Mifepristone

Identification

Summary

Mifepristone is a cortisol receptor blocker used to treat Cushing's syndrome, and to terminate pregnancies up to 70 days gestation.

Brand Names

Korlym, Mifegymiso

Generic Name

Mifepristone

DrugBank Accession Number

DB00834

Background

Mifepristone is 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. The two marketed forms of mifepristone are Mifeprex® (mifepristone 200mg) and Korlym™ (mifepristone 300mg). Currently under investigation for use in psychotic depression (phase 3 trials).

Type

Small Molecule

Groups

Approved, Investigational

Structure

Similar Structures

Weight: Average: 429.5937
Monoisotopic: 429.266779369
Chemical Formula: C₂₉H₃₅NO₂

Synonyms

Mifepriston
Mifepristona
Mifépristone
Mifepristone
Mifepristonum

External IDs

RU 38486
RU 486
RU-38486
RU-486
RU486

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Pharmacology

Indication

For the medical termination of intrauterine pregnancy through 49 days' pregnancy. Also indicated to control hyperglycemia secondary to hypercortisolism in adult patients with endogenous Cushing's syndrome who have type 2 diabetes mellitus or glucose intolerance and are not candidates for surgery or have had unsuccessful surgery.

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Management of	Hyperglycemia		••••••••••••

Associated Therapies

Medically induced abortion

Contraindications & Blackbox Warnings

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Pharmacodynamics

Mifepristone is a synthetic steroid with antiprogestational effects indicated for the medical termination of intrauterine pregnancy through 49 days' pregnancy. Doses of 1 mg/kg or greater of mifepristone have been shown to antagonize the endometrial and myometrial effects of progesterone in women. During pregnancy, the compound sensitizes the myometrium to the contraction-inducing activity of prostaglandins. Mifepristone also exhibits antiglucocorticoid and weak antiandrogenic activity. The activity of the glucocorticoid dexamethasone in rats was inhibited following doses of 10 to 25 mg/kg of mifepristone. Doses of 4.5 mg/kg or greater in human beings resulted in a compensatory elevation of adrenocorticotropic hormone (ACTH) and cortisol.

Mechanism of action

The anti-progestational activity of mifepristone results from competitive interaction with progesterone at progesterone-receptor sites. Based on studies with various oral doses in several animal species (mouse, rat, rabbit and monkey), the compound inhibits the activity of endogenous or exogenous progesterone. The termination of pregnancy results.

In the treatment of Cushing's syndrome, Mifepristone blocks the binding of cortisol to its receptor. It does not decrease cortisol production but reduces the effects of excess cortisol, such as high blood sugar levels.

Target	Actions	Organism
AProgesterone receptor	antagonist	Humans
AGlucocorticoid receptor	antagonist	Humans
UProstate-specific antigen	Not Available	Humans
UNuclear receptor subfamily 1 group I member 2	Not Available	Humans

Absorption

The absolute bioavailability of a 20 mg oral dose is 69%

Volume of distribution

Not Available

Protein binding

98% (bound to plasma proteins, albumin and a 1-acid glycoprotein)

Metabolism

Hepatic. Hepatic, by Cytochrome P450 3A4 isoenzyme to the N-monodemethylated metabolite (RU 42 633); RU 42 698, which results from the loss of two methyl groups from position 11 beta; and RU 42 698, which results from terminal hydroxylation of the 17–propynyl chain.

Hover over products below to view reaction partners

Mifepristone
- Monodemethylated mifepristone
- 17alpha-hydroxymifepristone

Route of elimination

Fecal: 83%; Renal: 9%.

Half-life

18 hours

Clearance

Not Available

Adverse Effects

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Toxicity

Nearly all of the women who receive mifepristone will report adverse reactions, and many can be expected to report more than one such reaction. About 90% of patients report adverse reactions following administration of misoprostol on day three of the treatment procedure. Side effects include more heavy bleeding than a heavy menstrual period, abdominal pain, uterine cramping, nausea, vomiting, and diarrhea.

Pathways

Not Available

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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Abametapir	The serum concentration of Mifepristone can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Mifepristone can be increased when combined with Abatacept.
Abciximab	The risk or severity of adverse effects can be increased when Mifepristone is combined with Abciximab.
Abemaciclib	The serum concentration of Abemaciclib can be decreased when it is combined with Mifepristone.
Abrocitinib	The metabolism of Abrocitinib can be decreased when combined with Mifepristone.

Food Interactions

Avoid grapefruit products. Grapefruit inhibits the metabolism of mifepristone through the CYP3A4 pathway causing increased serum levels of mifepristone.
Take with food. Taking mifepristone with meals has been shown to increase serum levels of mifepristone.

Products

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International/Other Brands

Corlux (Corcept Therapeutics Incorporated) / Mefipil (Abbott) / Mifegyne (Exelgyn Laboratories) / Mifeprex (Danco Laboratories)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Korlym	Tablet	300 mg/1	Oral	Corcept Therapeutics Incorporated	2012-02-17	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Mifepristone	Tablet	200 mg/1	Oral	PCI Pharma Services Canada, Inc.	2019-04-11	Not applicable
Mifepristone	Tablet	200 mg/1	Oral	GenBioPro, Inc.	2019-05-01	Not applicable
Mifepristone	Tablet, film coated	300 mg/1	Oral	Actavis Pharma, Inc.	2024-01-19	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
MEDABON	Mifepristone (200 MG) + Misoprostol (0.2 MG)	Tablet		บริษัท ฟาร์มาแลนด์ (1982) จำกัด	2014-12-30	2020-10-13
Mifegymiso	Mifepristone (200 mg) + Misoprostol (200 mcg)	Kit; Tablet	Buccal; Oral	Linepharma International Limited	2017-01-10	Not applicable
Mifiso	Mifepristone (200 mg) + Misoprostol (200 mcg)	Kit; Tablet	Buccal; Oral	Linepharma International Limited	Not applicable	Not applicable
Mpm Pak	Mifepristone (200 mg/1) + Ibuprofen (800 mg/1) + Misoprostol (200 ug/1) + Ondansetron (8 mg/1)	Kit; Tablet; Tablet, orally disintegrating	Oral	Nucare Pharmaceuticals,inc.	2023-02-24	Not applicable
Mpm Pak	Mifepristone (200 mg/1) + Ibuprofen (800 mg/1) + Misoprostol (200 ug/1) + Ondansetron (8 mg/1)	Kit; Tablet; Tablet, orally disintegrating	Oral	Nucare Pharmaceuticals,inc.	2023-02-24	Not applicable

Chemical Identifiers

UNII: 320T6RNW1F
CAS number: 84371-65-3
InChI Key: VKHAHZOOUSRJNA-GCNJZUOMSA-N
InChI: InChI=1S/C29H35NO2/c1-5-15-29(32)16-14-26-24-12-8-20-17-22(31)11-13-23(20)27(24)25(18-28(26,29)2)19-6-9-21(10-7-19)30(3)4/h6-7,9-10,17,24-26,32H,8,11-14,16,18H2,1-4H3/t24-,25+,26-,28-,29-/m0/s1
IUPAC Name: (1S,3aS,3bS,10R,11aS)-10-[4-(dimethylamino)phenyl]-1-hydroxy-11a-methyl-1-(prop-1-yn-1-yl)-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
SMILES: [H][C@@]12CC[C@@](O)(C#CC)[C@@]1(C)C[C@H](C1=CC=C(C=C1)N(C)C)C1=C3CCC(=O)C=C3CC[C@@]21[H]

References

Synthesis Reference

Narendra Joshi, Anil Khile, Nitin Pradhan, "Novel polymorph form M of mifepristone and process for its preparation." U.S. Patent US20070105828, issued May 10, 2007.

US20070105828

General References

Fiala C, Gemzel-Danielsson K: Review of medical abortion using mifepristone in combination with a prostaglandin analogue. Contraception. 2006 Jul;74(1):66-86. Epub 2006 May 19. [Article]
Heikinheimo O, Kekkonen R, Lahteenmaki P: The pharmacokinetics of mifepristone in humans reveal insights into differential mechanisms of antiprogestin action. Contraception. 2003 Dec;68(6):421-6. [Article]
Chabbert-Buffet N, Meduri G, Bouchard P, Spitz IM: Selective progesterone receptor modulators and progesterone antagonists: mechanisms of action and clinical applications. Hum Reprod Update. 2005 May-Jun;11(3):293-307. Epub 2005 Mar 24. [Article]
Spitz IM, Bardin CW, Benton L, Robbins A: Early pregnancy termination with mifepristone and misoprostol in the United States. N Engl J Med. 1998 Apr 30;338(18):1241-7. [Article]
Piaggio G, von Hertzen H, Heng Z, Bilian X, Cheng L: Meta-analyses of randomized trials comparing different doses of mifepristone in emergency contraception. Contraception. 2003 Dec;68(6):447-52. [Article]
Fjerstad M, Trussell J, Sivin I, Lichtenberg ES, Cullins V: Rates of serious infection after changes in regimens for medical abortion. N Engl J Med. 2009 Jul 9;361(2):145-51. doi: 10.1056/NEJMoa0809146. [Article]

External Links

Human Metabolome Database: HMDB0014972
KEGG Drug: D00585
KEGG Compound: C07652
PubChem Compound: 55245
PubChem Substance: 46505795
ChemSpider: 49889
BindingDB: 18627
RxNav: 6964
ChEBI: 50692
ChEMBL: CHEMBL1276308
ZINC: ZINC000003831128
Therapeutic Targets Database: DAP000090
PharmGKB: PA450500
Guide to Pharmacology: GtP Drug Page
PDBe Ligand: 486
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Mifepristone

PDB Entries

1nhz / 2w8y / 3h52 / 3qt0 / 4ltw / 5uc1 / 5uc3

FDA label

Download (46.5 KB)

MSDS

Download (57.1 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Health Services Research	Early Abortion / Pregnancy Related	1
4	Completed	Not Available	Anxiety Disorders / Post Traumatic Stress Disorder (PTSD)	1
4	Completed	Health Services Research	Abortion, Therapeutic	1
4	Completed	Health Services Research	Early Abortion / Pregnancy Related	1
4	Completed	Health Services Research	Menstrual Regulation	1

Pharmacoeconomics

Manufacturers

Danco laboratories llc

Packagers

Danco Labs LLC

Dosage Forms

Form	Route	Strength
Tablet	Oral	300 mg/1
Tablet
Kit; tablet	Buccal; Oral
Tablet	Oral	600 MG
Tablet	Oral	200 mg
Tablet	Oral
Tablet	Oral	200 mg/1
Tablet, film coated	Oral	300 mg/1
Kit; tablet; tablet, orally disintegrating	Oral
Tablet	Oral	200.00 mg
Tablet	Oral	200.000 mg

Prices

Unit description	Cost	Unit
Mifeprex 200 mg tablet	90.0USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US8921348	No	2014-12-30	2028-08-27
US9829495	No	2017-11-28	2036-08-15
US9943526	No	2018-04-17	2036-04-20
US10006924	No	2018-06-26	2036-08-12
US10166243	No	2019-01-01	2036-04-20
US10166242	No	2019-01-01	2036-04-20
US10151763	No	2018-12-11	2037-01-18
US10195214	No	2019-02-05	2037-06-19
US10231983	No	2019-03-19	2038-08-22
US10314850	No	2019-06-11	2038-08-22
US10500216	No	2019-12-10	2033-03-05
US10495650	No	2019-12-03	2036-08-12
US10660904	No	2020-05-26	2036-04-20
US10780097	No	2020-09-22	2038-08-22
US10842800	No	2020-11-24	2037-06-19
US10842801	No	2020-11-24	2032-11-15

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	191-196 °C	FDA Label
water solubility	Poorly soluble	FDA Label
logP	4.5	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00336 mg/mL	ALOGPS
logP	5.33	ALOGPS
logP	5.13	Chemaxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	12.87	Chemaxon
pKa (Strongest Basic)	4.89	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	3	Chemaxon
Hydrogen Donor Count	1	Chemaxon
Polar Surface Area	40.54 Å²	Chemaxon
Rotatable Bond Count	3	Chemaxon
Refractivity	132.58 m³·mol^-1	Chemaxon
Polarizability	50.69 Å³	Chemaxon
Number of Rings	5	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	1.0
Blood Brain Barrier	+	0.7135
Caco-2 permeable	+	0.6716
P-glycoprotein substrate	Substrate	0.643
P-glycoprotein inhibitor I	Inhibitor	0.8564
P-glycoprotein inhibitor II	Inhibitor	0.8387
Renal organic cation transporter	Non-inhibitor	0.8177
CYP450 2C9 substrate	Non-substrate	0.7606
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Substrate	0.8334
CYP450 1A2 substrate	Inhibitor	0.9106
CYP450 2C9 inhibitor	Non-inhibitor	0.6293
CYP450 2D6 inhibitor	Inhibitor	0.8931
CYP450 2C19 inhibitor	Inhibitor	0.8994
CYP450 3A4 inhibitor	Inhibitor	0.796
CYP450 inhibitory promiscuity	High CYP Inhibitory Promiscuity	0.6129
Ames test	Non AMES toxic	0.856
Carcinogenicity	Non-carcinogens	0.825
Biodegradation	Not ready biodegradable	0.9971
Rat acute toxicity	2.7705 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9177
hERG inhibition (predictor II)	Non-inhibitor	0.6879

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0w29-0356900000-2d8af6b9cc4537ce26fd
MS/MS Spectrum - , positive	LC-MS/MS	splash10-001i-0332900000-9cbfa7fe6866f246577a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-001i-0000900000-6cc132780bb114cc2304
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-000t-0958400000-90d89bf049821be45f72
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-004i-0000900000-bb15b020dd7dc0ff9e1e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-004i-0000900000-14e7dff7e75a31f8e8c2
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-000t-0942100000-daf78c1795dcbda71588
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-016u-0069800000-c4925dab8b09c3196848
1H NMR Spectrum	1D NMR	Not Applicable
13C NMR Spectrum	1D NMR	Not Applicable
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	228.3900568	predicted	DarkChem Lite v0.1.0
[M-H]-	216.6296007	predicted	DarkChem Lite v0.1.0
[M-H]-	226.0790568	predicted	DarkChem Lite v0.1.0
[M-H]-	201.22139	predicted	DeepCCS 1.0 (2019)
[M+H]+	228.0370568	predicted	DarkChem Lite v0.1.0
[M+H]+	218.2452362	predicted	DarkChem Lite v0.1.0
[M+H]+	226.6089568	predicted	DarkChem Lite v0.1.0
[M+H]+	203.61696	predicted	DeepCCS 1.0 (2019)
[M+Na]+	228.3637568	predicted	DarkChem Lite v0.1.0
[M+Na]+	229.2100829	predicted	DarkChem Lite v0.1.0
[M+Na]+	226.2535568	predicted	DarkChem Lite v0.1.0
[M+Na]+	209.5295	predicted	DeepCCS 1.0 (2019)

Targets

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Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	0.3	N/A	N/A	A29094
EC 50 (nM)	>10000	N/A	N/A	A28042
IC 50 (nM)	0.18	N/A	N/A	A28035 / A29087
IC 50 (nM)	0.35	N/A	N/A	A28035
IC 50 (nM)	0.3	N/A	N/A	A29088 / A29090 / A29092 / A28040
IC 50 (nM)	0.028	N/A	N/A	A29089
IC 50 (nM)	0.025	N/A	N/A	A29089
IC 50 (nM)	0.2	N/A	N/A	A29090 / A28048 / A29103 / A29104 / A28051 / A29109
IC 50 (nM)	0.13	N/A	N/A	A29092
IC 50 (nM)	0.1	N/A	N/A	A29093
IC 50 (nM)	3.3	N/A	N/A	A29094
IC 50 (nM)	3	N/A	N/A	A29095
IC 50 (nM)	2.9	N/A	N/A	A29096
IC 50 (nM)	0.25	N/A	N/A	A29098
IC 50 (nM)	1.4	N/A	N/A	A29099 / A29101 / A29106
IC 50 (nM)	2.6	N/A	N/A	A29100
IC 50 (nM)	0.054	N/A	N/A	A29102
IC 50 (nM)	0.6	N/A	N/A	A29103 / A28042
IC 50 (nM)	0.045	N/A	N/A	A29105
IC 50 (nM)	0.021	N/A	N/A	A29105
IC 50 (nM)	0.05	N/A	N/A	A29107
IC 50 (nM)	7.94	N/A	N/A	A29108
IC 50 (nM)	10	N/A	N/A	A29110
Ki (nM)	0.58	N/A	N/A	A28035
Ki (nM)	1.1	N/A	N/A	A29088 / A29090 / A28040 / A29094
Ki (nM)	15	N/A	N/A	A29091
Ki (nM)	0.64	N/A	N/A	A29097

Details1. Progesterone receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Antagonist

General Function: Zinc ion binding
Specific Function: The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor ...
Gene Name: PGR
Uniprot ID: P06401
Uniprot Name: Progesterone receptor
Molecular Weight: 98979.96 Da

References

Greb RR, Kiesel L, Selbmann AK, Wehrmann M, Hodgen GD, Goodman AL, Wallwiener D: Disparate actions of mifepristone (RU 486) on glands and stroma in the primate endometrium. Hum Reprod. 1999 Jan;14(1):198-206. [Article]
Sun M, Zhu G, Zhou L: [Effect of mifepristone on the expression of progesterone receptor messenger RNA and protein in uterine leiomyomata]. Zhonghua Fu Chan Ke Za Zhi. 1998 Apr;33(4):227-31. [Article]
Hazra BG, Basu S, Pore VS, Joshi PL, Pal D, Chakrabarti P: Synthesis of 11beta-(4-dimethylaminophenyl)-17beta-hydroxy-17alpha- (3-methyl-1-butynyl)-4, 9-estradien-3-one and 11beta-(4-acetophenyl)- 17beta-hydroxy-17alpha-(3-methyl-1-butynyl)-4, 9-estradien-3-one: two new analogs of mifepristone (RU-486). Steroids. 2000 Mar;65(3):157-62. [Article]
Gao Y, Cheng L, Liu Y: [Failure of mifepristone induced interruption of pregnancy: point mutation at genetic codon 722 in human progesterone receptor gene]. Zhonghua Fu Chan Ke Za Zhi. 1998 Sep;33(9):549-52. [Article]
Jiang J, Wu R, Wang Z: [Effects of mifepristone on expression of estrogen receptor and progesterone receptor in cultured human eutopic and ectopic endometria]. Zhonghua Fu Chan Ke Za Zhi. 2001 Apr;36(4):218-21. [Article]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	2	N/A	N/A	A29113
EC 50 (nM)	872	N/A	N/A	A28042
IC 50 (nM)	0.8	N/A	N/A	A28035 / A29092 / A29094
IC 50 (nM)	1.1	N/A	N/A	A29111 / A29096 / A29115
IC 50 (nM)	5	N/A	N/A	A29111 / A29095 / A29115
IC 50 (nM)	1	N/A	N/A	A29095
IC 50 (nM)	4.8	N/A	N/A	A29096 / A29112
IC 50 (nM)	0.008	N/A	N/A	A28680
IC 50 (nM)	>1000	N/A	N/A	A29114 / A29119
IC 50 (nM)	5.75	N/A	N/A	A29114 / A29119
IC 50 (nM)	4.68	N/A	N/A	A29114 / A29119
IC 50 (nM)	1.6	N/A	N/A	A29099 / A29101 / A29106
IC 50 (nM)	6.9	N/A	N/A	A29117
IC 50 (nM)	11	N/A	N/A	A29117
IC 50 (nM)	6	N/A	N/A	A29102
IC 50 (nM)	0.6	N/A	N/A	A29103 / A29104 / A28051 / A29109
IC 50 (nM)	3.2	N/A	N/A	A28052
IC 50 (nM)	>10000	N/A	N/A	A29108
IC 50 (nM)	6.31	N/A	N/A	A29108
IC 50 (nM)	0.95	N/A	N/A	A28042
Ki (nM)	0.68	N/A	N/A	A28035
Ki (nM)	0.24	N/A	N/A	A29091 / A29121
Ki (nM)	120	N/A	N/A	A29097
Ki (nM)	0.44	N/A	N/A	A29097
Ki (nM)	0.1	N/A	N/A	A29097
Ki (nM)	1.1	N/A	N/A	A29116
Ki (nM)	169	N/A	N/A	A29116
Ki (nM)	5	N/A	N/A	A29116
Ki (nM)	1	N/A	N/A	A29100
Ki (nM)	0.82	N/A	N/A	A29118
Ki (nM)	1.2	N/A	N/A	A29118 / A29120
Ki (nM)	0.4	N/A	N/A	A29118 / A29120
Ki (nM)	0.84	N/A	N/A	A28042

Details2. Glucocorticoid receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Antagonist

General Function: Zinc ion binding
Specific Function: Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modula...
Gene Name: NR3C1
Uniprot ID: P04150
Uniprot Name: Glucocorticoid receptor
Molecular Weight: 85658.57 Da

References

LeVan TD, Babin EA, Yamamura HI, Bloom JW: Pharmacological characterization of glucocorticoid receptors in primary human bronchial epithelial cells. Biochem Pharmacol. 1999 May 1;57(9):1003-9. [Article]
Attardi BJ, Burgenson J, Hild SA, Reel JR: In vitro antiprogestational/antiglucocorticoid activity and progestin and glucocorticoid receptor binding of the putative metabolites and synthetic derivatives of CDB-2914, CDB-4124, and mifepristone. J Steroid Biochem Mol Biol. 2004 Mar;88(3):277-88. [Article]
Aida K, Shi Q, Wang J, VandeBerg JL, McDonald T, Nathanielsz P, Wang XL: The effects of betamethasone (BM) on endothelial nitric oxide synthase (eNOS) expression in adult baboon femoral arterial endothelial cells. J Steroid Biochem Mol Biol. 2004 Aug;91(4-5):219-24. [Article]
Gu G, Hentunen TA, Nars M, Harkonen PL, Vaananen HK: Estrogen protects primary osteocytes against glucocorticoid-induced apoptosis. Apoptosis. 2005 May;10(3):583-95. [Article]
de Pablos RM, Villaran RF, Arguelles S, Herrera AJ, Venero JL, Ayala A, Cano J, Machado A: Stress increases vulnerability to inflammation in the rat prefrontal cortex. J Neurosci. 2006 May 24;26(21):5709-19. [Article]
Ayalasomayajula SP, Ashton P, Kompella UB: Fluocinolone inhibits VEGF expression via glucocorticoid receptor in human retinal pigment epithelial (ARPE-19) cells and TNF-alpha-induced angiogenesis in chick chorioallantoic membrane (CAM). J Ocul Pharmacol Ther. 2009 Apr;25(2):97-103. doi: 10.1089/jop.2008.0090. [Article]

Details3. Prostate-specific antigen

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: Hydrolyzes semenogelin-1 thus leading to the liquefaction of the seminal coagulum.
Specific Function: Endopeptidase activity
Gene Name: KLK3
Uniprot ID: P07288
Uniprot Name: Prostate-specific antigen
Molecular Weight: 28741.1 Da

References

Kang Z, Janne OA, Palvimo JJ: Coregulator recruitment and histone modifications in transcriptional regulation by the androgen receptor. Mol Endocrinol. 2004 Nov;18(11):2633-48. Epub 2004 Aug 12. [Article]

Details4. Nuclear receptor subfamily 1 group I member 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: Zinc ion binding
Specific Function: Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...
Gene Name: NR1I2
Uniprot ID: O75469
Uniprot Name: Nuclear receptor subfamily 1 group I member 2
Molecular Weight: 49761.245 Da

References

Kretschmer XC, Baldwin WS: CAR and PXR: xenosensors of endocrine disrupters? Chem Biol Interact. 2005 Aug 15;155(3):111-28. [Article]

Enzymes

Details1. Cytochrome P450 2D6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Steroid hydroxylase activity
Specific Function: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name: CYP2D6
Uniprot ID: P10635
Uniprot Name: Cytochrome P450 2D6
Molecular Weight: 55768.94 Da

References

He K, Woolf TF, Hollenberg PF: Mechanism-based inactivation of cytochrome P-450-3A4 by mifepristone (RU486). J Pharmacol Exp Ther. 1999 Feb;288(2):791-7. [Article]

Details2. Cytochrome P450 2C8

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Steroid hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP2C8
Uniprot ID: P10632
Uniprot Name: Cytochrome P450 2C8
Molecular Weight: 55824.275 Da

References

Mifepristone FDA Label [File]

Details3. Cytochrome P450 2C9

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Inhibitor

General Function: Steroid hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP2C9
Uniprot ID: P11712
Uniprot Name: Cytochrome P450 2C9
Molecular Weight: 55627.365 Da

References

PDR [Link]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	4700	N/A	N/A	A18342

Details4. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor
Inducer

General Function: Vitamin d3 25-hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

Yueh MF, Kawahara M, Raucy J: High volume bioassays to assess CYP3A4-mediated drug interactions: induction and inhibition in a single cell line. Drug Metab Dispos. 2005 Jan;33(1):38-48. Epub 2004 Oct 1. [Article]
Jang GR, Benet LZ: Antiprogestin pharmacodynamics, pharmacokinetics, and metabolism: implications for their long-term use. J Pharmacokinet Biopharm. 1997 Dec;25(6):647-72. [Article]
Jang GR, Benet LZ: Antiprogestin-mediated inactivation of cytochrome P450 3A4. Pharmacology. 1998 Mar;56(3):150-7. doi: 10.1159/000028193. [Article]
Ma B, Polsky-Fisher SL, Vickers S, Cui D, Rodrigues AD: Cytochrome P450 3A-dependent metabolism of a potent and selective gamma-aminobutyric acid Aalpha2/3 receptor agonist in vitro: involvement of cytochrome P450 3A5 displaying biphasic kinetics. Drug Metab Dispos. 2007 Aug;35(8):1301-7. doi: 10.1124/dmd.107.014753. Epub 2007 Apr 25. [Article]
Reinen J, Smit M, Wenker M: Evaluation of Strategies for the Assessment of Drug-Drug Interactions Involving Cytochrome P450 Enzymes. Eur J Drug Metab Pharmacokinet. 2018 Dec;43(6):737-750. doi: 10.1007/s13318-018-0485-7. [Article]
Flockhart Table of Drug Interactions [Link]
Mifeprex (Mifepristone) FDA Label [Link]

Details5. Cytochrome P450 3A5

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Oxygen binding
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP3A5
Uniprot ID: P20815
Uniprot Name: Cytochrome P450 3A5
Molecular Weight: 57108.065 Da

References

Soars MG, Grime K, Riley RJ: Comparative analysis of substrate and inhibitor interactions with CYP3A4 and CYP3A5. Xenobiotica. 2006 Apr;36(4):287-99. doi: 10.1080/00498250500446208 . [Article]
Khan KK, He YQ, Correia MA, Halpert JR: Differential oxidation of mifepristone by cytochromes P450 3A4 and 3A5: selective inactivation of P450 3A4. Drug Metab Dispos. 2002 Sep;30(9):985-90. [Article]
Flockhart Table of Drug Interactions [Link]

Transporters

Details1. P-glycoprotein 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor
Inducer

General Function: Xenobiotic-transporting atpase activity
Specific Function: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name: ABCB1
Uniprot ID: P08183
Uniprot Name: Multidrug resistance protein 1
Molecular Weight: 141477.255 Da

References

Geick A, Eichelbaum M, Burk O: Nuclear receptor response elements mediate induction of intestinal MDR1 by rifampin. J Biol Chem. 2001 May 4;276(18):14581-7. Epub 2001 Jan 31. [Article]
Lecureur V, Fardel O, Guillouzo A: The antiprogestatin drug RU 486 potentiates doxorubicin cytotoxicity in multidrug resistant cells through inhibition of P-glycoprotein function. FEBS Lett. 1994 Nov 28;355(2):187-91. [Article]

Details2. Multidrug resistance-associated protein 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Transporter activity
Specific Function: Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name: ABCC1
Uniprot ID: P33527
Uniprot Name: Multidrug resistance-associated protein 1
Molecular Weight: 171589.5 Da

References

Payen L, Delugin L, Courtois A, Trinquart Y, Guillouzo A, Fardel O: Reversal of MRP-mediated multidrug resistance in human lung cancer cells by the antiprogestatin drug RU486. Biochem Biophys Res Commun. 1999 May 19;258(3):513-8. [Article]

Details3. Bile salt export pump

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate

General Function: Transporter activity
Specific Function: Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name: ABCB11
Uniprot ID: O95342
Uniprot Name: Bile salt export pump
Molecular Weight: 146405.83 Da

References

Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [Article]

Details4. Solute carrier organic anion transporter family member 1B1

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Inhibitor

General Function: Sodium-independent organic anion transmembrane transporter activity
Specific Function: Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name: SLCO1B1
Uniprot ID: Q9Y6L6
Uniprot Name: Solute carrier organic anion transporter family member 1B1
Molecular Weight: 76447.99 Da

References

Gui C, Miao Y, Thompson L, Wahlgren B, Mock M, Stieger B, Hagenbuch B: Effect of pregnane X receptor ligands on transport mediated by human OATP1B1 and OATP1B3. Eur J Pharmacol. 2008 Apr 14;584(1):57-65. doi: 10.1016/j.ejphar.2008.01.042. Epub 2008 Feb 8. [Article]

Details5. Solute carrier organic anion transporter family member 1B3

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Inhibitor

General Function: Sodium-independent organic anion transmembrane transporter activity
Specific Function: Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
Gene Name: SLCO1B3
Uniprot ID: Q9NPD5
Uniprot Name: Solute carrier organic anion transporter family member 1B3
Molecular Weight: 77402.175 Da

References

Gui C, Miao Y, Thompson L, Wahlgren B, Mock M, Stieger B, Hagenbuch B: Effect of pregnane X receptor ligands on transport mediated by human OATP1B1 and OATP1B3. Eur J Pharmacol. 2008 Apr 14;584(1):57-65. doi: 10.1016/j.ejphar.2008.01.042. Epub 2008 Feb 8. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:45

Mifepristone

Identification

Structure for Mifepristone (DB00834)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

References

References

References

Enzymes

References

References

References

References

References

Transporters

References

References

References

References

References