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fluprostenol
An organofluorine compound that is racemic prostaglandin F2alpha in which the pentyl group is replaced by a 3-(trifluoromethyl)phenoxymethyl group. A synthetic analogue of prostaglandin F2alpha, 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.


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03. Biological Effects of Specific Chemicals: pharmacological uses [CHEBI:52210] > agonist [CHEBI:48705] > prostaglandin receptor agonist [CHEBI:66900]
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03. Biological Effects of Specific Chemicals 
03. Biological Effects of Specific Chemicals
 pharmacological uses [CHEBI:52210] (736) 
 agonist [CHEBI:48705] (68) 
 prostaglandin receptor agonist [CHEBI:66900] (3) 
 fluprostenol [CHEBI:60782] (1)
05. Industrial Uses 
05. Industrial Uses
 pharmaceutical [CHEBI:52217] (1978) 
 drug [CHEBI:23888] (1930) 
 antihypertensive agent [CHEBI:35674] (104) 
 fluprostenol [CHEBI:60782] (1)
 reproductive control drug [CHEBI:50689] (25) 
 contraceptive drug [CHEBI:49323] (15) 
 female contraceptive drug [CHEBI:49324] (10) 
 fluprostenol [CHEBI:60782] (1)
 abortifacient [CHEBI:50691] (5) 
 fluprostenol [CHEBI:60782] (1)
 ophthalmology drug [CHEBI:66981] (30) 
 antiglaucoma drug [CHEBI:39456] (28) 
 fluprostenol [CHEBI:60782] (1)
08. Chemical Category 
08. Chemical Category
 main group molecular entity [CHEBI:33579] (25650) 
 s-block molecular entity [CHEBI:33674] (7287) 
 hydrogen molecular entity [CHEBI:33608] (6932) 
 hydroxides [CHEBI:24651] (5641) 
 oxoacid [CHEBI:24833] (3119) 
 carbon oxoacid [CHEBI:35605] (3012) 
 carboxylic acid [CHEBI:33575] (3005) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 fluprostenol [CHEBI:60782] (1)
 monocarboxylic acid [CHEBI:25384] (1620) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 fluprostenol [CHEBI:60782] (1)
 organic hydroxy compound [CHEBI:33822] (3050) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 fluprostenol [CHEBI:60782] (1)
 p-block molecular entity [CHEBI:33675] (25343) 
 halogen molecular entity [CHEBI:24471] (1475) 
 fluorine molecular entity [CHEBI:24062] (288) 
 organofluorine compound [CHEBI:37143] (275) 
 fluprostenol [CHEBI:60782] (1)
 halide [CHEBI:37578] (1402) 
 organohalogen compound [CHEBI:36684] (976) 
 organofluorine compound [CHEBI:37143] (275) 
 fluprostenol [CHEBI:60782] (1)
 chalcogen molecular entity [CHEBI:33304] (15225) 
 oxygen molecular entity [CHEBI:25806] (14414) 
 hydroxides [CHEBI:24651] (5641) 
 oxoacid [CHEBI:24833] (3119) 
 carbon oxoacid [CHEBI:35605] (3012) 
 carboxylic acid [CHEBI:33575] (3005) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 fluprostenol [CHEBI:60782] (1)
 monocarboxylic acid [CHEBI:25384] (1620) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 fluprostenol [CHEBI:60782] (1)
 organic hydroxy compound [CHEBI:33822] (3050) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 fluprostenol [CHEBI:60782] (1)
 organooxygen compound [CHEBI:36963] (11352) 
 carbon oxoacid [CHEBI:35605] (3012) 
 carboxylic acid [CHEBI:33575] (3005) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 fluprostenol [CHEBI:60782] (1)
 monocarboxylic acid [CHEBI:25384] (1620) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 fluprostenol [CHEBI:60782] (1)
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic acid [CHEBI:33575] (3005) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 fluprostenol [CHEBI:60782] (1)
 monocarboxylic acid [CHEBI:25384] (1620) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 fluprostenol [CHEBI:60782] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 carbon oxoacid [CHEBI:35605] (3012) 
 carboxylic acid [CHEBI:33575] (3005) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 fluprostenol [CHEBI:60782] (1)
 monocarboxylic acid [CHEBI:25384] (1620) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 fluprostenol [CHEBI:60782] (1)
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic acid [CHEBI:33575] (3005) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 fluprostenol [CHEBI:60782] (1)
 monocarboxylic acid [CHEBI:25384] (1620) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 fluprostenol [CHEBI:60782] (1)
 carbon group molecular entity [CHEBI:33582] (23847) 
 organic molecular entity [CHEBI:50860] (23769) 
 heteroorganic entity [CHEBI:33285] (15197) 
 organohalogen compound [CHEBI:36684] (976) 
 organofluorine compound [CHEBI:37143] (275) 
 fluprostenol [CHEBI:60782] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 carbon oxoacid [CHEBI:35605] (3012) 
 carboxylic acid [CHEBI:33575] (3005) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 fluprostenol [CHEBI:60782] (1)
 monocarboxylic acid [CHEBI:25384] (1620) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 fluprostenol [CHEBI:60782] (1)
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic acid [CHEBI:33575] (3005) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 fluprostenol [CHEBI:60782] (1)
 monocarboxylic acid [CHEBI:25384] (1620) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 fluprostenol [CHEBI:60782] (1)
 organic hydroxy compound [CHEBI:33822] (3050) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 fluprostenol [CHEBI:60782] (1)
 fatty acid derivative [CHEBI:61697] (144) 
 icosanoid [CHEBI:23899] (138) 
 prostanoid [CHEBI:26347] (63) 
 prostaglandin [CHEBI:26333] (47) 
 prostaglandins F [CHEBI:26340] (20) 
 prostaglandins Falpha [CHEBI:36066] (18) 
 fluprostenol [CHEBI:60782] (1)
 organic acid [CHEBI:64709] (3008) 
 carboxylic acid [CHEBI:33575] (3005) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 fluprostenol [CHEBI:60782] (1)
 monocarboxylic acid [CHEBI:25384] (1620) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 fluprostenol [CHEBI:60782] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic oxo compound [CHEBI:36587] (5932) 
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic acid [CHEBI:33575] (3005) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 fluprostenol [CHEBI:60782] (1)
 monocarboxylic acid [CHEBI:25384] (1620) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 fluprostenol [CHEBI:60782] (1)
 polyatomic entity [CHEBI:36357] (18777) 
 molecule [CHEBI:25367] (11520) 
 organic molecule [CHEBI:72695] (11399) 
 organic oxo compound [CHEBI:36587] (5932) 
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic acid [CHEBI:33575] (3005) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 fluprostenol [CHEBI:60782] (1)
 monocarboxylic acid [CHEBI:25384] (1620) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 fluprostenol [CHEBI:60782] (1)
 heteroatomic molecular entity [CHEBI:37577] (13672) 
 hydroxides [CHEBI:24651] (5641) 
 oxoacid [CHEBI:24833] (3119) 
 carbon oxoacid [CHEBI:35605] (3012) 
 carboxylic acid [CHEBI:33575] (3005) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 fluprostenol [CHEBI:60782] (1)
 monocarboxylic acid [CHEBI:25384] (1620) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 fluprostenol [CHEBI:60782] (1)
 organic hydroxy compound [CHEBI:33822] (3050) 
 hydroxy carboxylic acid [CHEBI:24669] (422) 
 hydroxy monocarboxylic acid [CHEBI:35868] (396) 
 fluprostenol [CHEBI:60782] (1)
 halide [CHEBI:37578] (1402) 
 organohalogen compound [CHEBI:36684] (976) 
 organofluorine compound [CHEBI:37143] (275) 
 fluprostenol [CHEBI:60782] (1)
ChEBI Compound Accession Identifier  [CHEBI:60782]
ChEBI Compound Description  An organofluorine compound that is racemic prostaglandin F2alpha in which the pentyl group is replaced by a 3-(trifluoromethyl)phenoxymethyl group. A synthetic analogue of prostaglandin F2alpha, 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.
ChEBI Compound Identification Number  60782
ChEBI InChI Value  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
ChEBI InChIKey Value  WWSWYXNVCBLWNZ-QIZQQNKQSA-N
ChEBI Compound Name  fluprostenol
ChEBI SMILES Value  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
ChEBI Substance ID  104222381
ChEBI URL  ChEBI:60782
ChemSpider ID  4470630
Ontomatica Chemical Accession Key (OnChAKey)  WWSWYXNVCBLWNZ_QIZQQNKQSA_N_000_000000
PubChem Compound ID  5311100