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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: latanoprost

latanoprost (isopropyl ester) is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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 Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
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
Specialist databases
GPCRdb Ligand latanoprost (isopropyl ester)
Other databases
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
Search Google for chemical match using the InChIKey GGXICVAJURFBLW-CEYXHVGTSA-N
Search Google for chemicals with the same backbone GGXICVAJURFBLW
Search PubMed clinical trials latanoprost
Search PubMed titles latanoprost
Search PubMed titles/abstracts latanoprost
UniChem Compound Search for chemical match using the InChIKey GGXICVAJURFBLW-CEYXHVGTSA-N
UniChem Connectivity Search for chemical match using the InChIKey GGXICVAJURFBLW-CEYXHVGTSA-N
Wikipedia Latanoprost

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Tocris
Latanoprost (links to external site)
Cat. No. 4757