Perfluorohexyloctane

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
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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofDry eye syndrome (des)••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

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
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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

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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
MieboSolution1 mg/1mgOphthalmicBausch & Lomb Incorporated2023-05-18Not applicableUS flag

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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. FDA Approved Drug Products: MIEBO (perfluorohexyloctane ophthalmic solution), for topical ophthalmic use [Link]
  7. Ophthalmology Times: Bausch + Lomb, Novaliq announce FDA approval of perfluorohexyloctane ophthalmic solution for treatment of dry eye disease [Link]
Human Metabolome Database
HMDB0243805
ChemSpider
8653305
RxNav
2637547
ZINC
ZINC000100046937

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Not Yet RecruitingTreatmentDry Eye Syndrome (DES)1
4RecruitingTreatmentDry Eye Syndrome (DES) / Dry Eye, Evaporative / Dry Eyes / Evaporative Dry Eye / Evaporative Dry Eye Disease / Keratoconjunctivitis Sicca (KCS)1
3CompletedTreatmentDry Eye Syndrome (DES)3
2CompletedTreatmentDry Eye Syndrome (DES)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionOphthalmic1 mg/1mg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US11357738No2016-09-292036-09-29US flag
US10058615No2018-08-282033-09-12US flag
US10369117No2019-08-062033-09-12US flag
US10449164No2019-10-222033-09-12US flag
US10507132No2019-12-172037-06-21US flag
US10576154No2020-03-032033-09-12US flag

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)5https://store.apolloscientific.co.uk/storage/msds/PC7927_msds.pdf
Predicted Properties
PropertyValueSource
logP7.95Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count0Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area0 Å2Chemaxon
Rotatable Bond Count12Chemaxon
Refractivity67.75 m3·mol-1Chemaxon
Polarizability29.76 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Drug created at May 19, 2023 16:44 / Updated at May 27, 2023 01:26