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84371-65-3

Basic Information
CAS No.: 84371-65-3
Name: Mifepristone
Article Data: 2
Cas Database
Molecular Structure:
Molecular Structure of 84371-65-3 (Mifepristone)
Formula: C29H35NO2
Molecular Weight: 429.602
Synonyms: Estra-4,9-dien-3-one,11-[4-(dimethylamino)- phenyl]-17-hydroxy-17-(1-propynyl)-,(11a,- 17a)-;Mifepristone [USAN:BAN:INN];17-beta-Hydroxy-11-beta-(4-dimethylaminophenyl-1)-17-alpha-(prop-1-ynyl)oestra-4,9-dien-3-one;Mifeprex;Mifepristonum [Latin];R 38486;RU 38486;11beta-(4-(Dimethylamino)phenyl)-17beta-hydroxy-17-(1-propynyl)estra-4,9-dien-3-on;Estra-4,9-dien-3-one, 11-[4-(dimethylamino)phenyl]-17-hydroxy-17-(1-propynyl)-, (11b,17b)-;Prestwick_570;Mifegyne;(11beta,17beta)-11-(4-(Dimethylamino)-phenyl)-17-hydroxy-17-(1-propynyl)estra-4,9-dien-3-one;RU-486;RU486;11beta-(4-(Dimethylamino)phenyl)-17-hydroxy-21-methyl-19-nor-17alpha-pregna-4,9-dien-20-m-3-on;RU 486-6;17-(1-propynyl)estra-4,9-dien-3-one;
EINECS: 617-559-7
Density: 1.18 g/cm3
Melting Point: 195-198 °C
Boiling Point: 628.6 °C at 760 mmHg
Flash Point: 334 °C
Solubility: Soluble to 100 mM in DMSO and to 50 mM in Ethanol
Appearance: pale yellow solid
Hazard Symbols: ToxicT
Risk Codes: 60-61
Safety: 53-22-36/37/39-45
Transport Information: N/A
PSA: 40.54000
LogP: 5.40650
Synthetic route
84371-65-3

mifepristone

aglepristone

Conditions
ConditionsYield
With hydrogen In methanol under 3800.26 Torr; Reagent/catalyst; Solvent; Green chemistry; stereoselective reaction;99%
98-98-6

2-Picolinic acid

84371-65-3

mifepristone

N-(4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-(prop-1-yn-1-yl)-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl)-N-methylpicolinamide

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;98%
688-73-3

tri-n-butyl-tin hydride

84371-65-3

mifepristone

C41H63NO2Sn

Conditions
ConditionsYield
With [MoI2(CO)2(CNC6H3(C6H3iPr2-2,6)2-2,6)2] In benzene-d6 at 20℃; for 0.5h; Inert atmosphere; Schlenk technique; Glovebox;98%
84371-65-3

mifepristone

104004-96-8

Demethylmifepristone

Conditions
ConditionsYield
With lithium acetate; iodine In tetrahydrofuran; methanol at 0 - 20℃; for 24h; Reagent/catalyst; Temperature; Solvent;97%
With lithium acetate; iodine In tetrahydrofuran; methanol at 20℃;92%
With iodine; calcium oxide In tetrahydrofuran; methanol at 0℃; for 1h;82%
84371-65-3

mifepristone

79-04-9

chloroacetyl chloride

2-chloro-N-(4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-(prop-1-yn-1-yl)-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl)-N-methylacetamide

Conditions
ConditionsYield
With triethylamine In ethyl acetate at 0 - 20℃; for 16h;92%
358-23-6

trifluoromethylsulfonic anhydride

135053-66-6

methyl (3β,5β,7α,12α)-7,12-dixydroxy-3-(2-hydroxyethoxy)cholan-24-oate

84371-65-3

mifepristone

639520-78-8

methyl (3β,5β,7α,12α)-7,12-dihydroxy-3-{2-[{4-[(11β,17α)-17-hydroxy-3-oxo-17-prop-1-ynylestra-4,9-dien-11-yl]phenyl}(methyl)amino]ethoxy}cholan-24-oate

Conditions
ConditionsYield
Stage #1: trifluoromethylsulfonic anhydride; methyl (3β,5β,7α,12α)-7,12-dixydroxy-3-(2-hydroxyethoxy)cholan-24-oate With N-ethyl-N,N-diisopropylamine In dichloromethane at -55 - -45℃; for 3.28333h;
Stage #2: mifepristone In dichloromethane at -6℃; for 88h;
Stage #3: With N-ethyl-N,N-diisopropylamine; sodium iodide In acetonitrile for 45h; Heating / reflux;
82.7%
84371-65-3

mifepristone

65-85-0

benzoic acid

N-(4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-(prop-1-yn-1-yl)-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl)-N-methylbenzamide

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;77%
58574-03-1

4'-Hydroxybiphenyl-4-carboxylic acid

84371-65-3

mifepristone

N-(4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-(prop-1-yn-1-yl)-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl)-N-methyl-[1,1'-biphenyl]-4-carboxamide

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;73%
51-44-5

3,4-dichlorbenzoic acid

84371-65-3

mifepristone

3,4-dichloro-N-(4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-(prop-1-yn-1-yl)-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl)-N-methylbenzamide

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;71%
3262-89-3

triphenylboroxine

84371-65-3

mifepristone

(8S,11R,13S,14S)-11-(4-(dimethylamino)phenyl)-13-methyl-17-((S)-2-phenylprop-1-en-1-ylidene)-6,7,8,11,12,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-one

Conditions
ConditionsYield
With [Rh(OH)(cod)]2 In tetrahydrofuran at 75℃; for 12h; Inert atmosphere; diastereoselective reaction;69%
Downstream Products
104004-96-8
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    Name: Mifepristone Synonyms: 11-(4-(dimethylamino)phenyl)-17-hydroxy-17-(1-propynyl)-estra-9-dien-3-one;11beta-[4-(n,n-dimethylamino)phenyl]-17alpha-… Founded in 2014, as a professional international pharmaceutical corporation, headquarter

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    Product Name: Mifepristone Synonyms: 11-(4-(dimethylamino)phenyl)-17-hydroxy-17-(1-propynyl)-estra-9-dien-3-one;11beta-[4-(n,n-dimethylamino)phenyl]-17alpha-(prop-1-ynyl)-delta4,9-estradiene;17-beta)-(11-bet;17beta)-11-[4-(dimethylamin

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History

In 1980, Mifepristone (CAS NO.84371-65-3) was discovered by researchers at Roussel Uclaf of France 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. After license approval but before market release, Roussel Uclaf announced it would abandon distribution of the drug, bowing to pressure from pro-life groups and the threat of a boycott. However, two days later, the French government, part owner of Roussel Uclaf, intervened, leading to the resumption of production and distribution of RU-486.

Specification

1. Introduction of Mifepristone
Mifepristone is one kind of pale yellow solid. The IUPAC Name of this chemical is (8S,11R,13S,14S,17S)-11-[4-(dimethylamino)phenyl]-17-hydroxy-13-methyl-17-prop-1-ynyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one. Mifepristone belongs to Steroids;Hormone;Acetylenes;Biochemistry;Functionalized Acetylenes;Hydroxyketosteroids;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Intracellular receptor;Nuclear Receptors. Mifepristone is soluble in organic solvents but poorly soluble in water.

The Classification Code of this chemical is Abortifacient Agents; Abortifacient agents, steroidal; Contraception; Contraceptive Agents; Contraceptive Agents, Female; Contraceptives, Oral; Contraceptives, Postcoital; Contraceptives, oral, synthetic; Contraceptives, postcoital, synthetic; Hormone; Hormone antagonists; Hormones, Hormone Substitutes, and Hormone Antagonists; Human Data; Induction of abortion; Luteolytic agents; Menstruation-inducing agents; Reproductive Control Agents; Reproductive Effect; Treatment of gynecological disorders [progesterone antagonist].

2. Properties of Mifepristone
Physical properties about Mifepristone are:
(1)Index of Refraction: 1.623; (2)Molar Refractivity: 127.71 cm3; (3)Molar Volume: 362 cm3; (4)Polarizability: 50.62×10-24 cm3; (5)Surface Tension: 54 dyne/cm; (6)Density: 1.18 g/cm3; (7)Flash Point: 334 °C; (8)Enthalpy of Vaporization: 97.77 kJ/mol; (9)Melting Point: 195-198°C; (10)Boiling Point: 628.6 °C at 760 mmHg; (11)Vapour Pressure: 1.14E-16 mmHg at 25°C; (12)XLogP3-AA: 3.8; (13)H-Bond Donor: 1; (14)H-Bond Acceptor: 3.

3. Structure Descriptors of Mifepristone
(1)Canonical SMILES: CC#CC1(CCC2C1(CC(C3=C4CCC(=O)C=C4CCC23)C5=CC=C(C=C5)N(C)C)C)O
(2)InChIKey: VKHAHZOOUSRJNA-GCNJZUOMSA-N
(3)Isomeric SMILES: CC#C[C@@]1(CC[C@@H]2[C@@]1(C[C@@H](C3=C4CCC(=O)C=C4CC[C@@H]23)C5=CC=C(C=C5)N(C)C)C)O
(4)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
(5)Smiles: C1=2[C@H]([C@H]3[C@]([C@@](C#CC)(O)CC3)(C)C[C@@H]1c1ccc(N(C)C)cc1)CCC=1C2CCC(C1)=O

4. Safety information of Mifepristone
Hazard Codes: ToxicT
Risk Statements: 60-61 
S60:This material and its container must be disposed of as hazardous waste. 
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
Safety Statements: 53-22-36/37/39-45 
S53:Avoid exposure - obtain special instructions before use. 
S22:Do not breathe dust. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
WGK Germany: 3
RTECS: KG2955000

5. Uses of Mifepristone
Mifepristone (CAS NO.84371-65-3) 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. 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, prostate cancer, and some types of Cushing's syndrome.

6. Production of Mifepristone
(1)Steroidal 4,9 estrogen diene-3 ,17-dione 3 ketal compound (I) as raw material and propynyl magnesium bromide Grignard reagent, at 17 for introduction of the propargyl group, to obtain the compound (II). Followed by five ethylenically for selective epoxidation to give compound (III). Containing copper bromide - dimethyl sulfide complex in tetrahydrofuran, and dimethylaminophenyl magnesium bromide in 11 introduces dimethylaminophenyl to give the compound (IV). Finally, in methanol, by hydrolysis with hydrochloric acid and dehydrated to obtain a mifepristone. Yield is 21.5%.

Production of Mifepristone

(2) Another way to get the Mifepristone is showed as follows:

Production of Mifepristone