Naphazoline
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| 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  |
| ATC code | R01AA08 (WHO) S01GA01 (WHO) |
| PubChem | CID 4436 |
| IUPHAR/BPS | 5509 |
| DrugBank |
DB06711  |
| ChemSpider |
4283 |
| UNII |
H231GF11BV |
| KEGG |
D08253 |
| ChEMBL |
CHEMBL761 |
| Chemical data | |
| Formula | C14H14N2 |
| Molar 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]
References
- ↑ Green, S. M. (2008). "Ophthalmology: Naphazoline". Tarascon Pocket Pharmacopoeia 2009. Jones and Bartlett. ISBN 0-7637-6572-4.
- ↑ 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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