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Mifepristone

Description
Mifepristone
Mifepristone structure
CAS No.
84371-65-3
Chemical Name:
Mifepristone
Synonyms
RU486;C-1073;r38486;ru486-6;VGX 410;MIFEGYNE;RU-38486;Mifeprex;Mifestone;Mifepriston
CBNumber:
CB6351940
Molecular Formula:
C29H35NO2
Formula Weight:
429.6
MOL File:
84371-65-3.mol

Mifepristone Properties

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
form 
Yellow solid
pka
12.94±0.60(Predicted)
Water Solubility 
474.8ug/L(22.5 ºC)
Merck 
14,6186
InChIKey
VKHAHZOOUSRJNA-GCNJZUOMSA-N
CAS DataBase Reference
84371-65-3(CAS DataBase Reference)
FDA UNII
320T6RNW1F
NCI Dictionary of Cancer Terms
Mifeprex; mifepristone; RU 486
NCI Drug Dictionary
Mifeprex
ATC code
G03XB01,G03XB51
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS08,GHS07
Signal word  Danger
Hazard statements  H302+H312+H332-H360
Precautionary statements  P261-P264-P270-P271-P301+P312+P330-P302+P352+P312+P362+P364-P304+P340+P312-P501-P201-P280-P308+P313
Hazard Codes  T
Risk Statements  60-61
Safety Statements  53-22-36/37/39-45
WGK Germany  3
RTECS  KG2955000
HS Code  29372900

Mifepristone price More Price(35)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 475838 Mifepristone 84371-65-3 50mg $74.92 2021-12-16 Buy
Sigma-Aldrich 1443759 Mifepristone United States Pharmacopeia (USP) Reference Standard 84371-65-3 200mg $477 2021-12-16 Buy
TCI Chemical M1732 Mifepristone >98.0%(T)(HPLC) 84371-65-3 1g $192 2021-12-16 Buy
TCI Chemical M1732 Mifepristone >98.0%(T)(HPLC) 84371-65-3 5g $606 2021-12-16 Buy
Cayman Chemical 10006317 Mifepristone ≥98% 84371-65-3 5 g $520 2021-12-16 Buy

Mifepristone Chemical Properties,Uses,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

A progesterone receptor antagonist with partial agonist activity. Abortifacient.

Uses

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.

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.

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

Preparation Products


Mifepristone Suppliers

Global( 404)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Beijing Cooperate Pharmaceutical Co.,Ltd
010-60279497
010-60279497 sales01@cooperate-pharm.com CHINA 1817 55
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com China 22607 55
Nanjing ChemLin Chemical Industry Co., Ltd.
025-83697070
product@chemlin.com.cn CHINA 3013 60
Nanjing Finetech Chemical Co., Ltd.
025-85710122 17714198479
025-85710122 sales@fine-chemtech.com CHINA 890 55
Shanghai Zheyan Biotech Co., Ltd.
18017610038
zheyansh@163.com CHINA 3623 58
HEBEI YINGONG NEW MATERIAL TECHNOLOGY CO.,LTD
+8619933070948
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TianYuan Pharmaceutical CO.,LTD
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Hebei Guanlang Biotechnology Co., Ltd.
+8619930503282
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View Lastest Price from Mifepristone manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2022-01-18 Mifepristone
84371-65-3
US $9.90-9.90 / g/Bag 10g/Bag 99.99%HPLC.USP42——Powder、Oil、Pills、Capsules、Tablets,Customized packaging 100KG/Month Wuhan Biocar Pharmacy Co., Ltd.
2022-01-18 Mifepristone
84371-65-3
US $1.00 / g 10g 99.5% 1000kg Guangzhou Biocar Biotechnology Co.,Ltd.
2022-01-18 Mifepristone
84371-65-3
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD

Mifepristone Spectrum


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