2-(4-Tert-butyl-2,6-dimethyl-3-hydroxybenzyl)-2-imidazoline
3-[(4,5-dihydro-1H-Imidazol-2-yl)methyl]-6-(1,1-dimethylethyl)-2,4-dimethylphenol
6-t-Butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenol
6-Tert-butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenol
Oximetazolinum
Oxymetazolina
Oxymetazolinum
Oxymethazoline
Oxymetozoline

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Oxymetazoline hydrochloride	K89MJ0S5VY	2315-02-8	BEEDODBODQVSIM-UHFFFAOYSA-N

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Clirol Nasal Spray	Spray	0.5 %	Nasal	Complex Pharma Inc.	Not applicable	Not applicable
Rhofade	Cream	10 mg/g	Topical	Allergan	2017-01-18	Not applicable

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
12 Hour Nasal	Spray	.05 g/100mL	Nasal	Select Brands Distributors	2000-03-01	Not applicable
12 Hour Nasal	Spray	.05 g/100mL	Nasal	Altaire Pharmaceuticals Inc.	2001-06-01	Not applicable
12 Hour Nasal	Spray	.05 g/100mL	Nasal	Healthlife of Usa	2018-01-02	Not applicable
12 Hour Nasal	Spray	.05 g/100mL	Nasal	Meijer Distribution	2015-05-06	Not applicable
12 Hour Original Nasal Decongestant	Liquid	50 mg/100mL	Nasal	Faria Llc Dba Sheffield Pharmaceutcials	2014-05-30	Not applicable
12 Hour Original Nasal Decongestant	Liquid	50 mg/100mL	Nasal	Preferreed Pharmaceuticals Inc.	2018-01-02	Not applicable
7 Select Nasal	Spray	.05 g/100mL	Nasal	7 Eleven	2014-08-05	Not applicable
7 Select Original Nasal	Spray	.05 g/mL	Nasal	7 Eleven	2016-10-04	Not applicable
Afrin	Spray	.5 mg/mL	Topical	Navajo Manuracturing Company	2017-12-04	Not applicable
Afrin Cold	Spray	0.05 mg	Nasal	Schering Plough	2002-09-28	2006-08-01

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Kovanaze	Oxymetazoline hydrochloride (.5 mg/mL) + Tetracaine hydrochloride (30 mg/mL)	Spray	Nasal	St. Renatus	2016-09-01	Not applicable

International/Other Brands

Afrin / Dristan 12-Hour / Duramist Plus / Genasal Nasal Spray Up to 12 Hour Relief / Iliadin / Neo-Synephrine 12 Hour Spray / Nezeril / Nostrilla 12 Hour Nasal Decongestant / OcuClear / Vicks Sinex 12 Hour Nasal Spray / Vicks Sinex 12 Hour Ultra Fine Mist for Sinus Relief

Categories

UNII

8VLN5B44ZY

CAS number

1491-59-4

Weight

Average: 260.3746
Monoisotopic: 260.1888634

Chemical Formula

C₁₆H₂₄N₂O

InChI Key

WYWIFABBXFUGLM-UHFFFAOYSA-N

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)

IUPAC Name

6-tert-butyl-3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethylphenol

SMILES

CC1=CC(=C(O)C(C)=C1CC1=NCCN1)C(C)(C)C

Pharmacology

Indication

For treatment of nasal congestion and redness associated with minor irritations of the eye

Structured Indications

Pharmacodynamics

Oxymetazoline a adrenergic alpha-agonists, direct acting sympathomimetic used as a vasoconstrictor to relieve nasal congestion The sympathomimetic action of oxymetazoline constricts the smaller arterioles of the nasal passages, producing a prolonged (up to 12 hours), gentle and decongesting effect. Oxymetazoline elicits relief of conjunctival hyperemia by causing vasoconstriction of superficial conjunctival blood vessels. The drug's action has been demonstrated in acute allergic conjunctivitis and in chemical (chloride) conjunctivitis.

Mechanism of action

Oxymetazoline is a direct acting sympathomimetic amine, which acts on alpha-adrenergic receptors in the arterioles of the conjunctiva and nasal mucosa. It produces vasoconstriction, resulting in decreased conjunctival congestion in ophthalmic. In nasal it produces constriction, resulting in decreased blood flow and decreased nasal congestion.

Target	Actions	Organism
AAlpha-1A adrenergic receptor	agonist	Human
AAlpha-2A adrenergic receptor	agonist	Human
UAlpha-2C adrenergic receptor	agonist	Human
UAlpha-2B adrenergic receptor	binder	Human
UAlpha-1B adrenergic receptor	agonist	Human
UAlpha-1D adrenergic receptor	agonist	Human

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half life

Not Available

Clearance

Not Available

Toxicity

Not Available

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction	Drug group
Acebutolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Acebutolol.	Approved, Investigational
Alfuzosin	Alfuzosin may decrease the vasoconstricting activities of Oxymetazoline.	Approved, Investigational
Alprenolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Alprenolol.	Approved, Withdrawn
Amineptine	Amineptine may decrease the antihypertensive activities of Oxymetazoline.	Illicit, Withdrawn
Amitriptyline	Amitriptyline may decrease the antihypertensive activities of Oxymetazoline.	Approved
Amoxapine	Amoxapine may decrease the antihypertensive activities of Oxymetazoline.	Approved
Amphetamine	The risk or severity of adverse effects can be increased when Amphetamine is combined with Oxymetazoline.	Approved, Illicit, Investigational
Arotinolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Arotinolol.	Investigational
Atenolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Atenolol.	Approved
Atomoxetine	Atomoxetine may increase the hypertensive activities of Oxymetazoline.	Approved
Befunolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Befunolol.	Experimental
Benzphetamine	The risk or severity of adverse effects can be increased when Benzphetamine is combined with Oxymetazoline.	Approved, Illicit
Benzylpenicilloyl Polylysine	Oxymetazoline may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.	Approved
Betaxolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Betaxolol.	Approved, Investigational
Bevantolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Bevantolol.	Approved
Bisoprolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Bisoprolol.	Approved
Bopindolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Bopindolol.	Approved
Bromocriptine	Bromocriptine may increase the hypertensive and vasoconstricting activities of Oxymetazoline.	Approved, Investigational
Bucindolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Bucindolol.	Investigational
Bufuralol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Bufuralol.	Experimental, Investigational
Bunazosin	Bunazosin may decrease the vasoconstricting activities of Oxymetazoline.	Investigational
Bupranolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Bupranolol.	Approved
Cabergoline	Cabergoline may increase the hypertensive and vasoconstricting activities of Oxymetazoline.	Approved
Carteolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Carteolol.	Approved
Carvedilol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Carvedilol.	Approved, Investigational
Celiprolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Celiprolol.	Approved, Investigational
Chlorphentermine	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Chlorphentermine.	Illicit, Withdrawn
Clenbuterol	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Clenbuterol.	Approved, Investigational, Vet Approved
Clomipramine	Clomipramine may decrease the antihypertensive activities of Oxymetazoline.	Approved, Investigational, Vet Approved
Cloranolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Cloranolol.	Experimental
Cyclobenzaprine	Cyclobenzaprine may decrease the antihypertensive activities of Oxymetazoline.	Approved
Desipramine	Desipramine may decrease the antihypertensive activities of Oxymetazoline.	Approved, Investigational
Desvenlafaxine	Desvenlafaxine may increase the tachycardic activities of Oxymetazoline.	Approved, Investigational
Dibenzepin	Dibenzepin may decrease the antihypertensive activities of Oxymetazoline.	Experimental
Dihydroergotamine	Dihydroergotamine may increase the hypertensive and vasoconstricting activities of Oxymetazoline.	Approved, Investigational
Dobutamine	The risk or severity of adverse effects can be increased when Dobutamine is combined with Oxymetazoline.	Approved
Dopamine	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Dopamine.	Approved
Dosulepin	Dosulepin may decrease the antihypertensive activities of Oxymetazoline.	Approved
Doxazosin	Doxazosin may decrease the vasoconstricting activities of Oxymetazoline.	Approved
Doxepin	Doxepin may decrease the antihypertensive activities of Oxymetazoline.	Approved, Investigational
Doxofylline	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Doxofylline.	Approved, Investigational
Dronabinol	Dronabinol may increase the tachycardic activities of Oxymetazoline.	Approved, Illicit
Duloxetine	Duloxetine may increase the tachycardic activities of Oxymetazoline.	Approved
Epanolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Epanolol.	Experimental
Ephedrine	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Ephedrine.	Approved
Epinephrine	The risk or severity of adverse effects can be increased when Epinephrine is combined with Oxymetazoline.	Approved, Vet Approved
Ergoloid mesylate	Ergoloid mesylate may increase the hypertensive and vasoconstricting activities of Oxymetazoline.	Approved
Ergonovine	Ergonovine may increase the hypertensive and vasoconstricting activities of Oxymetazoline.	Approved
Ergotamine	Ergotamine may increase the hypertensive and vasoconstricting activities of Oxymetazoline.	Approved
Esmirtazapine	Esmirtazapine may decrease the antihypertensive activities of Oxymetazoline.	Investigational
Esmolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Esmolol.	Approved
Etilefrine	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Etilefrine.	Withdrawn
Fenoterol	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Fenoterol.	Approved, Investigational
Fenozolone	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Fenozolone.	Experimental
Hyaluronidase	Hyaluronidase may increase the vasoconstricting activities of Oxymetazoline.	Approved, Investigational
Hydroxyamphetamine	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Hydroxyamphetamine.	Approved
Imipramine	Imipramine may decrease the antihypertensive activities of Oxymetazoline.	Approved
Indenolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Indenolol.	Withdrawn
Indoramin	Indoramin may decrease the vasoconstricting activities of Oxymetazoline.	Withdrawn
Iobenguane	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Oxymetazoline.	Approved, Investigational
Iprindole	Iprindole may decrease the antihypertensive activities of Oxymetazoline.	Experimental
Isoprenaline	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Isoprenaline.	Approved, Investigational
Isoxsuprine	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Isoxsuprine.	Approved, Withdrawn
Labetalol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Labetalol.	Approved
Landiolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Landiolol.	Investigational
Levomilnacipran	Levomilnacipran may increase the tachycardic activities of Oxymetazoline.	Approved, Investigational
Linezolid	Linezolid may increase the hypertensive activities of Oxymetazoline.	Approved, Investigational
Lofepramine	Lofepramine may decrease the antihypertensive activities of Oxymetazoline.	Experimental
Mefenorex	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Mefenorex.	Experimental
Mephentermine	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Mephentermine.	Approved
Mepindolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Mepindolol.	Experimental
Metaraminol	The risk or severity of adverse effects can be increased when Metaraminol is combined with Oxymetazoline.	Approved, Investigational
Methamphetamine	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Methamphetamine.	Approved, Illicit
Methoxamine	The risk or severity of adverse effects can be increased when Methoxamine is combined with Oxymetazoline.	Approved, Investigational
Methylergometrine	Methylergometrine may increase the hypertensive and vasoconstricting activities of Oxymetazoline.	Approved
Metoprolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Metoprolol.	Approved, Investigational
Mianserin	The therapeutic efficacy of Oxymetazoline can be decreased when used in combination with Mianserin.	Approved, Investigational
Midodrine	The risk or severity of adverse effects can be increased when Midodrine is combined with Oxymetazoline.	Approved
Milnacipran	Milnacipran may increase the tachycardic activities of Oxymetazoline.	Approved, Investigational
Mirtazapine	Mirtazapine may decrease the antihypertensive activities of Oxymetazoline.	Approved
Nabilone	Nabilone may increase the tachycardic activities of Oxymetazoline.	Approved, Investigational
Nadolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Nadolol.	Approved
Nebivolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Nebivolol.	Approved, Investigational
Norepinephrine	The risk or severity of adverse effects can be increased when Norepinephrine is combined with Oxymetazoline.	Approved
Nortriptyline	Nortriptyline may decrease the antihypertensive activities of Oxymetazoline.	Approved
Nylidrin	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Nylidrin.	Approved
Opipramol	Opipramol may decrease the antihypertensive activities of Oxymetazoline.	Investigational
Orciprenaline	The risk or severity of adverse effects can be increased when Orciprenaline is combined with Oxymetazoline.	Approved
Oxprenolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Oxprenolol.	Approved
Patent Blue	The therapeutic efficacy of Oxymetazoline can be decreased when used in combination with Patent Blue.	Approved
Penbutolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Penbutolol.	Approved, Investigational
Phenmetrazine	The risk or severity of adverse effects can be increased when Phenmetrazine is combined with Oxymetazoline.	Approved, Illicit
Phentermine	The risk or severity of adverse effects can be increased when Phentermine is combined with Oxymetazoline.	Approved, Illicit
Phenylephrine	The risk or severity of adverse effects can be increased when Phenylephrine is combined with Oxymetazoline.	Approved
Phenylpropanolamine	The risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Oxymetazoline.	Approved, Vet Approved, Withdrawn
Pindolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Pindolol.	Approved, Investigational
Platelet Activating Factor	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Platelet Activating Factor.	Experimental
Practolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Practolol.	Approved
Prazosin	Prazosin may decrease the vasoconstricting activities of Oxymetazoline.	Approved
Prenalterol	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Prenalterol.	Experimental
Procaterol	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Procaterol.	Approved, Investigational
Propranolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Propranolol.	Approved, Investigational
Protriptyline	Protriptyline may decrease the antihypertensive activities of Oxymetazoline.	Approved
Pseudoephedrine	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Pseudoephedrine.	Approved
Racepinephrine	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Racepinephrine.	Approved
Ritodrine	The risk or severity of adverse effects can be increased when Ritodrine is combined with Oxymetazoline.	Approved, Investigational
Silodosin	Silodosin may decrease the vasoconstricting activities of Oxymetazoline.	Approved
Sotalol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Sotalol.	Approved
Spironolactone	Spironolactone may decrease the vasoconstricting activities of Oxymetazoline.	Approved
Synephrine	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Synephrine.	Experimental
Talinolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Talinolol.	Investigational
Tamsulosin	Tamsulosin may decrease the vasoconstricting activities of Oxymetazoline.	Approved, Investigational
Tedizolid Phosphate	Tedizolid Phosphate may increase the hypertensive activities of Oxymetazoline.	Approved
Terazosin	Terazosin may decrease the vasoconstricting activities of Oxymetazoline.	Approved
Terbutaline	The risk or severity of adverse effects can be increased when Terbutaline is combined with Oxymetazoline.	Approved
Tertatolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Tertatolol.	Experimental
Tetryzoline	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Tetryzoline.	Approved
Tianeptine	Tianeptine may decrease the antihypertensive activities of Oxymetazoline.	Approved, Investigational
Timolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Timolol.	Approved
Tramazoline	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Tramazoline.	Investigational
Tretoquinol	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Tretoquinol.	Experimental
Trimazosin	Trimazosin may decrease the vasoconstricting activities of Oxymetazoline.	Experimental
Trimipramine	Trimipramine may decrease the antihypertensive activities of Oxymetazoline.	Approved
Tyramine	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Tyramine.	Investigational, Nutraceutical
Urapidil	Urapidil may decrease the vasoconstricting activities of Oxymetazoline.	Investigational
Venlafaxine	Venlafaxine may increase the tachycardic activities of Oxymetazoline.	Approved

Food Interactions

Not Available

References

General References

Not Available

External Links

Human Metabolome Database: HMDB0015070
KEGG Compound: C07363
PubChem Compound: 4636
PubChem Substance: 46505622
ChemSpider: 4475
BindingDB: 30712
ChEBI: 7862
ChEMBL: CHEMBL762
Therapeutic Targets Database: DAP000235
PharmGKB: PA164748840
IUPHAR: 124
Guide to Pharmacology: GtP Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Oxymetazoline

ATC Codes

R01AA05 — Oxymetazoline

R01AB07 — Oxymetazoline

S01GA04 — Oxymetazoline

AHFS Codes

52:32.00 — Vasoconstrictors

MSDS

Download (74.6 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Completed	Not Available	Autonomic Failure / Idiopathic orthostatic hypotension	1
1	Completed	Basic Science	Anaesthesia therapy	1
1	Completed	Basic Science	Acute Rhinitis	1
1	Completed	Treatment	Allergic Rhinitis (AR)	2
1	Completed	Treatment	Assess Pharmacokinetics of Ketorolac Tromethamine Intranasal and Assess Effects of a Oxymetazoline Hydrochloride on the PK of Ketorolac Tromethamine / Healthy Volunteers	1
1, 2	Completed	Treatment	Incontinence, Fecal / Spinal Cord Injuries (SCI)	1
2	Completed	Prevention	Conjunctivitis, Seasonal Allergic	1
2	Completed	Treatment	Allergic Rhinitis (AR)	1
2	Completed	Treatment	Anaesthesia therapy	3
2	Completed	Treatment	Seasonal Allergic Rhinitis (SAR)	1
2	Withdrawn	Treatment	Anesthesia, Dental / Intranasal Drug Administration / Nasal Surgical Procedures	1
3	Completed	Treatment	Anaesthesia therapy	3
3	Completed	Treatment	Erythemas / Rosaceas	2
3	Completed	Treatment	Herpes Simplex Labialis	1
3	Recruiting	Treatment	Nasal Stuffiness / Rhinitis	1
3	Recruiting	Treatment	Rosaceas	1
3	Terminated	Treatment	Anaesthesia therapy	1
4	Completed	Treatment	Adenoidal Hypertrophy	1
4	Completed	Treatment	Allergic Rhinitis (AR)	1
4	Completed	Treatment	Nasal Obstruction Present Finding	1
4	Not Yet Recruiting	Other	Local Anesthetic Drug Adverse Reaction / Local Infiltration / Pulp Disease, Dental	1
4	Not Yet Recruiting	Treatment	Chronic Nasal Congestion / Sleep Apnea Syndrome	1
4	Recruiting	Treatment	Rosaceas	1
4	Withdrawn	Treatment	Allergic Rhinitis (AR) / Rhinitis Medicamentosa / Tachyphylaxis	1
Not Available	Completed	Treatment	Adenoidectomy / Functional Endoscopic Sinus Surgery (FESS) / Turbinate Surgery	1
Not Available	Completed	Treatment	Blood Pressures / Nasal Bleeding	1
Not Available	Completed	Treatment	Nasal Obstruction	1
Not Available	Recruiting	Basic Science	Middle Ear Disease / Nasal Allergies	1
Not Available	Terminated	Treatment	Chronic Rhinitis	1

Pharmacoeconomics

Manufacturers

Schering plough healthcare products inc
Johnson and johnson group consumer companies

Packagers

Altaire Pharmaceuticals
Bayer Healthcare
Chain Drug
CVS Pharmacy
Palmetto Pharmaceuticals Inc.
Perrigo Co.
Pfizer Inc.
S&P Healthcare
Spectrum Pharmaceuticals
Target Corp.
Walgreen Co.
Wyeth Pharmaceuticals

Dosage forms

Form	Route	Strength
Liquid	Nasal	50 mg/100mL
Spray	Topical	.5 mg/mL
Spray	Nasal	0.05 mg
Spray, metered	Nasal	.05 g/100mL
Spray, metered	Nasal	.05 mg/mL
Spray	Nasal	.05 g/100mL
Spray	Nasal	.05 mg/100mL
Spray	Nasal	.2 mg/.4mL
Spray	Nasal	.5 mg/mL
Spray	Nasal	0.5 %
Spray	Nasal	.0005 g/mL
Spray	Nasal
Spray	Nasal	.05 mg/100mg
Liquid	Nasal	0.05 %
Spray	Nasal	0.05 %
Solution	Nasal	.5 mg/mL
Solution	Nasal	.05 g/100mL
Solution	Nasal	.05 mg/100mL
Solution / drops; spray	Nasal	.025 %
Spray	Nasal	5 g/100mL
Spray	Nasal	.05 mg/mL
Liquid	Topical	.05 g/100mL
Spray, metered	Nasal	.0005 mL/100mL
Solution / drops	Ophthalmic	.25 mg
Spray, metered	Nasal	0.05 %
Spray	Oral	.5 mg/mL
Spray, metered	Nasal	.2 mg/.4mL
Spray, metered	Nasal	.5 mg/mL
Cream	Topical	10 mg/g
Spray	Nasal	7.5 mg/15mL
Spray	Nasal	50 mg/100mL
Spray	Nasal	.512 mg/mL
Spray	Nasal	.0005055 g/mL
Spray	Nasal	.000512 g/mL
Spray	Nasal	.0005095 g/mL
Liquid	Nasal	.05 %
Spray	Nasal	.05 g/mL
Liquid	Ophthalmic	.25 mg/mL
Liquid	Ophthalmic	.025 %
Solution / drops	Ophthalmic	0.025 %
Spray	Nasal	.005 g/100mL
Solution	Nasal	0.05 %

Prices

Unit description	Cost	Unit
Oxymetazoline hcl powder	84.42USD	g
Afrin 0.05% nose spray	0.62USD	ml
Drixoral cold & allergy tablet sa	0.4USD	tablet
Afrin no drip sinus pump mist	0.38USD	ml
Oxymetazoline 0.05% spray	0.38USD	ml
Anefrin 0.05% nasal spray	0.37USD	ml
Afrin sinus spray	0.33USD	ml
Dristan long lasting mist	0.32USD	ml
Neo-synephrine 12 hour spray	0.28USD	ml
Visine long lasting eye drops	0.27USD	ml
12 hour nasal relief spray	0.24USD	ml
Dristan cold multi-symp tablet	0.23USD	tablet
Ocuclear eye drops	0.23USD	ml
CVS Pharmacy nasal spray 0.05%	0.22USD	ml
No drip 0.05% nasal spray	0.13USD	ml
Nasal spray 0.05%	0.06USD	ml
Sinus nasal spray	0.06USD	ml
Nasal decongestant 0.05% spray	0.03USD	ml
Pv nasal spray 0.05%	0.03USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US8580282	No	2010-04-02	2030-04-02
US6413499	No	2000-03-20	2020-03-20
US9308191	No	2010-04-02	2030-04-02
US8883838	No	2011-12-01	2031-12-01
US7812049	No	2008-05-02	2028-05-02
US8420688	No	2004-08-02	2024-08-02

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	182 °C	PhysProp
logP	3.4	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0515 mg/mL	ALOGPS
logP	3.7	ALOGPS
logP	3.03	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	10.91	ChemAxon
pKa (Strongest Basic)	10.15	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	44.62 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	79.8 m³·mol^-1	ChemAxon
Polarizability	30.64 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.9761
Blood Brain Barrier	-	0.5388
Caco-2 permeable	-	0.567
P-glycoprotein substrate	Substrate	0.8858
P-glycoprotein inhibitor I	Non-inhibitor	0.9477
P-glycoprotein inhibitor II	Non-inhibitor	0.6585
Renal organic cation transporter	Inhibitor	0.6039
CYP450 2C9 substrate	Non-substrate	0.7585
CYP450 2D6 substrate	Non-substrate	0.5707
CYP450 3A4 substrate	Non-substrate	0.5394
CYP450 1A2 substrate	Non-inhibitor	0.9045
CYP450 2C9 inhibitor	Non-inhibitor	0.9071
CYP450 2D6 inhibitor	Inhibitor	0.8931
CYP450 2C19 inhibitor	Non-inhibitor	0.9026
CYP450 3A4 inhibitor	Non-inhibitor	0.854
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.8682
Ames test	Non AMES toxic	0.7951
Carcinogenicity	Non-carcinogens	0.8923
Biodegradation	Not ready biodegradable	1.0
Rat acute toxicity	4.4155 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.8402
hERG inhibition (predictor II)	Non-inhibitor	0.7432

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

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Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Taxonomy

Description: This compound belongs to the class of organic compounds known as xylenols. These are aromatic compounds that contain a xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups, and at least one hydroxyl group.
Kingdom: Organic compounds
Super Class: Benzenoids
Class: Benzene and substituted derivatives
Sub Class: Xylenes
Direct Parent: Xylenols
Alternative Parents: Phenylpropanes / m-Xylenes / Para cresols / Ortho cresols / Imidolactams / Imidazolines / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Carboxamidines / Azacyclic compounds
show 3 more
Substituents: Xylenol / Phenylpropane / M-xylene / O-cresol / P-cresol / Phenol / Imidolactam / 2-imidazoline / Amidine / Carboxylic acid amidine
show 12 more
Molecular Framework: Aromatic heteromonocyclic compounds
External Descriptors: phenols, carboxamidine, imidazolines (CHEBI:7862)

Targets

Details1. Alpha-1A adrenergic receptor

Kind: Protein
Organism: Human
Pharmacological action: Yes
Actions: Agonist

General Function: Protein heterodimerization activity
Specific Function: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name: ADRA1A
Uniprot ID: P35348
Uniprot Name: Alpha-1A adrenergic receptor
Molecular Weight: 51486.005 Da

References

Yang HT, Endoh M: (+/-)-tamsulosin, an alpha 1A-adrenoceptor antagonist, inhibits the positive inotropic effect but not the accumulation of inositol phosphates in rabbit heart. Eur J Pharmacol. 1996 Oct 3;312(3):281-91. [PubMed:8894610]
Deplanne V, Galzin AM: Functional characterization of alpha-1-adrenoceptor subtypes in the prostatic urethra and trigone of male rabbit. J Pharmacol Exp Ther. 1996 Aug;278(2):527-34. [PubMed:8768700]
Shibata K, Taketani K: [Excitatory effect of noradrenaline on rat airway parasympathetic ganglion neurons]. Fukuoka Igaku Zasshi. 2001 Nov;92(11):377-83. [PubMed:11774707]
Furukawa K, Rosario DJ, Smith DJ, Chapple CR, Uchiyama T, Chess-Williams R: Alpha 1A-adrenoceptor-mediated contractile responses of the human vas deferens. Br J Pharmacol. 1995 Sep;116(1):1605-10. [PubMed:8564226]
Gonzalez-Espinosa C, Romero-Avila MT, Mora-Rodriguez DM, Gonzalez-Espinosa D, Garcia-Sainz JA: Molecular cloning and functional expression of the guinea pig alpha(1a)-adrenoceptor. Eur J Pharmacol. 2001 Aug 31;426(3):147-55. [PubMed:11527538]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	1.28	N/A	N/A	7908054
Ki (nM)	1.3	N/A	N/A	8935801
Ki (nM)	1.36	N/A	N/A	12954796
Ki (nM)	1.44	N/A	N/A	7908054
Ki (nM)	3.3	N/A	N/A	1353247
Ki (nM)	4.9	N/A	N/A	11408545
Ki (nM)	7.24	N/A	N/A	9605427
Ki (nM)	9.68	N/A	N/A	7996470

Details2. Alpha-2A adrenergic receptor

Kind: Protein
Organism: Human
Pharmacological action: Yes
Actions: Agonist

General Function: Thioesterase binding
Specific Function: Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
Gene Name: ADRA2A
Uniprot ID: P08913
Uniprot Name: Alpha-2A adrenergic receptor
Molecular Weight: 48956.275 Da

References

MacKinnon AC, Kilpatrick AT, Kenny BA, Spedding M, Brown CM: [3H]-RS-15385-197, a selective and high affinity radioligand for alpha 2-adrenoceptors: implications for receptor classification. Br J Pharmacol. 1992 Aug;106(4):1011-8. [PubMed:1327384]
Mitrani P, Srinivasan M, Dodds C, Patel MS: Role of the autonomic nervous system in the development of hyperinsulinemia by high-carbohydrate formula feeding to neonatal rats. Am J Physiol Endocrinol Metab. 2007 Apr;292(4):E1069-78. Epub 2006 Dec 12. [PubMed:17164433]
Lepretre N, Mironneau J: Alpha 2-adrenoceptors activate dihydropyridine-sensitive calcium channels via Gi-proteins and protein kinase C in rat portal vein myocytes. Pflugers Arch. 1994 Dec;429(2):253-61. [PubMed:7892112]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	185	N/A	N/A	7996470
Ki (nM)	239.88	N/A	N/A	9605427
Ki (nM)	31	N/A	N/A	1353247

Details3. Alpha-2C adrenergic receptor

Kind: Protein
Organism: Human
Pharmacological action: Unknown
Actions: Agonist

General Function: Protein homodimerization activity
Specific Function: Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins.
Gene Name: ADRA2C
Uniprot ID: P18825
Uniprot Name: Alpha-2C adrenergic receptor
Molecular Weight: 49521.585 Da

References

Haenisch B, Walstab J, Herberhold S, Bootz F, Tschaikin M, Ramseger R, Bonisch H: Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline. Fundam Clin Pharmacol. 2010 Dec;24(6):729-39. doi: 10.1111/j.1472-8206.2009.00805.x. [PubMed:20030735]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	1778.28	N/A	N/A	9605427
Ki (nM)	213	N/A	N/A	2172775
Ki (nM)	2980	N/A	N/A	7996470
Ki (nM)	754	N/A	N/A	1353247

Details4. Alpha-2B adrenergic receptor

Kind: Protein
Organism: Human
Pharmacological action: Unknown
Actions: Binder

General Function: Epinephrine binding
Specific Function: Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine...
Gene Name: ADRA2B
Uniprot ID: P18089
Uniprot Name: Alpha-2B adrenergic receptor
Molecular Weight: 49565.8 Da

References

Uhlen S, Wikberg JE: Delineation of rat kidney alpha 2A- and alpha 2B-adrenoceptors with [3H]RX821002 radioligand binding: computer modelling reveals that guanfacine is an alpha 2A-selective compound. Eur J Pharmacol. 1991 Sep 17;202(2):235-43. [PubMed:1666366]
Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP: ChEMBL: a large-scale bioactivity database for drug discovery. Nucleic Acids Res. 2012 Jan;40(Database issue):D1100-7. doi: 10.1093/nar/gkr777. Epub 2011 Sep 23. [PubMed:21948594]

Details5. Alpha-1B adrenergic receptor

Kind: Protein
Organism: Human
Pharmacological action: Unknown
Actions: Agonist

General Function: Protein heterodimerization activity
Specific Function: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name: ADRA1B
Uniprot ID: P35368
Uniprot Name: Alpha-1B adrenergic receptor
Molecular Weight: 56835.375 Da

References

Haenisch B, Walstab J, Herberhold S, Bootz F, Tschaikin M, Ramseger R, Bonisch H: Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline. Fundam Clin Pharmacol. 2010 Dec;24(6):729-39. doi: 10.1111/j.1472-8206.2009.00805.x. [PubMed:20030735]
Akinaga J, Lima V, Kiguti LR, Hebeler-Barbosa F, Alcantara-Hernandez R, Garcia-Sainz JA, Pupo AS: Differential phosphorylation, desensitization, and internalization of alpha1A-adrenoceptors activated by norepinephrine and oxymetazoline. Mol Pharmacol. 2013 Apr;83(4):870-81. doi: 10.1124/mol.112.082313. Epub 2013 Jan 30. [PubMed:23364786]
Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP: ChEMBL: a large-scale bioactivity database for drug discovery. Nucleic Acids Res. 2012 Jan;40(Database issue):D1100-7. doi: 10.1093/nar/gkr777. Epub 2011 Sep 23. [PubMed:21948594]

Details6. Alpha-1D adrenergic receptor

Kind: Protein
Organism: Human
Pharmacological action: Unknown
Actions: Agonist

General Function: Alpha1-adrenergic receptor activity
Specific Function: This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium.
Gene Name: ADRA1D
Uniprot ID: P25100
Uniprot Name: Alpha-1D adrenergic receptor
Molecular Weight: 60462.205 Da

References

Haenisch B, Walstab J, Herberhold S, Bootz F, Tschaikin M, Ramseger R, Bonisch H: Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline. Fundam Clin Pharmacol. 2010 Dec;24(6):729-39. doi: 10.1111/j.1472-8206.2009.00805.x. [PubMed:20030735]
Akinaga J, Lima V, Kiguti LR, Hebeler-Barbosa F, Alcantara-Hernandez R, Garcia-Sainz JA, Pupo AS: Differential phosphorylation, desensitization, and internalization of alpha1A-adrenoceptors activated by norepinephrine and oxymetazoline. Mol Pharmacol. 2013 Apr;83(4):870-81. doi: 10.1124/mol.112.082313. Epub 2013 Jan 30. [PubMed:23364786]
Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP: ChEMBL: a large-scale bioactivity database for drug discovery. Nucleic Acids Res. 2012 Jan;40(Database issue):D1100-7. doi: 10.1093/nar/gkr777. Epub 2011 Sep 23. [PubMed:21948594]

Drug created on June 13, 2005 07:24 / Updated on April 17, 2018 01:02

Oxymetazoline

Identification

Structure for DB00935 (Oxymetazoline)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References

References

References

References

References

References