|Systematic (IUPAC) name|
|Licence data||US FDA:|
|Metabolism||Extensive, CYP not involved|
0.9–1.4 hours (main metabolite)
|Excretion||Renal (60%) and fecal (30%)|
|Mol. mass||390.462 g/mol|
Lubiprostone (rINN, marketed under the trade name Amitiza) is a medication used in the management of chronic idiopathic constipation, predominantly irritable bowel syndrome-associated constipation in women and opioid-induced constipation. It was initially approved by the U.S. Food and Drug Administration (FDA) in 2006.
Lubiprostone 24 mcg capsules twice daily is approved to treat chronic idiopathic constipation (CIC) in adults.
Lubiprostone 24 mcg twice daily is also approved to treat opioid-induced constipation, in adults with chronic non-cancer pain. The effectiveness of lubiprostone has not been established in patients who are taking a diphenylheptane opioid (e.g., methadone).
Lubiprostone 8 mcg capsules twice daily is approved to treat irritable bowel syndrome with constipation (IBS-C) in women 18 years of age and older.
As of 12 November 2014, lubiprostone has not been studied in children. There is current research underway to determine the safety and efficacy in postoperative bowel dysfunction.
In clinical trials, the most common adverse event was nausea (31%). Other adverse events (≥5% of patients) included diarrhea (13%), headache (13%), abdominal distention (5%), abdominal pain (5%), flatulence (6%), sinusitis (5%) and vomiting (5%).
There are no current data on use in people with liver or kidney complications. The effects on pregnancy have not been studied in humans but testing in Guinea pigs resulted in fetal loss. Amitiza is not approved for use in children. Lubiprostone is contraindicated in patients exhibiting chronic diarrhea, bowel obstruction, or diarrhea-predominant irritable bowel syndrome.
Mechanism of action
Lubiprostone is a bicyclic fatty acid derived from prostaglandin E1 that acts by specifically activating ClC-2 chloride channels on the apical aspect of gastrointestinal epithelial cells, producing a chloride-rich fluid secretion. These secretions soften the stool, increase motility, and promote spontaneous bowel movements (SBM).
Symptoms of constipation such as pain and bloating are usually improved within one week, and SBM may occur within one day.
Unlike many laxative products, lubiprostone does not show signs of tolerance, dependency, or altered serum electrolyte concentration. There was no rebound effect following withdrawal of treatment, but a gradual return to pre-treatment bowel movement frequency should be expected.
Minimal distribution of the drug occurs beyond the immediate gastrointestinal tissues. Lubiprostone is rapidly metabolized by reduction/oxidation, mediated by carbonyl reductase. There is no metabolic involvement of the hepatic cytochrome P450 system. The measurable metabolite, M3, exists in very low levels in plasma and makes up less than 10% of the total administered dose.
A laboratory synthesis of lubiprostone has been reported:
Lubiprostone received approval from the Food and Drug Administration in 2008 to treat irritable bowel syndrome with constipation (IBS-C). It is available through prescription only.
- "amitiza". The American Society of Health-System Pharmacists. Retrieved 3 April 2011.
- Sobrera, L. A.; Castaner, J. (2004). Drugs of the Future 29 (4): 336.
- Official Website