Naphazoline

Naphazoline
Systematic (IUPAC) name
2-(naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazole
Clinical data
Trade names Naphcon-a
AHFS/Drugs.com monograph
Pregnancy cat.  ?
Legal status  ?
Routes Topical
Identifiers
CAS number 835-31-4 YesY
ATC code R01AA08
PubChem CID 4436
DrugBank DB06711
ChemSpider 4283 YesY
UNII H231GF11BV N
KEGG D08253 YesY
ChEMBL CHEMBL761 YesY
Chemical data
Formula C14H14N2 
Mol. mass 210.274
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

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.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:

A possible association with stroke has been suggested.[2]

Chemistry

Naphazoline, 2-(1-naphthylmethyl)-2-imidazoline, is synthesized from (1-naphthyl)acetonitrile, which upon reaction with ethanol transforms into iminoester, and undergoes further heterocyclization into the desired imidazoline derivative upon reaction with ethylene diamine Naphazoline synthesis.png

References

  1. ^ "Ophthalmology: naphazoline". Tarascon Pocket Pharmacopoeia 2009. Jones and Bartlett Publishers. 2008. ISBN 0763765724. 
  2. ^ Zavala JA, Pereira ER, Zétola VH, Teive HA, Nóvak EM, Werneck LC (September 2004). "Hemorrhagic stroke after naphazoline exposition: case report". Arq Neuropsiquiatr 62 (3B): 889–91. doi:/S0004-282X2004000500030. PMID 15476091. http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0004-282X2004000500030&lng=en&nrm=iso&tlng=en. 

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Look at other dictionaries:

  • naphazoline — ● naphazoline ou naphtazoline nom féminin Médicament chimique utilisé à l état de nitrate pour son action vasoconstrictrice périphérique et décongestionnante. naphazoline [nafazɔlin] n. f. ÉTYM. Mil. XXe; de naph(tyl) , et (imid)azoline, de imide …   Encyclopédie Universelle

  • naphazoline — noun 2 (1 naphthylmethyl) 2 imidazoline hydrochloride, a sympathomimetic agent used as a vasoconstrictor …   Wiktionary

  • naphazoline — na·phaz·o·line nə faz ə .lēn n a base derived from naphthalene and imidazoline and used topically in the form of its hydrochloride C14H14N2·HCl esp. to relieve nasal congestion and itching and redness of the eyes …   Medical dictionary

  • naphazoline — na·phaz·o·line …   English syllables

  • naphazoline — noun vasoconstrictor (trade names Privine and Sudafed) used in nasal sprays to treat symptoms of nasal congestion and in eyedrops to treat eye irritation • Syn: ↑Privine, ↑Sudafed • Usage Domain: ↑trade name (for: ↑Sudafed), ↑trade name …   Useful english dictionary

  • naphazoline hydrochloride — A sympathomimetic amine, used as a topical vasoconstrictor; available as n. nitrate, with the same uses. SYN: naphthazoline hydrochloride. * * * naph·az·o·line hy·dro·chlo·ride (naf azґo lēn) [USP] an adrenergic used as a vasoconstrictor,… …   Medical dictionary

  • Нафазолин (Naphazoline) — сосудосуживающее лекарственное вещество; применяется для устранения заложенное (tm) носа при рините и синусйте. Назначается в каплях в нос; иногда может вызывать слабое раздражение. Торговое название: вазокон А (Vasocon A). НЕБО (palate) верхняя… …   Медицинские термины

  • naphtazoline — ● naphazoline ou naphtazoline nom féminin Médicament chimique utilisé à l état de nitrate pour son action vasoconstrictrice périphérique et décongestionnante …   Encyclopédie Universelle

  • НАФАЗОЛИН — (naphazoline) сосудосуживающее лекарственное вещество; применяется для устранения заложенное (tm) носа при рините и синусйте. Назначается в каплях в нос; иногда может вызывать слабое раздражение. Торговое название: вазокон А (Vasocon A) …   Толковый словарь по медицине

  • Guanethidine — Systematic (IUPAC) name 2 [2 (azocan 1 yl)ethyl]guanidine Clinical data AHFS/Drugs.com …   Wikipedia


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