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Naphazoline

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Naphazoline
Clinical data
Trade namesClear Eyes, Cleari,Naphcon-A,Rohto
AHFS/Drugs.comMonograph
Routes of
administration
Ophthalmic drug administration,nasal administration
ATC code
Legal status
Legal status
Identifiers
  • 2-(naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazole
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.011.492Edit this at Wikidata
Chemical and physical data
FormulaC14H14N2
Molar mass210.280 g·mol−1
3D model (JSmol)
  • N\1=C(\NCC/1)Cc2cccc3c2cccc3
  • 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) checkY
  • Key:CNIIGCLFLJGOGP-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Naphazoline is a medicine used as adecongestant, and avasoconstrictor added toeye drops to relievered eye. It has a rapid action in reducing swelling when applied tomucous membranes. It is asympathomimetic agent with markedalpha adrenergic activity that acts on alpha-receptors in thearterioles of theconjunctiva to produce constriction, resulting in decreased congestion.

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

Medical uses

[edit]
Red eyes can be treated with naphazoline.

Nasal administration

[edit]

Nasaldecongestant.[2]

Ophthalmic drug administration

[edit]

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.cannabis induced conjunctival vasodilation).[3] However, continuous use is not recommended without knowing an underlying condition.

Side effects

[edit]

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

Nasal administration

[edit]

Ophthalmic drug administration

[edit]

Known side-effect:[5][6]

Contraindications

[edit]

Pharmacology

[edit]

Naphazoline is a mixedα1- andα2-adrenergic receptoragonist.[2]

Chemistry

[edit]

The non-hydrochloride form of Naphazoline has themolecular formula C14H14N2 and amolar mass of 210.28 g/mol. The HCl salt form has a molar mass of 246.73 g/mol.

Society and culture

[edit]

It is anactive ingredient in severalover-the-countereye drop formulations including Clear Eyes,Rohto Cool, Eucool, andNaphcon-A.[7]

Illicit use

[edit]

The nasal or ophthalmic form of naphazoline has been abused byheroin orcocainedrug addicts.[8][9] It's used asCNS stimulant andvasoconstrictor to enhance primary drug effects.[9]

References

[edit]
  1. ^Fischer J, Ganellin CR (2006).Analogue-based Drug Discovery. John Wiley & Sons. p. 552.ISBN 9783527607495.
  2. ^abcHosten 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.PMC 7399465.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.PMC 2584875.PMID 18725316.
  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.com.
  6. ^"naphazoline ophthalmic (eye): Uses, Side Effects, Interactions, Pictures, Warnings & Dosing - WebMD".www.webmd.com.
  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.
  9. ^ab"Naphazoline abuse".Reactions Weekly.1815 (1): 251. 2020-08-01.doi:10.1007/s40278-020-81577-1.ISSN 1179-2051.S2CID 195174995.
Decongestants and other nasal preparations (R01)
Topical
Sympathomimetics, plain
Antiallergic agents,
excluding corticosteroids
Corticosteroids
Other nasal preparations
Combination products
Systemic use:
Sympathomimetics
α1
Agonists
Antagonists
α2
Agonists
Antagonists
β
Agonists
Antagonists
Phenethylamines
Amphetamines
Phentermines
Cathinones
Phenylisobutylamines
(and further-extended)
Catecholamines
(and close relatives)
Cyclized
phenethylamines
Phenylalkylpyrrolidines
2-Benzylpiperidines
(phenidates)
Phenylmorpholines
(phenmetrazines)
Phenyloxazolamines
(aminorexes)
Isoquinolines and
tetrahydroisoquinolines
2-Aminoindanes
2-Aminotetralins
Others / unsorted
Related compounds
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