CHEBI:60782 - fluprostenol

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name fluprostenol
ChEBI ID CHEBI:60782
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C23H29F3O6
Net Charge 0
Average Mass 458.46800
Monoisotopic Mass 458.19162
InChI InChI=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
InChIKey WWSWYXNVCBLWNZ-QIZQQNKQSA-N
SMILES O[C@@H](COc1cccc(c1)C(F)(F)F)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): prostaglandin receptor agonist
An agonist that binds to and activates prostaglandin receptors.
Application(s): 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.
antihypertensive agent
Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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 Sources
fluprosténol WHO MedNet
fluprostenol ChemIDplus
fluprostenol WHO MedNet
fluprostenolum ChemIDplus
Synonyms Sources
EINECS 255-029-3 ChemIDplus
ICI 81,008 ChemIDplus
travoprost acid ChEBI
travoprost free acid ChEBI
Registry Numbers Types Sources
40666-16-8 CAS Registry Number ChemIDplus
8368795 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11832489 PubMed citation Europe PMC
11929662 PubMed citation Europe PMC
550147 PubMed citation Europe PMC
6090118 PubMed citation Europe PMC
6911921 PubMed citation Europe PMC
6916556 PubMed citation Europe PMC
941381 PubMed citation Europe PMC
951924 PubMed citation Europe PMC
Last Modified
11 November 2014