4246 60409 63423754
Pregnancy 763.98 50.32 224 4635 36612 63447551
Endometritis 447.78 50.32 76 4783 942 63483221
Anaemia 267.56 50.32 202 4657 293228 63190935
Drug ineffective for unapproved indication 186.87 50.32 77 4782 33986 63450177
Induced abortion failed 183.26 50.32 29 4830 223 63483940
Muscle spasms 149.36 50.32 111 4748 156039 63328124
Retained products of conception 124.30 50.32 19 4840 113 63484050
Abortion induced incomplete 123.15 50.32 16 4843 19 63484144
Intermenstrual bleeding 115.84 50.32 37 4822 7889 63476274
Vaginal haemorrhage 101.32 50.32 47 4812 27440 63456723
Product use in unapproved indication 75.30 50.32 80 4779 179000 63305163
Ectopic pregnancy 72.70 50.32 20 4839 2547 63481616
Uterine haemorrhage 72.18 50.32 22 4837 4019 63480144
Pelvic inflammatory disease 71.30 50.32 18 4841 1644 63482519
Ruptured ectopic pregnancy 63.46 50.32 13 4846 463 63483700
Uterine rupture 57.88 50.32 14 4845 1072 63483091
Pelvic pain 55.71 50.32 25 4834 13494 63470669
Pain 52.58 50.32 149 4710 740479 62743684
Syncope 52.05 50.32 54 4805 117331 63366832

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 4832.30 47.65 662 3958 2402 79737366
Haemorrhage 2319.43 47.65 607 4013 90511 79649257
Pregnancy 896.23 47.65 224 4396 26627 79713141
Endometritis 442.29 47.65 70 4550 738 79739030
Anaemia 238.86 47.65 200 4420 444815 79294953
Induced abortion failed 189.39 47.65 28 4592 178 79739590
Muscle spasms 161.23 47.65 109 4511 174621 79565147
Retained products of conception 138.36 47.65 20 4600 106 79739662
Drug ineffective for unapproved indication 108.82 47.65 55 4565 51183 79688585
Abortion induced incomplete 103.42 47.65 13 4607 16 79739752
Intermenstrual bleeding 100.29 47.65 29 4591 5855 79733913
Vaginal haemorrhage 96.16 47.65 39 4581 21778 79717990
Pain 86.15 47.65 149 4471 703653 79036115
Ectopic pregnancy 85.92 47.65 20 4600 1723 79738045
Uterine haemorrhage 85.44 47.65 22 4598 2881 79736887
Pelvic inflammatory disease 79.46 47.65 18 4602 1374 79738394
Ruptured ectopic pregnancy 68.36 47.65 13 4607 418 79739350
Uterine rupture 61.69 47.65 13 4607 708 79739060
Pelvic pain 59.22 47.65 24 4596 13357 79726411
Heavy menstrual bleeding 54.78 47.65 23 4597 13988 79725780
Dizziness 53.43 47.65 103 4517 526338 79213430
Product use in unapproved indication 50.33 47.65 67 4553 250292 79489476

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




🐶 Veterinary Drug Use

None

🐶 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
Glucocorticoid receptor Nuclear hormone receptor ANTAGONIST IC50 9 WOMBAT-PK CHEMBL
Progesterone receptor Nuclear hormone receptor ANTAGONIST Ki 8.74 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
Glucocorticoid receptor Unclassified IC50 7.70 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
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
Korlym HUMAN PRESCRIPTION DRUG LABEL 1 76346-073 TABLET 300 mg ORAL NDA 28 sections