Name | Lubiprostone |
Synonyms | Ru 0211 SPI 0211 Rubiprostone Lubiprostone lubiprostone UNII-7662KG2R6K Lubiprostone API AMITIZA LUBIPROSTONE (11a)-16,16-Difluoro-11-hydroxy-9,15-dioxo-prostan-1-oic Acid (11α)-16,16-Difluoro-11-hydroxy-9,15-dioxo-prostan-1-oic Acid (11alpha,15R)-16,16-difluoro-15-hydroxy-9-oxo-11,15-epoxyprostan-1-oic acid (8beta,11alpha,15R)-16,16-difluoro-15-hydroxy-9-oxo-11,15-epoxyprostan-1-oic acid 7-[(1r,4r,6r,9r)-4-(1,1-difluoropentyl)-4-hydroxy-8-oxo-5-oxabicyclo[4.3.0]non-9-yl]heptanoic acid (2R,4aR,5R,7aR)-2-(1,1-Difluoropentyl)-2-hydroxy-6-oxo-3,4,4a,5,7,7a-hexahydrocyclopenta[b]pyran-5-heptanoic acid |
CAS | 136790-76-6 333963-40-9 |
EINECS | 634-172-9 |
InChI | InChI=1/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+/m0/s1 |
Molecular Formula | C20H32F2O5 |
Molar Mass | 390.47 |
Density | 1.143±0.06 g/cm3(Predicted) |
Melting Point | 56-59°C |
Boling Point | 539.1±50.0 °C(Predicted) |
Flash Point | 275.7°C |
Solubility | Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) |
Vapor Presure | 1.49E-13mmHg at 25°C |
Appearance | powder |
Color | white to beige |
pKa | 4.77±0.10(Predicted) |
Storage Condition | -20°C |
Refractive Index | 1.486 |
In vitro study | Lubiprostone induces a strong secretory response in T84 monolayers. Lubiprostone induced an increase in the level of cAMP in EP4 receptor-sensitive T84 Cells. Lubiprostone induced contraction of rat and human gastric longitudinal muscles, an effect that was inhibited by EP1 receptor antagonists but not by EP3 or EP4 receptor antagonists. In rat and human colonic circular muscles, Lubiprostone also reduced electrical stimulation, nerve contraction. Despite a lower I (SC) response, Lubiprostone(1 mM) stimulated terbium at a higher level than non-selective agonist-secreted PGE2(1 mM). Lubiprostone significantly reduces the flux of mucosal to serosal (3)H-labeled mannitol to control tissue levels and restores localization of occludin to tight junctions. Lubiprostone caused the largest increase in I(SC) of T84 Cells. Lubiprostone induced an increase in iodine outflow, which was 80% of that of forskolin. Lubiprostone activates chloride (-) secretion in T84 Cells, through cyclic adenosine monophosphate, protein kinase A, and by increasing apical membrane CFTR protein. Lubiprostone, applied to the small intestinal mucosa, evoked an increase in Isc in a concentration-dependent manner with an EC50 of 42.5 nM in 8 concentration gradients ranging from 1-3000 nM. Lubiprostone applied to the mucosa of the colon in 8 concentration gradients ranging from 1-3000 nM evoked an increase in Isc in a concentration-dependent manner with an EC50 of 31.7 nM. |
In vivo study | Lubiprostone induced a cadmium chloride (2)-insensitive secretory response in the intestine of mice, but did not affect CFTR-empty mice caused by intestinal Cl(-) secretion. |
RTECS | UK8257750 |