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84371-65-3

84371-65-3 Structure

84371-65-3 Structure
IdentificationMore
[Name]

Mifepristone
[CAS]

84371-65-3
[Synonyms]

(11B,17 B)-11-[4-(DIMETHYLAMINO)PHENYL]-17-HYDROXY-17-(1-PROPYNYL)-ESTRA-4,9-DIEN-3-ONE
(11BETA,17BETA)-11-(4-(DIMETHYLAMINO)PHENYL)-17-HYDROXY-17-(1-PROPYNYL)ESTRA-4,9-DIEN-3-ONE
11BETA-[4-(DIMETHYLAMINO)PHENYL]-17BETA-HYDROXY-17-(1-PROPYNYL)ESTRA-4,9-DIEN-3-ONE
11b-[p-(dimethylamino)phenyl]-17b-hydroxy-17-(1-propynyl)estra-4,9-dien-3-one
4,9-ESTRADIEN-17-ALPHA-PROPYNYL, 11-BETA-[4-DIMETHYNYLAMINO]PHENYL-17-BETA-OL-3-ONE
MIFEGYNE
MIFEPRISTONE
RU-38486
RU486
11-(4-(dimethylamino)phenyl)-17-hydroxy-17-(1-propynyl)-estra-9-dien-3-one
11beta-[4-(n,n-dimethylamino)phenyl]-17alpha-(prop-1-ynyl)-delta4,9-estradiene
17-beta)-(11-bet
17beta)-11-[4-(dimethylamino)-phenyl]-17-hydroxy-17-(1-propynyl)estra-(11bet
17-beta-hydroxy-11-beta-(4-dimethylaminophenyl-1)-17-alpha-(prop-1-ynyl)oest
-17beta-ol-3-one
4,9-dien-3-one
r38486
ra-4,9-dien-3-one
ru486-6
Mifepriston Dianhydride
[EINECS(EC#)]

617-559-7
[Molecular Formula]

C29H35NO2
[MDL Number]

MFCD00867226
[Molecular Weight]

429.59
[MOL File]

84371-65-3.mol
Chemical PropertiesBack Directory
[Appearance]

Pale Yellow Solid
[Melting point ]

195-198°C
[mp ]

195-198°C
[Boiling point ]

544.13°C (rough estimate)
[alpha ]

D20 +138.5° (c = 0.5 in chloroform)
[density ]

1.0731 (rough estimate)
[refractive index ]

1.6290 (estimate)
[storage temp. ]

2-8°C
[pka]

12.94±0.60(Predicted)
[form ]

Yellow solid
[Water Solubility ]

474.8ug/L(22.5 ºC)
[Usage]

A progesterone receptor antagonist with partial agonist activity. Abortifacient.
[Merck ]

6186
[InChIKey]

VKHAHZOOUSRJNA-GCNJZUOMSA-N
[CAS DataBase Reference]

84371-65-3(CAS DataBase Reference)
Safety DataBack Directory
[Hazard Codes ]

T
[Risk Statements ]

R60:May impair fertility.
R61:May cause harm to the unborn child.
[Safety Statements ]

S53:Avoid exposure-obtain special instruction before use .
S22:Do not breathe dust .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
[WGK Germany ]

3
[RTECS ]

KG2955000
[HS Code ]

29372900
[Hazardous Substances Data]

84371-65-3(Hazardous Substances Data)
Raw materials And Preparation ProductsBack Directory
【Raw materials】

Tetrahydrofuran-->N,N-Dimethylaniline-->Isopropyl ether-->Dimethyl sulfide-->1,2-Dibromoethane
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

11b-[p-(Dimethylamino)phenyl]-17b-hydroxy-17-(1-propynyl)estra-4,9-dien-3-one(84371-65-3).msds
Hazard InformationBack Directory
[Chemical Properties]

Pale Yellow Solid
[Originator]

Roussel-Uclaf (France)
[Uses]

A progesterone and glucocorticoid antagonist, suppresses VEGF production.
[Uses]

A progesterone receptor antagonist with partial agonist activity. Abortifacient.
[Uses]

glutamate uptake inhibitor, AMPA blocker
[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.
[Manufacturing Process]

1st method of synthesis of mifepristone:A solution of 24 g of 4-(N,N-dimethylaminoethoxy)bromobenzene was addeddropwise over 45 min to magnesium in 90 ml of anhydrous tetrahydrofuran. 2ml of 1,2-dibromoethane were added as catalyst. After the addition, themixture was stirred at 25°C for one hour to obtain a solution of 0.7 M of 4-(N,N-dimethylaminoethoxy)-benzene magnesium bromide which was thenadded to a solution of 6.16 g of dimethylsulfide-cuprous bromide complex in20 ml of tetrahydrofuran. The mixture was stirred at room temperature for 20min and a solution of 3.7 g of 3,3-[1,2-(ethanediyl-bisoxy)]-5α,10α-epoxy-17α-prop-1-ynyl-δ(9(11))-estrene-17β-ol in 50 ml of tetrahydrofuran was addedthereto dropwise over a few minutes. The mixture was stirred under an inertatmosphere for one hour and was then poured into a solution of 15 g ofammonium chloride in 20 ml of iced water. The mixture was extracted withether and the organic phase was washed with aqueous saturated sodiumchloride solution, was dried and evaporated to dryness under reducedpressure. The 18.3 g of oil were chromatographed over silica gel and elutedwith chloroform to obtain 4.5 g of 3,3-[1,2-ethanediyl-bisoxy]-11β-[4-(N,N-dimethylaminoethoxy)phenyl]-17α-(prop-1-ynyl)-δ9-estrene-5α,17β-diol with aspecific rotation of [α]D20=-44(+/-)1.5° (c = 1% in chloroform).
9.5 ml of 2 N hydrochloric acid were added to a solution of 4.5 g of 3,3-[1,2-ethanediyl-bisoxy]-11β-[4-(N,N-dimethylaminoethoxy)phenyl]-17α-(prop-1-ynyl)-δ9-estrene-5α,17β-diol in 20 ml of methanol and the solution was stirredat room temperature for 2 hours. 260 ml of ether and 110 ml of an aqueoussaturated sodium bicarbonate solution were added to the mixture which wasstirred at room temperature for 15 min. The decanted aqueous phase wasextracted with ether and the organic phase was dried and evaporated todryness under reduced pressure. The 3.3 g of residue were chromatographedover silica gel and eluted with a 92.5/7.5 methylene chloride-methanolmixture to obtain 1.8 g of amorphous 11β-[4-(N,N-dimethylaminoethoxy)phenyl]-17α-(prop-1-ynyl)-δ4,9-estradiene-17β-ol-3-one with a specificrotation of [α]D20=+71° (c = 1% in chloroform).
2th method of synthesis of mifepristone (see scheme):The oxidation of the diene I, which constitutes an intermediate for totalsynthesis of 19-nor steroids, with a reagent prepared from trifluoroaceticanhydride/hydrogen peroxide was obtained exclusively α-epoxide II. Thecondensation of II with the Grignard reagent from 4-bromo-N,N-dimethylaniline results in addition of the reagent at the 11β-position. Thisresults in rearragement of the olefin to 9,10 and opening of the epoxide. Thestereochemistry of the product obtained III is consistent with trans-opening ofthe oxirane, albeit at a remove of two carbon atoms. Mild hydrolysis removesthe silyl cyanohydrin protecting group at the 17-position to give a ketone IV.Reaction of the ketone with propargyl lithium leads to V. Hydrolysis of thatproduct under more strenuous condition results in removal of the acetal at 3;the resulting β-hydroxyketone then dehydrates to afford the 4,10(9)-dienoneVI. Another name of VI is estra-4,9-dien-3-one, 11-(4-(dimethylamino)phenyl)-17-hydroxy-17-(1-propynyl)-, (11β,17β)- or mifepristone.
[Brand name]

Mifeprex (Danco);Ru-486;Mifegyne.
[Therapeutic Function]

Antiprogesterone
[World Health Organization (WHO)]

Mifepristone, an antiprogesterone used in combination with a prostaglandin for the termination of early pregnancy, was introduced in 1990. Use of the combination has been associated with episodes of coronary spasm that are attributed to administration of the prostaglandin and which have resulted in several cases of cardiac infarction and ventricular fibrillation. At least one of these incidents has been fatal.
[Biological Activity]

Selective antagonist at progesterone (PR) and glucocorticoid (GR) receptors in vitro and in vivo . Is a silent antagonist at PR and has a higher affinity than progesterone. Has higher affinity for GR than dexamethasone.
[Pharmacokinetics]

Following oral administration, mifepristone is rapidly absorbed, with a peak plasmaconcentration in approximately 90 minutes , an oral bioavailability of approximately 70%, and a term inal elimination half-life of 18 hours. It is 98% protein bound, primarily to album in and α1-acid glycoprotein. Mifepristone is metabolized primarily via CYP3A4 pathways involving mono- and di-N-demethylation and terminal hydroxylation of the 17-propynyl chain. The fact that approximately 83% of the drug is recovered in the feces and 9% in the urine suggests a biliary route of elimination. Mifepristone also demonstrates antiglucocorticoid activity.
[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.
Questions And AnswerBack Directory
[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.  
Questions and Answers (Q&A)Back Directory
[References]

https://pubchem.ncbi.nlm.nih.gov/compound/mifepristone#section=Top
https://www.drugbank.ca/drugs/DB00834
https://www.drugs.com/cdi/mifepristone-tablets.html
Spectrum DetailBack Directory
[Spectrum Detail]

Mifepristone(84371-65-3)13CNMR
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

84371-65-3(sigmaaldrich)
[TCI AMERICA]

Mifepristone,>98.0%(LC)(T)(84371-65-3)
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