Structure via PubChem · Public domain (PubChem)
mifepristone
Sign in to saveAlso known as RU-486, RU486, Mifepristonum, Mifegyne, 11-(4-DIMETHYLAMINO-phenyl)-17-hydroxy-13-methyl-17-prop-1-ynyl-1,2,6,7,8,11,12,13,14,15,16,17-dodec ahydro-cyclopenta[a]phenanthren-3-one, Mifepriston, Corlux
Mifepristone, 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. This combination is 97% effective during the first 63 days (9 weeks) of pregnancy, and is effective in the second trimester as well. It is also used on its own to treat Cushing's syndrome or in low doses as an emergency contraceptive.
Key facts
- Drug.image
- Mifepristone structure.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 200
- Drug.image2
- Mifepristona3D.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 200
- Drug.tradename
- Mifegyne, others
- Drug.MedlinePlus
- a600042
- Drug.DailyMedID
- Mifepristone
- Drug.pregnancy_category
- Not recommended
- Drug.routes_of_administration
- By mouth
- Drug.class
- Antiprogestogen; antiglucocorticoid
- Drug.ATC_prefix
- G03
- Drug.ATC_suffix
- XB01
- Drug.legal_AU
- S4
- Drug.legal_CA
- Rx-only
- Drug.legal_US
- Rx-only
- Drug.legal_status
- Rx-only
via Wikipedia infobox
Chemical data
- Formula
- C29H35NO2
- Molecular weight
- 429.6 g/mol
- IUPAC name
- (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
- 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
- InChIKey
- VKHAHZOOUSRJNA-GCNJZUOMSA-N
- XLogP
- 3.8
- Polar surface area
- 40.5 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
8,361 papers- Mifepristone.The Annals of pharmacotherapy · 2001
- Mifepristone at home.BMJ (Clinical research ed.) · 2022
- Mifepristone-Induced Hypothyroidism.Journal of investigative medicine high impact case reports · 2023
- Mifepristone for uterine fibroids.The Cochrane database of systematic reviews · 2012
- Mifepristone: ten years later.Contraception · 2010
via PubMed
~26 min read
Encyclopedic overview
29 sectionsContents
- Medical uses
- Abortion
- Cushing's syndrome
- Medical management of early pregnancy loss
- Other uses
- Side effects
- Pregnancy
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- History
- 1980–1987
- 1988–1990
- 1991–1996
- 1997–1999
- 2000–present
- Society and culture
- Economics
- Frequency of use
- United States
- Europe
- Legal status
- United States
- European Union
- Other countries
- Controversy
- Research
- References
Mifepristone, 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. This combination is 97% effective during the first 63 days (9 weeks) of pregnancy, and is effective in the second trimester as well. It is also used on its own to treat Cushing's syndrome or in low doses as an emergency contraceptive.
The most common adverse effects include abdominal pain, feeling tired, and vaginal bleeding. Serious side effects may include heavy vaginal bleeding, bacterial infection, and, if pregnant, birth defects. When used, appropriate follow-up care needs to be available. Mifepristone is primarily an antiprogestogen. It works by blocking the effects of progesterone, making both the cervix and uterine vessels dilate and causing uterine contraction. Mifepristone also works, to a lesser extent, as an antiglucocorticoid and diminishes the effects of hypercortisolism.
Excerpted from Wikipedia’s “mifepristone” article, available under the CC BY-SA 4.0 licence.