Misoprostol

Misoprostol
Clinical data
Trade namesCytotec, Misodel, others
AHFS/Drugs.comMonograph
MedlinePlusa689009
License data
Pregnancy
category
Routes of
administration		By mouth, rectal, vaginal, under the tongue
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailabilityextensively absorbed
Protein binding80–90% (active metabolite, misoprostol acid)
MetabolismLiver (extensive to misoprostic acid)
Elimination half-life20–40 minutes
ExcretionUrine (80%)
Identifiers
IUPAC name
  • Methyl 7-((1R,2R,3R)-3-hydroxy-2-((S,E)-4-hydroxy-4-methyloct-1-enyl)-5-oxocyclopentyl)heptanoate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.190.521
Chemical and physical data
FormulaC22H38O5
Molar mass382.541 g·mol−1
3D model (JSmol)
SMILES
  • CCCC[C@](C)(O)C/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC
InChI
  • InChI=1S/C22H38O5/c1-4-5-14-22(2,26)15-10-12-18-17(19(23)16-20(18)24)11-8-6-7-9-13-21(25)27-3/h10,12,17-18,20,24,26H,4-9,11,13-16H2,1-3H3/b12-10+/t17-,18-,20-,22?/m1/s1 Y
  • Key:OJLOPKGSLYJEMD-URPKTTJQSA-N Y
  (verify)

Misoprostol is a synthetic prostaglandin medication used to prevent and treat stomach and duodenal ulcers, induce labor, cause an abortion, and treat postpartum bleeding due to poor contraction of the uterus.[9][10] It is taken by mouth when used to prevent gastric ulcers in people taking nonsteroidal anti-inflammatory drugs (NSAID).[10] For abortions it is typically used in conjunction with mifepristone or methotrexate, but can be used alone.[11] By itself, effectiveness for abortion is between 82% and 100%.[12] Its efficacy with mifepristone is higher, but varies based on gestational age.[13] The misoprostol-only abortion regimen is typically recommended only when mifepristone is not available.[14] For labor induction or abortion, it is taken by mouth, dissolved in the mouth, or placed in the vagina.[11][15][16][17][18] For postpartum bleeding it may also be used rectally.[19]

Common side effects include diarrhea and abdominal pain.[10] It is in pregnancy category X, meaning that it is known to result in negative outcomes for the fetus if taken during pregnancy.[10] In rare cases, uterine rupture may occur.[10] It is a prostaglandin analogue—specifically, a synthetic prostaglandin E1 (PGE1).[10]

Misoprostol was developed in 1973 and first created for the treatment of gastric ulcers.[20][12] Its first uses for abortion emerged in Latin America in the 1980s, as women noticed miscarriage was a side effect of the medication.[12] It is on the World Health Organization's List of Essential Medicines.[21] It is available as a generic medication.[10]

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  2. ^ "TGA eBS - Product and Consumer Medicine Information Licence". Archived from the original on 14 April 2023. Retrieved 14 April 2023.
  3. ^ "Angusta (Norgine Pty Ltd)". Therapeutic Goods Administration (TGA). 13 January 2023. Archived from the original on 18 March 2023. Retrieved 9 April 2023.
  4. ^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 15 August 2023.
  5. ^ "Angusta 25 microgram tablets - Summary of Product Characteristics (SmPC)". (emc). 8 April 2022. Archived from the original on 10 April 2023. Retrieved 9 April 2023.
  6. ^ "Cytotec- misoprostol tablet". DailyMed. 9 July 2021. Archived from the original on 18 April 2023. Retrieved 13 April 2023.
  7. ^ "List of nationally authorised medicinal products. Misoprostol (gastrointestinal indication). Procedure no.: PSUSA/00010353/202005" (PDF). European Medicines Agency. 14 January 2021. Archived (PDF) from the original on 29 June 2022. Retrieved 8 August 2021.
  8. ^ "List of nationally authorised medicinal products. Misoprostol (gastrointestinal indication). Procedure no.: PSUSA/00010291/202006" (PDF). European Medicines Agency. 14 January 2021. Archived (PDF) from the original on 29 June 2022. Retrieved 8 August 2021.
  9. ^ Rostom A, Dube C, Wells G, Tugwell P, Welch V, Jolicoeur E, et al. (2002). "Prevention of NSAID-induced gastroduodenal ulcers". The Cochrane Database of Systematic Reviews. 2011 (4): CD002296. doi:10.1002/14651858.CD002296. PMC 8439413. PMID 12519573. S2CID 1052260.
  10. ^ a b c d e f g "Misoprostol". The American Society of Health-System Pharmacists. Archived from the original on 21 February 2015. Retrieved 20 February 2015.
  11. ^ a b Zhang J, Zhou K, Shan D, Luo X (May 2022). "Medical methods for first trimester abortion". The Cochrane Database of Systematic Reviews. 2022 (5): CD002855. doi:10.1002/14651858.CD002855.pub5. PMC 9128719. PMID 35608608.
  12. ^ a b c Moseson H, Jayaweera R, Baum SE, Gerdts C (June 2024). "How Effective Is Misoprostol Alone for Medication Abortion?". NEJM Evidence. 3 (6): EVIDccon2300129. doi:10.1056/EVIDccon2300129. PMID 38804786.
  13. ^ Fjerstad M, Sivin I, Lichtenberg ES, Trussell J, Cleland K, Cullins V (September 2009). "Effectiveness of medical abortion with mifepristone and buccal misoprostol through 59 gestational days". Contraception. 80 (3): 282–286. doi:10.1016/j.contraception.2009.03.010. PMC 3766037. PMID 19698822.
  14. ^ Krugh M, Patel P, Maani CV (2025). "Misoprostol". StatPearls. Treasure Island (FL): StatPearls Publishing. PMID 30969695. Retrieved 12 March 2025.
  15. ^ Marret H, Simon E, Beucher G, Dreyfus M, Gaudineau A, Vayssière C, et al. (April 2015). "Overview and expert assessment of off-label use of misoprostol in obstetrics and gynaecology: review and report by the Collège national des gynécologues obstétriciens français". European Journal of Obstetrics, Gynecology, and Reproductive Biology. 187: 80–84. doi:10.1016/j.ejogrb.2015.01.018. PMID 25701235.
  16. ^ Prager S. "Early Pregnancy Loss" (PDF). ACOG Practice Bulletin (200). ACOG. Archived (PDF) from the original on 2 June 2021. Retrieved 2 June 2021.
  17. ^ Cite error: The named reference ACOG Practice Bulletin No. 200: Ear was invoked but never defined (see the help page).
  18. ^ "Early Pregnancy Loss". ACOG. 20 January 2015. Archived from the original on 19 January 2023. Retrieved 25 June 2023.
  19. ^ Blum J, Alfirevic Z, Walraven G, Weeks A, Winikoff B (December 2007). "Treatment of postpartum hemorrhage with misoprostol". International Journal of Gynaecology and Obstetrics. 99 (Suppl 2): S202 – S205. doi:10.1016/j.ijgo.2007.09.013. PMID 17961565. S2CID 10997666.
  20. ^ Paul M (2011). "Misoprostol". Management of Unintended and Abnormal Pregnancy: Comprehensive Abortion Care. John Wiley & Sons. ISBN 9781444358476. Archived from the original on 29 June 2022. Retrieved 18 August 2020.
  21. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
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