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    Lubiprostone (SPI-0211; RU0211)
    Lubiprostone (SPI-0211; RU0211)

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    This product is for research use only, not for human use. We do not sell to patients.
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    InvivoChem Cat #: V1692
    CAS #: 136790-76-6 Purity ≥98%

    Description: Lubiprostone (also known as SPI-0211; RU-0211), a potent activator of ClC-2 chloride channels, is a medication used in the management of idiopathic chronic constipation. It was approved by the U.S. Food and Drug Administration (FDA) in 2006 as a medication used in the treatment of chronic idiopathic constipation, predominantly irritable bowel syndrome-associated constipation in women and opioid-induced constipation. 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. 

    References: Br J Pharmacol. 2008 May;154(1):126-35; Gastroenterology. 2009 Sep;137(3):976-85. 

    Related CAS#: 333963-40-9 (hemiketal)

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    Molecular Weight (MW)390.46
    FormulaC20H32F2O5
    CAS No.136790-76-6
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: 78 mg/mL (199.8 mM)
    Water: <1 mg/mL
    Ethanol: 78 mg/mL (199.8 mM)
    Other infoChemical Name: 7-[(1R,3R,6R,7R)-3-(1,1-Difluoropentyl)-3-hydroxy-8-oxo-2-oxabicyclo[4.3.0]non-7-yl]heptanoic acid
    InChi Key: WGFOBBZOWHGYQH-MXHNKVEKSA-N
    InChi Code: 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
    SMILES Code: O=C(O)CCCCCC[[email protected]@H]1[[email protected]@]2([H])CC[[email protected]](O)(C(F)(F)CCCC)O[[email protected]]2([H])CC1=O
    SynonymsRU 0211; U-0211; RU 0211; RU0211; Spi 0211; Spi-0211; Spi0211; Lubiprostone hemiketal; Lubiprostone. trade name Amitiza.


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    In Vitro

    In vitro activity: Lubiprostone induces a robust secretory response in T84 monolayers. Lubiprostone induces a rise in cAMP levels that was sensitive to EP(4)-receptor blockage in T84 cells. Lubiprostone induces a contraction in rat and human stomach longitudinal muscle, which is inhibited by pretreatment with the EP(1) receptor antagonist but not by the EP(3) or EP(4) receptor antagonists. Lubiprostone also reduces electrically stimulated, neuronal contractions in rat and human colon circular muscle preparations. Lubiprostone (1 mM) stimulates higher elevations in TER despite lower I(sc) responses compared with the nonselective secretory agonist PGE(2) (1 mM). 


    Cell Assay: Lubiprostone significantly reduces mucosal-to-serosal fluxes of (3)H-labeled mannitol to levels comparable to those of normal control tissues and restored occludin localization to tight junctions. Lubiprostone causes comparable and maximal increases of I(sc) in T84 cells. Lubiprostone-induced increases in iodide efflux are ~80% of those obtained with forskolin. Lubiprostone activates Cl(-) secretion in T84 cells via cAMP, protein kinase A, and by increasing apical membrane CFTR protein. Lubiprostone, applied to the small intestinal mucosa in eight concentrations ranging from 1-3000 nM, evokes increases in Isc in a concentration-dependent manner with an EC50 of 42.5 nM. Lubiprostone applied to the mucosa of the colon in eight concentrations ranging from 1-3000 nM evokes increases in Isc in a concentration-dependent manner with an EC50 of 31.7 nM.

    In VivoLubiprostone induces a CdCl(2)-insensitive secretory response in mouse intestine, but fail to induce intestinal Cl(-) secretion in Cftr-null mice. 
    Animal modelMouse
    Formulation & DosageN/A
    ReferencesBr J Pharmacol. 2008 May;154(1):126-35; Gastroenterology. 2009 Sep;137(3):976-85. 


    These protocols are for reference only. InvivoChem does not independently validate these methods.

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