Lubiprostone

Lubiprostone
Clinical data
Trade names	Amitiza
Other names	RU-0211; SPI-0211
AHFS/Drugs.com	Monograph
MedlinePlus	a607034
License data	US DailyMed: Lubiprostone;
Routes of; administration	By mouth
ATC code	A06AX03 (WHO) ;
Legal status
Legal status	CA: ℞-only; US: ℞-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	Negligible
Protein binding	94%
Metabolism	Extensive, CYP not involved
Elimination half-life	Unknown (lubiprostone); 0.9–1.4 hours (main metabolite)
Excretion	Kidney (60%) and fecal (30%)
Identifiers
	IUPAC name 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	136790-76-6 ;
PubChem CID	157920;
IUPHAR/BPS	4242;
DrugBank	DB01046 ;
ChemSpider	138948 ;
UNII	7662KG2R6K;
KEGG	D04790 ;
ChEMBL	ChEMBL1201134 ;
CompTox Dashboard (EPA)	DTXSID80861338 DTXSID5048639, DTXSID80861338 ;
ECHA InfoCard	100.107.168
Chemical and physical data
Formula	C20H32F2O5
Molar mass	390.468 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES FC(F)(CCCC)[C@]2(O)O[C@@H]1CC(=O)[C@@H]([C@H]1CC2)CCCCCCC(=O)O;
	InChI 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 ; Key:WGFOBBZOWHGYQH-MXHNKVEKSA-N ;
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Lubiprostone, sold under the brand 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. The drug is owned by Mallinckrodt and is marketed by Takeda Pharmaceutical Company.

The drug was developed by Sucampo Pharmaceuticals and approved by the Food and Drug Administration (FDA) in 2006. It was recommended for use in the UK by the National Institute for Health and Care Excellence (NICE) in July 2014. Health Canada approved the drug in 2015. Lubiprostone received approval from the Food and Drug Administration in 2008, to treat irritable bowel syndrome with constipation (IBS-C), and in 2013, for the treatment of opioid-induced constipation in adults with chronic noncancer pain. It is available as a generic medication.