Mifepristone

Mifepristone, also known as RU-486, is a medication typically used in combination with misoprostol to bring about a medical abortion during pregnancy and manage early miscarriage. This combination is 97% effective during the first 63 days of pregnancy. It is also effective in the second trimester of pregnancy. It is taken by mouth.

For the song "RU486" by Stone Sour, see House of Gold & Bones – Part 1.

Mifepristone
Clinical data
Pronunciation/ˌmɪfəˈprɪˌstoʊn/
Trade namesMifegyne, Mifeprex, Korlym, others
Other namesRU-486; RU-38486; ZK-98296; 11β-[p-(Dimethylamino)phenyl]-17α-(1-propynyl)estra-4,9-dien-17β-ol-3-one
AHFS/Drugs.comMonograph
MedlinePlusa600042
License data
Pregnancy
category
  • Not recommended
Routes of
administration		By mouth
Drug classAntiprogestogen; Antiglucocorticoid
ATC code
Legal status
Legal status
  • US: WARNINGRx-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability69%
Protein binding98%
MetabolismLiver
ExcretionFeces: 83%
urine: 9%
Identifiers
  • (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
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.127.911
Chemical and physical data
FormulaC29H35NO2
Molar mass429.604 g·mol−1
3D model (JSmol)
Density1.189 g/cm3
Melting point194 °C (381 °F)
Boiling point629 °C (1,164 °F)
  • O=C5\C=C4/C(=C3/[C@@H](c1ccc(N(C)C)cc1)C[C@]2([C@@H](CC[C@]2(C#CC)O)[C@@H]3CC4)C)CC5
  • 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 Y
  • Key:VKHAHZOOUSRJNA-GCNJZUOMSA-N Y
  (verify)

The more common adverse effects include abdominal pain, feeling tired, and vaginal bleeding. Serious side effects may include heavy vaginal bleeding, bacterial infection, and birth defects if the pregnancy does not end. If used, appropriate follow-up care needs to be available. Mifepristone is an antiprogestogen. It works by blocking the effects of progesterone, making both the cervix and uterine vessels dilate and causing uterine contraction.

Mifepristone was developed in 1980 and came into use in France in 1987. It became available in the United States in 2000. It is on the World Health Organization's List of Essential Medicines. Mifepristone was approved in Canada in January 2017.

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