EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:60782 - fluprostenol

ChEBI IDCHEBI:60782
ChEBI Namefluprostenol
Stars
DefinitionAn organofluorine compound that is racemic prostaglandin F2α in which the pentyl group is replaced by a 3-(trifluoromethyl)phenoxymethyl group. A synthetic analogue of prostaglandin F2α, ophthalmic solutions of its isopropyl ester prodrug, travoprost, are used as a topical medication for controlling the progression of open-angle glaucoma and ocular hypertension, by reducing intraocular pressure. The isopropyl ester group of travoprost is hydrolysed to the biologically active free acid by esterases in the cornea.
Last Modified11 November 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC23H29F3O6
Net Charge0
Average Mass458.473
Monoisotopic Mass458.19162
SMILESO=C(O)CCC/C=C\C[C@@H]1[C@@H](/C=C/[C@@H](O)COc2cccc(C(F)(F)F)c2)[C@H](O)C[C@@H]1O
InChIInChI=1S/C23H29F3O6/c24-23(25,26)15-6-5-7-17(12-15)32-14-16(27)10-11-19-18(20(28)13-21(19)29)8-3-1-2-4-9-22(30)31/h1,3,5-7,10-12,16,18-21,27-29H,2,4,8-9,13-14H2,(H,30,31)/b3-1-,11-10+/t16-,18-,19-,20+,21-/m1/s1
InChIKeyWWSWYXNVCBLWNZ-QIZQQNKQSA-N
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
prostaglandin receptor agonist  An agonist that binds to and activates prostaglandin receptors.
Applications:
antihypertensive agent  Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
female contraceptive drug  A chemical substance or agent with contraceptive activity in females.
abortifacient  A chemical substance that interrupts pregnancy after implantation.
antiglaucoma drug  Any drug which can be used to prevent or alleviate glaucoma, a disease in which the optic nerve is damaged, resulting in progressive, irreversible loss of vision. It is often, though not always, associated with increased pressure of the fluid in the eye.
ChEBI Ontology
Outgoing Relation(s)
fluprostenol (CHEBI:60782) has role abortifacient (CHEBI:50691)
fluprostenol (CHEBI:60782) has role antiglaucoma drug (CHEBI:39456)
fluprostenol (CHEBI:60782) has role antihypertensive agent (CHEBI:35674)
fluprostenol (CHEBI:60782) has role female contraceptive drug (CHEBI:49324)
fluprostenol (CHEBI:60782) has role prostaglandin receptor agonist (CHEBI:66900)
fluprostenol (CHEBI:60782) is a (trifluoromethyl)benzenes (CHEBI:83565)
fluprostenol (CHEBI:60782) is a hydroxy monocarboxylic acid (CHEBI:35868)
fluprostenol (CHEBI:60782) is a prostaglandins Fα (CHEBI:36066)
Incoming Relation(s)
travoprost (CHEBI:746859) has functional parent fluprostenol (CHEBI:60782)
IUPAC Name 
rac-(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-{(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-en-1-yl}cyclopentyl]hept-5-enoic acid
INNs  Source
fluprostenolChemIDplus
fluprostenolumChemIDplus
fluprostenolWHO MedNet
fluprosténolWHO MedNet
Synonyms  Source
travoprost acidChEBI
travoprost free acidChEBI
ICI 81,008ChemIDplus
EINECS 255-029-3ChemIDplus
Registry NumbersSources
Reaxys:8368795Reaxys
CAS:40666-16-8ChemIDplus
Citations