Mifepristone
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MedKoo CAT#: 201870

CAS#: 84371-65-3

Description: Mifepristone is a synthetic steroid compound used as a pharmaceutical. It is used as an abortifacient in the first two months of pregnancy, and in smaller doses as an emergency contraceptive. During early trials, it was known as RU-486, its designation at the Roussel Uclaf company, which designed the drug. The drug was initially made available in France, and other countries then followed—often amid controversy. It is marketed under tradenames Mifegyne and Mifeprex.


Chemical Structure

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Mifepristone
CAS# 84371-65-3

Theoretical Analysis

MedKoo Cat#: 201870
Name: Mifepristone
CAS#: 84371-65-3
Chemical Formula: C29H35NO2
Exact Mass: 429.26678
Molecular Weight: 429.59
Elemental Analysis: C, 81.08; H, 8.21; N, 3.26; O, 7.45

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1.0g USD 90.0 Same day
2.0g USD 150.0 Same day
5.0g USD 250.0 Same day
10.0g USD 450.0 Same day
20.0g USD 750.0 Same day
50.0g USD 1450.0 Same day
100.0g USD 2450.0 Same day
500.0g USD 6950.0 2 Weeks
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Synonym: RU-486; RU 486; RU486; C-1073; C 1073; C1073; C-1073; Brand name: Mifegyne;Mifepriston;Pictovir; Mifepristonum; Mifepristona; Corlux.

IUPAC/Chemical Name: (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 Key: VKHAHZOOUSRJNA-GCNJZUOMSA-N

InChi Code: 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

SMILES Code: O=C1CCC2=C3[C@@H](C4=CC=C(N(C)C)C=C4)C[C@]5(C)[C@@](C#CC)(O)CC[C@@]5([H])[C@]3([H])CCC2=C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not soluble in water.

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Biological target: Mifepristone (RU486) is a progesterone receptor (PR) and glucocorticoid receptor (GR) antagonist with IC50s of 0.2 nM and 2.6 nM in in vitro assay.
In vitro activity: As early as 24 h, it was evident that MF (mifepristone) inhibited the growth of the cells, even at the lowest concentration of 5 μM. It was also evident that the growth inhibition had a dose-dependent fashion. The decreased rate of proliferation in the presence of MF was reflected by the longer doubling times of the cells subjected to the various concentrations of MF. In both cell lines, doubling times consistently increased with increased concentration of MF (Fig. 2b, e). Notice that the extremely large doubling times for cells treated with the largest dose of MF (40 μM), represents a theoretical number as the cells no longer proliferate—they actually die—when subjected to this high concentration of the antiprogestin/antiglucocorticoid. Reference: Cancer Cell Int. 2018; 18: 185. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6238342/
In vivo activity: The Inhα/Tag TG mice treated with these doses of MF (mifepristone) shown increased testis weights (Figure 2A). Histopathological analyses demonstrated in non-treated LCTs severe cellular atypia, only a few peripheral tubular structures with spermatogenic cells up to elongated spermatids and in some regions rapid tumor growth with necrosis (Figure 2B). The MF-treated LCTs showed overall destroyed histological morphology with blood-filled cavities, infiltrating lymphocytes, and with almost no normal testicular structures left (Figure 2D,F). Reference: Cancers (Basel). 2020 Nov; 12(11): 3263. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7694279/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 62.0 144.32
DMF 30.0 69.83
DMF:PBS (pH 7.2) (1:4) 0.2 0.47
Ethanol 42.16 98.14

Preparing Stock Solutions

The following data is based on the product molecular weight 429.59 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Casulari LA, Dondi D, Pratesi G, Piva F, Milani M, Piccolella M, Maggi R. Antiproliferative effect of mifepristone (RU486) on human neuroblastoma cells (SK-N-SH): in vitro and in vivo studies. Braz J Med Biol Res. 2020 Oct 7;53(11):e10067. doi: 10.1590/1414-431X202010067. PMID: 33053110; PMCID: PMC7552897. 2. Kapperman HE, Goyeneche AA, Telleria CM. Mifepristone inhibits non-small cell lung carcinoma cellular escape from DNA damaging cisplatin. Cancer Cell Int. 2018 Nov 15;18:185. doi: 10.1186/s12935-018-0683-z. PMID: 30479564; PMCID: PMC6238342. 3. Ponikwicka-Tyszko D, Chrusciel M, Pulawska K, Bernaczyk P, Sztachelska M, Guo P, Li X, Toppari J, Huhtaniemi IT, Wołczyński S, Rahman NA. Mifepristone Treatment Promotes Testicular Leydig Cell Tumor Progression in Transgenic Mice. Cancers (Basel). 2020 Nov 4;12(11):3263. doi: 10.3390/cancers12113263. PMID: 33158280; PMCID: PMC7694279. 4. Miguel-Hidalgo JJ, Carter K, Deloach PH, Sanders L, Pang Y. Glucocorticoid-Induced Reductions of Myelination and Connexin 43 in Mixed Central Nervous System Cell Cultures Are Prevented by Mifepristone. Neuroscience. 2019 Jul 15;411:255-269. doi: 10.1016/j.neuroscience.2019.05.050. Epub 2019 Jun 1. PMID: 31163207; PMCID: PMC6664452.
In vitro protocol: 1. Casulari LA, Dondi D, Pratesi G, Piva F, Milani M, Piccolella M, Maggi R. Antiproliferative effect of mifepristone (RU486) on human neuroblastoma cells (SK-N-SH): in vitro and in vivo studies. Braz J Med Biol Res. 2020 Oct 7;53(11):e10067. doi: 10.1590/1414-431X202010067. PMID: 33053110; PMCID: PMC7552897. 2. Kapperman HE, Goyeneche AA, Telleria CM. Mifepristone inhibits non-small cell lung carcinoma cellular escape from DNA damaging cisplatin. Cancer Cell Int. 2018 Nov 15;18:185. doi: 10.1186/s12935-018-0683-z. PMID: 30479564; PMCID: PMC6238342.
In vivo protocol: 1. Ponikwicka-Tyszko D, Chrusciel M, Pulawska K, Bernaczyk P, Sztachelska M, Guo P, Li X, Toppari J, Huhtaniemi IT, Wołczyński S, Rahman NA. Mifepristone Treatment Promotes Testicular Leydig Cell Tumor Progression in Transgenic Mice. Cancers (Basel). 2020 Nov 4;12(11):3263. doi: 10.3390/cancers12113263. PMID: 33158280; PMCID: PMC7694279. 2. Miguel-Hidalgo JJ, Carter K, Deloach PH, Sanders L, Pang Y. Glucocorticoid-Induced Reductions of Myelination and Connexin 43 in Mixed Central Nervous System Cell Cultures Are Prevented by Mifepristone. Neuroscience. 2019 Jul 15;411:255-269. doi: 10.1016/j.neuroscience.2019.05.050. Epub 2019 Jun 1. PMID: 31163207; PMCID: PMC6664452.

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 1: Cossu G, Levivier M, Daniel RT, Messerer M. The Role of Mifepristone in Meningiomas Management: A Systematic Review of the Literature. Biomed Res Int. 2015;2015:267831. doi: 10.1155/2015/267831. Epub 2015 Jun 3. Review. PubMed PMID: 26146614; PubMed Central PMCID: PMC4469754.

2: Grossman D, White K, Harris L, Reeves M, Blumenthal PD, Winikoff B, Grimes DA. Continuing pregnancy after mifepristone and "reversal" of first-trimester medical abortion: a systematic review. Contraception. 2015 Jun 7. pii: S0010-7824(15)00226-7. doi: 10.1016/j.contraception.2015.06.001. [Epub ahead of print] Review. PubMed PMID: 26057457.

3: Chen J, Wang J, Shao J, Gao Y, Xu J, Yu S, Liu Z, Jia L. The unique pharmacological characteristics of mifepristone (RU486): from terminating pregnancy to preventing cancer metastasis. Med Res Rev. 2014 Sep;34(5):979-1000. doi: 10.1002/med.21311. Epub 2014 Mar 1. Review. PubMed PMID: 24585714.

4: Kakade AS, Kulkarni YS. Mifepristone: current knowledge and emerging prospects. J Indian Med Assoc. 2014 Jan;112(1):36-40. Review. PubMed PMID: 25935948.

5: Sun Y, Fang M, Davies H, Hu Z. Mifepristone: a potential clinical agent based on its anti-progesterone and anti-glucocorticoid properties. Gynecol Endocrinol. 2014 Mar;30(3):169-73. doi: 10.3109/09513590.2013.856410. Epub 2013 Nov 11. Review. PubMed PMID: 24205903.

6: Howland RH. Mifepristone as a therapeutic agent in psychiatry. J Psychosoc Nurs Ment Health Serv. 2013 Jun;51(6):11-4. Review. PubMed PMID: 23814820.

7: Shaw KA, Topp NJ, Shaw JG, Blumenthal PD. Mifepristone-misoprostol dosing interval and effect on induction abortion times: a systematic review. Obstet Gynecol. 2013 Jun;121(6):1335-47. doi: 10.1097/AOG.0b013e3182932f37. Review. PubMed PMID: 23812471.

8: Morgan FH, Laufgraben MJ. Mifepristone for management of Cushing's syndrome. Pharmacotherapy. 2013 Mar;33(3):319-29. doi: 10.1002/phar.1202. Epub 2013 Feb 21. Review. PubMed PMID: 23436494.

9: Fleseriu M, Molitch ME, Gross C, Schteingart DE, Vaughan TB 3rd, Biller BM. A new therapeutic approach in the medical treatment of Cushing's syndrome: glucocorticoid receptor blockade with mifepristone. Endocr Pract. 2013 Mar-Apr;19(2):313-26. doi: 10.4158/EP12149.RA. Review. PubMed PMID: 23337135.

10: Carmichael JD, Fleseriu M. Mifepristone: is there a place in the treatment of Cushing's disease? Endocrine. 2013 Aug;44(1):20-32. doi: 10.1007/s12020-012-9846-1. Epub 2012 Nov 29. Review. PubMed PMID: 23192246.

11: Raymond EG, Shannon C, Weaver MA, Winikoff B. First-trimester medical abortion with mifepristone 200 mg and misoprostol: a systematic review. Contraception. 2013 Jan;87(1):26-37. doi: 10.1016/j.contraception.2012.06.011. Epub 2012 Aug 13. Review. PubMed PMID: 22898359.

12: Tristan M, Orozco LJ, Steed A, Ramírez-Morera A, Stone P. Mifepristone for uterine fibroids. Cochrane Database Syst Rev. 2012 Aug 15;8:CD007687. doi: 10.1002/14651858.CD007687.pub2. Review. PubMed PMID: 22895965.

13: Gómez García MT, Aguarón Benitez G, Barberá Belda B, Callejón Rodríguez C, González Merlo G. Medical therapy (methotrexate and mifepristone) alone or in combination with another type of therapy for the management of cervical or interstitial ectopic pregnancy. Eur J Obstet Gynecol Reprod Biol. 2012 Nov;165(1):77-81. doi: 10.1016/j.ejogrb.2012.06.024. Epub 2012 Jul 7. Review. PubMed PMID: 22771188.

14: Castinetti F, Brue T, Conte-Devolx B. The use of the glucocorticoid receptor antagonist mifepristone in Cushing's syndrome. Curr Opin Endocrinol Diabetes Obes. 2012 Aug;19(4):295-9. doi: 10.1097/MED.0b013e32835430bf. Review. PubMed PMID: 22543346.

15: Hou SP, Fang AH, Chen QF, Huang YM, Chen OJ, Cheng LN. Termination of second-trimester pregnancy by mifepristone combined with misoprostol versus intra-amniotic injection of ethacridine lactate (Rivanol®): a systematic review of Chinese trials. Contraception. 2011 Sep;84(3):214-23. doi: 10.1016/j.contraception.2011.01.018. Epub 2011 Mar 11. Review. PubMed PMID: 21843683.

16: Chen QJ, Hou SP, Meads C, Huang YM, Hong QQ, Zhu HP, Cheng LN; EBM-CONNECT Collaboration. Mifepristone in combination with prostaglandins for termination of 10-16 weeks' gestation: a systematic review. Eur J Obstet Gynecol Reprod Biol. 2011 Dec;159(2):247-54. doi: 10.1016/j.ejogrb.2011.06.034. Epub 2011 Jul 8. Review. PubMed PMID: 21741747.

17: Guo SW, Liu M, Shen F, Liu X. Use of mifepristone to treat endometriosis: a review of clinical trials and trial-like studies conducted in China. Womens Health (Lond Engl). 2011 Jan;7(1):51-70. doi: 10.2217/whe.10.79. Review. PubMed PMID: 21175391.

18: Spitz IM. Mifepristone: where do we come from and where are we going? Clinical development over a quarter of a century. Contraception. 2010 Nov;82(5):442-52. doi: 10.1016/j.contraception.2009.12.012. Epub 2010 Feb 1. Review. PubMed PMID: 20933118.

19: Wedisinghe L, Elsandabesee D. Flexible mifepristone and misoprostol administration interval for first-trimester medical termination. Contraception. 2010 Apr;81(4):269-74. doi: 10.1016/j.contraception.2009.09.007. Epub 2009 Oct 29. Review. PubMed PMID: 20227541.

20: Im A, Appleman LJ. Mifepristone: pharmacology and clinical impact in reproductive medicine, endocrinology and oncology. Expert Opin Pharmacother. 2010 Feb;11(3):481-8. doi: 10.1517/14656560903535880. Review. PubMed PMID: 20102310.



Additional Information

According to http://en.wikipedia.org/wiki/Mifepristone, the compound was discovered by researchers at Roussel Uclaf of France in 1980 (the "RU" in RU-486) while they were studying glucocorticoid receptor antagonists. Étienne-Émile Baulieu recognized its anti-progesterone activities and saw its potential for the induction of a medical abortion. Clinical testing began in 1982. The drug was first licensed in France in 1988, for use in combination with a prostaglandin, under the name Mifegyne.
 
Mifegyne is sold outside the U.S. by Exelgyn Laboratories, made in France, and is approved for: 1. Medical termination of intrauterine pregnancies of up to 49 days gestation (up to 63 days gestation in Britain and Sweden); 2. Softening and dilatation of the cervix prior to mechanical cervical dilatation for pregnancy termination; 3. Use in combination with gemeprost for termination of pregnancies between 13 and 24 weeks gestation; 4. Labor induction in fetal death in utero.
Mifeprex is sold in the U.S. by Danco Laboratories, made in China, and is U.S. Food and Drug Administration-approved to terminate intrauterine pregnancies of up to 49 days gestation.  see http://en.wikipedia.org/wiki/Mifepristone.  
 
 
Other medical applications of mifepristone that have been studied in Phase II clinical trials include regular long-term use as an oral contraceptive, and treatment of: uterine fibroids, endometriosis, major depression with psychotic features, glaucoma, meningiomas, breast cancer, ovarian cancer, and prostate cancer. Mifepristone has been used to treat Cushing's syndrome with treatment durations being as long as 10 years without noticeable adverse effect.