Naphazoline

Naphazoline

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Systematic (IUPAC) name
2-(naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazole
Clinical data
Routes of administration	Topical
Identifiers
CAS Number	835-31-4
ATC code	R01AA08 (WHO)
PubChem	CID 4436
Chemical data
Formula	C14H14N2
Molar mass	210.274[[]]

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.

It has the molecular formula C₁₄H₁₄N₂.HCl and a molecular weight 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:

• Hypersensitivity to naphazoline
• Patients taking MAO inhibitors can experience a severe hypertensive crisis if given a sympathomimetic drug such as naphazoline HCl
• Use in infants and children can result in central nervous system depression, leading to coma and marked reduction in body temperature
• Should be used with caution in patients with severe cardiovascular disease including cardiac arrythmia and in patients with diabetes, especially those with a tendency toward diabetic ketoacidosis
• Drug interactions can occur with anaesthetics that sensitize the myocardium to sympathomimetics (e.g. cyclopropane or halothane cautiously)
• Exercise caution when applying prior to use of phenylephrine.

A possible association with stroke has been suggested.

References

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