Naphazoline

Naphazoline
Clinical data
Trade names	Clear Eyes, Cleari,Naphcon-A,Rohto
AHFS/Drugs	Monograph
Routes of; administration	Ophthalmic drug administration,nasal administration
ATC code	R01AA08(WHO)S01GA01(WHO);
Legal status
Legal status	In general:Over-the-counter(OTC);
Identifiers
	IUPAC name 2-(naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazole;
CAS Number	835-31-4;
PubChemCID	4436;
IUPHAR/BPS	5509;
DrugBank	DB06711;
ChemSpider	4283;
UNII	H231GF11BV;
KEGG	D08253;
ChEMBL	ChEMBL761;
CompTox Dashboard(EPA)	DTXSID3048449;
ECHA InfoCard	100.011.492
Chemical and physical data
Formula	C14H14N2
Molar mass	210.280g·mol−1
3D model (JSmol)	Interactive image;
	SMILES N\1=C(\NCC/1)Cc2cccc3c2cccc3;
	InChI InChI=1S/C14H14N2/c1-2-7-13-11(4-1)5-3-6-12(13)10-14-15-8-9-16-14/h1-7H,8-10H2,(H,15,16); Key:CNIIGCLFLJGOGP-UHFFFAOYSA-N;
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Naphazolineis a medicine used as adecongestant,and avasoconstrictoradded toeye dropsto relievered eye.It has a rapid action in reducing swelling when applied tomucous membranes.It is asympathomimeticagent with markedAlpha adrenergicactivity that acts on Alpha -receptors in thearteriolesof theconjunctivato produce constriction, resulting in decreased congestion.

It was patented in 1934 and came into medical use in 1942.^[1]

Medical uses

Red eyes can be treated with naphazoline.

Nasal administration

Nasaldecongestant.^[2]

Ophthalmic drug administration

Eye drops(brand names Clear Eyes, and Cleari) narrowing swollen blood vessels (ophthalmic arteries,andophthalmic veins) to relievered eye.^[2]

Temporary red eye can safely be treated when the cause of the redness is established (e.g.cannabisinduced conjunctival vasodilation).^[3]However, continuous use is not recommended without knowing an underlying condition.

Side effects

A few warnings andcontraindicationsthat apply to all naphazoline-containing substances intended for medicinal use are:

Hypersensitivity to naphazoline
Use in infants and children can result incentral nervous systemdepression, leading to coma and marked reduction inbody temperature
Should be used with caution in patients with severecardiovascular diseaseincludingcardiac arrhythmiaand in patients withdiabetes,especially those with a tendency toward diabeticketoacidosis
A possible association with stroke has been suggested.^[4]

Nasal administration

Extended use may causerhinitis medicamentosa,a condition ofrebound nasal congestion.

Ophthalmic drug administration

Known side-effect:^[5]^[6]

Stinging
Discomfort
Irritation
Increasedred eyes
Blurred vision
Mydriasis
Punctate keratitis
Lacrimation(tears)
Increasedintraocular pressure

Contraindications

Patients takingMAO inhibitorscan experience a severehypertensivecrisis if given asympathomimeticdrug such as naphazoline HCl
Drug interactions can occur withanaestheticsthat sensitize themyocardiumto sympathomimetics (e.g.cyclopropaneorhalothanecautiously)
Exercise caution when applying prior to use ofphenylephrine.

Pharmacology

Naphazoline is a mixedα₁-andα₂-adrenergic receptor agonist.^[2]

Chemistry

The non-hydrochloride form of Naphazoline has themolecular formulaC₁₄H₁₄N₂and amolar massof 210.28 g/mol. The HCl salt form has a molar mass of 246.73 g/mol.

Society and culture

It is anactive ingredientin severalover-the-counter eye dropformulations including Clear Eyes,RohtoCool, Eucool, andNaphcon-A.^[7]

Illicit use

The nasal or ophthalmic form of naphazoline has been abused byheroinorcocaine drug addicts.^[8]^[9]It's used asCNS stimulantandvasoconstrictorto enhance primary drug effects.^[9]

References

^Fischer J, Ganellin CR (2006).Analogue-based Drug Discovery.John Wiley & Sons. p. 552.ISBN 9783527607495.
^^a ^b ^cHosten LO, Snyder C (2020)."Over-the-Counter Ocular Decongestants in the United States - Mechanisms of Action and Clinical Utility for Management of Ocular Redness".Clinical Optometry.12:95–105.doi:10.2147/OPTO.S259398.PMC7399465.PMID 32801982.
^Yazulla S (September 2008)."Endocannabinoids in the retina: from marijuana to neuroprotection".Progress in Retinal and Eye Research.27(5):501–526.doi:10.1016/j.preteyeres.2008.07.002.PMC2584875.PMID 18725316.
^Zavala JA, Pereira ER, Zétola VH, Teive HA, Nóvak EM, Werneck LC (September 2004)."Hemorrhagic stroke after naphazoline exposition: case report".Arquivos de Neuro-Psiquiatria.62(3B):889–891.doi:10.1590/S0004-282X2004000500030.PMID 15476091.
^"Naphazoline - FDA prescribing information, side effects and uses".Drugs.
^"naphazoline ophthalmic (eye): Uses, Side Effects, Interactions, Pictures, Warnings & Dosing - WebMD".webmd.
^Green SM (2008). "Ophthalmology: Naphazoline".Tarascon Pocket Pharmacopoeia 2009.Jones and Bartlett.ISBN 978-0-7637-6572-9.
^van Montfrans GA, van Steenwijk RP, Vyth A, Borst C (1981). "Intravenous naphazoline intoxication".Acta Medica Scandinavica.209(5):429–430.doi:10.1111/j.0954-6820.1981.tb11622.x.PMID 7246278.
^^a ^b"Naphazoline abuse".Reactions Weekly.1815(1): 251. 2020-08-01.doi:10.1007/s40278-020-81577-1.ISSN 1179-2051.S2CID 195174995.

[Fis2006-1] Fischer J, Ganellin CR (2006).Analogue-based Drug Discovery.John Wiley & Sons. p. 552.ISBN 9783527607495.

[pmid32801982-2] Hosten LO, Snyder C (2020)."Over-the-Counter Ocular Decongestants in the United States - Mechanisms of Action and Clinical Utility for Management of Ocular Redness".Clinical Optometry.12:95–105.doi:10.2147/OPTO.S259398.PMC7399465.PMID 32801982.

[3] Yazulla S (September 2008)."Endocannabinoids in the retina: from marijuana to neuroprotection".Progress in Retinal and Eye Research.27(5):501–526.doi:10.1016/j.preteyeres.2008.07.002.PMC2584875.PMID 18725316.

[pmid15476091-4] Zavala JA, Pereira ER, Zétola VH, Teive HA, Nóvak EM, Werneck LC (September 2004)."Hemorrhagic stroke after naphazoline exposition: case report".Arquivos de Neuro-Psiquiatria.62(3B):889–891.doi:10.1590/S0004-282X2004000500030.PMID 15476091.

[5] "Naphazoline - FDA prescribing information, side effects and uses".Drugs.

[6] "naphazoline ophthalmic (eye): Uses, Side Effects, Interactions, Pictures, Warnings & Dosing - WebMD".webmd.

[7] Green SM (2008). "Ophthalmology: Naphazoline".Tarascon Pocket Pharmacopoeia 2009.Jones and Bartlett.ISBN 978-0-7637-6572-9.

[8] van Montfrans GA, van Steenwijk RP, Vyth A, Borst C (1981). "Intravenous naphazoline intoxication".Acta Medica Scandinavica.209(5):429–430.doi:10.1111/j.0954-6820.1981.tb11622.x.PMID 7246278.

[:0-9] "Naphazoline abuse".Reactions Weekly.1815(1): 251. 2020-08-01.doi:10.1007/s40278-020-81577-1.ISSN 1179-2051.S2CID 195174995.

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