Misoprostol information

Misoprostol
Clinical data
Trade names	Cytotec, Misodel, others
AHFS/Drugs.com	Monograph
MedlinePlus	a689009
License data	US DailyMed: Misoprostol;
Pregnancy; category	AU: X (High risk); Used for terminating pregnancy;
Routes of; administration	By mouth, rectal vaginal, under the tongue
ATC code	A02BB01 (WHO) G02AD06 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances) Hospital use only; CA: ℞-only; UK: POM (Prescription only); US: WARNINGRx-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	extensively absorbed
Protein binding	80–90% (active metabolite, misoprostol acid)
Metabolism	Liver (extensive to misoprostic acid)
Elimination half-life	20–40 minutes
Excretion	Urine (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	59122-46-2 ;
PubChem CID	5282381;
IUPHAR/BPS	1936;
DrugBank	DB00929 ;
ChemSpider	4445541 ;
UNII	0E43V0BB57;
KEGG	D00419 ;
ChEMBL	ChEMBL606 ;
CompTox Dashboard (EPA)	DTXSID7020897 ;
ECHA InfoCard	100.190.521
Chemical and physical data
Formula	C22H38O5
Molar mass	382.541 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:OJLOPKGSLYJEMD-URPKTTJQSA-N ;
	(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.^[10]^[11] It is taken by mouth when used to prevent gastric ulcers in people taking nonsteroidal anti-inflammatory drugs (NSAID).^[11] For abortions it is used by itself or in conjunction with mifepristone or methotrexate.^[12] By itself, effectiveness for abortion is between 66% and 90%.^[13]^[14] For labor induction or abortion, it is taken by mouth, dissolved in the mouth, or placed in the vagina.^[12]^[15]^[16]^[17]^[18] For postpartum bleeding it may also be used rectally.^[19]

Common side effects include diarrhea and abdominal pain.^[11] It is in pregnancy category X, meaning that it is known to result in negative outcomes for the fetus if taken during pregnancy.^[11] In rare cases, uterine rupture may occur.^[11] It is a prostaglandin analogue—specifically, a synthetic prostaglandin E₁ (PGE₁).^[11]

Misoprostol was developed in 1973.^[20] It is on the World Health Organization's List of Essential Medicines.^[21] It is available as a generic medication.^[11]

^ "TGA eBS - Product and Consumer Medicine Information Licence". Archived from the original on 14 April 2023. Retrieved 14 April 2023.
^ "TGA eBS - Product and Consumer Medicine Information Licence". Archived from the original on 14 April 2023. Retrieved 14 April 2023.
^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
^ "Angusta (Norgine Pty Ltd)". Therapeutic Goods Administration (TGA). 13 January 2023. Archived from the original on 18 March 2023. Retrieved 9 April 2023.
^ 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.
^ "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.
^ "Cytotec- misoprostol tablet". DailyMed. 9 July 2021. Archived from the original on 18 April 2023. Retrieved 13 April 2023.
^ "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.
^ "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.
^ 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.
^ ^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.
^ ^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.
^ Bryant AG, Regan E, Stuart G (January 2014). "An overview of medical abortion for clinical practice". Obstetrical & Gynecological Survey. 69 (1): 39–45. doi:10.1097/OGX.0000000000000017. PMID 25102250. S2CID 28486936.
^ Raymond EG, Harrison MS, Weaver MA (January 2019). "Efficacy of Misoprostol Alone for First-Trimester Medical Abortion: A Systematic Review". Obstetrics and Gynecology. 133 (1): 137–147. doi:10.1097/AOG.0000000000003017. PMC 6309472. PMID 30531568.
^ 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: 80–4. doi:10.1016/j.ejogrb.2015.01.018. PMID 25701235.
^ Prager S. "Early Pregnancy Loss" (PDF). ACOG Practice Bulletin (200). ACOG. Archived (PDF) from the original on 2 June 2021. Retrieved 2 June 2021.
^ Cite error: The named reference ACOG Practice Bulletin No. 200: Ear was invoked but never defined (see the help page).
^ "Early Pregnancy Loss". ACOG. 20 January 2015. Archived from the original on 19 January 2023. Retrieved 25 June 2023.
^ 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): S202-5. doi:10.1016/j.ijgo.2007.09.013. PMID 17961565. S2CID 10997666.
^ 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.
^ 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.

[1] "TGA eBS - Product and Consumer Medicine Information Licence". Archived from the original on 14 April 2023. Retrieved 14 April 2023.

[2] "TGA eBS - Product and Consumer Medicine Information Licence". Archived from the original on 14 April 2023. Retrieved 14 April 2023.

[FDA-AllBoxedWarnings-3] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.

[4] "Angusta (Norgine Pty Ltd)". Therapeutic Goods Administration (TGA). 13 January 2023. Archived from the original on 18 March 2023. Retrieved 9 April 2023.

[5] 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.

[6] "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.

[7] "Cytotec- misoprostol tablet". DailyMed. 9 July 2021. Archived from the original on 18 April 2023. Retrieved 13 April 2023.

[8] "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.

[9] "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.

[Ros2002-10] 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.

[AHFS2015-11] ^ ^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.

[:3-12] 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.

[13] Bryant AG, Regan E, Stuart G (January 2014). "An overview of medical abortion for clinical practice". Obstetrical & Gynecological Survey. 69 (1): 39–45. doi:10.1097/OGX.0000000000000017. PMID 25102250. S2CID 28486936.

[14] Raymond EG, Harrison MS, Weaver MA (January 2019). "Efficacy of Misoprostol Alone for First-Trimester Medical Abortion: A Systematic Review". Obstetrics and Gynecology. 133 (1): 137–147. doi:10.1097/AOG.0000000000003017. PMC 6309472. PMID 30531568.

[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: 80–4. 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.

[ACOG_Practice_Bulletin_No._200:_Ear-17] Cite error: The named reference ACOG Practice Bulletin No. 200: Ear was invoked but never defined (see the help page).

[Early_Pregnancy_Loss-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): S202-5. 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.

[WHO22nd-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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