Mifepristone
Overview
Description
Mifepristone, also known by its developmental code name RU-486, is a synthetic steroid compound with the chemical formula C29H35NO2 . It is primarily known for its use in medical abortions and the management of early miscarriages. This compound works by blocking the hormone progesterone, which is essential for pregnancy continuation .
Scientific Research Applications
Mifepristone has a wide range of scientific research applications, including:
Chemistry: Used as a model compound to study steroidal synthesis and reactions.
Biology: Investigated for its effects on hormone receptors and cellular pathways.
Industry: Utilized in the development of new pharmaceutical formulations and drug delivery systems.
Mechanism of Action
Target of Action
Mifepristone primarily targets the progesterone receptor and the glucocorticoid receptor . It acts as a progestational and glucocorticoid hormone antagonist . The compound’s antagonistic action on the progesterone receptor is particularly significant in its use for medical termination of pregnancy .
Mode of Action
This compound’s mode of action involves a competitive interaction with progesterone at progesterone-receptor sites . This interaction results in the inhibition of progesterone, which induces bleeding during the luteal phase and in early pregnancy by releasing endogenous prostaglandins from the endometrium or decidua . As a glucocorticoid receptor antagonist, this compound has been used to treat hypercortisolism in patients with nonpituitary Cushing syndrome .
Biochemical Pathways
The biochemical pathways affected by this compound primarily involve the progesterone and glucocorticoid pathways . By inhibiting the activity of endogenous or exogenous progesterone, this compound impacts these pathways and their downstream effects .
Pharmacokinetics
This compound exhibits complex pharmacokinetics. It is rapidly absorbed and has a long half-life of 25 to 30 hours . The serum transport protein α1-acid glycoprotein (AAG) regulates the serum kinetics of this compound . Binding to AAG limits the tissue availability of this compound, explaining the low metabolic clearance rate and the low volume of distribution of this compound . Following oral intake, this compound is extensively metabolized by demethylation and hydroxylation, the initial metabolic steps are catalyzed by the cytochrome P450 (CYP) enzyme CYP3A4 .
Result of Action
The primary result of this compound’s action is the termination of pregnancy up to 70 days gestation . Its inhibition of progesterone induces bleeding during the luteal phase and in early pregnancy . In addition, it has been used to control hyperglycemia secondary to hypercortisolism in adult patients with endogenous Cushing’s syndrome .
Action Environment
The action of this compound can be influenced by various environmental factors. For instance, the timing of administration relative to intercourse and ovulation can impact its efficacy as an emergency contraceptive . Additionally, the compound’s action may be affected by the patient’s hormonal status and other individual physiological factors .
Future Directions
The fate of the abortion pill lies with the Supreme Court. The high court, which has a conservative supermajority, holds the power to maintain full access to the drug or reverse regulation changes that made medication abortion more accessible in recent years . This includes allowing the pills to be prescribed via telemedicine, delivered in the mail, and used up to 10 weeks of pregnancy instead of seven .
Biochemical Analysis
Biochemical Properties
Mifepristone acts as a competitive progesterone receptor antagonist . In the absence of progesterone, this compound acts as a partial agonist . It works by blocking the effects of progesterone, making both the cervix and uterine vessels dilate and causing uterine contraction . This compound is also a glucocorticoid receptor antagonist .
Cellular Effects
This compound has been shown to inhibit ovarian cancer cell proliferation in a dose- and time-dependent manner . It also induced fewer alveoli, enlarged alveolar lumina, and altered the levels of hormones such as estrogen, progesterone, prolactin, growth hormone, corticosterone, and oxytocin, as well as the mRNA expression of these hormonal receptors during pregnancy or early lactation .
Molecular Mechanism
This compound is a selective antagonist of the progesterone receptor at low doses and blocks the glucocorticoid receptor (GR-II) at higher doses . It works by blocking the effects of progesterone, which is necessary for a pregnancy to continue . This compound’s inhibition of progesterone induces bleeding during the luteal phase and in early pregnancy by releasing endogenous prostaglandins from the endometrium or decidua .
Temporal Effects in Laboratory Settings
In a 24-week multicenter, open-label trial, this compound produced significant clinical and metabolic improvement in patients with Cushing’s syndrome with an acceptable risk-benefit profile during 6 months of treatment . This compound treatment reduced cellular proliferation and viability of all UM cell lines studied in a concentration-dependent manner .
Dosage Effects in Animal Models
In animal models, this compound administration at the dose of 1.20 mg/kg body weight on pregnancy day 4 caused a significant reduction in milk production on lactation day 1, lactation day 2, and lactation day 3 . This compound also induced an increase in the weight of epididymal, perirenal, and gluteofemoral adipose tissues .
Metabolic Pathways
This compound is extensively metabolised by demethylation and hydroxylation, the initial metabolic steps are catalysed by the cytochrome P450 (CYP) enzyme CYP3A4 . The three most proximal metabolites, namely the monodemethylated, didemethylated, and hydroxylated metabolites of this compound, all retain considerable affinity toward the human progesterone and glucocorticoid receptors .
Transport and Distribution
The serum transport protein α1-acid glycoprotein (AAG) regulates the serum kinetics of this compound . Binding to AAG limits the tissue availability of this compound, explaining the low metabolic clearance rate of 0.55 L/kg/day and the low volume of distribution of this compound .
Subcellular Localization
This compound markedly reduces cdk2 activity likely due to increased association of cdk2 with the cdk inhibitors p21 cip1 and p27 kip1 and reduced nuclear cdk2/cyclin E complex availability . This suggests that this compound may regulate mitochondrial function through the control of mitochondrial gene expression .
Preparation Methods
Synthetic Routes and Reaction Conditions: Mifepristone is synthesized through a multi-step process involving several key intermediates. The synthesis begins with the preparation of 11β-[4-(dimethylamino)phenyl]-17β-hydroxy-17α-(1-propynyl)estra-4,9-dien-3-one. This intermediate is then subjected to various chemical reactions, including hydroxylation and alkylation, to produce the final compound .
Industrial Production Methods: In industrial settings, this compound is produced using a wet granulation method. This involves mixing the active pharmaceutical ingredient with excipients such as starch and microcrystalline cellulose, followed by granulation with a water/alcohol mixture. The granules are then dried and compressed into tablets .
Chemical Reactions Analysis
Types of Reactions: Mifepristone undergoes several types of chemical reactions, including:
Oxidation: this compound can be oxidized to form various metabolites.
Reduction: Reduction reactions can modify the ketone group in this compound.
Substitution: Substitution reactions can occur at the dimethylamino group.
Common Reagents and Conditions:
Oxidation: Common oxidizing agents include potassium permanganate and chromium trioxide.
Reduction: Reducing agents such as sodium borohydride and lithium aluminum hydride are used.
Substitution: Reagents like alkyl halides and amines are employed for substitution reactions.
Major Products Formed: The major products formed from these reactions include various hydroxylated and demethylated metabolites, such as N-desmethyl-mifepristone and 22-hydroxy-mifepristone .
Comparison with Similar Compounds
Mifepristone belongs to a class of compounds known as progesterone receptor antagonists. Similar compounds include:
Levonorgestrel: Used for emergency contraception, but works primarily as a progestin rather than an antagonist.
Ulipristal acetate: Another progesterone receptor modulator used for emergency contraception and treatment of fibroids.
Asoprisnil: A selective progesterone receptor modulator with applications in treating endometriosis and uterine fibroids.
Uniqueness of this compound: this compound’s unique ability to act as both a progesterone and glucocorticoid receptor antagonist sets it apart from other compounds in its class. This dual action makes it highly effective for a range of medical applications, from terminating pregnancies to managing hormonal disorders .
Properties
IUPAC Name |
(8S,11R,13S,14S,17S)-11-[4-(dimethylamino)phenyl]-17-hydroxy-13-methyl-17-prop-1-ynyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
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 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
VKHAHZOOUSRJNA-GCNJZUOMSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CC#CC1(CCC2C1(CC(C3=C4CCC(=O)C=C4CCC23)C5=CC=C(C=C5)N(C)C)C)O |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Isomeric SMILES |
CC#C[C@@]1(CC[C@@H]2[C@@]1(C[C@@H](C3=C4CCC(=O)C=C4CC[C@@H]23)C5=CC=C(C=C5)N(C)C)C)O |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C29H35NO2 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID5023322 |
Source
|
| Record name | Mifepristone | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID5023322 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
429.6 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Solid |
Source
|
| Record name | Mifepristone | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014972 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Solubility |
7 [ug/mL] (The mean of the results at pH 7.4), Poorly soluble, Very soluble in methanol, chloroform, and acetone and poorly soluble in water, hexane, and isopropyl ether., In water, 5.0X10-2 mg/L at 25 °C /Estimated/, 3.36e-03 g/L |
Source
|
| Record name | SID11533034 | |
| Source | Burnham Center for Chemical Genomics | |
| URL | https://pubchem.ncbi.nlm.nih.gov/bioassay/1996#section=Data-Table | |
| Description | Aqueous solubility in buffer at pH 7.4 | |
| Record name | Mifepristone | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00834 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | MIFEPRISTONE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/6841 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| Record name | Mifepristone | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014972 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Vapor Pressure |
8.0X10-14 mm Hg at 25 °C /Estimated/ |
Source
|
| Record name | MIFEPRISTONE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/6841 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
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., Mifepristone competitively inhibits the actions of progesterone at progesterone-receptor sites, resulting in termination of pregnancy.The combination of mifepristone and misoprostol causes expulsion of the products of conception through decidual necrosis, myometrial contractions, and cervical softening., When administered in the early stages of pregnancy, mifepristone causes decidual breakdown by blockade of uterine progesterone receptors. This leads to detachment of the blastocyte, which decreases hCG production. This in turn causes a decrease in progesterone secretion from the corpus luteum, which further accentuates decidual breakdown. Decreased endogenous progesterone coupled with blockade of progesterone receptors in the uterus increases prostaglandin levels and sensitizes the myometrium to the contractile actions of prostaglandins., In addition, mifepristone promotes uterine contractions and softening of the cervix and sensitizes the myometrium to effects of prostaglandins (e.g., misoprostol) that stimulate uterine contraction and expulsion of the products of conception. In the absence of progesterone, mifepristone acts as a partial progestin agonist. At dosages higher than those used for termination of pregnancy, mifepristone also exhibits antiglucocorticoid activity. The drug also has been shown to have weak antiandrogenic activity. |
Source
|
| Record name | Mifepristone | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00834 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | MIFEPRISTONE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/6841 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
Color/Form |
Yellow powder | |
CAS No. |
84371-65-3 |
Source
|
| Record name | Mifepristone | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=84371-65-3 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
| Explanation | The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated. | |
| Record name | Mifepristone [USAN:INN:BAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0084371653 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
| Record name | Mifepristone | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00834 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | Mifepristone | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID5023322 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
| Record name | Estra-4,9-dien-3-one, 11-[4-(dimethylamino)phenyl]-17-hydroxy-17-(1-propyn-1-yl)-, (11β,17β) | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/substance-information/-/substanceinfo/100.127.911 | |
| Description | The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness. | |
| Explanation | Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. | |
| Record name | MIFEPRISTONE | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/320T6RNW1F | |
| Description | The FDA Global Substance Registration System (GSRS) enables the efficient and accurate exchange of information on what substances are in regulated products. Instead of relying on names, which vary across regulatory domains, countries, and regions, the GSRS knowledge base makes it possible for substances to be defined by standardized, scientific descriptions. | |
| Explanation | Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. | |
| Record name | MIFEPRISTONE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/6841 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| Record name | Mifepristone | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014972 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Melting Point |
191-196 °C, 150 °C, 191 - 196 °C |
Source
|
| Record name | Mifepristone | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00834 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | MIFEPRISTONE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/6841 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| Record name | Mifepristone | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014972 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Retrosynthesis Analysis
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Strategy Settings
| Precursor scoring | Relevance Heuristic |
|---|---|
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| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
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