Misoprostol
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Overview
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| Misoprostol
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| Systematic (IUPAC) name | |
| Methyl 7-{3-hydroxy-2- [(E)-4-hydroxy-4-methyloct-1-enyl]- 5-oxocyclopentyl}heptanoate | |
| Identifiers | |
| CAS number | |
| ATC code | A02 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C22H38O5 |
| Mol. mass | 382.5 g/mol |
| Pharmacokinetic data | |
| Bioavailability | extensively absorbed |
| Metabolism | de-esterified to misoprostol acid, then to prostaglandin F analogs |
| Half life | 20–40 minutes |
| Excretion | Renal:80% Fecal:15% |
| Therapeutic considerations | |
| Pregnancy cat. |
X |
| Legal status |
℞ Prescription only |
| Routes | Oral, Vaginal, Sublingual |
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Misoprostol is a drug that is FDA-approved in the United States for the prevention of NSAID-induced gastric ulcers. It is also used (and approved in other countries) to induce labor and as an abortifacient. It was invented and marketed by G.D. Searle & Company (now Pfizer) under the trade name Cytotec, but other brand-name and generic formulations are now available as well.
Chemically, misoprostol is a synthetic prostaglandin E1 (PGE1) analogue.
Indicated (in the United States) use
Misoprostol stimulates increased secretion of the protective mucus that lines the gastrointestinal tract and increases mucosal blood flow, thereby increasing mucosal integrity. It is sometimes co-prescribed with non-steroidal anti-inflammatory drugs to prevent their common adverse effect of gastric ulceration (e.g. with Diclofenac in Arthrotec).
Off label (in the United States) uses
Obstetric and gynecological
Labor Induction
Misoprostol is commonly prescribed off-label to cause birth induction by uterine contractions and the ripening (effacement or thinning) of the cervix. Misoprostol is highly effective and much less expensive than pitocin and dinoprostone, the FDA-approved drugs for medically necessary labor induction. Trial meta-analysis by the Cochrane Collaboration demonstrates no difference in efficacy or side effects between inductions undertaken with dinoprostone or misoprostol (when used at the correct dosage).
Concern has been expressed about the overuse or misuse of misoprostol for labor induction. High doses can cause uterine rupture (especially in women who have previously had a caesarean section), fetal death and severe fetal brain damage, according to a CBS Evening News story by correspondent Sharyn Alfonsi.[1] All induction agents cause uterine contractions – this can affect the blood supply to the fetus, especially if contractions become very frequent. Induction agents therefore need to be used with great care and with close fetal monitoring. One of the problems with induction using prostaglandins (either cervidil or misoprostol) is that once given, the process is difficult to reverse. In contrast, Pitocin (oxytocin, a hormone that also causes contractions) has a half-life of about 10 minutes and is administered via intravenous drip, which can be stopped immediately in the event of adverse reaction, according to a Salon.com webzine article by midwife Ina May Gaskin.[1] A clinical trial is currently underway to establish a controlled delivery method for misoprostol.[1]
The manufacturers of misoprostol have never sought to license misoprostol for labor induction. Recently, however, generic forms of misoprostol have become available, and it is now licensed for labor induction in Egypt and Brazil, and a licensed induction product is expected in the UK in 2008.[1] [1]
The American College of Obstetricians and Gynecologists advocates misoprostol for labor inductions, and it is on the WHO essential drug list for labour induction.[1] Other agencies await more evidence as to its safety, including obstetric organizations in Britain, Canada and Scandinavia, according to a Midwifery Today magazine article by neonatologist Marsden Wagner.[1]
Abortion
Misoprostol is one of the drugs used for medical abortions. In many countries it is used in conjunction with mifepristone (RU-486). After mifepristone is taken orally, misoprostol is taken 24–72 hours later causing the expulsion of the fetus and associated matter in approximately 92% of the cases. No large studies have established a protocol for the use of misoprostol alone,[1] and the range of efficacy is 65%–93% depending on sample size, gestational age, and other test variables;[1] Misoprostol alone may be more effective in earlier gestation.[1] The side effects associated with the misoprostol-only regimen are generally much more severe than those associated with the combined regimens. Misoprostol is used for self-induced abortions in Brazil, where black market prices exceed US $100 per dose. Illegal medically-unsupervised misoprostol abortions in Brazil are associated with a lower complication rate than other forms of illegal self-induced abortion, but are still associated with a higher complication rate than legal, medically supervised surgical and chemical abortions. Failed misoprostol abortions are associated with birth defects in some cases. [1] [1][1] [1] [1] Poor immigrant populations in New York have also been observed to use self-administered misoprostol to induce abortions, as this method is much cheaper than a surgical abortion (about $2 per dose).[1]
Misoprostol is sometimes used to treat early fetal death in the absence of spontaneous miscarriage, but further research is needed to establish a a safe, effective protocol. [1] It can also be used to dilate the cervix in preparation for a surgical abortion. Misoprostol is also used to prevent and treat post-partum hemorrhage, but it has more side effects and is less effective than oxytocin for this purpose. [1]
Erectile dysfunction
A 1998 study found misoprostol to be helpful as a supplement to a vacuum pump (VED) in the treatment of erectile dysfunction, but not effective by itself.[1] The paper concluded "The intraurethral application of misoprostol significantly improves the quality of VED-induced erections. This agent seems to be a cheap intraurethral adjunct to VED with mild to moderate local side-effects".
Side effects and contraindications
The most commonly reported adverse effect of taking a misoprostol 200 µg tablet by mouth four times a day to reduce the risk of NSAID-induced gastric ulcers is diarrhea. In clinical trials, an average 13% of patients reported diarrhea, which was dose-related and usually developed early in the course of therapy (after 13 days) and was usually self-limiting (often resolving within 8 days), but sometimes (in 2% of patients) required discontinuation of misoprostol.[1]
The next most commonly reported adverse effects of taking a misoprostol 200 µg tablet by mouth four times a day to reduce the risk of NSAID-induced gastric ulcers are: abdominal pain, nausea, flatulence, headache, dyspepsia, vomiting, and constipation, but none of these adverse effects occurred significantly more often than when taking placebos.[1]
Misoprostol should not be taken by pregnant women to reduce the risk of NSAID-induced gastric ulcers because it increases uterine tone and contractions in pregnancy which may cause partial or complete abortions, and because its use in pregnancy has been associated with birth defects.[1][1]
References
External links and further reading
- Misoprostol from Drugdigest
- Misoprostol.org an independent website containing dosage guidelines and advice on misoprostol use.
Drugs for acid related disorders: Drugs for peptic ulcer and GERD/GORD (A02B) | |
|---|---|
| H2 antagonists | Cimetidine, Famotidine, Nizatidine, Ranitidine, Roxatidine |
| Prostaglandins/analogues | Misoprostol, Enprostil |
| Proton pump inhibitors | Esomeprazole, Lansoprazole, Omeprazole, Pantoprazole, Rabeprazole, Tenatoprazole |
| Other | Carbenoxolone, Sucralfate, Pirenzepine |
Eicosanoids: prostaglandins | |
|---|---|
| Endogenous/series 2 | D2 - E2 (Dinoprostone) - F2 (Dinoprost) - H2 - I2 (Prostacyclin) |
| Prostaglandin analogues | E: Alprostadil - Enprostil - Misoprostol
F: Bimatoprost - Carboprost - Latanoprost - Travoprost I: Beraprost - Iloprost - Treprostinil |
de:Misoprostolnl:Misoprostol ja:ミソプロストール
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
