7-[(2R,4aR,5S,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxo-octahydrocyclopenta[b]pyran-5-yl]heptanoic acid
Basic information
- CAS
136790-76-6- Standard SMILES
CCCCC(F)(F)[C@@]1(O)CC[C@@H]2[C@H](CCCCCCC(=O)O)C(=O)C[C@H]2O1- InChIKey
WGFOBBZOWHGYQH-DKYLXPRQSA-N- Molecular formula
- C20H32F2O5
- Average molar mass
- 390.5 g/mol
- Monoisotopic mass
- 390.22178044
Overview
RU-0211 is a prostanoid.
Names & identifiers
- Preferred name
- 7-[(2R,4aR,5S,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxo-octahydrocyclopenta[b]pyran-5-yl]heptanoic acid
- IUPAC
- 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
- English name
- Lubiprostone
- Molecular formula
- C20H32F2O5
- Molecular weight
- 390.47
Names & synonyms
1263283-38-07-[(2R,4aR,5S,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxo-octahydrocyclopenta[b]pyran-5-yl]heptanoic acidRU-02111808535-45-67-((2R,4aR,5S,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxooctahydrocyclopenta[b]pyran-5-yl)heptanoic acid7-((2R,4aR,5S,7aR)-rel-2-(1,1-Difluoropentyl)-2-hydroxy-6-oxooctahydrocyclopenta[b]pyran-5-yl)heptanoic acidLubiprostone Impurity 3YB5CA7ESQ3SCHEMBL454016CHEBI:34945EBC-61026AKOS015896617
Show more names
C13707Ru 0211RubiprostonelubiprostoneRubyprostoneLubiprostoneLubipristoneLubiprostone APILubiprostone CASLubiprostone, >=99%
Cyclopenta[b]pyran-5-heptanoic acid, 2-(1,1-difluoropentyl)octahydro-2-hydroxy-6-oxo-, (2R,4aR,5S,7aR)-
Properties
Computed structural properties
- XLogP
- 4
- Topological polar surface area
- 83.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 11
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 525
Experimental & physicochemical properties
LogP4.3
Solubility2.56e-02 g/L
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 56 · 56-59°C
- Boiling point
- 539.1 · 539.1±50.0 °C(Predicted)
- Density
- 1.143 · 1.143±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
- pka
- 4.77 · 4.77±0.10(Predicted)
- form
- powder
- color
- white to beige
- InChI
- InChI=1/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-/s3
- InChIKey
- DBVFKLAGQHYVGQ-LRVNMBRDNA-N
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- WGK 3
- rtecs
- UK8257750
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Applications
General DescriptionLubiprostone (brand name: Amitiza) is a drug that is prescribed as a treatment for acute idiopathic constipation that is associated with bloating, stomach pain and straining in bowel movements. The drug is prescribed in cases where a patient is experiencing infrequent bowel movements that may persist for about 3 months or a longer period of time without necessarily being resultant of certain medications or diseases. The drug may also be used to relieve constipation that may result from specific opioid (narcotic) use amongst people who have persistent pain that is not caused by cancer. Lubiprostone is classified as a laxative and its mechanism of action entails enhancing the flow of fluid into the bowel for easier bowel movements.
UsesLubiprostone is a bicyclic fatty acid metabolite analog of Prostaglandin E1. It activates specific chloride channels in the gastrointestinal tract to stimulate intestinal fluid secretion, increase gastrointestinal transit, and improve symptoms of constipation.
Upstream & downstream products
Upstream raw materials
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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