Oxymetazoline

Oxymetazoline
Clinical data
Trade names	Afrin, others
Other names	DA-020; DA020
AHFS/Drugs.com	Monograph
Dependence; liability	Moderate
Routes of; administration	Intranasal, ophthalmic, topical
ATC code	D11AX27 (WHO) ; R01AA05 (WHO), R01AB07 (WHO) (combinations), S01GA04 (WHO);
Legal status
Legal status	UK: General sales list (GSL, OTC); US: OTC / Rx-only;
Pharmacokinetic data
Elimination half-life	5–6 hours
Excretion	Kidney: 30% Bile: 10%
Identifiers
	IUPAC name 3-(4,5-Dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethyl-6-tert-butyl-phenol;
CAS Number	1491-59-4 ;
PubChem CID	4636;
IUPHAR/BPS	124;
DrugBank	DB00935 ;
ChemSpider	4475 ;
UNII	8VLN5B44ZY;
KEGG	D08322 ;
ChEBI	CHEBI:7862 ;
ChEMBL	ChEMBL762 ;
CompTox Dashboard (EPA)	DTXSID3040691 ;
ECHA InfoCard	100.014.618
Chemical and physical data
Formula	C16H24N2O
Molar mass	260.381 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	182 °C (360 °F)
	SMILES Oc1c(c(c(cc1C(C)(C)C)C)CC/2=N/CCN\2)C;
	InChI InChI=1S/C16H24N2O/c1-10-8-13(16(3,4)5)15(19)11(2)12(10)9-14-17-6-7-18-14/h8,19H,6-7,9H2,1-5H3,(H,17,18) ; Key:WYWIFABBXFUGLM-UHFFFAOYSA-N ;
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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.

In 2022, it was the 305th most commonly prescribed medication in the United States, with more than 300,000 prescriptions.