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Identification
- Summary
Perfluorohexyloctane is a drug used to treat dry eye disease.
- Brand Names
- Miebo
- Generic Name
- Perfluorohexyloctane
- DrugBank Accession Number
- DB17823
- Background
Perfluorohexyloctane is a semifluorinated alkane that contains six perfluorinated carbon atoms and eight hydrogenated carbon atoms.6 It is an inert, slightly amphiphilic compound.3 Because it is a completely non-aqueous liquid, microbial growth is not possible; therefore, its drug products do not need to be combined with any preservative.3,4
Perfluorohexyloctane has been used in the field of ophthalmology as a vitreous substitute.2 It was approved by the FDA on May 18, 2023 for the treatment of dry eye disease.7
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Perfluorohexyloctane (DB17823)
- Weight
- Average: 432.269
Monoisotopic: 432.112266666 - Chemical Formula
- C14H17F13
- Synonyms
- 1-(perfluorohexyl)octane
- F6H8
- NOV03
- Tetradecane, 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-
Pharmacology
- Indication
Perfluorohexyloctane ophthalmic formulation is indicated for the treatment of the signs and symptoms of dry eye disease.6
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Dry eye syndrome (des) •••••••••••• - Contraindications & Blackbox Warnings
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Perfluorohexyloctane is administered ophthalmically to alleviate symptoms of dry eye disease, increase tear film breakup time, and increase lipid layer thickness.3 Having low surface and interface tensions, perfluorohexyloctane spreads rapidly across the ocular surface. It is reported to cause minimal visual disturbances, attributed to its refractive index being similar to that of water.1,3,4
- Mechanism of action
Perfluorohexyloctane mediates its actions in the lipid layer and meibomian glands.5 While the exact mechanism of action is not fully understood, perfluorohexyloctane is believed to interact with the air-liquid interface of the tear film and form a monolayer, preventing the evaporation of the aqueous phase of the tears.5,3,6
- Absorption
Perfluorohexyloctane penetrates meibomian glands, where it has been reported to interact with and dissolve the altered, viscous meibum in the glands.5 A single pharmacokinetic study showed low systemic perfluorohexyloctane blood levels after topical ocular administration.6 In rabbits, perfluorohexyloctane was detected in tears at six hours and in meibomian glands at 24 hours following ophthalmic administration, with minimal systemic exposure.1
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Perfluorohexyloctane was not metabolized by human liver microsomes in vitro.6
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
There is limited information regarding acute toxicity (LD50) or overdosage of perfluorohexyloctane.
- 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.Not Available
- Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Miebo Solution 1 mg/1mg Ophthalmic Bausch & Lomb Incorporated 2023-05-18 Not applicable US 
Categories
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 7VYX4ELWQM
- CAS number
- 133331-77-8
- InChI Key
- WRYIIOKOQSICTB-UHFFFAOYSA-N
- InChI
- InChI=1S/C14H17F13/c1-2-3-4-5-6-7-8-9(15,16)10(17,18)11(19,20)12(21,22)13(23,24)14(25,26)27/h2-8H2,1H3
- IUPAC Name
- 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorotetradecane
- SMILES
- CCCCCCCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
References
- General References
- Tauber J, Berdy GJ, Wirta DL, Krosser S, Vittitow JL: NOV03 for Dry Eye Disease Associated with Meibomian Gland Dysfunction: Results of the Randomized Phase 3 GOBI Study. Ophthalmology. 2023 May;130(5):516-524. doi: 10.1016/j.ophtha.2022.12.021. Epub 2022 Dec 24. [Article]
- Zeana D, Becker J, Kuckelkorn R, Kirchhof B: Perfluorohexyloctane as a long-term vitreous tamponade in the experimental animal. Experimental perfluorohexyloctane substitution. Int Ophthalmol. 1999;23(1):17-24. doi: 10.1023/a:1006444615412. [Article]
- Delicado-Miralles M, Velasco E, Diaz-Tahoces A, Gallar J, Acosta MC, Aracil-Marco A: Deciphering the Action of Perfluorohexyloctane Eye Drops to Reduce Ocular Discomfort and Pain. Front Med (Lausanne). 2021 Oct 26;8:709712. doi: 10.3389/fmed.2021.709712. eCollection 2021. [Article]
- Steven P, Scherer D, Krosser S, Beckert M, Cursiefen C, Kaercher T: Semifluorinated Alkane Eye Drops for Treatment of Dry Eye Disease--A Prospective, Multicenter Noninterventional Study. J Ocul Pharmacol Ther. 2015 Oct;31(8):498-503. doi: 10.1089/jop.2015.0048. Epub 2015 Aug 21. [Article]
- Tauber J, Wirta DL, Sall K, Majmudar PA, Willen D, Krosser S: A Randomized Clinical Study (SEECASE) to Assess Efficacy, Safety, and Tolerability of NOV03 for Treatment of Dry Eye Disease. Cornea. 2021 Sep 1;40(9):1132-1140. doi: 10.1097/ICO.0000000000002622. [Article]
- FDA Approved Drug Products: MIEBO (perfluorohexyloctane ophthalmic solution), for topical ophthalmic use [Link]
- Ophthalmology Times: Bausch + Lomb, Novaliq announce FDA approval of perfluorohexyloctane ophthalmic solution for treatment of dry eye disease [Link]
- External Links
- Human Metabolome Database
- HMDB0243805
- ChemSpider
- 8653305
- 2637547
- ZINC
- ZINC000100046937
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data4 Completed Treatment Dry Eye Syndrome (DES) 1 somestatus stop reason just information to hide 4 Completed Treatment Dry Eye Syndrome (DES) / Dry Eyes / Evaporative Dry Eye / Evaporative Dry Eye Disease / Keratoconjunctivitis Sicca (KCS) 1 somestatus stop reason just information to hide 4 Completed Treatment Dry Eyes 1 somestatus stop reason just information to hide 4 Recruiting Treatment Dry Eyes 2 somestatus stop reason just information to hide 3 Completed Treatment Dry Eye Syndrome (DES) 3 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Ophthalmic 1 mg/1mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US11357738 No 2016-09-29 2036-09-29 US US10058615 No 2018-08-28 2033-09-12 US US10369117 No 2019-08-06 2033-09-12 US US10449164 No 2019-10-22 2033-09-12 US US10507132 No 2019-12-17 2037-06-21 US US10576154 No 2020-03-03 2033-09-12 US
Properties
- State
- Liquid
- Experimental Properties
Property Value Source melting point (°C) 5 https://store.apolloscientific.co.uk/storage/msds/PC7927_msds.pdf - Predicted Properties
Property Value Source logP 7.95 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 0 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 0 Å2 Chemaxon Rotatable Bond Count 12 Chemaxon Refractivity 67.75 m3·mol-1 Chemaxon Polarizability 29.76 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No 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 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Drug created at May 19, 2023 16:44 / Updated at May 27, 2023 01:26