Naphazoline
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| Systematic (IUPAC) name | |
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2-(naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazole
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| Clinical data | |
| Trade names | Naphcon-a |
| AHFS/Drugs.com | monograph |
| Routes of administration |
Topical |
| Identifiers | |
| CAS Number | 835-31-4  |
| ATC code | R01AA08 (WHO) S01GA01 |
| PubChem | CID: 4436 |
| IUPHAR/BPS | 5509 |
| DrugBank | DB06711  |
| ChemSpider | 4283 |
| UNII | H231GF11BV |
| KEGG | D08253 |
| ChEMBL | CHEMBL761 |
| Chemical data | |
| Formula | C14H14N2 |
| Molecular mass | 210.274 |
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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:
- 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 arrhythmia 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.
- Extended use may cause rhinitis medicamentosa, a condition of rebound nasal congestion.
A possible association with stroke has been suggested.[2]
