Naphazoline

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Naphazoline
Naphazoline.svg
Naphazoline.png
Names
Trade namesNaphcon-a, Clear Eyes Red Relief, Visine A, others
  • 2-(naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazole
Clinical data
Drug classAlpha adrenergic agonist[1]
Main usesStuffy nose, eye redness[1]
Side effectsBurning, blurry vision[1]
Routes of
use
Nasal spray, eye drops
External links
AHFS/Drugs.comMonograph
US NLMNaphazoline
Legal
Legal status
Chemical and physical data
FormulaC14H14N2
Molar mass210.274 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, sold under many brand names, is a medication used to treat a stuffy nose or eye redness due to minor irritation.[1] It is available as a nasal spray or eye drops.[1]

Common side effects include blurry vision and stinging.[1] Other side effects may include recurrence of stuffiness following stopping use, headache, palpitations, and nervousness.[1] Safety in pregnancy is unclear.[1] It works by activating alpha adrenergic receptor which cases small arteries to narrow.[1]

Naphazoline was patented in 1934 and came into medical use in 1942.[2] It is available as a generic medication and over the counter.[1] In the United States 15 ml of solution costs about 14 USD.[3]

Medical use

Dosage

It is used at a dose of 1 to 2 eye drops every 3 to 4 hours.[1]

Side effects

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.[4]

Chemistry

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

Society and culture

Brand names

It is an active ingredient in several over-the-counter formulations including Rohto, Eucool, Clear Eyes and Naphcon eye drops.[5]

References

  1. 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 1.10 "Naphazoline Monograph for Professionals". Drugs.com. Retrieved 11 November 2021.
  2. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 552. ISBN 9783527607495.
  3. "Naphazoline ophthalmic Prices, Coupons & Patient Assistance Programs". Drugs.com. Retrieved 11 November 2021.
  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): 889–91. doi:10.1590/S0004-282X2004000500030. PMID 15476091.
  5. Green SM (2008). "Ophthalmology: Naphazoline". Tarascon Pocket Pharmacopoeia 2009. Jones and Bartlett. ISBN 978-0-7637-6572-9.

External links

Identifiers: