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Merck

M8046

Mifepristone

synthetic (organic), ≥98%, Progesterone receptor antagonist, powder

Synonyme(s) :

11β-(4-Dimethyl­amino)­phenyl-17β-hydroxy-17-(1-propynyl)­estra-4,9-dien-3-one, RU-38486, RU-486

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A propos de cet article

Formule empirique (notation de Hill) :
C29H35NO2
Numéro CAS:
84371-65-3
Poids moléculaire :
429.59
UNSPSC Code:
51111800
PubChem Substance ID:
24278572
NACRES:
NA.77
MDL number:
MFCD00867226

Principaux documents

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Nom du produit

Mifepristone, ≥98%

SMILES string

[H][C@@]12CCC3=CC(=O)CCC3=C1[C@H](C[C@@]4(C)[C@@]2([H])CC[C@@]4(O)C#CC)c5ccc(cc5)N(C)C

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

InChI key

VKHAHZOOUSRJNA-GCNJZUOMSA-N

biological source

synthetic (organic)

sterility

non-sterile

assay

≥98%

form

powder

technique(s)

inhibition assay: suitable

solubility

ethanol: 50 mg/mL, clear, greenish-yellow

originator

Danco Laboratories

shipped in

ambient

storage temp.

2-8°C

Gene Information

human ... AR(367), ESR1(2099), ESR2(2100), HTR1A(3350), HTR1B(3351), HTR1D(3352), HTR1E(3354), HTR1F(3355), HTR2A(3356), HTR2B(3357), HTR2C(3358), HTR3A(3359), HTR3B(9177), HTR3C(170572), HTR3D(200909), HTR3E(285242), HTR4(3360), HTR5A(3361), HTR5B(645694), HTR6(3362), HTR7(3363), NR3C1(2908), NR3C2(4306), PGR(5241)
mouse ... Nr3c1(14815)
rat ... Nr3c1(24413), Tat(24813)

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Catégories apparentées

Application

Mifepristone has been used:
  • to induce damage against the proliferative and secretory phase of endometrial stromal cells
  • to establish a preterm birth (PTB) mice model in order to study the difference in cervical ripening mechanism between term and PTBs
  • to activate geneswitch gal4 in flies
  • to study the effects of sex steroids on prostaglandin secretion

Biochem/physiol Actions

Mifepristone (RU-486) has activity as both a progesterone receptor antagonist and a glucocorticoid receptor antagonist.
Therefore, mifepristone is considered to be a potent abortifacient. It is also known to inhibit human chorionic gonadotropin. Mifepristone results in decidual necrosis.

Features and Benefits

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Danco Laboratories. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

General description

Mifepristone, a synthetic steroid, can be utilized for the management of Cushing′s syndrome and uterine leiomyomas. At low doses, it selectively antagonizes progesterone by binding to the intracellular progesterone receptor. At higher doses, mifepristone blocks cortisol at the glucocorticoid receptor, affecting the hypothalamic-pituitary-adrenal axis and leading to increased circulating cortisol, thereby controlling hyperglycemia in some patients. Additionally, mifepristone has a higher affinity for the glucocorticoid II receptor than for the glucocorticoid I receptor. In cases of pregnancy termination, mifepristone disrupts progesterone.

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H360

Hazard Classifications

Repr. 1B

Classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificats d'analyse (COA)

Lot/Batch Number
WXBF3658V
WXBF0030V
WXBD7927V
WXBD5791V
WXBD2264V

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. What is Mifepristone, Product M8046, soluble in?

    Mifepristone is soluble in ethanol at 50 mg/mL; heat may be required to dissolve the compound at this concentration.  It is also soluble in DMSO at 20 mg/mL.

  4. Can solutions of Mifepristone, Product M8046, be stored?

    Stock solutions of 1 mM mifepristone in ethanol can be stored at -20 °C. The top of the container should be sealed with Parafilm to prevent solvent evaporation. Solutions in ethanol, properly stored and handled, are probably good for several months (based on the structure of the compound), but we have no specific information on this.

  5. Where can I find information on usage of Mifepristone, Product M8046?

    The Sigma-Aldrich website listing has several cited articles with hyperlinks to the abstracts. These references can be found under the reference tab on the M8046 product webpage.

  6. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  7. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  8. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Ovarian steroids regulate prostaglandin secretion in the feline endometrium
Siemieniuch MJ, et al.
Animal Reproduction Science, 120(1-4), 142-150 (2010)
Nynne Sharma et al.
Nucleic acids research, 36(11), e67-e67 (2008-05-24)
Nonviral integration systems are widely used genetic tools in transgenesis and play increasingly important roles in strategies for therapeutic gene transfer. Methods to efficiently regulate the activity of transposases and site-specific recombinases have important implications for their spatiotemporal regulation in
Pfenninger and Fowler's Procedures for Primary Care, 874-874 (2010)
Mifepristone
Autry BM and Wadhwa R
StatPearls [Internet] (2020)
The molecular mechanisms of cervical ripening differ between term and preterm birth
Holt R, et al.
Endocrinology, 152(3), 1036-1046 (2011)
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