Naphazoline
{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 462258437
| IUPAC_name = 2-(naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazole
| image = Naphazoline.svg
| width = 175
| image2 = Naphazoline.png
| width2 = 175
| tradename = Clear Eyes, Cleari, Naphcon-A, Rohto
| Drugs.com = {{drugs.com|monograph|naphazoline-hydrochloride}}
| pregnancy_category =
| legal_status = otc
| routes_of_administration =Ophthalmic drug administration, nasal administration
| bioavailability =
| metabolism =
| excretion =
| IUPHAR_ligand = 5509
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 835-31-4
| ATC_prefix = R01
| ATC_suffix = AA08
| ATC_supplemental = {{ATC|S01|GA01}}
| PubChem = 4436
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB06711
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4283
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = H231GF11BV
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08253
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 761
| C=14 | H=14 | N=2
| smiles = N\1=C(\NCC/1)Cc2cccc3c2cccc3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = CNIIGCLFLJGOGP-UHFFFAOYSA-N
}}
Naphazoline is a medicine used as a decongestant, and a vasoconstrictor added to eye drops to relieve red eye. It has a rapid action in reducing swelling when applied to mucous membranes. It is a sympathomimetic agent with marked alpha adrenergic activity that acts on alpha-receptors in the arterioles of the conjunctiva to produce constriction, resulting in decreased congestion.
It was patented in 1934 and came into medical use in 1942.{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=552 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA552 |language=en}}
Medical uses
=Nasal administration=
Nasal decongestant.
=Ophthalmic drug administration=
Eye drops (brand names Clear Eyes, and Cleari) narrowing swollen blood vessels (ophthalmic arteries, and ophthalmic veins) to relieve red eye.
Temporary red eye can safely be treated when the cause of the redness is established (e.g. cannabis induced conjunctival vasodilation).{{cite journal | vauthors = Yazulla S | title = Endocannabinoids in the retina: from marijuana to neuroprotection | journal = Progress in Retinal and Eye Research | volume = 27 | issue = 5 | pages = 501–526 | date = September 2008 | pmid = 18725316 | pmc = 2584875 | doi = 10.1016/j.preteyeres.2008.07.002 }} However, continuous use is not recommended without knowing an underlying condition.
Side effects
A few warnings and contraindications that apply to all naphazoline-containing substances intended for medicinal use are:
- Hypersensitivity to naphazoline
- 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
- A possible association with stroke has been suggested.{{cite journal | vauthors = Zavala JA, Pereira ER, Zétola VH, Teive HA, Nóvak EM, Werneck LC | title = Hemorrhagic stroke after naphazoline exposition: case report | journal = Arquivos de Neuro-Psiquiatria | volume = 62 | issue = 3B | pages = 889–891 | date = September 2004 | pmid = 15476091 | doi = 10.1590/S0004-282X2004000500030 | doi-access = free }}
=Nasal administration=
- Extended use may cause rhinitis medicamentosa, a condition of rebound nasal congestion.
=Ophthalmic drug administration=
Known side-effect:{{cite web |title=Naphazoline - FDA prescribing information, side effects and uses |url=https://www.drugs.com/pro/naphazoline.html |website=Drugs.com |language=en}}{{cite web |title=naphazoline ophthalmic (eye): Uses, Side Effects, Interactions, Pictures, Warnings & Dosing - WebMD |url=https://www.webmd.com/drugs/2/drug-5611/naphazoline-ophthalmic-eye/details |website=www.webmd.com |language=en}}
- Stinging
- Discomfort
- Irritation
- Increased red eyes
- Blurred vision
- Mydriasis
- Punctate keratitis
- Lacrimation (tears)
- Increased intraocular pressure
Contraindications
- Patients taking MAO inhibitors can experience a severe hypertensive crisis if given a sympathomimetic drug such as naphazoline HCl
- 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.
Pharmacology
Naphazoline is a mixed α1- and α2-adrenergic receptor agonist.{{cite journal | vauthors = Hosten LO, Snyder C | title = Over-the-Counter Ocular Decongestants in the United States - Mechanisms of Action and Clinical Utility for Management of Ocular Redness | journal = Clinical Optometry | volume = 12 | issue = | pages = 95–105 | date = 2020 | pmid = 32801982 | pmc = 7399465 | doi = 10.2147/OPTO.S259398 | doi-access = free }}
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
It is an active ingredient in several over-the-counter eye drop formulations including Clear Eyes, Rohto Cool, Eucool, and Naphcon-A.{{cite encyclopedia | vauthors = Green SM | year = 2008 | title = Ophthalmology: Naphazoline | encyclopedia = Tarascon Pocket Pharmacopoeia 2009 | publisher = Jones and Bartlett | isbn = 978-0-7637-6572-9 }}
Illicit use
The nasal or ophthalmic form of naphazoline has been abused by heroin or cocaine drug addicts.{{cite journal | vauthors = van Montfrans GA, van Steenwijk RP, Vyth A, Borst C | title = Intravenous naphazoline intoxication | journal = Acta Medica Scandinavica | volume = 209 | issue = 5 | pages = 429–430 | date = 1981 | pmid = 7246278 | doi = 10.1111/j.0954-6820.1981.tb11622.x }}{{Cite journal |date=2020-08-01 |title=Naphazoline abuse |url=https://doi.org/10.1007/s40278-020-81577-1 |journal=Reactions Weekly |language=en |volume=1815 |issue=1 |pages=251 |doi=10.1007/s40278-020-81577-1 |s2cid=195174995 |issn=1179-2051}} It's used as CNS stimulant and vasoconstrictor to enhance primary drug effects.
References
{{Reflist}}
{{Nasal preparations}}
{{Adrenergic receptor modulators}}
{{Phenethylamines}}
Category:Alpha-1 adrenergic receptor agonists