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sepetaprost   Click here for help

GtoPdb Ligand ID: 9875

Synonyms: ONO-9054 | ONO9054 | Setaneo®
Approved drug
sepetaprost is an approved drug
Compound class: Synthetic organic
Comment: Sepetaprost (ONO-9054) is dual agonist of the prostanoid FP and EP3 receptors [1-2,7-8]. It was designed to reduce intraocular pressure [3].
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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

sepetaprost 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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 2
Rotatable bonds 11
Topological polar surface area 85.22
Molecular weight 482.25
XLogP 4.03
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CC(OC(=O)CCCC1CCC2C(OC1)CC(C2C=CC(COc1cc(F)ccc1F)O)O)C
Isomeric SMILES CC(OC(=O)CCC[C@H]1CC[C@H]2[C@@H](OC1)C[C@H]([C@@H]2/C=C/[C@H](COc1cc(F)ccc1F)O)O)C
InChI InChI=1S/C26H36F2O6/c1-16(2)34-26(31)5-3-4-17-6-9-21-20(23(30)13-24(21)32-14-17)10-8-19(29)15-33-25-12-18(27)7-11-22(25)28/h7-8,10-12,16-17,19-21,23-24,29-30H,3-6,9,13-15H2,1-2H3/b10-8+/t17-,19+,20+,21+,23+,24-/m0/s1
InChI Key BKVUSNOUTQMSBE-XCMGCKIWSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Harris A, Ward CL, Rowe-Rendleman CL, Ouchi T, Wood A, Fujii A, Serle JB. (2016)
Ocular Hypotensive Effect of ONO-9054, an EP3/FP Receptor Agonist: Results of a Randomized, Placebo-controlled, Dose Escalation Study.
J Glaucoma, 25 (10): e826-e833. [PMID:27300645]
2. Klimko PG, Sharif NA. (2019)
Discovery, characterization and clinical utility of prostaglandin agonists for the treatment of glaucoma.
Br J Pharmacol, 176 (8): 1051-1058. [PMID:29665040]
3. Maki K, Kimura E, Yamamoto Y, Fuwa M, Toris CB, Fan S, Shimazaki A, Kato M. (2026)
The Role of EP3 Agonism in Intraocular Pressure-Lowering by Sepetaprost, a Novel Dual Agonist of FP and EP3 Receptors, in Monkeys.
J Ocul Pharmacol Ther, 42 (3): 172-178. [PMID:41420459]
4. Miller Ellis E, Berlin MS, Ward CL, Sharpe JA, Jamil A, Harris A. (2017)
Ocular hypotensive effect of the novel EP3/FP agonist ONO-9054 versus Xalatan: results of a 28-day, double-masked, randomised study.
Br J Ophthalmol, 101 (6): 796-800. [PMID:27649982]
5. Wirta DL, El-Harazi SM, Tepedino ME, Bacharach J. (2025)
Sepetaprost 0.002% Noninferiority vs. Timolol 0.5% in Patients with Primary Open-Angle Glaucoma or Ocular Hypertension: ANGEL-2.
Ophthalmol Glaucoma, 8 (4): 384-392. [PMID:40043909]
6. Wirta DL, Kuwayama Y, Lu F, Shao H, Odani-Kawabata N. (2022)
Phase 2b, Randomized, 3-Month, Dose-Finding Study of Sepetaprost in Patients with Primary Open-Angle Glaucoma or Ocular Hypertension: The ANGEL Study.
J Ocul Pharmacol Ther, 38 (3): 240-251. [PMID:35167779]
7. Yamagishi-Kimura R, Honjo M, Aihara M. (2022)
The Roles Played by FP/EP3 Receptors During Pressure-lowering in Mouse Eyes Mediated by a Dual FP/EP3 Receptor Agonist.
Invest Ophthalmol Vis Sci, 63 (2): 24. [PMID:35147658]
8. Yamane S, Karakawa T, Nakayama S, Nagai K, Moriyuki K, Neki S, Suto F, Kambe T, Hirota Y, Kawabata K. (2015)
IOP-Lowering Effect of ONO-9054, A Novel Dual Agonist of Prostanoid EP3 and FP Receptors, in Monkeys.
Invest Ophthalmol Vis Sci, 56 (4): 2547-52. [PMID:25788650]