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CHEBI:6384 - latanoprost

ChEBI IDCHEBI:6384
ChEBI Namelatanoprost
Stars
DefinitionA prostaglandin Fα that is the isopropyl ester prodrug of latanoprost free acid. Used in the treatment of open-angle glaucoma and ocular hypertension.
Last Modified9 March 2018
DownloadsMolfile
FormulaC26H40O5
Net Charge0
Average Mass432.601
Monoisotopic Mass432.28757
SMILESCC(C)OC(=O)CCC/C=C\C[C@@H]1[C@@H](CC[C@@H](O)CCc2ccccc2)[C@H](O)C[C@@H]1O
InChIInChI=1S/C26H40O5/c1-19(2)31-26(30)13-9-4-3-8-12-22-23(25(29)18-24(22)28)17-16-21(27)15-14-20-10-6-5-7-11-20/h3,5-8,10-11,19,21-25,27-29H,4,9,12-18H2,1-2H3/b8-3-/t21-,22+,23+,24-,25+/m0/s1
InChIKeyGGXICVAJURFBLW-CEYXHVGTSA-N
Wikipedia
Roles Classification
Biological Role:
EC 4.2.1.1 (carbonic anhydrase) inhibitor  An EC 4.2.1.* (hydro-lyases) inhibitor that interferes with the action of carbonic anhydrase (EC 4.2.1.1). Such compounds reduce the secretion of H+ ions by the proximal kidney tubule.
Applications:
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.
antihypertensive agent  Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
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)
latanoprost (CHEBI:6384) has functional parent latanoprost free acid (CHEBI:63925)
latanoprost (CHEBI:6384) has role antiglaucoma drug (CHEBI:39456)
latanoprost (CHEBI:6384) has role antihypertensive agent (CHEBI:35674)
latanoprost (CHEBI:6384) has role EC 4.2.1.1 (carbonic anhydrase) inhibitor (CHEBI:23018)
latanoprost (CHEBI:6384) has role prodrug (CHEBI:50266)
latanoprost (CHEBI:6384) is a isopropyl ester (CHEBI:35725)
latanoprost (CHEBI:6384) is a prostaglandins Fα (CHEBI:36066)
latanoprost (CHEBI:6384) is a triol (CHEBI:27136)
IUPAC Name 
isopropyl (5Z,9α,11α,15R)-9,11,15-trihydroxy-17-phenyl-18,19,20-trinorprost-5-en-1-oate
INNs  Source
latanoprostWHO MedNet
latanoprostWHO MedNet
latanoprostWHO MedNet
latanoprostumWHO MedNet
Synonyms  Source
propan-2-yl (5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoateIUPAC
PhXA 41ChemIDplus
XalatanChemIDplus
isopropyl (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((3R)-3-hydroxy-5-phenylpentyl)cyclopentyl)-5-heptenoateChemIDplus
Manual XrefsDatabases
D00356KEGG DRUG
LatanoprostWikipedia
DB00654DrugBank
HMDB0014792HMDB
1551DrugCentral
Registry NumbersSources
Reaxys:5912370Reaxys
CAS:130209-82-4ChemIDplus
Citations