Unoprostone
Identification
- Summary
Unoprostone is a prostaglandin analogue used to lower intraocular pressure in patients with open-angle glaucoma or ocular hypertension who are clinically unresponsive to other ocular antihypertensive agents.
- Generic Name
- Unoprostone
- DrugBank Accession Number
- DB06826
- Background
Unoprostone isopropyl is a prostaglandin analogue. Ophthalmic Solution 0.15% is a synthetic docosanoid. Unoprostone isopropyl has the chemical name isopropyl (+)-(Z)-7-[(1R,2R,3R,5S)-3,5 dihydroxy-2-(3-oxodecyl)cyclopentyl]-5-heptenoate. The main indication of Unoprostane is treatment of glucoma.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Unoprostone (DB06826)
- Weight
- Average: 382.541
Monoisotopic: 382.271924324 - Chemical Formula
- C22H38O5
- Synonyms
- 13,14-dihydro-15-keto-20-ethyl PGF2α
- Unoprostone
- External IDs
- UF 021
- UF-021
- UF021
Pharmacology
- Indication
For the lowering of intraocular pressure in patients with open-angle glaucoma or ocular hypertension who are intolerant of other intraocular pressure lowering medications or insufficiently responsive (failed to achieve target IOP determined after multiple measurements over time) to another intraocular pressure lowering medication.
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- Contraindications & Blackbox Warnings
Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- Pharmacodynamics
Unoprostone will begin to reduce IOP 30 minutes after ocular instillation.
- Mechanism of action
Unoprostone is believed to reduce elevated intraocular pressure (IOP), by increasing the outflow of aqueous humor. The mechanism of action for the IOP-lowering effect of unoprostone is controversial. Early studies showed that unoprostone increases aqueous humor outflow through the uveoscleral pathway similar to the 20-carbon prostaglandin analogs, such as latanoprost.8 More recent evidence, however, shows that it may work, at least in part, through stimulation of Ca2+-activated BK and CIC-2 type channels, leading to increased trabecular meshwork outflow.
- Absorption
After application to the eye, unoprostone isopropyl is absorbed through the cornea and conjunctival epithelium where it is hydrolyzed by esterases to unoprostone free acid. mean peak unoprostone free acid plasma concentration was <1.5 ng/mL and dro pped below the lower limit of quantitation (<0.250 ng/mL) 1 hour following instillation, indicating low systemic absorption and rapid plasma excretion.
- Volume of distribution
Intended for local use only, very low systemic absorption.
- Protein binding
Intended for local use only, very low systemic absorption.
- Metabolism
After ocular application, unoprostone isopropyl is hydrolyzed by esterases in the cornea to its biological active metabolite, unoprostone free acid. Unoprostone free acid is then metabolized to several inactive metabolites with lower molecular weight and increased polarity via ε- or β-oxidation. No secondary conjugation is found and no significant effect on hepatic microsomal enzyme activity has been observed.
- Route of elimination
Elimination of unoprostone free acid from human plasma is rapid. Plasma levels of unoprostone free acid dropped below the lower limit of quantitation ( < 0.25 ng/mL) 1 hour following ocular instillation. Urinary elimination is the predominant elimination route.
- Half-life
Half-life of Unoprostone is 14 minutes.
- Clearance
Intended for local use only, very low systemic absorption.
- Adverse Effects
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LD50 in rats: 1g/Kg (subcutaneous), 93500 µg/Kg (IV).
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcebutolol Acebutolol may increase the hypotensive activities of Unoprostone. Aceclofenac The therapeutic efficacy of Unoprostone can be decreased when used in combination with Aceclofenac. Acemetacin The therapeutic efficacy of Unoprostone can be decreased when used in combination with Acemetacin. Acetylsalicylic acid The therapeutic efficacy of Unoprostone can be decreased when used in combination with Acetylsalicylic acid. Alclofenac The therapeutic efficacy of Unoprostone can be decreased when used in combination with Alclofenac. Aliskiren Unoprostone may increase the hypotensive activities of Aliskiren. Ambrisentan Ambrisentan may increase the hypotensive activities of Unoprostone. Aminophenazone The therapeutic efficacy of Unoprostone can be decreased when used in combination with Aminophenazone. Amlodipine Amlodipine may increase the hypotensive activities of Unoprostone. Antipyrine The therapeutic efficacy of Unoprostone can be decreased when used in combination with Antipyrine. 
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- Not Available
Products
Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets- Product Ingredients
Ingredient UNII CAS InChI Key Unoprostone isopropyl 5M161S5O5P 120373-24-2 XXUPXHKCPIKWLR-JHUOEJJVSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Rescula Solution 0.15 % Ophthalmic Novartis Ophthalmics Novartis Pharmaceuticals (Canada) Inc 2002-05-27 2006-01-18 Canada 
Rescula Solution / drops 1.5 mg/1mL Ophthalmic Sucampo Pharma Americas, Llc 2013-01-07 2014-12-31 US 
Categories
- ATC Codes
- S01EE02 — Unoprostone
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Fatty Acyls
- Sub Class
- Eicosanoids
- Direct Parent
- Prostaglandins and related compounds
- Alternative Parents
- Long-chain fatty acids / Hydroxy fatty acids / Unsaturated fatty acids / Cyclopentanols / Ketones / Cyclic alcohols and derivatives / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
- Substituents
- Alcohol / Aliphatic homomonocyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Cyclic alcohol / Cyclopentanol / Fatty acid / Hydrocarbon derivative / Hydroxy fatty acid
- Molecular Framework
- Aliphatic homomonocyclic compounds
- External Descriptors
- oxo monocarboxylic acid, prostaglandins Falpha, ketone (CHEBI:39455) / Prostaglandins (LMFA03010204)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 6X4F561V3W
- CAS number
- 120373-36-6
- InChI Key
- TVHAZVBUYQMHBC-SNHXEXRGSA-N
- InChI
- InChI=1S/C22H38O5/c1-2-3-4-5-8-11-17(23)14-15-19-18(20(24)16-21(19)25)12-9-6-7-10-13-22(26)27/h6,9,18-21,24-25H,2-5,7-8,10-16H2,1H3,(H,26,27)/b9-6-/t18-,19-,20+,21-/m1/s1
- IUPAC Name
- (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl]hept-5-enoic acid
- SMILES
- CCCCCCCC(=O)CC[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O
References
- General References
- External Links
- PubChem Compound
- 5311236
- PubChem Substance
- 347827802
- ChemSpider
- 4470755
- 1546408
- ChEBI
- 39455
- ChEMBL
- CHEMBL1201407
- ZINC
- ZINC000008214703
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Unoprostone
- FDA label
- Download (36.9 KB)
- MSDS
- Download (32.4 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Terminated Treatment Retinitis Pigmentosa (RP) 1 2 Completed Treatment Dry Age-related Macular Degeneration 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Ophthalmic 0.15 % Solution / drops Ophthalmic 1.5 mg/1mL - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US6458836 No 2002-10-01 2021-07-09 US US6770675 No 2004-08-03 2018-11-24 US
Properties
- State
- Liquid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0306 mg/mL ALOGPS logP 3.99 ALOGPS logP 3.91 ChemAxon logS -4.1 ALOGPS pKa (Strongest Acidic) 4.31 ChemAxon pKa (Strongest Basic) -2.9 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 94.83 Å2 ChemAxon Rotatable Bond Count 15 ChemAxon Refractivity 107.68 m3·mol-1 ChemAxon Polarizability 45.47 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Drug created on September 14, 2010 16:21 / Updated on February 21, 2021 18:52