IUPAC name
7-[(2R,4aR,5S,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxo-octahydrocyclopenta[b]pyran-5-yl]heptanoic acid
SMILES
[H][C@@]12CC(=O)[C@@H](CCCCCCC(O)=O)[C@@]1([H])CC[C@@](O)(O2)C(F)(F)CCCC
Compound class
Laxatives; Alimentary Tract and Metabolism; Drugs for Constipation; Chloride Channel Agonists;
Therapeutic area
For the treatment of chronic idiopathic constipation in the adult population. Also used for the treatment of irritable bowel syndrome with constipation in women who are 18 years of age or older.
Common name
Lubiprostone
IUPAC name
7-[(2R,4aR,5S,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxo-octahydrocyclopenta[b]pyran-5-yl]heptanoic acid
SMILES
[H][C@@]12CC(=O)[C@@H](CCCCCCC(O)=O)[C@@]1([H])CC[C@@](O)(O2)C(F)(F)CCCC
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
FORMULA
C20H32F2O5
Common name
Lubiprostone
IUPAC name
7-[(2R,4aR,5S,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxo-octahydrocyclopenta[b]pyran-5-yl]heptanoic acid
Molecular weight
390.462
clogP
4.515
clogS
-4.391
HBond Acceptor
5
HBond Donor
2
Total Polar Surface Area
83.83
Number of Rings
2
Rotatable Bond
11
| Drug ID | Common name | Structure CAS | SMILE | Frequency |
|---|---|---|---|---|
| FDBF00007 | propane |
|
C(C)C | 0.2412 |
| FDBF00062 | pentanoic acid |
|
CCCCC(=O)O | 0.0079 |
| FDBF00067 | butane |
|
CCCC | 0.0680 |
| FDBF00370 | difluoromethane |
|
FCF | 0.0151 |
| FDBF02128 | 1,1-difluoroethane |
|
FC(F)C | 0.0021 |
| FDBF02328 | (2S,4aR,5R,7aR)-2-hydroxy-5-methyl-3,4,4a,5,7,7a-hexahydro-2H-cyclopenta[b]pyran-6-one |
|
O1C2C(C(C(=O)C2)C)CCC1O | 0.0003 |
| FDBF02329 | (2R,4aR,7aR)-2-(difluoromethyl)-2-hydroxy-3,4,4a,5,7,7a-hexahydrocyclopenta[b]pyran-6-one |
|
O1C2C(CC(=O)C2)CCC1(O)C(F)F | 0.0003 |
| FDBF02331 | (2R,4aR,7aR)-2-(1,1-difluoroethyl)-2-hydroxy-3,4,4a,5,7,7a-hexahydrocyclopenta[b]pyran-6-one |
|
CC(C1(OC2C(CC(=O)C2)CC1)O)(F)F | 0.0003 |
| FDBF02333 | (2R,4aR,5R,7aR)-2-(difluoromethyl)-5-ethyl-2-hydroxy-3,4,4a,5,7,7a-hexahydrocyclopenta[b]pyran-6-one |
|
O1C2C(C(C(=O)C2)CC)CCC1(O)C(F)F | 0.0003 |
| FDBF02336 | 1,1-difluoropentane |
|
C(CCC)C(F)F | 0.0003 |
