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Mifepristone

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

Mifepristone
Clinical data
Pronunciation/ˌmɪfəˈprɪˌstoʊn/[1]
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
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 Edit this at Wikidata
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 checkY
  • Key:VKHAHZOOUSRJNA-GCNJZUOMSA-N checkY
  (verify)

Mifepristone, and also known by its developmental code name RU-486, is a drug typically used in combination with misoprostol to bring about a medical abortion during pregnancy.[7] This combination is 97% effective[8] during the first 63 days (9 weeks) of pregnancy, yet effective in the second trimester as well.[9][10] It is also used on its own to treat Cushing's Syndrome or for use as a low-dose emergency contraceptive.[11][12]

The most common adverse effects include abdominal pain, feeling tired, and vaginal bleeding.[7] Serious side effects may include heavy vaginal bleeding, bacterial infection, and, if pregnant, birth defects.[7] When used, appropriate follow-up care needs to be available.[7][13] Mifepristone is primarily an antiprogestogen.[7] It works by blocking the effects of progesterone, making both the cervix and uterine vessels dilate and causing uterine contraction.[7] Mifepristone also works, to a less extent, as an antiglucocorticoid and diminishes the effects of hypercortisolism.[14]

Mifepristone was developed in 1980 and came into use in France in 1987.[15] It became available in the United States in 2000, for medication abortion, and in 2010, for Cushing's syndrome.[16][9][11] It is on the World Health Organization's List of Essential Medicines.[17] Mifepristone was approved in Canada in January 2017.[18][19]

  1. ^ "mifepristone". Mifepristone Definition & Meaning - Merriam-Webster. Merriam-Webster.com Dictionary. Merriam-Webster. Archived from the original on 3 March 2023. Retrieved 3 March 2023.
  2. ^ Cite error: The named reference Mifepristone Linepharma PI 2015 was invoked but never defined (see the help page).
  3. ^ "Mifegymiso Product information". Health Canada. 10 January 2017. Retrieved 5 September 2024.
  4. ^ "Mifiso Product information". Health Canada. 16 December 2022. Retrieved 5 September 2024.
  5. ^ Cite error: The named reference Korlym FDA label was invoked but never defined (see the help page).
  6. ^ "Mifepristone tablet". DailyMed. 30 March 2023. Archived from the original on 10 April 2023. Retrieved 24 April 2023.
  7. ^ a b c d e f "Mifepristone". American Society of Health System Pharmacists. Archived from the original on 22 December 2015. Retrieved 25 February 2023 – via Drugs.com.
  8. ^ Chen MJ, Creinin MD (July 2015). "Mifepristone With Buccal Misoprostol for Medical Abortion: A Systematic Review". Obstetrics and Gynecology. 126 (1): 12–21. doi:10.1097/AOG.0000000000000897. PMID 26241251. S2CID 20800109. Archived from the original on 26 July 2020. Retrieved 27 July 2019 – via eScholarship.
  9. ^ a b Goldman MB, Troisi R, Rexrode KM, eds. (2012). Women and Health (2nd ed.). Oxford: Academic Press. p. 236. ISBN 978-0-12-384979-3. Archived from the original on 8 September 2017. Retrieved 5 September 2017 – via Google Books.
  10. ^ Wildschut H, Both MI, Medema S, Thomee E, Wildhagen MF, Kapp N (January 2011). "Medical methods for mid-trimester termination of pregnancy". The Cochrane Database of Systematic Reviews. 2011 (1): CD005216. doi:10.1002/14651858.CD005216.pub2. PMC 8557267. PMID 21249669.
  11. ^ a b Tribble S (8 April 2018). "How an abortion pill turned out to be a treatment for a rare disease". Washington Post. Retrieved 11 January 2025.
  12. ^ Cite error: The named reference Trussell 20162 was invoked but never defined (see the help page).
  13. ^ "Mifepristone Use During Pregnancy". Drugs.com. 20 January 2023. Archived from the original on 23 April 2023. Retrieved 22 April 2023.
  14. ^ Cite error: The named reference :0 was invoked but never defined (see the help page).
  15. ^ Corey EJ, Czakó B, Kürti L (2012). "Mifepristone". Molecules and Medicine. John Wiley & Sons. ISBN 978-1-118-36173-3. Archived from the original on 8 September 2017 – via Google Books.
  16. ^ "Drug Approval Package: Mifeprex (Mifepristone) NDA #20687". U.S. Food and Drug Administration (FDA). 18 June 2001. Archived from the original on 21 April 2023. Retrieved 24 April 2023.
  17. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  18. ^ "Mifepristone Product information". Health Canada. 22 October 2009. Archived from the original on 24 April 2023. Retrieved 24 April 2023.
  19. ^ Kingston A (5 February 2017). "How the arrival of the abortion pill reveals a double standard". Maclean's. Archived from the original on 21 February 2017. Retrieved 21 February 2017.

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