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latanoprost (CHEBI:6384)

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ChEBI Name latanoprost
ChEBI ID CHEBI:6384
Definition A prostaglandin Fα that is the isopropyl ester prodrug of latanoprost free acid. Used in the treatment of open-angle glaucoma and ocular hypertension.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula Source
C26H40O5 KEGG DRUG
Net Charge 0
Average Mass 432.59280
InChI
InChI=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
InChIKey
GGXICVAJURFBLW-CEYXHVGTSA-N
SMILES
CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@@H](O)CCc1ccccc1
Roles Classification
Chemical Role(s): 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.
Biological Role(s): 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.
Application(s): 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.
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.
View more on the ChEBI Ontology
ChEBI Ontology
Outgoing 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 carboxylic ester (CHEBI:33308)
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 Sources
latanoprost WHO MedNet
latanoprost WHO MedNet
latanoprost WHO MedNet
latanoprostum WHO MedNet
Synonyms Sources
isopropyl (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((3R)-3-hydroxy-5-phenylpentyl)cyclopentyl)-5-heptenoate ChemIDplus
PhXA 41 ChemIDplus
propan-2-yl (5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoate IUPAC
Xalatan ChemIDplus
Database Links Databases
D00356 KEGG DRUG
DB00654 DrugBank
HMDB14792 HMDB
Latanoprost Wikipedia
View more database links
Registry Numbers Types Sources
130209-82-4 CAS Registry Number ChemIDplus
5912370 Reaxys Registry Number Reaxys
5912370 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
21278589 PubMed citation CiteXplore
21858678 PubMed citation CiteXplore
22040280 PubMed citation CiteXplore
22049909 PubMed citation CiteXplore
22167538 PubMed citation CiteXplore
22167539 PubMed citation CiteXplore
22275814 PubMed citation CiteXplore
22275828 PubMed citation CiteXplore
22283238 PubMed citation CiteXplore
22289195 PubMed citation CiteXplore
22289196 PubMed citation CiteXplore
22320418 PubMed citation CiteXplore
22323882 PubMed citation CiteXplore
Last Modified
22 April 2013

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