Xylometazoline

Last updated

Xylometazoline
Xylometazoline.svg
Clinical data
Pronunciation /ˌzlˌmɛtəˈzln/
ZY-lo-MET-ə-ZOH-leen
Trade names Otrivin, Otrivine, others
AHFS/Drugs.com Monograph
MedlinePlus a608026
License data
Pregnancy
category
  • C
Dependence
liability
Moderate [1]
Routes of
administration
intranasal (spray or drops)
Drug class α1 and α2 Adrenergic receptor agonist,
Decongestant
ATC code
Legal status
Legal status
Pharmacokinetic data
Elimination half-life 2–3 hours [ citation needed ]
Excretion Urinary
Identifiers
  • 2-[(4-tert-butyl-2,6-dimethylphenyl)methyl]-
    4,5-dihydro-1H-imidazole
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.007.629 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C16H24N2
Molar mass 244.382 g·mol−1
3D model (JSmol)
  • N\1=C(\NCC/1)Cc2c(cc(cc2C)C(C)(C)C)C
  • InChI=1S/C16H24N2/c1-11-8-13(16(3,4)5)9-12(2)14(11)10-15-17-6-7-18-15/h8-9H,6-7,10H2,1-5H3,(H,17,18) Yes check.svgY
  • Key:HUCJFAOMUPXHDK-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Xylometazoline, also spelled xylomethazoline, is a drug used to reduce symptoms of nasal congestion, allergic rhinitis, and sinusitis. [2] Use is not recommended for more than seven days. [3] Use is also not recommended in those less than three months of age and some say not less than 6 years of age. [3] [4] It is used directly in the nose as a spray or drops. [3]

Contents

Side effects include trouble sleeping, irritation of the nose, nausea, nosebleed (3%), period pain (10%) and headache (3%). [5] [2] [3] Long term use (> 10 days) is not recommended due to a rhinitis medicamentosa when stopped. [5] [6] Use is not recommended during pregnancy. [2] Xylometazoline is in the decongestant and alpha-adrenergic agonist families of medication. [6] [7]

One study classified it with selectivity ratios in alpha 2 adrenergic receptors of 151 for a2A vs a2B, 4.5 a2A vs a2C, and 33.9 a2B vs a2C.  Making it a highly selective a2A agonist. [8]

Xylometazoline was patented in 1956 and came into medical use in 1959. [9] [10] It is on the World Health Organization's List of Essential Medicines. [4] [11] Xylometazoline is available as a generic medication. [3]

Mechanism of action

The drug works by stimulating adrenergic receptors on the lamina propria of blood vessels in the nose. The decongestant effect is due to constriction of large veins in the nose which swell up during the inflammation of any infection or allergy of the nose. The smaller arteries are also constricted and this causes the colour of the nasal epithelium to be visibly paler after dosage.

Xylometazoline is an imidazole derivative which is designed to mimic the molecular shape of adrenaline. It binds to α1 and α2 adrenergic receptors [12] in the nasal mucosa. Due to its sympathomimetic effects, it should not be used by people with high blood pressure, or other heart problems.

Extended usage of xylometazoline can result in decreased effectiveness or a buildup of tolerance against the drug. [13] The number of receptors decreases, and when the administration of the drug is ceased, chronic congestion can occur; this is called rhinitis medicamentosa, commonly referred to as rebound congestion. Moreover, long-term overdosing can cause degenerative changes in nasal mucous membranes that pose another health problem.[ citation needed ]

Society and culture

Brand names

The most common name for over-the-counter products containing xylometazoline internationally is "Otrivin" (used in Australia, [14] Canada, Estonia, Finland, Greece, Hungary, India, [15] Israel, Jordan, Netherlands, New Zealand, Norway, Poland, South Africa, Egypt, Sweden, Vietnam, Hong Kong), "Otrivine" (United Kingdom, Ireland, Turkey, Belgium), or "Otriven" (Germany). A product marketed as "Otrivin Oxy" contains oxymetazoline instead of xylometazoline.

Other product names used include Antazol (Square, in Bangladesh), Xylomet (Opsonin, Bangladesh), Cirovin, Klarigen (in Denmark), Nasolin (in Finland), Neo-Rinoleina, Novorin, Olynth, Otrinoz, Galazolin (Russia, Ukraine, Belarus), Nasomist-X, Otrix, Rhinoset, Zenfresh, Naphthyzinium, Xymelyn (in Latvia), Sinutab Nasal Spray, Snup akut, Sudafed, Xylo-COMOD, Xylolin (in the United Arab Emirates), Xylovit, Olynth (in Serbia, the Czech Republic, Lithuania and Slovakia), Meralys (in Croatia) Xynosine (in Pakistan, Afghanistan, Kyrgyzstan and Kazakhstan), Xymelin, Zymelin, Xylostar, Xylorin (in Poland), Nasobol, Xylo Mepha and others (Switzerland), Decozal (in Jordan), Nasic, Orinox (Romania), Narhimed (Italy), nasa Rhinathiol (Belgium), Zolinol, Nasorhinathiol, and Vibrocil (Portugal).

In 2021, a U.S. FDA Drug Safety Communication stated that, while a U.S. Consumer Product Safety Commission (CPSC) proposed rule regarding child-resistant packaging covered products containing xylometazoline, no such products were marketed in the United States at that time. [16]

Formulations

The standard adult solution strength is 0.1%  w/v xylometazoline (or 1 mg per 1 mL solution), and the dose for children under 12 is usually 0.05% (0.5 mg/mL). [17]

Related Research Articles

<span class="mw-page-title-main">Allergic rhinitis</span> Nasal inflammation due to allergens in the air

Allergic rhinitis, of which the seasonal type is called hay fever, is a type of inflammation in the nose that occurs when the immune system overreacts to allergens in the air. Signs and symptoms include a runny or stuffy nose, sneezing, red, itchy, and watery eyes, and swelling around the eyes. The fluid from the nose is usually clear. Symptom onset is often within minutes following allergen exposure, and can affect sleep and the ability to work or study. Some people may develop symptoms only during specific times of the year, often as a result of pollen exposure. Many people with allergic rhinitis also have asthma, allergic conjunctivitis, or atopic dermatitis.

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">Rhinitis</span> Irritation and inflammation of the mucous membrane inside the nose

Rhinitis, also known as coryza, is irritation and inflammation of the mucous membrane inside the nose. Common symptoms are a stuffy nose, runny nose, sneezing, and post-nasal drip.

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">Ipratropium bromide</span> Type of anticholinergic

Ipratropium bromide, sold under the trade name Atrovent among others, is a type of anticholinergic medication which is applied by different routes: inhaler, nebulizer, or nasal spray, for different reasons.

<span class="mw-page-title-main">Nasal spray</span> Spray that delivers medications locally in the nasal cavities or systemically

Nasal sprays are used to deliver medications locally in the nasal cavities or systemically. They are used locally for conditions such as nasal congestion and allergic rhinitis. In some situations, the nasal delivery route is preferred for systemic therapy because it provides an agreeable alternative to injection or pills. Substances can be assimilated extremely quickly and directly through the nose. Many pharmaceutical drugs exist as nasal sprays for systemic administration. Other applications include hormone replacement therapy, treatment of Alzheimer's disease and Parkinson's disease. Nasal sprays are seen as a more efficient way of transporting drugs with potential use in crossing the blood–brain barrier.

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

Phenylephrine, sold under the brand names Neosynephrine and Sudafed PE among numerous others, 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, applied to the skin, or as a rectal suppository.

<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 eye drops 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.

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

Olopatadine, sold under the brand name Patanol among others, is an antihistamine medication used to decrease the symptoms of allergic conjunctivitis and allergic rhinitis. It is used as eye drops or as a nasal spray. The eye drops generally result in an improvement within half an hour.

<span class="mw-page-title-main">Nasal congestion</span> Partial or complete blockage of nasal passages

Nasal congestion is the partial or complete blockage of nasal passages, leading to impaired nasal breathing, usually due to membranes lining the nose becoming swollen from inflammation of blood vessels.

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

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.

<span class="mw-page-title-main">Triamcinolone acetonide</span> Medicinal chemical compound, steroid

Triamcinolone acetonide, sold under the brand name Kenalog among others, is a synthetic corticosteroid medication used topically to treat various skin conditions, to relieve the discomfort of mouth sores, and by injection into joints to treat various joint conditions. It is also injected into lesions to treat inflammation in some parts of the body, particularly the skin. In nasal spray form, it is used to treat allergic rhinitis. It is used for the treatment of macular edema associated with uveitis. It is a more potent derivative of triamcinolone, and is about eight times as potent as prednisone.

<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">Alpha-2 adrenergic receptor</span> Protein family

The alpha-2 (α2) adrenergic receptor is a G protein-coupled receptor (GPCR) associated with the Gi heterotrimeric G-protein. It consists of three highly homologous subtypes, including α2A-, α2B-, and α2C-adrenergic. Some species other than humans express a fourth α2D-adrenergic receptor as well. Catecholamines like norepinephrine (noradrenaline) and epinephrine (adrenaline) signal through the α2-adrenergic receptor in the central and peripheral nervous systems.

<span class="mw-page-title-main">Alpha-adrenergic agonist</span> Class of drugs

Alpha-adrenergic agonists are a class of sympathomimetic agents that selectively stimulates alpha adrenergic receptors. The alpha-adrenergic receptor has two subclasses α1 and α2. Alpha 2 receptors are associated with sympatholytic properties. Alpha-adrenergic agonists have the opposite function of alpha blockers. Alpha adrenoreceptor ligands mimic the action of epinephrine and norepinephrine signaling in the heart, smooth muscle and central nervous system, with norepinephrine being the highest affinity. The activation of α1 stimulates the membrane bound enzyme phospholipase C, and activation of α2 inhibits the enzyme adenylate cyclase. Inactivation of adenylate cyclase in turn leads to the inactivation of the secondary messenger cyclic adenosine monophosphate and induces smooth muscle and blood vessel constriction.

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

Amidephrine, or amidefrine, sold under the brand name Fentrinol among others, is a selective α1-adrenergic receptor agonist which is described as an adrenergic or sympathomimetic, vasoconstrictor, and topical nasal decongestant used to treat allergic rhinitis. It is used as the mesylate salt, which has the generic names amidefrine mesilate and amidephrine mesylate. The drug is a substituted phenethylamine derivative and is also known as 3-methylsulfonamidyl-β-hydroxy-N-methylphenethylamine. As of 2000, it remained marketed only in Austria.

Mirabegron, sold under the brand name Myrbetriq among others, is a medication used to treat overactive bladder. Its benefits are similar to antimuscarinic medication such as solifenacin or tolterodine. It is taken by mouth.

Nonallergic rhinitis is rhinitis—inflammation of the inner part of the nose—not caused by an allergy. Nonallergic rhinitis displays symptoms including chronic sneezing or having a congested, drippy nose, without an identified allergic reaction with allergy testing being normal. Other common terms for nonallergic rhinitis are vasomotor rhinitis and perennial rhinitis. The prevalence of nonallergic rhinitis in otolaryngology is 40%. Allergic rhinitis is more common than nonallergic rhinitis; however, both conditions have similar presentation, manifestation and treatment. Nasal itching and paroxysmal sneezing are usually associated with nonallergic rhinitis rather than allergic rhinitis. Other symptoms that are more specific to non-allergic rhinitis include ear plugging or discomfort with eustachian tube dysfunction, headaches, sinus pressure, and muffled hearing. Common triggers for non-allergic rhinitis include irritants such as tobacco smoke, cleaning agents, or abrupt changes in ambient temperature.

<span class="mw-page-title-main">Epinephrine (medication)</span> Hormone used as a medicine

Epinephrine, also known as adrenaline, is a medication and hormone. As a medication, it is used to treat several conditions, including anaphylaxis, cardiac arrest, asthma, and superficial bleeding. Inhaled epinephrine may be used to improve the symptoms of croup. It may also be used for asthma when other treatments are not effective. It is given intravenously, by injection into a muscle, by inhalation, or by injection just under the skin.

Anti-allergic agents are medications used to treat allergic reactions. Anti-allergic agents have existed since 3000 B.C in countries such as China and Egypt. It was not until 1933 when antihistamines, the first type of anti-allergic agents, were developed. Common allergic diseases include allergic rhinitis, allergic asthma and atopic dermatitis with varying symptoms, including runny nose, watery eyes, itchiness, coughing, and shortness of breath. More than one-third of the world's population is currently being affected by one or more allergic conditions.

References

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