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

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. Archived from the original on 23 January 2021. Retrieved 11 November 2021.
  2. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 552. ISBN 9783527607495. Archived from the original on 2016-12-29. Retrieved 2020-10-19.
  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: