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MedKoo Cat#: 318281 | Name: Misoprostol
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Misoprostol is a medication used to start labor, cause an abortion, prevent and treat stomach ulcers, and treat postpartum bleeding due to poor contraction of the uterus. For abortions it is often used with mifepristone or methotrexate. By itself effectiveness for this purpose is between 66% and 90%.

Chemical Structure

Misoprostol
Misoprostol
CAS#59122-46-2

Theoretical Analysis

MedKoo Cat#: 318281

Name: Misoprostol

CAS#: 59122-46-2

Chemical Formula: C22H38O5

Exact Mass: 382.2719

Molecular Weight: 382.53

Elemental Analysis: C, 69.07; H, 10.01; O, 20.91

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 550.00 2 Weeks
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Related CAS #
No Data
Synonym
Misoprostol, Cytotec, Misoprostolum, Isprelor, Misopess, SC-29333, SC-30249
IUPAC/Chemical Name
methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(E)-4-hydroxy-4-methyloct-1-enyl]-5-oxocyclopentyl]heptanoate
InChi Key
OJLOPKGSLYJEMD-URPKTTJQSA-N
InChi Code
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
SMILES Code
O=C(OC)CCCCCC[C@@H]1[C@@H](/C=C/CC(C)(O)CCCC)[C@H](O)CC1=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Misoprostol (SC-29333) is an orally active synthetic prostaglandin E1 (PGE1) analog that is used for gastric ulcers research.
In vitro activity:
In vitro, misoprostol suppressed macrophage TNF-alpha and chemokine generation following C. sordellii or peptidoglycan challenge, impaired leukocyte phagocytosis of C. sordellii, and inhibited uterine epithelial cell human beta-defensin expression. These immunosuppressive effects of misoprostol, which were not shared by mifepristone, correlated with the activation of the G(s) protein-coupled E prostanoid (EP) receptors EP2 and EP4 (macrophages) or EP4 alone (uterine epithelial cells). Reference: J Immunol. 2008 Jun 15;180(12):8222-30. https://pubmed.ncbi.nlm.nih.gov/18523288/
In vivo activity:
This study tested whether misoprostol, a PGE(2) receptor agonist that is utilized clinically as an anti-ulcer agent and signals through the protective PGE(2) EP2, EP3, and EP4 receptors, would reduce brain injury in the murine middle cerebral artery occlusion-reperfusion (MCAO-RP) model. Administration of misoprostol, at the time of MCAO or 2h after MCAO, resulted in significant rescue of infarct volume at 24 and 72h. Reference: Neurosci Lett. 2008 Jun 20;438(2):210-5. https://pubmed.ncbi.nlm.nih.gov/18472336/
Solvent mg/mL mM comments
Solubility
DMSO 46.4 121.34
Ethanol 24.1 63.07
Water 18.5 48.36
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 382.53 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Aronoff DM, Hao Y, Chung J, Coleman N, Lewis C, Peres CM, Serezani CH, Chen GH, Flamand N, Brock TG, Peters-Golden M. Misoprostol impairs female reproductive tract innate immunity against Clostridium sordellii. J Immunol. 2008 Jun 15;180(12):8222-30. doi: 10.4049/jimmunol.180.12.8222. PMID: 18523288; PMCID: PMC2667109. 2. Moreland RB, Kim NN, Nehra A, Parulkar BG, Traish A. Misoprostol induces relaxation of human corpus cavernosum smooth muscle: comparison to prostaglandin E1. Int J Impot Res. 2000 Apr;12(2):107-10. doi: 10.1038/sj.ijir.3900497. PMID: 11052637. 3. Li J, Liang X, Wang Q, Breyer RM, McCullough L, Andreasson K. Misoprostol, an anti-ulcer agent and PGE2 receptor agonist, protects against cerebral ischemia. Neurosci Lett. 2008 Jun 20;438(2):210-5. doi: 10.1016/j.neulet.2008.04.054. Epub 2008 Apr 20. PMID: 18472336; PMCID: PMC2621308. 4. Lyons C, Beharry K, Akmal Y, Attenello F, Nageotte MP. In vitro response of prostaglandin E2 receptor (EP3) in the term pregnant rat uterus and cervix to misoprostol. Prostaglandins Other Lipid Mediat. 2003 Jan;70(3-4):317-29. doi: 10.1016/s0090-6980(02)00146-6. PMID: 12611496.
In vitro protocol:
1. Aronoff DM, Hao Y, Chung J, Coleman N, Lewis C, Peres CM, Serezani CH, Chen GH, Flamand N, Brock TG, Peters-Golden M. Misoprostol impairs female reproductive tract innate immunity against Clostridium sordellii. J Immunol. 2008 Jun 15;180(12):8222-30. doi: 10.4049/jimmunol.180.12.8222. PMID: 18523288; PMCID: PMC2667109. 2. Moreland RB, Kim NN, Nehra A, Parulkar BG, Traish A. Misoprostol induces relaxation of human corpus cavernosum smooth muscle: comparison to prostaglandin E1. Int J Impot Res. 2000 Apr;12(2):107-10. doi: 10.1038/sj.ijir.3900497. PMID: 11052637.
In vivo protocol:
1. Li J, Liang X, Wang Q, Breyer RM, McCullough L, Andreasson K. Misoprostol, an anti-ulcer agent and PGE2 receptor agonist, protects against cerebral ischemia. Neurosci Lett. 2008 Jun 20;438(2):210-5. doi: 10.1016/j.neulet.2008.04.054. Epub 2008 Apr 20. PMID: 18472336; PMCID: PMC2621308. 2. Lyons C, Beharry K, Akmal Y, Attenello F, Nageotte MP. In vitro response of prostaglandin E2 receptor (EP3) in the term pregnant rat uterus and cervix to misoprostol. Prostaglandins Other Lipid Mediat. 2003 Jan;70(3-4):317-29. doi: 10.1016/s0090-6980(02)00146-6. PMID: 12611496.
1: Zhuo Z, Yu H, Jiang X. A systematic review and meta-analysis of randomized controlled trials on the effectiveness of cervical ripening with misoprostol administration before hysteroscopy. Int J Gynaecol Obstet. 2016 Mar;132(3):272-7. doi: 10.1016/j.ijgo.2015.07.039. Epub 2015 Dec 11. Review. PubMed PMID: 26797202. 2: Chen W, Xue J, Peprah MK, Wen SW, Walker M, Gao Y, Tang Y. A systematic review and network meta-analysis comparing the use of Foley catheters, misoprostol, and dinoprostone for cervical ripening in the induction of labour. BJOG. 2016 Feb;123(3):346-54. doi: 10.1111/1471-0528.13456. Epub 2015 Nov 5. Review. PubMed PMID: 26538408. 3: Smith HJ, Colvin CJ, Richards E, Roberson J, Sharma G, Thapa K, Gülmezoglu AM. Programmes for advance distribution of misoprostol to prevent post-partum haemorrhage: a rapid literature review of factors affecting implementation. Health Policy Plan. 2016 Feb;31(1):102-13. doi: 10.1093/heapol/czv012. Epub 2015 Mar 21. Review. PubMed PMID: 25797470. 4: Iavazzo C, Mamais I, Gkegkes ID. Use of misoprostol in myomectomy: a systematic review and meta-analysis. Arch Gynecol Obstet. 2015 Dec;292(6):1185-91. doi: 10.1007/s00404-015-3779-x. Epub 2015 Jun 4. Review. PubMed PMID: 26041328. 5: Rath W, Tsikouras P. Misoprostol for Labour Induction after Previous Caesarean Section - Forever a "No Go"? Geburtshilfe Frauenheilkd. 2015 Nov;75(11):1140-1147. Review. PubMed PMID: 26719597; PubMed Central PMCID: PMC4678051. 6: Stephenson ML, Wing DA. Misoprostol for induction of labor. Semin Perinatol. 2015 Oct;39(6):459-62. doi: 10.1053/j.semperi.2015.07.008. Review. PubMed PMID: 26601733. 7: Zhang Y, Wang J, Yu Y, Xie C, Xiao M, Ren L. Misoprostol versus prostaglandin E2 gel for labor induction in premature rupture of membranes after 34 weeks of pregnancy. Int J Gynaecol Obstet. 2015 Sep;130(3):214-8. doi: 10.1016/j.ijgo.2015.04.031. Epub 2015 Jun 10. Review. PubMed PMID: 26118328. 8: Chen MJ, Creinin MD. Mifepristone With Buccal Misoprostol for Medical Abortion: A Systematic Review. Obstet Gynecol. 2015 Jul;126(1):12-21. doi: 10.1097/AOG.0000000000000897. Review. PubMed PMID: 26241251. 9: Chen W, Xue J, Gaudet L, Walker M, Wen SW. Meta-analysis of Foley catheter plus misoprostol versus misoprostol alone for cervical ripening. Int J Gynaecol Obstet. 2015 Jun;129(3):193-8. doi: 10.1016/j.ijgo.2015.01.005. Epub 2015 Mar 10. Review. PubMed PMID: 25794821. 10: Ghinea N, Lipworth W, Little M, Kerridge I, Day R. Overcoming entrenched disagreements: the case of misoprostol for post-partum haemorrhage. Dev World Bioeth. 2015 Apr;15(1):48-54. Review. PubMed PMID: 25897445. 11: Marret H, Simon E, Beucher G, Dreyfus M, Gaudineau A, Vayssière C, Lesavre M, Pluchon M, Winer N, Fernandez H, Aubert J, Bejan-Angoulvant T, Jonville-Bera AP, Clouqueur E, Houfflin-Debarge V, Garrigue A, Pierre F; Collège national des gynécologues obstétriciens français. 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. Eur J Obstet Gynecol Reprod Biol. 2015 Apr;187:80-4. doi: 10.1016/j.ejogrb.2015.01.018. Epub 2015 Jan 31. Review. PubMed PMID: 25701235. 12: McMaster K, Sanchez-Ramos L, Kaunitz AM. Balancing the efficacy and safety of misoprostol: a meta-analysis comparing 25 versus 50 micrograms of intravaginal misoprostol for the induction of labour. BJOG. 2015 Mar;122(4):468-76. doi: 10.1111/1471-0528.12935. Epub 2014 Jul 3. Review. PubMed PMID: 24989790. 13: Stephenson ML, Wing DA. A novel misoprostol delivery system for induction of labor: clinical utility and patient considerations. Drug Des Devel Ther. 2015 Apr 22;9:2321-7. doi: 10.2147/DDDT.S64227. eCollection 2015. Review. PubMed PMID: 25960635; PubMed Central PMCID: PMC4410824. 14: Patte C, Deruelle P. A critical appraisal of the misoprostol removable, controlled-release vaginal delivery system of labor induction. Int J Womens Health. 2015 Nov 12;7:889-99. doi: 10.2147/IJWH.S62372. eCollection 2015. Review. PubMed PMID: 26648758; PubMed Central PMCID: PMC4648618. 15: Alfirevic Z, Aflaifel N, Weeks A. Oral misoprostol for induction of labour. Cochrane Database Syst Rev. 2014 Jun 13;6:CD001338. doi: 10.1002/14651858.CD001338.pub3. Review. PubMed PMID: 24924489. 16: Radoff KA. Orally administered misoprostol for induction of labor with prelabor rupture of membranes at term. J Midwifery Womens Health. 2014 May-Jun;59(3):254-63. doi: 10.1111/jmwh.12195. Epub 2014 Apr 28. Review. PubMed PMID: 24773622. 17: Liu A, Lv J, Hu Y, Lang J, Ma L, Chen W. Efficacy and safety of intravaginal misoprostol versus intracervical dinoprostone for labor induction at term: a systematic review and meta-analysis. J Obstet Gynaecol Res. 2014 Apr;40(4):897-906. doi: 10.1111/jog.12333. Review. PubMed PMID: 24698022. 18: Clouqueur E, Coulon C, Vaast P, Chauvet A, Deruelle P, Subtil D, Houfflin-Debarge V. [Use of misoprostol for induction of labor in case of fetal death or termination of pregnancy during second or third trimester of pregnancy: Efficiency, dosage, route of administration, side effects, use in case of uterine scar]. J Gynecol Obstet Biol Reprod (Paris). 2014 Feb;43(2):146-61. doi: 10.1016/j.jgyn.2013.11.008. Epub 2014 Jan 22. Review. French. PubMed PMID: 24461423. 19: Gaudineau A, Vayssière C. [Cervical ripening with misoprostol with a live fetus]. J Gynecol Obstet Biol Reprod (Paris). 2014 Feb;43(2):169-78. doi: 10.1016/j.jgyn.2013.11.010. Epub 2014 Jan 13. Review. French. PubMed PMID: 24433989. 20: Garrigue A, Pierre F. [Misoprostol: off-label use in the treatment of post-partum hemorrhage]. J Gynecol Obstet Biol Reprod (Paris). 2014 Feb;43(2):179-89. doi: 10.1016/j.jgyn.2013.11.011. Epub 2014 Jan 20. Review. French. PubMed PMID: 24457021.