Mifepristone

Base Information

• Chemical Name: Mifepristone
• CAS No.: 84371-65-3
• Deprecated CAS: 122742-25-0,83203-42-3
• Molecular Formula: C29H35NO2
• Molecular Weight: 429.602
• Hs Code.: 29372900
• European Community (EC) Number: 617-559-7
• UNII: 320T6RNW1F
• DSSTox Substance ID: DTXSID5023322
• Nikkaji Number: J23.743D
• Wikipedia: Mifepristone
• Wikidata: Q411240
• NCI Thesaurus Code: C655
• RXCUI: 6964
• Pharos Ligand ID: WGH879VG45KF
• Metabolomics Workbench ID: 43122
• ChEMBL ID: CHEMBL1276308
• Mol file: 84371-65-3.mol

Synonyms:Mifégyne;Mifegyne;Mifeprex;Mifepristone;R 38486;R-38486;R38486;RU 38486;RU 486;RU-38486;RU-486;RU38486;RU486;ZK 98296;ZK-98296;ZK98296

Chemical Property of Mifepristone

Chemical Property:

• Appearance/Colour: pale yellow solid
• Vapor Pressure: 1.14E-16mmHg at 25°C
• Melting Point: 195-198 °C
• Refractive Index: 1.623
• Boiling Point: 628.6 °C at 760 mmHg
• PKA: 12.94±0.60(Predicted)
• Flash Point: 334 °C
• PSA: 40.54000
• Density: 1.18 g/cm³
• LogP: 5.40650
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMSO (up to 40 mg/ml) or in Ethanol (up to 20 mg/ml).
• Water Solubility.: 474.8ug/L(22.5 oC)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 429.266779359
• Heavy Atom Count: 32
• Complexity: 921

Purity/Quality:

98.0%min ^*data from raw suppliers

Mifepristone ≥99%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 60-61
• Safety Statements: 53-22-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Pregnancy Termination Agents
• Canonical SMILES: CC#CC1(CCC2C1(CC(C3=C4CCC(=O)C=C4CCC23)C5=CC=C(C=C5)N(C)C)C)O
• 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
• Recent ClinicalTrials: Mifepristone for Labor Induction
• Recent EU Clinical Trials: REStoring mood after Early life Trauma – Glucocorticoid Receptor (GR) blockade as disease-modifying treatment for depression with childhood trauma
• Description: Mifepristone is a kind of antagonist of the progestational and glucocorticoid hormone. It is mainly used for the treatment of hypercortisolism in patients with nonpituitary cushing syndrome. During the treatment of Cushing’s syndrome, mifepristone takes effect through interfering with the binding of cortisol to its receptor. It reduces the effects of excess cortisol (e.g., high blood sugar levels) without causing decreased cortisol production. It can also be used to end a pregnancy. Its inhibition on progesterone can induce bleeding during the luteal phase and in early pregnancy. Mifepristone is an orally-active progesterone and glucocorticoid receptor antagonist indicated for use as a post-coital contraceptive. In addition to being an abortifacient, mifepristone is reported to be effective in the treatment of ocular hypertension; its potential therapeutic effect in hormone-dependent tumors is currently under investigation.
• Uses: glutamate uptake inhibitor, AMPA blocker A progesterone and glucocorticoid antagonist, suppresses VEGF production. A progesterone receptor antagonist with partial agonist activity. Abortifacient. Mifepristone is a progesterone receptor antagonist with partial agonist activity. Abortifacient.
• Indications: Mifepristone is a progesterone receptor antagonist that has a high affinity for glucocorticoid receptors and little agonist effect.This drug has recently been approved for use in the United States for the treatment of hypercortisolism. At high doses, mifepristone blocks negative feedback of the hypothalamic–pituitary axis, thereby increasing endogenous corticotrophin and cortisol levels. Because mifepristone exerts its effects at the receptor level and not by altering glucocorticoid production, elevated serum cortisol and corticotrophin levels may not accurately reflect the effectiveness of the therapeutic regimen. Mifepristone does not inhibit cortisol binding to the mineralocorticoid receptor, so that the resulting corticotrophin disinhibition may cause potassium depletion. Thus, administration of a mineralocorticoid receptor antagonist such as spironolactone may be indicated with mifepristone. Hypoadrenalism, nausea, and drowsiness have been reported during prolonged administration of mifepristone.
• Therapeutic Function: Antiprogesterone
• Clinical Use: An antiprogestin is a substance that competes with progesterone for its receptor and, ultimately, prevents progesterone from binding to and activating its receptor. Because progesterone is integral to the continuation of an early pregnancy, it is expected that antipro-gestins will interfere with pregnancy maintenance. In 1982, the first antiproges tin, mifepristone (RU 486), was reported. Mifepristone was shown to interrupt early stages of implantation and pregnancy in humans.

Technology Process of Mifepristone

There total 1 articles about Mifepristone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ mifepristone (84371-65-3)

Guidance literature:

Reference yield: 99.0%

mifepristone (84371-65-3) → aglepristone

Guidance literature:

With hydrogen; In methanol; under 3800.26 Torr; Reagent/catalyst; Solvent; stereoselective reaction; Green chemistry;

DOI:10.1039/c8gc01522h

Reference yield: 98.0%

2-Picolinic acid (98-98-6) + mifepristone (84371-65-3) → N-(4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-(prop-1-yn-1-yl)-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl)-N-methylpicolinamide

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃;

Downstream raw materials:

(8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-11-(4-(methylamino)phenyl)-17-(prop-1-yn-1-yl)-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one

N-(4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-(prop-1-yn-1-yl)-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl)-N-methylformamide

(S)-2-Amino-4-{[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-prop-1-ynyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)-phenyl]-methyl-carbamoyl}-butyric acid methyl ester

11β-{4-((4(S)-t-Butoxycarbonylamino-4(S)-methoxycarbonyl)butyryl-methyl-amino)phenyl}-17β-hydroxy-17α-(1-propynyl)estra-4,9-dien-3-one

Refernces

• 1、 -. "Steroid derivatives". . . Retrieved 2008/06/13.