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
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

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 TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofHyperglycemia••••••••••••
Associated Therapies
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.

TargetActionsOrganism
AProgesterone receptor
antagonist
Humans
AGlucocorticoid receptor
antagonist
Humans
UProstate-specific antigenNot AvailableHumans
UNuclear receptor subfamily 1 group I member 2Not AvailableHumans
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

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
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
AbametapirThe serum concentration of Mifepristone can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Mifepristone can be increased when combined with Abatacept.
AbciximabThe risk or severity of adverse effects can be increased when Mifepristone is combined with Abciximab.
AbemaciclibThe serum concentration of Abemaciclib can be decreased when it is combined with Mifepristone.
AbrocitinibThe 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
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
KorlymTablet300 mg/1OralCorcept Therapeutics Incorporated2012-02-17Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
MifepristoneTablet200 mg/1OralGenBioPro, Inc.2019-05-01Not applicableUS flag
MifepristoneTablet, film coated300 mg/1OralActavis Pharma, Inc.2024-01-19Not applicableUS flag
MifepristoneTablet200 mg/1OralPCI Pharma Services Canada, Inc.2019-04-11Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
MEDABONMifepristone (200 MG) + Misoprostol (0.2 MG)Tabletบริษัท ฟาร์มาแลนด์ (1982) จำกัด2014-12-302020-10-13Thailand flag
MifegymisoMifepristone (200 mg) + Misoprostol (200 mcg)Kit; TabletBuccal; OralLinepharma International Limited2017-01-10Not applicableCanada flag
MifisoMifepristone (200 mg) + Misoprostol (200 mcg)Kit; TabletBuccal; OralLinepharma International LimitedNot applicableNot applicableCanada flag
Mpm PakMifepristone (200 mg/1) + Ibuprofen (800 mg/1) + Misoprostol (200 ug/1) + Ondansetron (8 mg/1)Kit; Tablet; Tablet, orally disintegratingOralNucare Pharmaceuticals,inc.2023-02-24Not applicableUS flag
Mpm PakMifepristone (200 mg/1) + Ibuprofen (800 mg/1) + Misoprostol (200 ug/1) + Ondansetron (8 mg/1)Kit; Tablet; Tablet, orally disintegratingOralNucare Pharmaceuticals,inc.2023-06-14Not applicableUS flag

Categories

ATC Codes
G03XB01 — MifepristoneG03XB51 — Mifepristone, combinations
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Oxosteroids
Direct Parent
Oxosteroids
Alternative Parents
3-oxosteroids / 17-hydroxysteroids / Dialkylarylamines / Aniline and substituted anilines / Cyclohexenones / Ynones / Tertiary alcohols / Cyclic alcohols and derivatives / Organopnictogen compounds / Organic oxides
show 1 more
Substituents
17-hydroxysteroid / 3-oxosteroid / Alcohol / Amine / Aniline or substituted anilines / Aromatic homopolycyclic compound / Benzenoid / Carbonyl group / Cyclic alcohol / Cyclic ketone
show 17 more
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
3-oxo steroid (CHEBI:50692) / Estrane and derivatives (C07652)
Affected organisms
  • Humans and other mammals

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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. 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]
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
PhaseStatusPurposeConditionsCount
4Active Not RecruitingHealth Services ResearchEarly Abortion / Pregnancy Related1
4CompletedNot AvailableAnxiety Disorders / Post Traumatic Stress Disorder (PTSD)1
4CompletedHealth Services ResearchAbortion, Therapeutic1
4CompletedHealth Services ResearchEarly Abortion / Pregnancy Related1
4CompletedHealth Services ResearchMenstrual Regulation1

Pharmacoeconomics

Manufacturers
  • Danco laboratories llc
Packagers
  • Danco Labs LLC
Dosage Forms
FormRouteStrength
TabletOral300 mg/1
Tablet
Kit; tabletBuccal; Oral
TabletOral600 MG
TabletOral200 mg
TabletOral
TabletOral200 mg/1
Tablet, film coatedOral300 mg/1
Kit; tablet; tablet, orally disintegratingOral
TabletOral200.00 mg
TabletOral200.000 mg
Prices
Unit descriptionCostUnit
Mifeprex 200 mg tablet90.0USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US8921348No2014-12-302028-08-27US flag
US9829495No2017-11-282036-08-15US flag
US9943526No2018-04-172036-04-20US flag
US10006924No2018-06-262036-08-12US flag
US10166243No2019-01-012036-04-20US flag
US10166242No2019-01-012036-04-20US flag
US10151763No2018-12-112037-01-18US flag
US10195214No2019-02-052037-06-19US flag
US10231983No2019-03-192038-08-22US flag
US10314850No2019-06-112038-08-22US flag
US10500216No2019-12-102033-03-05US flag
US10495650No2019-12-032036-08-12US flag
US10660904No2020-05-262036-04-20US flag
US10780097No2020-09-222038-08-22US flag
US10842800No2020-11-242037-06-19US flag
US10842801No2020-11-242032-11-15US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)191-196 °CFDA Label
water solubilityPoorly solubleFDA Label
logP4.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00336 mg/mLALOGPS
logP5.33ALOGPS
logP5.13Chemaxon
logS-5.1ALOGPS
pKa (Strongest Acidic)12.87Chemaxon
pKa (Strongest Basic)4.89Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area40.54 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity132.58 m3·mol-1Chemaxon
Polarizability50.69 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.7135
Caco-2 permeable+0.6716
P-glycoprotein substrateSubstrate0.643
P-glycoprotein inhibitor IInhibitor0.8564
P-glycoprotein inhibitor IIInhibitor0.8387
Renal organic cation transporterNon-inhibitor0.8177
CYP450 2C9 substrateNon-substrate0.7606
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.8334
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorNon-inhibitor0.6293
CYP450 2D6 inhibitorInhibitor0.8931
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorInhibitor0.796
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6129
Ames testNon AMES toxic0.856
CarcinogenicityNon-carcinogens0.825
BiodegradationNot ready biodegradable0.9971
Rat acute toxicity2.7705 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9177
hERG inhibition (predictor II)Non-inhibitor0.6879
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0w29-0356900000-2d8af6b9cc4537ce26fd
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-0332900000-9cbfa7fe6866f246577a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0000900000-6cc132780bb114cc2304
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000t-0958400000-90d89bf049821be45f72
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0000900000-bb15b020dd7dc0ff9e1e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0000900000-14e7dff7e75a31f8e8c2
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000t-0942100000-daf78c1795dcbda71588
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-016u-0069800000-c4925dab8b09c3196848
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[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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Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
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Details
1. 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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Details
2. 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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. 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]
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
  1. 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]
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
  1. Kretschmer XC, Baldwin WS: CAR and PXR: xenosensors of endocrine disrupters? Chem Biol Interact. 2005 Aug 15;155(3):111-28. [Article]

Enzymes

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
  1. 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]
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
  1. Mifepristone FDA Label [File]
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
  1. PDR [Link]
Details
4. 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
  1. 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]
  2. 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]
  3. Jang GR, Benet LZ: Antiprogestin-mediated inactivation of cytochrome P450 3A4. Pharmacology. 1998 Mar;56(3):150-7. doi: 10.1159/000028193. [Article]
  4. 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]
  5. 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]
  6. Flockhart Table of Drug Interactions [Link]
  7. Mifeprex (Mifepristone) FDA Label [Link]
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
  1. 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]
  2. 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]
  3. Flockhart Table of Drug Interactions [Link]

Transporters

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
  1. 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]
  2. 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]
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
  1. 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]
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
  1. 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]
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
  1. 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]
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
  1. 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