lubiprostone (amitiza) Report issue

Small molecule Approved FDA
AACT ChEMBL DrugBank Drug Central Drugs@FDA KEGG MeSH PubChem repoDB

Active Ingredient History

NOW
  • Now
Lubiprostone is a medication used in the management of idiopathic chronic constipation. It is a bicyclic fatty acid (prostaglandin E1 derivative) which 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). Lubiprostone acts by specifically activating ClC-2 chloride channels, which is a normal constituent of the apical membrane of the human intestine, in a protein kinase A action independent fashion. Activation of ClC-2 chloride channels causes an efflux of chloride ions into the lumen, which in turn leads to an efflux of sodium ions through a paracellular pathway to maintain isoelectric neutrality. As a result, water follows sodium into the lumen in order to maintain isotonic equilibrium, thereby increasing intestinal fluid secretion. By increasing intestinal fluid secretion, lubiprostone increases motility in the intestine, thereby increasing the passage of stool and alleviating symptoms associated with chronic idiopathic constipation. Activation of ClC-2 chloride channels may also stimulate the recovery of muscosal barrier function by restoring tight junction protein complexes in the intestine. Patch clamp cell studies in human cell lines have indicated that the majority of the beneficial biological activity of lubiprostone and its metabolites is observed only on the apical (luminal) portion of the gastrointestinal epithelium. Lubiprostone is marketed under the trade name Amitiza among others.   NCATS

Chemistry

  • SMILES: CCCCC(F)(F)[C@@]1(O)CC[C@H]2[C@@H](CC(=O)[C@@H]2CCCCCCC(O)=O)O1
  • InChIKey: WGFOBBZOWHGYQH-MXHNKVEKSA-N
  • Mol. Mass: 390.4619
  • ALogP: 4.31
  • ChEMBL Molecule:
    lubiprostone  
More Chemistry

Pharmacology

  • Mechanism of Action:
  • Multi-specific: Missing data
  • Black Box: No
  • Availability: Prescription Only
  • Delivery Methods: Oral
  • Pro Drug: No

Drug Pricing (per unit)

United States

$3.7037 - $6.0297
More Pricing Detail

Note: This drug pricing data is preliminary, incomplete, and may contain errors.

Alternative names

amitiza | lubiprostone | ru-0211

Organizations (45)

Research & Development (41)

Organization Org Type FDA approvals Clinical Trials involvement Org ID Force Sort

Marketing (7)

Organization Org Type FDA approvals Clinical Trials involvement Org ID Force Sort

Indications (15)

Approved Indications (2)


 

Constipation

Irritable Bowel Syndrome

Experimental Indications - Clinical Trial Phases 1-4 (15)


 

Colonoscopy (Phase 4)

Colorectal Neoplasms (Phase 3)

Constipation ()

Diabetes Mellitus (Phase 4)

Diagnosis (Phase 4)

Drug-Related Side Effects and Adverse Reactions (Phase 3)

Healthy Volunteers (Phase 4)

HIV (Phase 2)

Inflammatory Bowel Diseases (Phase 4)

Irritable Bowel Syndrome ()

Multiple Sclerosis (Phase 4)

Non-alcoholic Fatty Liver Disease (Phase 3)

Opioid-Induced Constipation (Phase 3)

Parkinson Disease (Phase 4)

Treatment Outcome (Phase 3)

Overview

  • Highest Phase: Phase 4
  • # of Trials: 47
  • # of Trial Organizations: 41

Trials by Phase

Trial Phase Start Date Organizations Indications

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