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Revision as of 12:45, 20 February 2016

Lubiprostone
Clinical data
Trade namesAmitiza
Other namesAmitiza
RU-0211
SPI-0211
AHFS/Drugs.comMonograph
MedlinePlusa607034
License data
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityNegligible
Protein binding94%
MetabolismExtensive, CYP not involved
Elimination half-lifeUnknown (lubiprostone)
0.9–1.4 hours (main metabolite)
ExcretionRenal (60%) and fecal (30%)
Identifiers
  • 7-[(1R,3R,6R,7R)-3-(1,1-Difluoropentyl)-3-hydroxy-8-oxo-2-oxabicyclo[4.3.0]non-7-yl]heptanoic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.107.168 Edit this at Wikidata
Chemical and physical data
FormulaC20H32F2O5
Molar mass390.462 g/mol g·mol−1
3D model (JSmol)
  • FC(F)(CCCC)[C@]2(O)O[C@@H]1CC(=O)[C@@H]([C@H]1CC2)CCCCCCC(=O)O
  • InChI=1S/C20H32F2O5/c1-2-3-11-19(21,22)20(26)12-10-15-14(16(23)13-17(15)27-20)8-6-4-5-7-9-18(24)25/h14-15,17,26H,2-13H2,1H3,(H,24,25)/t14-,15-,17-,20-/m1/s1 checkY
  • Key:WGFOBBZOWHGYQH-MXHNKVEKSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Lubiprostone (rINN, marketed under the trade name Amitiza among others) 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. It is very expensive as of 2012.[1]

Medical uses

Lubiprostone is used for the treatment of chronic constipation of unknown cause in adults, as well as irritable bowel syndrome associated with constipation in women.[2]

Lubiprostone is approved to treat chronic idiopathic constipation (CIC) in adults.

Lubiprostone 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 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.

Adverse effects

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%) Vomiting (5%) and Fecal Incontinence (1%).

Contraindications

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.

Pharmacokinetics

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.

Data indicate that metabolism occurs locally in the stomach and jejunum.

Society and culture

Legal status

Lubiprostone received approval from the Food and Drug Administration in 2008 to treat irritable bowel syndrome with constipation (IBS-C) and is available through prescription only. As of 2014, the drug is available in the United States, Japan, Switzerland and the United Kingdom; review by Health Canada began in late 2014.[3]

Brand names

In Bangladesh under the trade name Lubilax marketed by Beacon Pharmaceuticals Limited

References

  1. ^ Hamilton, Richard J. (2013). Tarascon pocket pharmacopoeia : 2013 classic shirt-pocket edition (27 ed.). Burlington, Ma.: Jones & Bartlett Learning. p. 112. ISBN 9781449665869.
  2. ^ "amitiza". The American Society of Health-System Pharmacists. Retrieved 3 April 2011.
  3. ^ House, Douglas W. (31 December 2014). "Canada accepts Sucampo's NDS for constipation med". Seeking Alpha.

External links


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