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84371-65-3 (Mifepristone)

1

Identification

Mifepristone Mifepristone
Name Mifepristone
Formula C29H35NO2
MW 429.59
CAS No. 84371-65-3
EINECS
Smiles C[[email protected]@]12[[email protected]](CC[[email protected]@]2(O)C#CC)([H])[[email protected]@](CC3)([H])C([[email protected]@H](C4=CC=C(N(C)C)C=C4)C1)=C(CC5)C3=CC5=O
Synonyms 11b-[p-(Dimethylamino)phenyl]-17b-hydroxy-17-(1-propynyl)estra-4,9-dien-3-one; (8S,11R,13S,14S,17S)-11-(4-(dimethylamino)phenyl)-17-hydroxy-13-methyl-17-(prop-1-yn-1-yl)-6,7,8,11,12,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-one
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
2

Introduction

Mifepristone(RU-38486; RU486) is a progesterone receptor antagonist(IC50= 0.2 nM) used as an abortifacient in the first months of pregnancy, and in smaller doses as an emergency contraceptive. IC50 Value: 0.2 nM (Progesterone receptor); 2.6 nM (Glucocorticoid receptor) [1] Target: Progesterone receptor Mifepristone is a synthetic steroid compound used as a pharmaceutical.

Background Information

A synthetic steroidal antiprogestogen and antiglucocorticoid drug. ......by AOBIOUS INC
Mifepristone(RU-38486; RU486) is a progesterone receptor antagonist(IC50= 0.2 nM) used as an abortifacient in the first months of pregnancy, and in smaller doses as an emergency contraceptive. IC50 Value: 0.2 nM (Progesterone receptor); 2.6 nM (Glucocorticoid receptor) [1] Target: Progesterone receptor Mifepristone is a synthetic steroid compound used as a pharmaceutical. It is a progesterone receptor antagonist used as an abortifacient in the first months of pregnancy, and in smaller doses as an emergency contraceptive. Mifepristone is also a powerful glucocorticoid receptor antagonist, and has occasionally been used in refractory Cushing's Syndrome. in vitro: Mifepristone had no effect onHeLa cell proliferation inhibition rate during 24 and 48 hours (p > 0.05). Mifepristone at low concentrations (< or = 10 micromol/l) combined withcisplatin can significantly enhance the inhibitory effect of cisplatin on HeLa cell line [2]. The effect of mifepristone on cytotoxicity of cisplatin could be mediated, at least partially, by an increase of intracellularcisplatin accumulation, but not by changes in Bcl-2/Bax gene relation expression in CaSki cells [3]. in vivo: Mifepristone administration did not alter food intake or weight during the 4-day regimen, nor were there drug-dependent differences in BEL or BCL on withdrawal day. Although mifepristone produced no significant changes in behavior of EtOH-na?ve animals, pretreatment withmifepristone (40 mg/kg) significantly reduced the severity of EtOH withdrawal [4]. Clinical trial: Mifepristone 10 or 5 mg for 6 Months to Treat Uterine Fibroids. Phase 3 ......by MedChemexpress Co., Ltd.
Shelf life: >2 years if stored properly Drug formulation: ......by MedKoo Biosciences, Inc.
Mifepristone is a remarkably active antagonist of progesterone receptor and glucocorticoid receptor with IC50 of 0.2 nM and 2.6 nM, respectively. ......by Selleck Chemicals LLC
Mifepristone is a progestational and glucocorticoid hormone antagonist. Its inhibition of progesterone induces bleeding during the luteal phase and in early pregnancy by releasing endogenous prostaglandins from the endometrium or decidua. As a glucocorticoid receptor antagonist, the drug has been used to treat hypercortisolism in patients with nonpituitary CUSHING SYNDROME. ......by Target Molecule Corp.
3

Protocol(Only for Reference)

Cell Experiment

Cell lines OV2008 and SK-OV-3 cells
Conditions 0-20 μM; 24 hours
Method Cell growth is evaluated in various ovarian cancer cell lines that are subjected to dose-response or time course treatments. Media containing each of the doses of fresh steroids is replaced every 24 hours. Control groups of cells are treated with vehicle ethanol at a final concentration of less than 0.05%. Number of viable cells is evaluated by trypsinization and counting in a hemocytometer chamber using trypan blue dye exclusion. Experiments are conducted in media without phenol red and supplemented with charcoal extracted fetal bovine serum, or media containing unextracted serum and having phenol red. Similar results are obtained with both media preparations; therefore, after performing the growth curves, all subsequent experiments are conducted using media with unextracted serum and in the presence of phenol red. When indicated, the proliferation IC50s are calculated using software designed to study drug interaction.
Source Selleck Chemicals LLC

Animal Experiment

Animal Models SK-OV-3 ovarian cancer cells are injected into immunosuppressed mice.
Dosage 0.5 or 1 mg/day
Formulation Constant release pellets (Innovative Research of America)
Administration Implanted s.c. with pellets
Source Selleck Chemicals LLC
4

Physical and Chemical Properties

Appearance:White to off-white Solid EBNumber:EB000016166

Storage condition

Solubility

DMSO 86 mg/mL; Water <1 mg/mL; Ethanol 79 mg/mL by MedChemexpress Co., Ltd.
(25°C) * In vitro DMSO 85 mg/mL (197.86 mM); Ethanol19 mg/mL (44.22 mM); Water<1 mg/mL (<1 mM) by Selleck Chemicals LLC
5

Mechanism and Indication

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Clinical Information

Product Name Sponsor & Collaborators Indications Start Date End Date Phase
Mifepristone Mount Sinai School of Medicine Hyperglycemia 2013/11/30 2014/9/30 Phase 4 Clinical
Mifepristone Gynuity Health Projects Planned abortion 2013/4/30 2013/9/30 Phase 4 Clinical
Mifepristone The University of Hong Kong Planned abortion 2010/8/31 2011/8/31 Phase 4 Clinical
Mifepristone Gynuity Health Projects 2012/11/30 2014/8/31 Phase 4 Clinical
Mifepristone Massachusetts General Hospital Post traumatic stress disorder 2009/3/31 2013/5/31 Phase 4 Clinical
Mifepristone - Launched
7

Safety Data of Mifepristone

Hazard Symbols : T
Risk Statements : 60-61
Safety Statements : 53-22-36/37/39-45
RTECS : KG2955000
WGKGermany : 3
8

Spectral Information

9

Suppliers List

Company Price and Availability Country/Region
AOBIOUS INC 1mg/USD9() USA
Abcam 100mg/USD79() USA
Apexbio Technology LLC 100mg/USD43(In stock) USA
BioVision, Inc., 50mg/USD209() USA
CHEMSCENE, LLC USA
Carbosynth Limited 2g/USD60()
Cayman Chemical Company 100mg/USD19() USA
EMD Millipore 50mg/USD69() USA
Hangzhou Deli Chemical Co., Ltd. China
Hubei Gedian Humanwell Pharmaceutical Co., Ltd. China
MedChemexpress Co., Ltd. 100mg/USD50(In stock);500mg/USD85(In stock) USA
MedKoo Biosciences, Inc. 10mg/USD80() USA
Santa Cruz Biotechnology, Inc. 100mg/USD38() USA
Selleck Chemicals LLC 50mg/USD180(In stock);10mM/1mLIn DMSO/USD230(In stock) USA
Shanghai Haoyuan Chemexpress Co., Ltd. 100mg/USD19(Get quote);500mg/USD85(Get quote) China
Sigma-Aldrich, Inc. 100mg/USD71() USA
Spectrum Chemical Mfg. Corp. 1g/USD191() USA
Taizhou Yojoy Chemical Co., Ltd. China
Target Molecule Corp. 2mg/USD55();10mg/USD78();50mg/USD168() USA
Tocris Bioscience Inc. 100mg/USD89() USA
Tokyo Chemical Industry Co., Ltd. 1g/USD153() Japan
Zhejiang Xianju Junye Pharmaceutical Co., Ltd. China
Zhejiang Xianju Xianle Pharmaceutical Co., Ltd. China
10

Related Products

Other Forms of 84371-65-3

Name CAS No Formula MW

Recommended Compounds in Progesterone Receptor Glucocorticoid Receptor Autophagy

Name CAS No Formula MW
Etonogestrel 54048-10-1 C22H28O2 324.46
Medroxyprogesterone 520-85-4 C22H32O3 344.49
Norethindrone 68-22-4 C20H26O2 298.42
Altrenogest 850-52-2 C21H26O2 310.43
Medroxyprogesterone (acetate) 71-58-9 C24H34O4 386.52
Dydrogesterone 152-62-5 C21H28O2 312.45
Levonorgestrel 797-63-7 C21H28O2 312.45
Drospirenone 67392-87-4 C24H30O3 366.49
Gestodene 60282-87-3 C21H26O2 310.43
Dienogest 65928-58-7 C20H25NO2 311.42
Progesterone 57-83-0 C21H30O2 314.46
Tanaproget 304853-42-7 C16H15N3OS 297.37
Megestrol (Acetate) 595-33-5 C24H32O4 384.51
Ulipristal (acetate) 126784-99-4 C30H37NO4 475.62
Nestoron 7759-35-5 C23H30O4 370.48
19-Norethindrone acetate 51-98-9 C22H28O3 340.46
Hydroxyprogesterone 68-96-2 C21H30O3 330.46
Ethynodiol diacetate 297-76-7 C24H32O4 384.51
Chlormadinone acetate 302-22-7 C23H29ClO4 404.93
Gestonorone caproate 1253-28-7 C26H38O4 414.58

Recommended Compounds in Same Indication

Name CAS No Formula MW
Asenapine 65576-45-6 C17H16ClNO 285.77
Asenapine (maleate) 85650-56-2 C21H20ClNO5 401.84
Nepicastat hydrochloride 170151-24-3 C14H16ClF2N3S 331.81
Nepicastat 173997-05-2 C14H15F2N3S 295.35
Vilazodone (Hydrochloride) 163521-08-2 C26H28ClN5O2 477.99
Vilazodone 163521-12-8 C26H28ClN5O2 477.99
11

Route of Synthesis

12

References

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More Information

Mifepristone

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