latanoprost (isopropyl ester)   Click here for help

GtoPdb Ligand ID: 1961

Synonyms: PHXA-41 | XA-41 | Xalatan®
Approved drug
latanoprost (isopropyl ester) is an approved drug (FDA (1996))
Compound class: Synthetic organic
Comment: Latanoprost is administered in the isopropyl ester form shown here, which is then hydrolysed in vivo in to active metabolite lanoprost free acid.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 14
Topological polar surface area 86.99
Molecular weight 432.29
XLogP 4.4
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES OC(CCc1ccccc1)CCC1C(O)CC(C1CC=CCCCC(=O)OC(C)C)O
Isomeric SMILES O[C@@H](CCc1ccccc1)CC[C@H]1[C@H](O)C[C@@H]([C@@H]1C/C=C\CCCC(=O)OC(C)C)O
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
InChI Key GGXICVAJURFBLW-CEYXHVGTSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1996))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
Is prodrug? Yes
Active form latanoprost (free acid form)
IUPAC Name Click here for help
propan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate
International Nonproprietary Names Click here for help
INN number INN
6980 latanoprost
Synonyms Click here for help
PHXA-41 | XA-41 | Xalatan®
Database Links Click here for help
CAS Registry No. 130209-82-4 (source: Scifinder)
ChEBI CHEBI:6384
ChEMBL Ligand CHEMBL1051
DrugBank Ligand DB00654
DrugCentral Ligand 1551
GtoPdb PubChem SID 135650509
PubChem CID 5311221
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Wikipedia Latanoprost

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Tocris
Latanoprost
Cat. No. 4757