Oxymetazoline

Oxymetazoline

Clinical data
Trade names	Afrin, Ocuclear, Drixine
AHFS/Drugs.com	Monograph
Pregnancy category	C
Dependence liability	Moderate
Routes of administration	Intranasal
ATC code	R01AA05 (WHO) R01AB07 (WHO) (combinations), S01GA04 (WHO)
Legal status
Legal status	UK: General sales list (GSL, OTC) US: OTC
Pharmacokinetic data
Metabolism	Kidney (30%), fecal (10%)
Biological half-life	5–6 hours
Identifiers
IUPAC name 3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethyl-6-tert-butyl-phenol
CAS Number	1491-59-4 Y
PubChem CID	4636
IUPHAR/BPS	124
DrugBank	DB00935 Y
ChemSpider	4475 Y
UNII	8VLN5B44ZY
KEGG	D08322 Y
ChEBI	CHEBI:7862 N
ChEMBL	CHEMBL762 Y
ECHA InfoCard	100.014.618
Chemical and physical data
Formula	C16H24N2O
Molar mass	260.375 g·mol−1
3D model (Jmol)	Interactive image
Melting point	301.5 °C (574.7 °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) Y Key:WYWIFABBXFUGLM-UHFFFAOYSA-N Y
NY (what is this?)

Oxymetazoline is a selective α₁ adrenergic receptor agonist and α₂ adrenergic receptor partial agonist. It is a topical decongestant, used in the form of oxymetazoline hydrochloride. It was developed from xylometazoline at E. Merck Darmstadt by Fruhstorfer in 1961. Oxymetazoline is generally available as a nasal spray.

Oxymetazoline is available over-the-counter as a topical decongestant in the form of oxymetazoline hydrochloride in nasal sprays such as Afrin, Operil, Dristan, Dimetapp, oxyspray, Facimin, Nasivin, Nostrilla, Sudafed OM, Vicks Sinex, Zicam, SinuFrin, and Mucinex Full Force.

Due to its vasoconstricting properties, oxymetazoline is also used to treat nose bleeds and eye redness due to minor irritation (marketed as Visine L.R. in the form of eye drops).

It is recommended that oxymetazoline not be used for more than three days, as rebound congestion, or rhinitis medicamentosa, may occur. Patients who continue to use oxymetazoline beyond this point may become dependent on the medication to relieve their chronic congestion.

Some studies have found that benzalkonium chloride, a common additive to oxymetazoline nasal sprays, may damage nasal epithelia and exacerbate rhinitis medicamentosa. However, the majority of studies find benzalkonium chloride to be a safe preservative.

The Food and Drug Administration places oxymetazoline in category C, indicating risk to the fetus cannot be ruled out. While it has been shown that a single dose does not significantly alter either maternal or fetal circulation, this subject has not been studied extensively enough to draw reliable conclusions.