Naphazoline

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Naphazoline
Naphazoline.svg
Naphazoline.png
Clinical data
Trade names Clear Eyes, Cleari, Naphcon-A, Rohto
AHFS/Drugs.com Monograph
Routes of
administration 		Ophthalmic drug administration, nasal administration
ATC code
Legal status
Legal status
Identifiers
  • 2-(naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazole
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.011.492 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C14H14N2
Molar mass 210.280 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) Yes check.svgY
  • Key:CNIIGCLFLJGOGP-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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.

Contents

It was patented in 1934 and came into medical use in 1942. [1]

Medical uses

Red eyes can be treated with naphazoline. Bloodshot eye.jpg
Red eyes can be treated with naphazoline.

Nasal administration

Nasal decongestant. [2]

Ophthalmic drug administration

Eye drops (brand names Clear Eyes, and Cleari) narrowing swollen blood vessels (ophthalmic arteries, and ophthalmic veins) to relieve red eye. [2]

Temporary red eye can safely be treated when the cause of the redness is established (e.g. cannabis induced corneal vasodilation) [3] . 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:

Nasal administration

Ophthalmic drug administration

Known side-effect: [5] [6]

Contraindications

Pharmacology

Naphazoline is a mixed α1- and α2-adrenergic receptor agonist. [2]

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, Eucool, and Naphcon-A. [7]

Illicit use

The nasal or ophthalmic form of naphazoline has been abused by heroin or cocaine drug addicts. [8] [9] It's used as CNS stimulant and vasoconstrictor to enhance primary drug effects. [9]

Related Research Articles

<span class="mw-page-title-main">Xylometazoline</span> Nasal decongestant

Xylometazoline, also spelled xylomethazoline, is a medication used to reduce symptoms of nasal congestion, allergic rhinitis, and sinusitis. Use is not recommended for more than seven days. Use is also not recommended in those less than three months of age and some say not less than 6 years of age. It is used directly in the nose as a spray or drops.

A decongestant, or nasal decongestant, is a type of pharmaceutical drug that is used to relieve nasal congestion in the upper respiratory tract. The active ingredient in most decongestants is either pseudoephedrine or phenylephrine. Intranasal corticosteroids can also be used as decongestants and antihistamines can be used to alleviate runny nose, nasal itch, and sneezing.

<span class="mw-page-title-main">Cyclopentolate</span> Pair of enantiomers

Cyclopentolate is a muscarinic antagonist. It is commonly used as an eye drop during pediatric eye examinations to dilate the eye (mydriatic) and prevent the eye from focusing/accommodating (cycloplegic). Cyclopentolate or atropine can also be administered to reverse muscarinic and central nervous system effects of indirect cholinomimetic (anti-AChase) administration.

Topical decongestants are decongestants applied directly to the nasal cavity. Their effectiveness by themselves in the common cold appears to have a small benefit in adults.

<span class="mw-page-title-main">Tetryzoline</span> Chemical compound

Tetryzoline (INN), also known as tetrahydrozoline, is a drug used in some over-the-counter eye drops and nasal sprays. Tetryzoline was patented in 1954, and came into medical use in 1959.

<span class="mw-page-title-main">Phenylephrine</span> Decongestant medication

Phenylephrine is a medication used as a decongestant for uncomplicated nasal congestion, used to dilate the pupil, used to increase blood pressure, and used to relieve hemorrhoids. It can be taken by mouth, as a nasal spray, given by injection into a vein or muscle, or applied to the skin.

<span class="mw-page-title-main">Oxymetazoline</span> Topical decongestant

Oxymetazoline, sold under the brand name Afrin among others, is a topical decongestant and vasoconstrictor medication. It is available over-the-counter as a nasal spray to treat nasal congestion and nosebleeds, as eyedrops to treat eye redness due to minor irritation, and as a prescription topical cream to treat persistent facial redness due to rosacea in adults. Its effects begin within minutes and last for up to six hours. Intranasal use for longer than three days may cause congestion to recur or worsen, resulting in physical dependence. It is estimated that 700,000 people in Norway could be dependent on nasal sprays.

<span class="mw-page-title-main">Betaxolol</span> Chemical compound

Betaxolol is a selective beta1 receptor blocker used in the treatment of hypertension and angina. It is also a adrenergic blocker with no partial agonist action and minimal membrane stabilizing activity. Being selective for beta1 receptors, it typically has fewer systemic side effects than non-selective beta-blockers, for example, not causing bronchospasm as timolol may. Betaxolol also shows greater affinity for beta1 receptors than metoprolol. In addition to its effect on the heart, betaxolol reduces the pressure within the eye. This effect is thought to be caused by reducing the production of the liquid within the eye. The precise mechanism of this effect is not known. The reduction in intraocular pressure reduces the risk of damage to the optic nerve and loss of vision in patients with elevated intraocular pressure due to glaucoma.

<span class="mw-page-title-main">Prazosin</span> Antihypertensive drug

Prazosin, sold under the brand name Minipress among others, is a medication used to treat high blood pressure, symptoms of an enlarged prostate, and nightmares related to post-traumatic stress disorder (PTSD). It is an α1 blocker. It is a less preferred treatment of high blood pressure. Other uses may include heart failure and Raynaud syndrome. It is taken by mouth.

<span class="mw-page-title-main">Rhinitis medicamentosa</span> Medical condition

Rhinitis medicamentosa is a condition of rebound nasal congestion suspected to be brought on by extended use of topical decongestants and certain oral medications that constrict blood vessels in the lining of the nose, although evidence has been contradictory.

<span class="mw-page-title-main">Levomethamphetamine</span> Nasal decongestant and optical isomer of methamphetamine

Levomethamphetamine is the levorotatory (L-enantiomer) form of methamphetamine. Levomethamphetamine is a sympathomimetic vasoconstrictor that is the active ingredient in some over-the-counter (OTC) nasal decongestant inhalers in the United States.

<span class="mw-page-title-main">Emedastine</span> Chemical compound

Emedastine (trade name Emadine) is a second generation antihistamine used in eye drops to alleviate the symptoms of allergic conjunctivitis. It acts as a H1 receptor antagonist. It works by blocking the action of histamine that causes allergic symptoms. It is used in form of the difumarate. The emedastine difumarate is a white, crystalline, water-soluble fine powder. Emedastine eye drops is usually applied twice a day to the affected eye. When the patients with allergic conjunctivitis were treated with 0.05% emedastine difumarate ophthalmic solution for six weeks, the signs and symptoms such as redness, itching and swelling of the eyes were relieved. Emedastine appears to be devoid of effects on adrenergic, dopaminergic and serotonin receptors. This drug was developed by Alcon, which is global medical company specializing in eye care products.

<span class="mw-page-title-main">Tropicamide</span> Chemical compound

Tropicamide, sold under the brand name Mydriacyl among others, is a medication used to dilate the pupil and help with examination of the eye. Specifically it is used to help examine the back of the eye. It is applied as eye drops. Effects occur within 40 minutes and last for up to a day.

<span class="mw-page-title-main">Brimonidine</span> Chemical compound

Brimonidine is an α2 agonist medication used to treat open-angle glaucoma, ocular hypertension, and rosacea. In rosacea it improves the redness. It is used as eye drops or applied to the skin.

<span class="mw-page-title-main">Cyclopentamine</span> Decongestant and stimulant drug

Cyclopentamine is a sympathomimetic alkylamine, classified as a vasoconstrictor. Cyclopentamine was indicated in the past as an over-the-counter (OTC) medication for use as a nasal decongestant, notably in Europe and Australia, but has now been largely discontinued.

<span class="mw-page-title-main">Apraclonidine</span> Chemical compound

Apraclonidine (INN), also known under the brand name Iopidine, is a sympathomimetic used in glaucoma therapy. It is an α2 adrenergic receptor agonist and a weak α1 adrenergic receptor agonist.

<span class="mw-page-title-main">Levobunolol</span> Chemical compound

Levobunolol is a non-selective beta blocker. It is used topically in the form of eye drops to manage ocular hypertension and open-angle glaucoma.

<span class="mw-page-title-main">Ibopamine</span> Chemical compound

Ibopamine is a sympathomimetic drug, designed as a prodrug of epinine, used in ophthalmology. It induces mydriasis. It also has been investigated for use in the treatment of congestive heart failure.

<span class="mw-page-title-main">Antazoline</span> Chemical compound

Antazoline is a 1st generation antihistamine with anticholinergic properties used to relieve nasal congestion and in eye drops, usually in combination with naphazoline, to relieve the symptoms of allergic conjunctivitis. To treat allergic conjunctivitis, antazoline can be combined in a solution with tetryzoline. The drug is a Histamine H1 receptor antagonist: selectively binding to but not activating the receptor, thereby blocking the actions of endogenous histamine and subsequently leading to the temporary relief of the negative symptoms brought on by histamine.

<span class="mw-page-title-main">Tuaminoheptane</span> Sympathomimetic agent

Tuaminoheptane is a sympathomimetic agent and vasoconstrictor which was formerly used as a nasal decongestant. It has also been used as a stimulant.

References

  1. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 552. ISBN   9783527607495.
  2. 1 2 3 Hosten LO, Snyder C (2020). "Over-the-Counter Ocular Decongestants in the United States - Mechanisms of Action and Clinical Utility for Management of Ocular Redness". Clinical Optometry. 12: 95–105. doi: 10.2147/OPTO.S259398 . PMC   7399465 . PMID   32801982.
  3. ↑ Yazulla S (September 2008). "Endocannabinoids in the retina: from marijuana to neuroprotection". Progress in Retinal and Eye Research. 27 (5): 501–526. doi:10.1016/j.preteyeres.2008.07.002. PMC   2584875 . PMID   18725316.
  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): 889–891. doi: 10.1590/S0004-282X2004000500030 . PMID   15476091.
  5. ↑ "Naphazoline - FDA prescribing information, side effects and uses". Drugs.com.
  6. ↑ "naphazoline ophthalmic (eye): Uses, Side Effects, Interactions, Pictures, Warnings & Dosing - WebMD". www.webmd.com.
  7. ↑ Green SM (2008). "Ophthalmology: Naphazoline". Tarascon Pocket Pharmacopoeia 2009. Jones and Bartlett. ISBN   978-0-7637-6572-9.
  8. ↑ van Montfrans GA, van Steenwijk RP, Vyth A, Borst C (1981). "Intravenous naphazoline intoxication". Acta Medica Scandinavica. 209 (5): 429–430. doi:10.1111/j.0954-6820.1981.tb11622.x. PMID   7246278.
  9. 1 2 "Naphazoline abuse". Reactions Weekly. 1815 (1): 251. 2020-08-01. doi:10.1007/s40278-020-81577-1. ISSN   1179-2051. S2CID   195174995.
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