CHEBI:63925 - latanoprost free acid

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ChEBI Name latanoprost free acid
ChEBI ID CHEBI:63925
Definition A prostaglandin Fα that is an analogue of prostaglandin F in which the pentyl group has been replaced by 2-phenylethyl and where the the 13,14-double bond has undergone formal hydrogenation. Its isopropyl ester prodrug, latanoprost, is 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 C23H34O5
Net Charge 0
Average Mass 390.51310
Monoisotopic Mass 390.241
InChI InChI=1S/C23H34O5/c24-18(13-12-17-8-4-3-5-9-17)14-15-20-19(21(25)16-22(20)26)10-6-1-2-7-11-23(27)28/h1,3-6,8-9,18-22,24-26H,2,7,10-16H2,(H,27,28)/b6-1-/t18-,19+,20+,21-,22+/m0/s1
InChIKey HNPFPERDNWXAGS-NFVOFSAMSA-N
SMILES O[C@H](CC[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O)CCc1ccccc1
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): 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): 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 latanoprost free acid (CHEBI:63925) has role antiglaucoma drug (CHEBI:39456)
latanoprost free acid (CHEBI:63925) has role antihypertensive agent (CHEBI:35674)
latanoprost free acid (CHEBI:63925) has role EC 4.2.1.1 (carbonic anhydrase) inhibitor (CHEBI:23018)
latanoprost free acid (CHEBI:63925) is a hydroxy monocarboxylic acid (CHEBI:35868)
latanoprost free acid (CHEBI:63925) is a prostaglandins Fα (CHEBI:36066)
Incoming 17-phenyl-trinor-prostaglandin F (CHEBI:73773) has functional parent latanoprost free acid (CHEBI:63925)
latanoprost (CHEBI:6384) has functional parent latanoprost free acid (CHEBI:63925)
IUPAC Name
(5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoic acid
Synonyms Sources
13,14-dihydro-17-phenyl-18,19,20-trinor-PGF ChEBI
latanoprost acid ChEBI
Phxa 85 ChemIDplus
Registry Numbers Types Sources
41639-83-2 CAS Registry Number ChemIDplus
5911495 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
18451496 PubMed citation Europe PMC
19084521 PubMed citation Europe PMC
19289115 PubMed citation Europe PMC
20019365 PubMed citation Europe PMC
21396362 PubMed citation Europe PMC
21788077 PubMed citation Europe PMC
21791206 PubMed citation Europe PMC
22124989 PubMed citation Europe PMC
22136089 PubMed citation Europe PMC
Last Modified
23 May 2013