Naphazoline

Naphazoline
Systematic (IUPAC) name
2-(naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazole
Clinical data
Trade names Naphcon-a
AHFS/Drugs.com monograph
Routes of
administration
Topical
Identifiers
CAS Number 835-31-4 N
ATC code R01AA08 (WHO) S01GA01 (WHO)
PubChem CID 4436
IUPHAR/BPS 5509
DrugBank DB06711 YesY
ChemSpider 4283 YesY
UNII H231GF11BV YesY
KEGG D08253 YesY
ChEMBL CHEMBL761 YesY
Chemical data
Formula C14H14N2
Molar mass 210.274
 NYesY (what is this?)  (verify)

Naphazoline (in the hydrochloride form) is the common name for 2-(1-naphthylmethyl)-2-imidazoline hydrochloride. It is a sympathomimetic agent with marked alpha adrenergic activity. It is a vasoconstrictor with a rapid action in reducing swelling when applied to mucous membrane. It acts on alpha-receptors in the arterioles of the conjunctiva to produce constriction, resulting in decreased congestion. It is an active ingredient in several over-the-counter formulations including Clear Eyes and Naphcon eye drops.[1]

It has the molecular formula C14H14N2 and a molar mass of 246.73 g/mol.

Warnings and contraindications

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

A possible association with stroke has been suggested.[2]

References

  1. Green, S. M. (2008). "Ophthalmology: Naphazoline". Tarascon Pocket Pharmacopoeia 2009. Jones and Bartlett. ISBN 0-7637-6572-4.
  2. Zavala, J. A.; Pereira, E. R.; Zétola, V. H.; Teive, H. A.; Nóvak, E. M.; Werneck, L. C. (2004). "Hemorrhagic stroke after naphazoline exposition: case report". Arquivos de Neuro-Psiquiatrica 62 (3B): 889–891. doi:10.1590/S0004-282X2004000500030. PMID 15476091.
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