Lubiprostone


Catalog No. Size PriceQuantity
M7282-2 2mg solid $90
M7282-10 10mg solid $270

Description

Lubiprostone is an ClC-2 chloride channel activator used in the treatment of idiopathic chronic constipation.

Product information

CAS Number: 136790-76-6

Molecular Weight: 390.46

Formula: C20H32F2O5

Synonym:

RU 0211

SPI-0211

Chemical Name: 7-[(1R,2R,3R)-2-(4,4-difluoro-3-oxooctyl)-3-hydroxy-5-oxocyclopentyl]heptanoic acid

Smiles: CCCCC(F)(F)C(=O)CC[C@@H]1[C@@H](CCCCCCC(O)=O)C(=O)C[C@H]1O

InChiKey: DBVFKLAGQHYVGQ-BFYDXBDKSA-N

InChi: InChI=1S/C20H32F2O5/c1-2-3-12-20(21,22)18(25)11-10-15-14(16(23)13-17(15)24)8-6-4-5-7-9-19(26)27/h14-15,17,24H,2-13H2,1H3,(H,26,27)/t14-,15-,17-/m1/s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO : 100 mg/mL (256.11 mM; Need ultrasonic)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥360 days if stored properly.

Stock Solution Storage: 0 - 4 oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

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. [1] 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. [2] Lubiprostone (1 mM) stimulates higher elevations in TER despite lower I(sc) responses compared with the nonselective secretory agonist PGE(2) (1 mM). 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. [3] 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. [4] 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. [5]

In Vivo:

Lubiprostone induces a CdCl(2)-insensitive secretory response in mouse intestine, but fail to induce intestinal Cl(-) secretion in Cftr-null mice. [1]

References:

  1. Bijvelds MJ, et al. Gastroenterology, 2009, 137(3), 976-985.
  2. Bassil AK, et al. Br J Pharmacol, 2008, 154(1), 126-135.
  3. Moeser AJ, et al. Am J Physiol Gastrointest Liver Physiol, 2007, 292(2), G647-656.
  4. Ao M, et al. Dig Dis Sci, 2011, 56(2), 339-351.
  5. Fei G, et al. Am J Physiol Gastrointest Liver Physiol, 2009, 296

Products are for research use only. Not for human use.

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