Description
ChemicalBook > CAS DataBase List > Mifepristone

Mifepristone

Description
Product Name
Mifepristone
CAS No.
84371-65-3
Chemical Name
Mifepristone
Synonyms
RU486;Mifeprestone;Mifepristone INN;C-1073;r38486;ru486-6;VGX 410;MIFEGYNE;RU-38486;Mifeprex
CBNumber
CB6351940
Molecular Formula
C29H35NO2
Formula Weight
429.59
MOL File
84371-65-3.mol
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Mifepristone Property

Melting point:
195-198°C
alpha 
D20 +138.5° (c = 0.5 in chloroform)
Boiling point:
544.13°C (rough estimate)
Density 
1.0731 (rough estimate)
refractive index 
1.6290 (estimate)
storage temp. 
2-8°C
solubility 
Soluble in DMSO (up to 40 mg/ml) or in Ethanol (up to 20 mg/ml).
form 
Yellow solid
pka
12.94±0.60(Predicted)
color 
Yellow
biological source
synthetic (organic)
Water Solubility 
474.8ug/L(22.5 ºC)
Merck 
14,6186
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
InChIKey
VKHAHZOOUSRJNA-GCNJZUOMSA-N
CAS DataBase Reference
84371-65-3(CAS DataBase Reference)
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Safety

Hazard Codes 
T
Risk Statements 
60-61
Safety Statements 
53-22-36/37/39-45
WGK Germany 
3
RTECS 
KG2955000
HS Code 
29372900
Hazardous Substances Data
84371-65-3(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H360May damage fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
475838
Product name
Mifepristone
Packaging
50mg
Price
$99.4
Updated
2024/03/01
Sigma-Aldrich
Product number
1443759
Product name
Mifepristone
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$572
Updated
2024/03/01
TCI Chemical
Product number
M1732
Product name
Mifepristone
Purity
>98.0%(T)(HPLC)
Packaging
1g
Price
$210
Updated
2024/03/01
TCI Chemical
Product number
M1732
Product name
Mifepristone
Purity
>98.0%(T)(HPLC)
Packaging
5g
Price
$693
Updated
2024/03/01
Cayman Chemical
Product number
10006317
Product name
Mifepristone
Purity
≥98%
Packaging
100mg
Price
$33
Updated
2024/03/01
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Mifepristone Chemical Properties,Usage,Production

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.  

Description

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.

Chemical Properties

Pale Yellow Solid

Originator

Roussel-Uclaf (France)

Uses

glutamate uptake inhibitor, AMPA blocker

Uses

A progesterone and glucocorticoid antagonist, suppresses VEGF production.

Uses

Mifepristone is a progesterone receptor antagonist with partial agonist activity. Abortifacient.

Uses

A progesterone receptor antagonist with partial agonist activity. Abortifacient.

Definition

ChEBI: Mifepristone is a 3-oxo-Delta(4) steroid, an acetylenic compound and a tertiary amino compound. It has a role as an abortifacient, a contraceptive drug, a synthetic oral contraceptive and a hormone antagonist. It derives from a hydride of an estrane.

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.

Biochem/physiol Actions

Therefore, mifepristone is considered to be a potent abortifacient. It is also known to inhibit human chorionic gonadotropin. Mifepristone results in decidual necrosis.

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.

storage

Room temperature

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

Mifepristone Preparation Products And Raw materials

Raw materials

Propyne bromide Grignard reagent Dimethyl sulfide Tetrahydrofuran N,N-Dimethylaniline Diisopropyl ether

Preparation Products

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View Lastest Price from Mifepristone manufacturers

Hebei Miaoyin Technology Co.,Ltd
Product
Mifepristone 84371-65-3
Price
US $20.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
10000
Release date
2023-04-06
Hebei Mujin Biotechnology Co.,Ltd
Product
Mifepristone 84371-65-3
Price
US $0.00/Kg/Bag
Min. Order
1KG
Purity
99%
Supply Ability
20ton
Release date
2021-06-03
Hebei Zhuanglai Chemical Trading Co Ltd
Product
Mifepristone 84371-65-3
Price
US $79.00-38.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-11-19

84371-65-3, MifepristoneRelated Search:

CHLOROPHOSPHONAZO III Phenylhydrazine PHENYL VALERATE Misoprostol Levonorgestrel Metronidazole Estr-9-en-3-one, 11-[4-(dimethylamino)phenyl]-5,17-dihydroxy-17-(1-propynyl)-, cyclic 1,2-ethanediyl acetal, (5a,11b,17b)- Didemethyl Mifepristone,DIDESMETHYL MIFEPRISTONE,N-Didesmethyl Mifepristone Mifepristone-d3 22-Hydroxy Mifepristone-d6 N-DESMETHYL MIFEPRISTONE,N-Demethyl Mifepristone MIFEPRISTONE, [N-METHYL-3H] HYDROXY MIFEPRISTONE,22-Hydroxy Mifepristone Mifepristone Toripristone Mifepristone(RU486) mifepristone methochloride RU-486 (MIFEPRISTONE), [N-METHYL-3H]

  • ra-4,9-dien-3-one
  • ru486-6
  • MIFEGYNE
  • MIFEPRISTONE
  • RU-38486
  • RU486
  • 11BETA-[4-(DIMETHYLAMINO)PHENYL]-17BETA-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
  • (11B,17 B)-11-[4-(DIMETHYLAMINO)PHENYL]-17-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
  • Mifepristone - CAS 84371-65-3 - Calbiochem
  • 4,9-ESTRADIEN-17-ALPHA-PROPYNYL, 11-BETA-[4-DIMETHYNYLAMINO]PHENYL-17-BETA-OL-3-ONE
  • Mifepriston Dianhydride
  • MifepristoneTablets/Mifeprex/(Ru-486)
  • RU-486, RU-38486, Mifegyne,
  • Mifepristone(Mifeprex)
  • Mifepristone (200 mg)
  • Mifepristone-D6
  • Mifepriston
  • (10S,11S,14S,15S,17R)-17-[4-(diMethylaMino)phenyl]-14-hydroxy-15-Methyl-14-(prop-1-yn-1-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1,6-dien-5-one
  • C-1073
  • Mifepristone 11b-[p-(Dimethylamino)phenyl]-17b-hydroxy-17-(1-propynyl)estra-4,9-dien-3-one
  • Mifepristone, >=99%
  • Mifepristone INN
  • 11-[4-(dimethylamino)phenyl]-17-hydroxy-17-(1-propyn-1-yl)estra-4,9-dien-3-one
  • (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
  • Mifeprestone
  • 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
  • 11β-(4-dimethyl-amino)-phenyl-17β-hydroxy-17-(1-propynyl)-estra-4,9-dien-3-one
  • 11β -[4-(N,N-dimethylaminyl)]-phenyl-17β -hydroxy-17α-(1-propynyl)-estra-4,9-diene-3-one
  • 11b-(4-Dimethyl amino) phenyl-17b-hydroxy-17-(1-propynyl) estra-4,9-dien-3-one
  • 17-beta-Hydroxy-11-beta-(4-dimethylaminophenyl-1)-17-alpha-(prop-1-ynyl)oestra-4,9-dien-3-one
  • Estra-4,9-dien-3-one, 11-(4-(dimethylamino)phenyl)-17-hydroxy-17-(1-propynyl)-, (11-beta, 17-beta)
  • 11-(4-Dimethylaminophenyl)-17-hydroxy-13-methyl-17-prop-1-ynyl-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
  • (11β,17β)-11-[4-(Dimethylamino)phenyl]-17-hydroxy-17-(1-propynyl)-estra-4,9-dien-3-one
  • Mifepristone,11β-(4-Dimethyl-amino)-phenyl-17β-hydroxy-17-(1-propynyl)-estra-4,9-dien-3-one, RU-38486, RU-486
  • (11,17)-11-[4-(Dimethylamino)phenyl]-17-hydroxy-17-(1-propyn-1-yl)estra-4,9-dien-3-one
  • Mifeprex
  • Mifestone
  • VGX 410
  • RU-38486, RU-486, 11β-(4-Dimethylamino)phenyl-17β-hydroxy-17-(1-propynyl)estra-4,9-dien-3-one
  • (1lβ，17β)-11-[4- (Dimethylamino)phenyl]-17-hydroxy-17-(1-propynyl)estra-4，9-dien-3-one
  • 11β-(p-Dimethylaminophenyl)-17β-hydroxy-17α-(1-propynyl)estra-4,9-dien-3-one
  • RU486, RU 38486
  • Mifepristone&gt
  • Mifepristone Solution
  • Mifepristone Mifepristone
  • Estra-4,9-dien-3-one, 11-[4-(dimethylamino)phenyl]-17-hydroxy-17-(1-propyn-1-yl)-, (11β,17β)-
  • (8S,11R,13S,14S,17S)-11-(4-(Dimethylamino)phenyl)-17-hydroxy-13-methyl-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
  • Mifepristone USP/EP/BP
  • (11β,17β)-11-[4-(Dimethylamino)phenyl]-17-hydroxy-17-(1-propyn-1-yl)estra-4,9-dien-3-one