Perfluorohexyloctane (NOV03; Miebo) is a semifluorinated alkane that reduces tear film instability in meibomian gland dysfunction and evaporative dry eye disease. Perfluorohexyloctane is a long-term tamponade agent. Perfluorohexyloctane increases tear film break-up time and lipid layer thickness. Approved in 2023 by FDA for treating dry eye disease.

Physicochemical Properties

Molecular Formula	C14H17F13
Molecular Weight	432.26
Exact Mass	432.112
Elemental Analysis	C, 38.90; H, 3.96; F, 57.14
CAS #	133331-77-8
PubChem CID	10477896
Appearance	Colorless to light yellow liquid（Density：1.331 g/cm3）
LogP	7.475
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	13
Rotatable Bond Count	11
Heavy Atom Count	27
Complexity	464
Defined Atom Stereocenter Count	0
SMILES	FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCCCCCCC
InChi Key	WRYIIOKOQSICTB-UHFFFAOYSA-N
InChi Code	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
Chemical Name	1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorotetradecane
Synonyms	Miebo; 1-(Perfluorohexyl)octane; 133331-77-8; perfluorohexyloctane; 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorotetradecane; MIEBO;
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	Interact with the air-liquid interface of the tear film and form a monolayer, preventing the evaporation of the aqueous phase of the tears.
ln Vitro	Perfluorohexyloctane mediates its actions in the lipid layer and meibomian glands. 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.
ln Vivo	Perfluorohexyloctane is administered ophthalmically to alleviate symptoms of dry eye disease, increase tear film breakup time, and increase lipid layer thickness. 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. PERFLUOROHEXYLOCTANE is a small molecule drug with a maximum clinical trial phase of IV (across all indications) that was first approved in 2023 and is indicated for dry eye syndrome and has 1 investigational indication.
ADME/Pharmacokinetics	Absorption, Distribution and Excretion Perfluorohexyloctane penetrates meibomian glands, where it has been reported to interact with and dissolve the altered, viscous meibum in the glands. A single pharmacokinetic study showed low systemic perfluorohexyloctane blood levels after topical ocular administration. In rabbits, perfluorohexyloctane was detected in tears at six hours and in meibomian glands at 24 hours following ophthalmic administration, with minimal systemic exposure. Metabolism / Metabolites Perfluorohexyloctane was not metabolized by human liver microsomes _in vitro_.
Toxicity/Toxicokinetics	Effects During Pregnancy and Lactation ◉ Summary of Use during Lactation No information is available on the use of perfluorohexyloctane during breastfeeding. Because perfluorohexyloctane is poorly absorbed, it is not likely to reach the bloodstream of the infant or cause any adverse effects in breastfed infants. No special precautions are required. ◉ Effects in Breastfed Infants Relevant published information was not found as of the revision date. ◉ Effects on Lactation and Breastmilk Relevant published information was not found as of the revision date.
References	[1]. Deciphering the Action of Perfluorohexyloctane Eye Drops to Reduce Ocular Discomfort and Pain. Front Med (Lausanne). 2021 Oct 26;8:709712. [2]. https://pubchem.ncbi.nlm.nih.gov/compound/10477896
Additional Infomation	Perfluorohexyloctane is a fluoroalkane that is tetradecane in which all of the hydrogen atoms at positions 1, 2, 3, 4, 5, and 6 have been replaced by fluorine atoms. It is an ophthalmic solution used to treat the signs and symptoms of dry eye disease. It has a role as an ophthalmology drug and a nonionic surfactant. It is a fluorohydrocarbon and a fluoroalkane. It derives from a hydride of a tetradecane. Perfluorohexyloctane is a semifluorinated alkane that contains six perfluorinated carbon atoms and eight hydrogenated carbon atoms. It is an inert, slightly amphiphilic compound. 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. Perfluorohexyloctane has been used in the field of ophthalmology as a vitreous substitute. It was approved by the FDA on May 18, 2023 for the treatment of dry eye disease. Drug Indication Perfluorohexyloctane ophthalmic formulation is indicated for the treatment of the signs and symptoms of dry eye disease. Mechanism of Action Perfluorohexyloctane mediates its actions in the lipid layer and meibomian glands. 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. Pharmacodynamics Perfluorohexyloctane is administered ophthalmically to alleviate symptoms of dry eye disease, increase tear film breakup time, and increase lipid layer thickness. 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.

Solubility Data

Solubility (In Vitro)

DMSO: ~100 mg/mL (~231 mM)

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.3134 mL	11.5671 mL	23.1342 mL
	5 mM	0.4627 mL	2.3134 mL	4.6268 mL
	10 mM	0.2313 mL	1.1567 mL	2.3134 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.