Structure via PubChem · Public domain (PubChem)
oxymetazoline
Sign in to saveAlso known as Afrin®, oxymethazoline, SCH-9384, Vicks Sinex®, Afrin, 6-t-butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenol, 2-(4-tert-butyl-2,6-dimethyl-3-hydroxybenzyl)-2-imidazoline, 6-tert-butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenol
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 (in the United States) 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 to five days may cause congestion to recur or worsen, resulting in physical dependence. Fluticasone propionate
Key facts
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 462267467
- Drug.image
- Oxymetazoline.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 200
- Drug.tradename
- Afrin, others
- Drug.dependency_liability
- Moderate
- Drug.routes_of_administration
- Intranasal, ophthalmic, topical
- Drug.ATC_prefix
- D11
- Drug.ATC_suffix
- AX27
- Drug.ATC_supplemental
- , (combinations),
- Drug.legal_UK
- GSL
- Drug.legal_US
- OTC
- Drug.legal_US_comment
- / Rx-only
- Drug.elimination_half life
- 5–6 hours
- Drug.excretion
- Kidney: 30% Bile: 10%
- Drug.CAS_number
- 1491-59-4
via Wikipedia infobox
Chemical data
- Formula
- C16H24N2O
- Molecular weight
- 260.37 g/mol
- IUPAC name
- 6-tert-butyl-3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethylphenol
- SMILES
- CC1=CC(=C(C(=C1CC2=NCCN2)C)O)C(C)(C)C
- InChIKey
- WYWIFABBXFUGLM-UHFFFAOYSA-N
- XLogP
- 2.9
- Polar surface area
- 44.6 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
1,241 papersvia PubMed
Wikidata facts
- Mass
- 260.188863
Show 5 more facts
- canonical SMILES
- CC1=CC(=C(C(=C1CC2=NCCN2)C)O)C(C)(C)C
- chemical formula
- C₁₆H₂₄N₂O
- World Health Organisation international non-proprietary name
- oxymetazoline
- Commons category
- Oxymetazoline
- defined daily dose
- 0.4
via Wikidata · CC0
~6 min read
Article
15 sectionsContents
- Medical uses
- Side effects
- Rebound congestion
- Nosebleeds
- Australian regulatory submission
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- History
- Society and culture
- Brand names
- Research
- Hair loss
- See also
- References
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 (in the United States) 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 to five days may cause congestion to recur or worsen, resulting in physical dependence. Fluticasone propionate (Flonase) and other intranasal glucocorticoids are known to treat oxymetazoline dependence.
Oxymetazoline is a derivative of imidazole. It was developed from xylometazoline at Merck by Wolfgang Fruhstorfer and Helmut Müller-Calgan in 1961. A direct sympathomimetic, oxymetazoline binds to and activates α1 adrenergic receptors and α2 adrenergic receptors, most notably.