Perfluorohexyloctane

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H17F13
Molecular Weight	432.264
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCCCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F

InChI

InChIKey=WRYIIOKOQSICTB-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.novaliq.com/products/nov03|https://www.accessdata.fda.gov/drugsatfda_docs/label/2023/216675s000lbl.pdf|https://pubmed.ncbi.nlm.nih.gov/36929413

Perfluorohexyloctane (NOV03, MIEBO), a semifluorinated alkane, is the first drug developed to treat dry eye disease (DED) associated with Meibomian gland dysfunction in a highly effective way. Perfluorohexyloctane is an investigational, proprietary, water-free, non-steroidal, single-component preservative-free eye drop. Perfluorohexyloctane prevents excessive tear evaporation and has the ability to restore tear film balance. The investigational drug has a unique mode of action: it stabilizes the lipid layer for hours to protect the tear film and has the ability to penetrate the Meibomian glands. Perfluorohexyloctane contains 6 perfluorinated carbon atoms and 8 hydrogenated carbon atoms. Perfluorohexyloctane forms a monolayer at the air-liquid interface of the tear film which can be expected to reduce evaporation. The exact mechanism of action for perfluorohexyloctane in DED is not known.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Dry eye disease 1 Sources: https://pubmed.ncbi.nlm.nih.gov/31417241/	Primary		Approved 8583	MIEBO Approved Use MIEBO (perfluorohexyloctane ophthalmic solution) is a semifluorinated alkane indicated for treatment of the signs and symptoms of dry eye disease. Launch Date 2023

PubMed

Title	Date	PubMed
Perfluorohexyloctane Eye Drops for Dry Eye Disease Associated With Meibomian Gland Dysfunction in Chinese Patients: A Randomized Clinical Trial.	2023-04-01	36929413
VEGF TrapR1R2 Suspended in the Semifluorinated Alkane F6H8 Inhibits Inflammatory Corneal Hem- and Lymphangiogenesis.	2020-10	33117607
Interactions of Perfluorohexyloctane With Polyethylene and Polypropylene Pharmaceutical Packaging Materials.	2020-07	32240694
Influence of Perfluorohexyloctane Eye Drops on Tear Film Thickness in Patients with Mild to Moderate Dry Eye Disease: A Randomized Controlled Clinical Trial.	2020-04	31895638

Patents

Sample Use Guides

In Vivo Use Guide

https://www.accessdata.fda.gov/drugsatfda_docs/label/2023/216675s000lbl.pdf

Route of Administration: Topical

In Vitro Use Guide

PBMC were incubated in PBS with either F6H8-Pluronic, F6H8-lecithin, or the pure surfactant stock solutions (Pluronic or lecithin alone) at various concentrations. The original F6H8-emulsions (containing 40 wt.% F6H8) were diluted 1:10, 1:100, 1:1,000, and 1:10,000 in order to yield the organic phase end concentrations used in the experiments of 4%, 0.4%, 0.04%, and 0.004%, respectively.

Name

Type

Language

Perfluorohexyloctane

Official Name

English

MIEBO

Preferred Name

English

perfluorohexyloctane [INN]

Common Name

English

1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorotetradecane

Systematic Name

English

PERFLUOROHEXYLOCTANE [USAN]

Common Name

English

Perfluorohexyloctane [WHO-DD]

Common Name

English

Tetradecane, 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-

Systematic Name

English

NOV03

Code

English

NOV-03

Code

English

1-(Perfluorohexyl)octane

Systematic Name

English

Code System Code Type Description

NCI_THESAURUS

C199090