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Details

Stereochemistry ABSOLUTE
Molecular Formula C29H35NO2
Molecular Weight 429.5937
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MIFEPRISTONE

SMILES

[H][C@@]12CC[C@@](O)(C#CC)[C@@]1(C)C[C@H](C3=CC=C(C=C3)N(C)C)C4=C5CCC(=O)C=C5CC[C@@]24[H]

InChI

InChIKey=VKHAHZOOUSRJNA-GCNJZUOMSA-N
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

HIDE SMILES / InChI

Molecular Formula C29H35NO2
Molecular Weight 429.5937
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Mifepristone is a synthetic steroid with antiprogestational effects indicated for the medical termination of intrauterine pregnancy through 49 days' pregnancy. Doses of 1 mg/kg or greater of mifepristone have been shown to antagonize the endometrial and myometrial effects of progesterone in women. During pregnancy, the compound sensitizes the myometrium to the contraction-inducing activity of prostaglandins. Mifepristone also exhibits antiglucocorticoid and weak antiandrogenic activity. The activity of the glucocorticoid dexamethasone in rats was inhibited following doses of 10 to 25 mg/kg of mifepristone. Doses of 4.5 mg/kg or greater in human beings resulted in a compensatory elevation of adrenocorticotropic hormone (ACTH) and cortisol. The anti-progestational activity of mifepristone results from competitive interaction with progesterone at progesterone-receptor sites. Based on studies with various oral doses in several animal species (mouse, rat, rabbit and monkey), the compound inhibits the activity of endogenous or exogenous progesterone. The termination of pregnancy results. In the treatment of Cushing's syndrome, Mifepristone blocks the binding of cortisol to its receptor. It does not decrease cortisol production but reduces the effects of excess cortisol, such as high blood sugar levels. Mifepristone is used for the medical termination of intrauterine pregnancy through 49 days' pregnancy. Also indicated to control hyperglycemia secondary to hypercortisolism in adult patients with endogenous Cushing's syndrome who have type 2 diabetes mellitus or glucose intolerance and are not candidates for surgery or have had unsuccessful surgery.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.35 nM [IC50]
0.8 nM [IC50]
5.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
MIFEPREX

Cmax

ValueDoseCo-administeredAnalytePopulation
3.8 μM
200 mg single, oral
MIFEPRISTONE plasma
Homo sapiens
1.77 mg/L
200 mg single, oral
MIFEPRISTONE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
25.8 mg × h/L
200 mg single, oral
MIFEPRISTONE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
85 h
600 mg 1 times / day multiple, oral
MIFEPRISTONE plasma
Homo sapiens
25 h
200 mg single, oral
MIFEPRISTONE plasma
Homo sapiens
18 h
200 mg single, oral
MIFEPRISTONE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
0.8%
600 mg 1 times / day multiple, oral
MIFEPRISTONE plasma
Homo sapiens
2%
200 mg single, oral
MIFEPRISTONE plasma
Homo sapiens

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Abortion -Day One: 200 mg mifepristone (MIFEPREX) orally as a single dose -Day Two or Three: 800 mcg misoprostol buccally 24 to 48 hours after the first dose of mifepristone (Two 200 mcg misoprostol tablets should be placed in each cheek pouch [the area between the cheek and gums] for 30 minutes and then swallow any remnants with water or another liquid).
Route of Administration: Oral
In Vitro Use Guide
Exposure to a low concentration (0.5uM) of mifepristone during the receptive period successfully inhibits human embryo implantation process in vitro.
Substance Class Chemical
Record UNII
320T6RNW1F
Record Status Validated (UNII)
Record Version