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Lubiprostone

  • Name Lubiprostone
  • EINECSN/A
  • CAS No. 136790-76-6
  • Density1.052 g/cm3
  • PSA83.83000
  • LogP4.30990
  • SolubilityN/A
  • Melting Point56-59 °C
  • FormulaC20H32F2O5
  • Boiling Point548.169 °C at 760 mmHg
  • Molecular Weight390.468
  • Flash Point299.385 °C
  • Transport InformationN/A
  • Appearancewhite solid
  • Safety
  • Risk CodesN/A
  • Molecular Structure
    Molecular Structure of 136790-76-6 (Lubiprostone)
  • Hazard SymbolsN/A
  • SynonymsN/A
  • Article Data3

Lubiprostone Specification

1. Introduction of Lubiprostone
Lubiprostone is one kind of white solid. The IUPAC Name of this chemical is 7-[(2R,4aR,5S,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxo-3,4,4a,5,7,7a-hexahydrocyclopenta[b]pyran-5-yl]heptanoic acid. Besides, Lubiprostone belongs to Prostaglandin; Chiral Reagents; Intermediates & Fine Chemicals; Pharmaceuticals. In addition, its Classification Code is Treatment of constipation and bowel preparation. Lubiprostone is sparingly soluble in aqueous buffers. And it is practically insoluble in water.

2. Properties of Lubiprostone
Physical properties about Lubiprostone are:
(1)Melting Point: 56-59°C; (2)Boiling point: 532.3 °C at 760 mmHg; (3)Flash Point: 275.7 °C; (4)Density: 1.175 g/cm3; (5)Index of Refraction: 1.486; (6)Molar Refractivity: 95.38 cm3; (7)Molar Volume: 332 cm3; (8)Surface Tension:  41.2 dyne/cm; (9)Enthalpy of Vaporization: 92.94 kJ/mol; (10)Vapour Pressure: 1.49E-13 mmHg at 25°C; (11)XLogP3-AA: 4; (12)H-Bond Donor: 2; (13)H-Bond Acceptor: 7.

3. Structure Descriptors of Lubiprostone
Canonical SMILES: CCCCC(C1(CCC2C(O1)CC(=O)C2CCCCCCC(=O)O)O)(F)F
Isomeric SMILES: CCCCC([C@]1(CC[C@H]2[C@H](O1)CC(=O)[C@H]2CCCCCCC(=O)O)O)(F)F
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+/m0/s1  
InChIKey: WGFOBBZOWHGYQH-DKYLXPRQSA-N
Smiles: C(CCCCCC[C@H]1C(C[C@@H]2[C@@H]1CC[C@](O2)(O)C(CCCC)(F)F)=O)(O)=O

4. Safety information of Lubiprostone
In clinical trials, the most common adverse event was nausea (31%). Other adverse events (≥5% of patients) included diarrhea (13%), headache (13%), abdominal distention (7%), abdominal pain (7%), flatulence (6%), sinusitis (5%) and vomiting (5%).

5. Uses of Lubiprostone
A locally acting chloride channel activator for the treatment of gastrointestinal disorders. 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.

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