M8046

Mifepristone

≥98%

• Synonym(s): 11β-(4-Dimethyl­amino)­phenyl-17β-hydroxy-17-(1-propynyl)­estra-4,9-dien-3-one, RU-38486, RU-486
• Empirical Formula (Hill Notation): C₂₉H₃₅NO₂
• CAS Number: 84371-65-3
• Molecular Weight: 429.59
• MDL number: MFCD00867226
• UNSPSC Code: 51111800
• PubChem Substance ID: 24278572
• NACRES: NA.77

Properties

• 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.

Safety Information

• pictograms: GHS08
• signalword: Danger
• hcodes: H360
• pcodes: P201 - P308 + P313
• Hazard Classifications: Repr. 1B
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges