CHEBI:746859 - travoprost

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ChEBI Name travoprost
ChEBI ID CHEBI:746859
Definition The isopropyl ester of prostaglandin F in which the pentyl group is replaced by a 3-(trifluoromethyl)phenoxymethyl group. A synthetic analogue of prostaglandin F, ophthalmic solutions of travoprost are used as a topical medication for controlling the progression of open-angle glaucoma and ocular hypertension, by reducing intraocular pressure. It is a pro-drug; the isopropyl ester group is hydrolysed by esterases in the cornea to the biologically active free acid, fluprostenol.
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Formula C26H35F3O6
Net Charge 0
Average Mass 500.54770
Monoisotopic Mass 500.239
InChI InChI=1S/C26H35F3O6/c1-17(2)35-25(33)11-6-4-3-5-10-21-22(24(32)15-23(21)31)13-12-19(30)16-34-20-9-7-8-18(14-20)26(27,28)29/h3,5,7-9,12-14,17,19,21-24,30-32H,4,6,10-11,15-16H2,1-2H3/b5-3-,13-12+/t19-,21-,22-,23+,24-/m1/s1
InChIKey MKPLKVHSHYCHOC-AHTXBMBWSA-N
SMILES CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)COc1cccc(c1)C(F)(F)F
Roles Classification
Biological Role(s): prostaglandin receptor agonist
An agonist that binds to and activates prostaglandin receptors.
Application(s): ophthalmology drug
Any compound used for the treatment of eye conditions or eye diseases.
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.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
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ChEBI Ontology
Outgoing travoprost (CHEBI:746859) has functional parent fluprostenol (CHEBI:60782)
travoprost (CHEBI:746859) has role antiglaucoma drug (CHEBI:39456)
travoprost (CHEBI:746859) has role antihypertensive agent (CHEBI:35674)
travoprost (CHEBI:746859) has role ophthalmology drug (CHEBI:66981)
travoprost (CHEBI:746859) has role prodrug (CHEBI:50266)
travoprost (CHEBI:746859) has role prostaglandin receptor agonist (CHEBI:66900)
travoprost (CHEBI:746859) is a (trifluoromethyl)benzenes (CHEBI:83565)
travoprost (CHEBI:746859) is a carboxylic ester (CHEBI:33308)
travoprost (CHEBI:746859) is a prostaglandins Fα (CHEBI:36066)
IUPAC Name
propan-2-yl (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-enoate
INNs Sources
travoprost WHO MedNet
travoprost WHO MedNet
travoprost ChemIDplus
travoprostum WHO MedNet
Synonyms Sources
isopropyl (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-{(1E,3R)-3-hydroxy-4-[(α,α,α-trifluoro-m-tolyl)oxy]-1-butenyl}cyclopentyl)-5-heptenoate ChEBI
Travoprost ChEMBL
Brand Names Sources
Travatan KEGG DRUG
Travatan Z ChEBI
Database Links Databases
2716 DrugCentral
D01964 KEGG DRUG
DB00287 DrugBank
HMDB0014432 HMDB
Travoprost Wikipedia
View more database links
Registry Numbers Types Sources
157283-68-6 CAS Registry Number ChemIDplus
157283-68-6 CAS Registry Number KEGG DRUG
8739060 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
22050687 PubMed citation Europe PMC
22167541 PubMed citation Europe PMC
22259229 PubMed citation Europe PMC
Last Modified
22 February 2017