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CHEBI:63925 - latanoprost free acid

ChEBI IDCHEBI:63925
ChEBI Namelatanoprost free acid
Stars
DefinitionA prostaglandin Fα that is an analogue of prostaglandin F2α in which the pentyl group has been replaced by 2-phenylethyl and where the the 13,14-double bond has undergone formal hydrogenation.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.
Last Modified23 May 2013
SubmitterSteve
DownloadsMolfile
FormulaC23H34O5
Net Charge0
Average Mass390.520
Monoisotopic Mass390.24062
SMILESO=C(O)CCC/C=C\C[C@@H]1[C@@H](CC[C@@H](O)CCc2ccccc2)[C@H](O)C[C@@H]1O
InChIInChI=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
InChIKeyHNPFPERDNWXAGS-NFVOFSAMSA-N
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
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:
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.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
17-phenyl-trinor-prostaglandin F2α (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  Source
13,14-dihydro-17-phenyl-18,19,20-trinor-PGF2αChEBI
latanoprost acidChEBI
Phxa 85ChemIDplus
Registry NumbersSources
Reaxys:5911495Reaxys
CAS:41639-83-2ChemIDplus
Citations