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M8046

Mifepristone

Name: Mifepristone
Brand: SIGMA

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

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₂₉H₃₅NO₂

CAS Number:

84371-65-3

Molecular Weight:

429.59

UNSPSC Code:

51111800

PubChem Substance ID:

24278572

NACRES:

NA.77

MDL number:

MFCD00867226

Assay:

≥98%

Form:

powder

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Properties

Product Name

Mifepristone, ≥98%

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

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

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)

Description

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.

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

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

Mifepristone (RU-486) has activity as both a progesterone receptor antagonist and a glucocorticoid receptor antagonist.

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.

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Pictograms

GHS08

Signal Word

Danger

Hazard Codes

H360

Precautionary Statements

P201 - P308 + P313

Hazard Classifications

Repr. 1B

Storage Class

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)