Chemistry and synthetic development of misoprostol

Collins, Paul W.; Pappo, Raphael; Dajani, Esam Z.

doi:10.1007/bf01309395

Cited by 50 publications

(27 citation statements)

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“…Misoprostol is a potent anti-secretory prostaglandin, structurally related to PGE1 (Collins et al, 1985). It is believed that it exerts its gastric anti-secretory effects via EP3-receptors (Reeves et al, 1988).…”

Section: Introductionmentioning

confidence: 99%

In vitro characterization of prostanoid EP‐receptors in the non‐pregnant human myometrium

Senior

Marshall

Sangha

et al. 1991

British J Pharmacology

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Postgraduate Studies in Pharmacology, University of Bradford, Bradford, BD7 lDP and *The Royal Infirmary, Bradford, BD9 6RJ1 Prostaglandin receptors of the PGE type have been characterized in the non-pregnant human myometrium in vitro according to the scheme of Coleman et al. (1984) by use of the agonists PGE2, sulprostone, rioprostil, AY23626, butaprost, misoprostol, 16,16-dimethylprostaglandin E2, enprostil and iloprost, and, the antagonist AH6809. 2 All prostanoids tested were active in non-pregnant human myometrium either as stimulators and/or inhibitors of spontaneous activity or both. Biphasic responses to PGE2 indicate that at least two receptor types of the EP-receptor exist, one mediating relaxation and the other mediating contraction. 3 Further evidence for the EP-receptor mediating excitation and relaxation was provided by the action of the EP2-/EP3-receptor selective prostanoids rioprostil, AY23626 and misoprostol, and the EP1-/EP2-receptor selective agonist 16,16-dimethylprostaglandin E2. 4 Butaprost, an EP2-receptor selective agonist, produced potent inhibition of spontaneous activity in the tissue which was generally longer-lasting than that evoked by the natural prostanoid PGE2. 5 The EP1-/EP3-receptor selective agonist sulprostone and the EP3-receptor agonist enprostil produced potent contractile responses supporting the presence of contractile EP3-receptors in the non-pregnant human myometrium in vitro.6 The EP,-/IP-receptor selective agonist, iloprost, produced mixed responses in non-pregnant human myometrium. The contractile response was inhibited by the EP,-receptor antagonist AH6809. However, responses to the EP1-/EP3-receptor selective agonist sulprostone were unaffected by AH6809 which may indicate that only a small population of EP1-receptors is present.

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Section: Introductionmentioning

confidence: 99%

In vitro characterization of prostanoid EP‐receptors in the non‐pregnant human myometrium

Senior

Marshall

Sangha

et al. 1991

British J Pharmacology

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“…Agonists and antagonists. Misoprostol (Collins et al, 1985), in which the 15-hydroxyl group of PGE 1 is displaced to C16, shows modest selectivity for EP 2 and EP 3 receptors, whereas the related butaprost (TR4979) is EP 2 -selective (Gardiner, 1986). However, tissue-dependent hydrolysis of its C1 ester is required to obtain full bioactivity (K i : butaprost, 3500 nM; butaprost-free acid, 91 nM for human rc-EP 2 receptor; Abramovitz et al, 2000).…”

Section: Distribution and Biological Functionsmentioning

confidence: 99%

International Union of Basic and Clinical Pharmacology. LXXXIII: Classification of Prostanoid Receptors, Updating 15 Years of Progress

Woodward

Jones

Narumiya³

2011

Pharmacol Rev

391

414

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“…7,8 The drug is absorbed through mucous membranes and can be administered sublingually, orally, vaginally, and rectally. 9,10 Misoprostol used alone for nonviable first-trimester pregnancy resulted in uterine expulsion in 13% to 96% of women.…”

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confidence: 99%

A randomized trial of saline solution–moistened misoprostol versus dry misoprostol for first-trimester pregnancy failure

Gilles

Creinin

Barnhart

et al. 2004

American Journal of Obstetrics and Gynecology

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Objective-The purpose of this study was to estimate whether the efficacy of treatment with intravaginal misoprostol for first-trimester pregnancy failure is enhanced by the addition of saline solution.Study design-Eighty women with embryonic/fetal death or anembryonic pregnancy were assigned randomly to receive either 800 μg of misoprostol with saline solution (group I, 41 women) or without (group II, 39 women). Treatment was repeated on day 3 if the gestational sac remained. Curettage was performed if the gestational sac remained on day 8 or as necessary during at least 30 days of follow-up. Data were analyzed with the Student t test and the χ 2 or Fisher exact test.Results-By the first follow-up visit, 73% (group I) and 64% (group II) of women passed the gestational sac (P = .38). By the second follow-up visit, expulsion rates were 83% and 87%, respectively (P = .59). Five subjects in each group underwent curettage. Conclusion-Misoprostol is effective for the treatment of failed first-trimester pregnancy. The expulsion rate is not improved by adding saline solution. KeywordsMissed abortion; Misoprostol; Anembryonic pregnancy; Fetal death; Spontaneous abortion Approximately 15% of clinically evident pregnancies result in first-trimester loss. 1 Curettage, commonly performed for this condition, is comparatively costly when performed in the operating room. 2 Although curettage is relatively safe, it can be associated with intrauterine infection, adhesion, perforation, and cervical stenosis. 3 An alternative may be expectant or medical treatment. Expectant treatment usually results in the complete expulsion of the products of conception 4 ; however, the interval after diagnosis and expulsion varies. Luise et al 5 reported that most women passed products within 2 weeks of diagnosis. Jurkovic et al 6 found only a 25% success rate in women whose cases were followed for >6 weeks. MedicalReprints not available from the authors. NIH Public Access Author ManuscriptAm J Obstet Gynecol. Author manuscript; available in PMC 2010 May 10.Published in final edited form as: Am J Obstet Gynecol. 2004 February ; 190(2): 389-394. doi:10.1016/j.ajog.2003 NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author Manuscript treatment may provide prompt expulsion and avoid costs and complications that are associated with surgery and the uncertainties of expectant treatment.A uterotonic drug that is proposed for medical treatment is misoprostol, an inexpensive widely available prostaglandin E 1 analog that is stable at room temperature. 7,8 The drug is absorbed through mucous membranes and can be administered sublingually, orally, vaginally, and rectally. 9,10 Misoprostol used alone for nonviable first-trimester pregnancy resulted in uterine expulsion in 13% to 96% of women. 11,12 Explanations for this wide range include different indications for treatment, dosing regimen, routes of administration, and measures of success. Vaginal administration appears to be more effective than oral administration for the inducement of ut...

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Chemistry and synthetic development of misoprostol

Cited by 50 publications

References 6 publications

In vitro characterization of prostanoid EP‐receptors in the non‐pregnant human myometrium

In vitro characterization of prostanoid EP‐receptors in the non‐pregnant human myometrium

International Union of Basic and Clinical Pharmacology. LXXXIII: Classification of Prostanoid Receptors, Updating 15 Years of Progress

A randomized trial of saline solution–moistened misoprostol versus dry misoprostol for first-trimester pregnancy failure

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