Oxymetazoline - DrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (6)

Targets (6)Biointeractions (6)

Identification

Name

Oxymetazoline

Accession Number

DB00935 (APRD01158)

Type

Small Molecule

Groups

Approved

Description

A direct acting sympathomimetic used as a vasoconstrictor to relieve nasal congestion. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1251)

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

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

External IDs

Not Available

Product Ingredients

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

Approved 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	Canada
Rhofade	Cream	10 mg/g	Topical	Allergan	2017-01-18	Not applicable	US

Approved Generic Prescription Products

Not Available

Approved Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
12 Hour Nasal	Spray	.05 g/100mL	Nasal	Altaire Pharmaceuticals Inc.	2001-06-01	Not applicable	US
12 Hour Nasal	Spray	.05 g/100mL	Nasal	Select Brands Distributors	2000-03-01	Not applicable	US
12 Hour Nasal	Spray	.05 g/100mL	Nasal	Meijer Distribution	2015-05-06	Not applicable	US
12 Hour Original Nasal Decongestant	Liquid	50 mg/100mL	Nasal	Faria Llc Dba Sheffield Pharmaceutcials	2014-05-30	Not applicable	US
7 Select Nasal	Spray	.05 g/100mL	Nasal	7 Eleven	2014-08-05	Not applicable	US
7 Select Original Nasal	Spray	.05 g/mL	Nasal	7 Eleven	2016-10-04	Not applicable	US
Afrin Cold	Spray	0.05 mg	Nasal	Schering Plough	2002-09-28	2006-08-01	Canada
Afrin No Drip Extra Moisturizing	Spray, metered	.05 g/100mL	Nasal	Famar Montreal Inc	2000-08-31	2017-05-04	US
Afrin No Drip Extra Moisturizing	Spray, metered	.05 g/100mL	Nasal	Bayer	2000-08-31	Not applicable	US
Afrin No Drip Original Pump Mist	Spray, metered	.05 g/100mL	Nasal	Famar Montreal Inc	1999-08-31	2017-05-04	US
Afrin No Drip Original Pump Mist	Spray, metered	.05 g/100mL	Nasal	Bayer	1999-08-31	Not applicable	US
Afrin No Drip Severe Congestion	Spray, metered	.05 g/100mL	Nasal	Bayer	2000-08-31	Not applicable	US
Afrin No Drip Severe Congestion	Spray, metered	.05 g/100mL	Nasal	Famar Montreal Inc	2000-08-31	2017-05-04	US
Afrin No Drip Sinus Pump Mist	Spray, metered	.05 g/100mL	Nasal	Msd Consumer Care Inc.	2000-08-31	Not applicable	US
Afrin No-drip Allergy Sinus	Spray, metered	.05 mg/mL	Nasal	Bayer	2016-08-30	Not applicable	US
Afrin Original	Spray	.05 g/100mL	Nasal	Bayer Health Care Llc.	1975-07-14	Not applicable	US
Afrin Original Pump Mist	Spray, metered	.05 g/100mL	Nasal	Msd Consumer Care Inc.	1975-07-14	Not applicable	US
Afrin Severe Congestion	Spray	.05 g/100mL	Nasal	Msd Consumer Care Inc.	2000-08-31	Not applicable	US
Afrin Sinus	Spray	.05 g/100mL	Nasal	Msd Consumer Care Inc.	1996-08-30	Not applicable	US
Anefrin Nasal	Spray	.05 g/100mL	Nasal	Walgreen	2009-08-28	Not applicable	US
Anefrin Nasal Extra Moisturizing	Spray	.05 g/100mL	Nasal	Walgreen	1994-07-01	Not applicable	US
Anefrin Nasal Original	Spray	.05 g/100mL	Nasal	Walgreen	1995-09-28	Not applicable	US
Assured Nasal Relief	Spray	.05 mg/100mL	Nasal	United Exchange Corporation	2013-11-20	Not applicable	US
Assured Nasal Relief	Spray	.05 mg/100mL	Nasal	Greenbrier International, Inc.	2013-04-30	Not applicable	US
Assured Nasal Relief Original	Spray	.05 g/100mL	Nasal	Greenbrier International, Inc.	2011-03-08	Not applicable	US
Assured Severe Congestion Nasal Relief	Spray	.2 mg/.4mL	Nasal	Greenbrier International, Inc.	2015-05-14	Not applicable	US
Being Well Nasal 12 Hour	Spray	.05 g/100mL	Nasal	Save A Lot Food Stores, Ltd.	2006-02-25	Not applicable	US
Breaze Nasal Moisturizing	Spray	.5 mg/mL	Nasal	Samson Pharmaceutical	2015-01-01	Not applicable	US
Breaze Nasal Sinus Colds and Allergies	Spray	.5 mg/mL	Nasal	Samson Pharmaceutical	2015-01-01	Not applicable	US
Care One Nasal	Spray	.05 g/100mL	Nasal	American Sales Company	2004-07-20	Not applicable	US
Care One Nasal Extra Moisturizing	Spray	.05 g/100mL	Nasal	American Sales Company	2004-06-01	Not applicable	US
Care One Nasal Original	Spray	.05 g/100mL	Nasal	American Sales Company	2004-05-24	Not applicable	US
Care One Nasal Sinus	Spray	.05 g/100mL	Nasal	American Sales Company	2004-05-24	Not applicable	US
Careone Severe Congestion Nasal	Spray	.05 g/100mL	Nasal	American Sales Company	2016-08-31	Not applicable	US
Circle K Congestion Relief	Spray	.05 g/100mL	Nasal	Lil' Drug Store Products, Inc.	2014-11-01	Not applicable	US
Claritin Allergy Decongestant	Solution	0.05 %	Nasal	Bayer Inc Consumer Care	2001-05-02	Not applicable	Canada
Claritin Eye Allergy Relief	Solution / drops	.25 mg	Ophthalmic	Schering Plough	2001-05-02	2012-07-24	Canada
Clear Time	Spray	.05 g/100mL	Nasal	Hyvee	2015-07-19	Not applicable	US
Cleartime	Spray	.05 g/100mL	Nasal	Western Family Foods	2015-05-13	Not applicable	US
Congestion Relief Lil Drug Store Products	Spray	.05 g/100mL	Nasal	Lil' Drug Store Products, Inc.	2014-12-01	Not applicable	US
Cooling Menthol Nasal Spray	Spray, metered	0.05 %	Nasal	Teva	2015-07-08	Not applicable	Canada
Cooling Menthol Nasal Spray	Spray, metered	0.05 %	Nasal	Juno Otc Inc	Not applicable	Not applicable	Canada
Cvs Health Nasal Mist	Spray	.05 g/100mL	Nasal	Cvs Health	2015-08-25	Not applicable	US
Cvs Health Sinus Relief	Spray	.0005 g/mL	Nasal	Cvs Health	2015-04-21	Not applicable	US
Decongestant Nasal	Solution	.05 g/100mL	Nasal	Salado Sales, Inc.	2000-02-01	Not applicable	US
Decongestant Nasal Mist Long Lasting	Solution	0.05 %	Nasal	Laboratoires Confab Inc	1996-10-31	Not applicable	Canada
Dg Health Clear Time	Spray	.05 g/100mL	Nasal	Dolgencorp	2015-05-01	Not applicable	US
Dg Health Nasal	Spray	.05 g/100mL	Nasal	Dolgencorp	2016-07-03	Not applicable	US
Dg Health Nasal Original	Spray	.05 g/100mL	Nasal	Dolgencorp	2010-01-08	Not applicable	US
Dg Health Sinus Relief	Spray	.05 mg/100mL	Nasal	Dolgencorp	2010-02-22	Not applicable	US
Dristan 12 Hr	Spray	.5 mg/mL	Nasal	Pfizer	2004-01-01	Not applicable	US
Drixoral Decongestant Nasal Spray	Solution	0.05 %	Nasal	Bayer Inc Consumer Care	1986-12-31	Not applicable	Canada
Drixoral Nasal Congestion	Spray	0.05 %	Nasal	Bayer Inc Consumer Care	2012-08-15	Not applicable	Canada
Drixoral No Drip Extra Moisturizing	Spray	0.05 %	Nasal	Bayer Inc Consumer Care	2002-09-28	Not applicable	Canada
Drixoral No Drip Original Unscented	Spray	0.05 %	Nasal	Bayer Inc Consumer Care	2002-09-28	Not applicable	Canada
Drixoral No Drip With Calming Chamomile	Spray	0.05 %	Nasal	Bayer Inc Consumer Care	2011-07-07	Not applicable	Canada
Drixoral No Drip With Cooling Menthol	Spray	0.05 %	Nasal	Bayer Inc Consumer Care	2002-09-28	Not applicable	Canada
Equaline Nasal	Spray	.05 g/100mL	Nasal	Supervalu	2014-07-15	Not applicable	US
Equaline Nasal	Spray	.05 g/100mL	Nasal	Supervalu	2016-07-03	Not applicable	US
Equaline Oxymetazoline HCl Nasal Decongestant No Drip	Spray	.05 g/100mL	Nasal	Supervalu	2015-06-12	Not applicable	US
Equate Nasal	Spray	.05 g/100mL	Nasal	Walmart Stores	2007-07-27	Not applicable	US
Equate Nasal Original	Spray	.05 g/100mL	Nasal	Walmart Stores	1990-08-15	Not applicable	US
Exchange Select Nasal	Spray	.05 g/100mL	Nasal	Army + Air Force Exchange Service	2014-01-06	Not applicable	US
Exchange Select Nasal	Spray	.05 g/100mL	Nasal	Army + Air Force Exchange Service	2011-10-28	Not applicable	US
Extra Moisturizing	Spray	.05 g/100mL	Nasal	Publix Supermarkets, Inc.	1998-05-07	Not applicable	US
Extra Moisturizing Nasal Spray	Spray, metered	0.05 %	Nasal	Teva	2015-07-08	Not applicable	Canada
Extra Moisturizing Nasal Spray	Spray, metered	0.05 %	Nasal	Juno Otc Inc	Not applicable	Not applicable	Canada
Extra Moisturizing No Drip Nasal Walgreens	Liquid	.05 g/100mL	Topical	Walgreens	2016-07-01	Not applicable	US
Family Care Nasal Relief	Spray	.05 g/100mL	Nasal	United Exchange Corporation	2013-06-30	Not applicable	US
Family Care Nasal Relief	Spray	5 g/100mL	Nasal	United Exchange Corporation	2013-05-31	Not applicable	US
Formucare Nasal Spray Original	Spray	.05 g/100mL	Nasal	Access Business Group	2007-07-10	Not applicable	US
Good Neighbor Pharmacy Nasal	Spray	.05 g/100mL	Nasal	Amerisource Bergen	2002-03-06	Not applicable	US
Good Neighbor Pharmacy Nasal	Spray	.05 g/100mL	Nasal	Amerisource Bergen	2016-07-11	Not applicable	US
Good Neighbor Pharmacy Nasal	Spray	.05 g/100mL	Nasal	Amerisource Bergen	1995-03-16	Not applicable	US
Good Neighbor Pharmacy Nasal	Spray	.05 g/100mL	Nasal	Amerisource Bergen	1990-01-15	Not applicable	US
Good Neighbor Pharmacy Nasal Extra Moisturizing	Spray	.05 g/100mL	Nasal	Amerisource Bergen	1995-05-04	Not applicable	US
Good Sense Nasal	Spray	.05 g/100mL	Nasal	L. Perrigo Company	2002-05-13	Not applicable	US
Good Sense Nasal	Spray	.5 mg/mL	Nasal	L. Perrigo Company	1989-09-15	Not applicable	US
Good Sense Nasal	Spray	.05 g/100mL	Nasal	L. Perrigo Company	1996-04-18	Not applicable	US
Good Sense Nasal	Spray	.05 g/100mL	Nasal	L. Perrigo Company	1994-03-23	Not applicable	US
Health Mart Nasal	Spray	.05 g/100mL	Nasal	Mc Kesson	2012-01-11	Not applicable	US
Health Mart Nasal	Spray	.05 g/100mL	Nasal	Mc Kesson	2012-01-12	Not applicable	US
Health Mart Nasal	Spray	.05 g/100mL	Nasal	Mc Kesson	2012-01-11	Not applicable	US
Healthy Accents Nasal	Spray	.05 g/100mL	Nasal	Dza Brands,	2008-02-24	Not applicable	US
Healthy Accents Nasal Original	Spray	.05 g/100mL	Nasal	Dza Brands,	2008-04-01	Not applicable	US
Heb Nasal Decongestant No Drip Extra Moisturizing	Solution	.05 g/100mL	Nasal	H.E.B.	2016-06-15	Not applicable	US
Leader Extra Moisturizing Nasal	Spray	.05 mg/100mg	Nasal	Cardinal Health	2013-08-29	Not applicable	US
Leader Nasal	Spray	.05 g/100mL	Nasal	Cardinal Health	2014-12-11	Not applicable	US
Leader Nasal	Spray	.05 g/100mL	Nasal	Cardinal Health	1996-12-05	Not applicable	US
Leader Nasal	Spray	.05 g/100mL	Nasal	Cardinal Health	1992-01-22	Not applicable	US
Leader Nasal	Spray	.05 g/100mL	Nasal	Cardinal Health	2014-12-04	Not applicable	US
Leader Original Nasal	Spray	.05 g/100mL	Nasal	Cardinal Health	2012-09-30	Not applicable	US
Leader Original Nasal	Spray	.05 mg/100mg	Nasal	Cardinal Health	2013-08-29	Not applicable	US
Leader Severe Congestion Nasal	Spray	.05 g/100mL	Nasal	Cardinal Health	2012-02-14	Not applicable	US
Long Lasting Decongestant Nasal Spray	Spray	0.05 %	Nasal	Crls	Not applicable	Not applicable	Canada
Long Lasting Dristan Mentholated Nasal Spray	Spray	0.05 %	Nasal	Pfizer Laboratories Div Pfizer Inc.	1992-12-31	Not applicable	Canada
Long Lasting Dristan Nasal Mist	Spray	0.05 %	Nasal	Pfizer Laboratories Div Pfizer Inc.	1992-12-31	Not applicable	Canada
Long Lasting Nasal Mist	Liquid	0.05 %	Nasal	Stanley Pharmaceuticals, A Division Of Vita Health Products Inc.	1999-03-08	2002-07-31	Canada
Long Lasting Nasal Mist	Solution	0.05 %	Nasal	Jamp Pharma Corporation	2004-06-30	Not applicable	Canada
Long Lasting Nasal Mist	Spray	0.05 %	Nasal	Pharmascience Inc	2003-02-01	Not applicable	Canada
Maximum Strenth Nasal	Liquid	.05 g/100mL	Topical	Walgreens	2016-07-15	Not applicable	US
Mucinex Full Force	Solution	.05 g/100mL	Nasal	Reckitt Benckiser	2011-07-01	Not applicable	US
Mucinex Moisture Smart	Solution	.05 g/100mL	Nasal	Reckitt Benckiser	2011-07-01	Not applicable	US
Mucinex Nasal Full Force	Solution	.5 mg/mL	Nasal	Reckitt Benckiser	2010-06-30	Not applicable	US
Mucinex Nasal Moisture Smart	Solution	.05 g/100mL	Nasal	Reckitt Benckiser	2011-10-20	Not applicable	US
Mucinex Sinus-action Congestion & Sinus Nasal Spray	Spray	0.05 %	Nasal	Reckitt Benckiser	Not applicable	Not applicable	Canada
Mucinex Sinus-action Moisture Smart Nasal Spray	Spray	0.05 %	Nasal	Reckitt Benckiser	Not applicable	Not applicable	Canada
Mucinex Sinus-max Full Force	Solution	.05 mg/100mL	Nasal	Reckitt Benckiser	2015-04-15	Not applicable	US
Mucinex Sinus-max Full Force	Solution	.05 mg/100mL	Nasal	Reckitt Benckiser	2012-09-01	Not applicable	US
Nafrine Pediatric Nasal Spray/drops 0.025%	Solution / drops; Spray	.025 %	Nasal	Schering Plough	1964-12-31	2001-07-18	Canada
Nasal	Spray	5 g/100mL	Nasal	Remedy Repack	2017-06-01	Not applicable	US
Nasal	Spray	5 g/100mL	Nasal	Major	2009-03-17	Not applicable	US
Nasal	Spray	5 g/100mL	Nasal	Preferreed Pharmaceuticals Inc.	2009-03-17	Not applicable	US
Nasal	Spray	.05 g/100mL	Nasal	Hyvee	2016-08-12	Not applicable	US
Nasal	Spray	.05 g/100mL	Nasal	Rite Aid	2013-09-30	Not applicable	US
Nasal	Spray	.05 g/100mL	Nasal	Hyvee	2002-05-13	Not applicable	US
Nasal	Spray	.05 g/100mL	Nasal	Kroger	2002-11-20	Not applicable	US
Nasal	Spray	5 g/100mL	Nasal	Lake Erie Medical Dba Quality Care Produts Llc	2009-03-17	Not applicable	US
Nasal	Spray	.05 g/100mL	Nasal	Kroger	2001-09-24	Not applicable	US
Nasal	Spray	5 g/100mL	Nasal	A S Medication Solutions	2009-03-17	2017-06-20	US
Nasal	Spray	.05 g/100mL	Nasal	Shopko Stores Operating	2013-08-19	Not applicable	US
Nasal	Spray	.05 g/100mL	Nasal	Shopko Stores Operating	2016-08-03	Not applicable	US
Nasal	Spray	5 g/100mL	Nasal	We Care Distributor Inc.	2016-08-23	Not applicable	US
Nasal	Spray	.05 g/100mL	Nasal	L. Perrigo Company	1991-07-29	Not applicable	US
Nasal	Spray	.05 g/100mL	Nasal	H.E.B.	2014-12-02	Not applicable	US
Nasal	Spray	.05 g/100mL	Nasal	Rite Aid	1996-12-05	Not applicable	US
Nasal	Spray	.05 g/100mL	Nasal	H.E.B.	2015-02-19	Not applicable	US
Nasal	Spray	5 g/100mL	Nasal	A S Medication Solutions	2009-03-17	2017-06-20	US
Nasal	Spray	.05 g/100mL	Nasal	Shopko Stores Operating	2013-07-11	Not applicable	US
Nasal	Spray	.05 g/100mL	Nasal	Meijer Distribution	1996-12-13	Not applicable	US
Nasal	Spray	.05 g/100mL	Nasal	Kroger	2016-06-21	Not applicable	US
Nasal	Spray	.05 g/100mL	Nasal	Cvs Health	1994-07-01	Not applicable	US
Nasal	Spray	.05 g/100mL	Nasal	Meijer Distribution	2002-09-11	Not applicable	US
Nasal	Spray	.05 g/100mL	Nasal	H.E.B.	2015-02-03	Not applicable	US
Nasal	Spray	.05 g/100mL	Nasal	Kroger	1990-11-15	Not applicable	US
Nasal	Spray	.05 g/100mL	Nasal	Rite Aid	2013-12-19	Not applicable	US
Nasal	Spray	5 g/100mL	Nasal	Proficient Rx LP	2009-03-17	Not applicable	US
Nasal 12 Hour	Spray	.05 g/100mL	Nasal	Meijer Distribution	1991-12-06	Not applicable	US
Nasal 12 Hour	Spray	.05 g/100mL	Nasal	Meijer Distribution	1994-05-03	Not applicable	US
Nasal Congestion Spray	Spray, metered	0.05 %	Nasal	Juno Otc Inc	Not applicable	Not applicable	Canada
Nasal Congestion Spray	Spray, metered	0.05 %	Nasal	Teva	2015-07-08	Not applicable	Canada
Nasal D	Spray	.05 g/100mL	Nasal	Western Family Foods	2015-01-26	Not applicable	US
Nasal D	Spray	.05 g/100mL	Nasal	Western Family Foods	2014-11-17	Not applicable	US
Nasal D Original	Spray	.05 g/100mL	Nasal	Western Family Foods	2014-11-13	Not applicable	US
Nasal Decongestant	Solution	.05 mg/100mL	Nasal	H.E.B.	2016-06-15	Not applicable	US
Nasal Decongestant	Spray	.05 g/100mL	Nasal	Navarro Discount Pharmacies, LLC	2012-10-26	Not applicable	US
Nasal Decongestant	Spray	.05 g/100mL	Nasal	Safeway	2004-06-07	Not applicable	US
Nasal Decongestant	Spray	.05 g/100mL	Nasal	Kareway Product, Inc.	2011-08-12	Not applicable	US
Nasal Decongestant	Spray	.05 g/100mL	Nasal	Safeway	1994-08-17	Not applicable	US
Nasal Decongestant	Spray	.05 g/100mL	Nasal	Kareway Product, Inc.	2015-11-23	Not applicable	US
Nasal Decongestant	Spray	.05 g/100mL	Nasal	Pro Mex Llc	2013-12-09	Not applicable	US
Nasal Decongestant	Spray	.05 g/100mL	Nasal	Safeway	2014-03-05	Not applicable	US
Nasal Decongestant Extra Moisturizing	Spray	.05 g/100mL	Nasal	Kareway Product, Inc.	2011-08-12	Not applicable	US
Nasal Decongestant Extra Moisturizing Premier Value	Spray	.05 mg/mL	Nasal	Chain Drug Consortium	2014-11-04	Not applicable	US
Nasal Decongestant Premier Value	Spray	.05 mg/mL	Nasal	Chain Drug Consortium	2014-11-04	Not applicable	US
Nasal Decongestant Sinus Premier Value	Spray	.05 mg/mL	Nasal	Chain Drug Consortium	2014-11-04	Not applicable	US
Nasal Extra Moisturizing	Spray	.05 g/100mL	Nasal	Hannaford Brothers Company	2006-04-21	Not applicable	US
Nasal Extra Moisturizing	Spray	.05 g/100mL	Nasal	Hyvee	1999-04-02	Not applicable	US
Nasal Extra Moisturizing	Spray	.05 g/100mL	Nasal	Kroger	1994-06-17	Not applicable	US
Nasal Mist	Spray	.05 g/100mL	Nasal	Cvs Health	2002-09-04	Not applicable	US
Nasal Mist	Spray	.05 g/100mL	Nasal	Shopko Stores Operating	2014-09-24	Not applicable	US
Nasal Mist Cvs	Liquid	.05 g/100mL	Topical	Cvs Health	2015-10-01	Not applicable	US
Nasal Mist Cvs	Liquid	.05 g/100mL	Topical	Cvs Health	2015-10-01	Not applicable	US
Nasal Mist Walgreens	Liquid	.05 g/100mL	Topical	Walgreens	2016-07-01	Not applicable	US
Nasal Original	Spray	.05 g/100mL	Nasal	Cvs Health	1991-09-18	Not applicable	US
Nasal Original	Spray	.05 g/100mL	Nasal	Cvs Health	1989-09-15	Not applicable	US
Nasal Original	Spray	.05 g/100mL	Nasal	Hyvee	1991-11-18	Not applicable	US
Nasal Relief	Spray	.5 mg/mL	Nasal	Rugby	2014-07-14	Not applicable	US
Nasal Relief 12-hour	Spray	.05 g/100mL	Nasal	Rugby	2012-10-29	Not applicable	US
Nasal Sinus	Spray	.05 g/100mL	Nasal	Cvs Health	1999-10-05	Not applicable	US
Nasalub Nasal Relief	Spray	.05 g/100mL	Nasal	Genomma Lab	2014-12-02	Not applicable	US
No Drip	Spray	.05 g/100mL	Nasal	Publix Supermarkets, Inc.	2002-12-26	Not applicable	US
No Drip Nasal Mist Original	Spray	.05 g/100mL	Nasal	Cvs Health	2012-09-01	Not applicable	US
No Drip Premier Value	Spray	.05 mg/mL	Nasal	Chain Drug Consortium	2014-11-04	Not applicable	US
No Drip Severe Congestion Premier Value	Spray	.05 mg/mL	Nasal	Chain Drug Consortium	2014-11-04	Not applicable	US
Nostrilla	Spray, metered	.0005 mL/100mL	Nasal	Insight Pharmaceuticals	2009-06-08	Not applicable	US
Nostrilla	Spray, metered	.0005 mL/100mL	Nasal	Insight Pharmaceuticals	2009-06-08	Not applicable	US
Ocuclear Oph Dps 0.025%	Solution / drops	.25 mg	Ophthalmic	Schering Plough	1982-12-31	2003-07-14	Canada
Original	Spray	.05 g/100mL	Nasal	Publix Supermarkets, Inc.	1991-11-13	Not applicable	US
Original No Drip Nasal Walgreens	Liquid	.05 g/100mL	Topical	Walgreens	2016-07-01	Not applicable	US
Original Unscented Nasal Spray	Spray, metered	0.05 %	Nasal	Actavis Pharma Company	Not applicable	Not applicable	Canada
Oxymetazoline HCl	Spray	.05 g/100mL	Nasal	Perrigo New York Inc.	2005-12-05	Not applicable	US
Oxymetazoline HCl	Spray	.5 mg/mL	Oral	Purine Pharma Llc	2015-02-09	Not applicable	US
Oxymetazoline HCl	Spray	.5 mg/mL	Oral	Kingston Pharma Llc	2017-03-01	2017-05-05	US
Oxymetazoline Hydrochloride	Spray, metered	.5 mg/mL	Nasal	Cadila Pharnmaceuticals	2009-09-24	Not applicable	US
Oxymetazoline Hydrochloride	Spray, metered	.2 mg/.4mL	Nasal	Dynamic Pharmaceuticals	2009-11-04	Not applicable	US
Oxymetazoline Hydrochloride	Spray, metered	.5 mg/mL	Nasal	Rebel Distributors	2008-12-11	Not applicable	US
Oxymetazoline Hydrochloride	Spray, metered	.2 mg/.4mL	Nasal	Dynamic Pharmaceuticals	2009-11-04	Not applicable	US
Oxymetazoline Hydrochloride	Spray, metered	.5 mg/mL	Nasal	Zydus Pharmaceuticals Usa, Inc.	2009-09-24	Not applicable	US
Oxymetazoline Hydrochloride 12-hour	Spray	.05 g/100mL	Nasal	Taro Pharmaceuticals U.S.A., Inc.	2006-02-25	Not applicable	US
Oxymetazoline Hydrochloride Nasal Spray 0.05%	Spray	0.05 %	Nasal	Glaxosmithkline Inc	Not applicable	Not applicable	Canada
Oxymetazoline Hydrochloride Nasal Spray 0.05% With Moisturizers	Spray	0.05 %	Nasal	Glaxosmithkline Inc	Not applicable	Not applicable	Canada
Preferred Plus 12 Hour Nasal Extra Moisturizing	Spray	50 mg/100mL	Nasal	Kinray	2008-01-31	Not applicable	US
Preferred Plus 12 Hour Nasal Original	Spray	50 mg/100mL	Nasal	Kinray	2008-01-31	Not applicable	US
Preferred Plus Nasal	Spray	.05 g/100mL	Nasal	Kinray	2014-11-24	Not applicable	US
Preferred Plus Nasal	Spray	.05 g/100mL	Nasal	Kinray	2014-11-24	Not applicable	US
Rx Act Nasal Extra Moisturizing	Spray	.05 g/100mL	Nasal	H.E.B.	1995-10-12	Not applicable	US
Rx Act Nasal Original	Spray	.05 g/100mL	Nasal	H.E.B.	1992-02-03	Not applicable	US
Rx Act Nasal Sinus	Spray	.05 g/100mL	Nasal	H.E.B.	2000-08-25	Not applicable	US
Severe Congestion Nasal No Drip Walgreens	Liquid	.05 g/100mL	Topical	Walgreens	2016-07-01	Not applicable	US
Shopko Extra Moisturizing Nasal	Spray	.05 g/100mL	Nasal	United Exchange Corporation	2012-03-01	Not applicable	US
Shopko Original Nasal	Spray	.05 g/100mL	Nasal	United Exchange Corporation	2012-03-01	Not applicable	US
Shopko Severe Congestion Nasal	Spray	.05 g/100mL	Nasal	United Exchange Corporation	2012-03-01	Not applicable	US
Shoprite Nasal	Spray	.05 g/100mL	Nasal	Wakfern Food Corporation	2013-07-09	Not applicable	US
Signature Care Nasal Decongestant	Spray	.05 g/100mL	Nasal	Safeway	2015-07-09	Not applicable	US
Signature Care Nasal Decongestant	Spray	.05 g/100mL	Nasal	Safeway	2015-07-30	Not applicable	US
Signature Care Nasal Decongestant	Spray	.05 g/100mL	Nasal	Safeway	2015-08-11	Not applicable	US
Sinex Complete	Spray	0.05 %	Nasal	Procter And Gamble	Not applicable	Not applicable	Canada
Sinex Complete Ultra Fine Mist	Spray	0.05 %	Nasal	Procter And Gamble	Not applicable	Not applicable	Canada
Sinex Moisturizing Ultra Fine Mist	Spray	0.05 %	Nasal	Procter And Gamble	Not applicable	Not applicable	Canada
Sinex Scent Free Ultra Fine Mist	Spray	0.05 %	Nasal	Procter And Gamble	Not applicable	Not applicable	Canada
Sinufrin	Spray	0.05 %	Nasal	Neil Med	2015-05-10	Not applicable	Canada
Sinufrin Neilmed	Spray	7.5 mg/15mL	Nasal	Neil Med	2012-07-15	Not applicable	US
Sinufrin Plus	Spray	0.05 %	Nasal	Neil Med	2015-05-10	Not applicable	Canada
Sinufrin Plus Neilmed	Spray	7.5 mg/15mL	Nasal	Neil Med	2012-07-15	Not applicable	US
Sinus Relief	Spray	.05 mg/100mL	Nasal	Meijer Distribution	2003-08-13	Not applicable	US
Sinus Relief	Spray	.05 mg/100mL	Nasal	Western Family Foods	2010-01-07	Not applicable	US
Sinus Relief	Spray	.05 mg/100mL	Nasal	Hyvee	2009-12-07	Not applicable	US
Smart Sense Nasal	Spray	.05 mg/100mL	Nasal	Kmart Corporation	2014-04-01	Not applicable	US
Smart Sense Nasal	Spray	.05 g/100mL	Nasal	Kmart Corporation	2011-01-26	Not applicable	US
Smart Sense Nasal Extra Moisturizing	Spray	.05 g/100mL	Nasal	Kmart Corporation	2010-11-12	Not applicable	US
Smart Sense Nasal Original	Spray	.05 g/100mL	Nasal	Kmart Corporation	2010-09-03	Not applicable	US
Smart Sense Pump Mist	Spray	.05 g/100mL	Nasal	Kmart Corporation	2014-01-28	Not applicable	US
Smart Sense Pump Mist	Spray	.05 g/100mL	Nasal	Kmart Corporation	2017-05-30	Not applicable	US
Smart Sense Sinus Relief	Spray	.05 mg/100mL	Nasal	Kmart Corporation	2011-01-26	Not applicable	US
Sound Body 12 Hour Nasal Original	Spray	50 mg/100mL	Nasal	Lee Pharmaceuticals	2008-01-31	Not applicable	US
Sound Body Nasal	Spray	.05 g/100mL	Nasal	Big Lots Stores, Inc.	2016-05-03	Not applicable	US
Sunmark Nasal	Spray	.05 g/100mL	Nasal	Mc Kesson	2014-09-26	Not applicable	US
Sunmark Nasal	Spray	.05 g/100mL	Nasal	Mc Kesson	2003-09-13	Not applicable	US
Sunmark Nasal	Spray	.05 g/100mL	Nasal	Mc Kesson	2003-09-19	Not applicable	US
Sunmark Nasal	Spray	.05 g/100mL	Nasal	Mc Kesson	2003-06-24	Not applicable	US
Sunmark Nasal Original	Spray	.5 mg/mL	Nasal	Mc Kesson	2003-06-27	Not applicable	US
Sunmark No Drip	Spray	.05 g/100mL	Nasal	Mc Kesson	2003-09-19	Not applicable	US
Todays Health Nasal Relief Extra Moisturizing	Spray	.05 g/100mL	Nasal	TAI GUK PHARM. CO., LTD.	2010-11-11	Not applicable	US
Todays Health Nasal Relief Original	Spray	.05 g/100mL	Nasal	TAI GUK PHARM. CO., LTD.	2010-10-22	Not applicable	US
Todays Health Sinus Nasal Relief	Spray	.05 g/100mL	Nasal	TAI GUK PHARM. CO., LTD.	2010-10-25	Not applicable	US
Topcare Clear Time	Spray	.05 g/100mL	Nasal	Topco Associates	2015-06-29	Not applicable	US
Topcare Nasal	Spray	.05 g/100mL	Nasal	Topco Associates	2015-02-04	Not applicable	US
Topcare Nasal	Spray	.05 g/100mL	Nasal	Topco Associates	1989-12-15	Not applicable	US
Topcare Nasal	Spray	.05 g/100mL	Nasal	Topco Associates	1996-08-06	Not applicable	US
Topcare Nasal	Spray	.05 g/100mL	Nasal	Topco Associates	2002-11-26	Not applicable	US
Topcare Nasal	Spray	.05 g/100mL	Nasal	Topco Associates	2016-07-14	Not applicable	US
Topcare Sinus Relief	Spray	.05 mg/100mL	Nasal	Topco Associates	2009-07-29	Not applicable	US
Ultra Fine Mist Premier Value	Spray	.05 mg/mL	Nasal	Chain Drug Consortium	2014-11-04	Not applicable	US
Up and Up Nasal	Spray	.05 g/100mL	Nasal	Target Corporation.	2009-08-12	Not applicable	US
Up and Up Nasal	Spray	.05 g/100mL	Nasal	Target Corporation.	2016-07-11	Not applicable	US
Up and Up Nasal Extra Moisturizing	Spray	.05 g/100mL	Nasal	Target Corporation.	2010-07-21	Not applicable	US
Vicks Qlearquil 12 Hour Decongestant Moisturizing	Spray	.512 mg/mL	Nasal	Procter And Gamble	2014-03-01	Not applicable	US
Vicks Sinex 12 Hour Decongestant	Spray	.0005095 g/mL	Nasal	Procter And Gamble	2015-04-27	Not applicable	US
Vicks Sinex 12 Hour Decongestant Nasal	Spray	.0005055 g/mL	Nasal	Procter And Gamble	2010-07-06	Not applicable	US
Vicks Sinex 12 Hour Decongestant Ultra Fine Mist	Spray	.0005095 g/mL	Nasal	Procter And Gamble	2010-07-06	Not applicable	US
Vicks Sinex 12 Hour Decongestant Ultra Fine Mist	Spray	.0005095 g/mL	Nasal	Procter And Gamble	2015-04-27	Not applicable	US
Vicks Sinex 12 Hour Decongestant Ultra Fine Mist Moisturizing	Spray	.000512 g/mL	Nasal	Procter And Gamble	2010-07-06	Not applicable	US
Vicks Sinex 12 Hour Nasal Decongestant Ultra Fine Mist Moisturizing	Spray	.0005095 g/mL	Nasal	Procter And Gamble	2015-04-27	Not applicable	US
Vicks Sinex Decongestant Nasal Spray 0.05%	Liquid	.05 %	Nasal	Procter And Gamble	1985-12-31	Not applicable	Canada
Vicks Sinex Scent Free	Spray	.05 g/mL	Nasal	Procter And Gamble	2015-01-31	Not applicable	US
Visine L.R.	Liquid	.25 mg/mL	Ophthalmic	Johnson & Johnson	2010-04-05	2016-08-01	US
Visine L.R. Ophthalmic Sol 0.025%	Liquid	.025 %	Ophthalmic	Pfizer Canada Inc., Consumer Healthcare Division	1991-12-31	1996-09-09	Canada
Visine Workplace	Solution / drops	0.025 %	Ophthalmic	Johnson & Johnson	1995-12-31	2016-08-04	Canada
Winco Foods Extra Moisturizing Nasal Relief	Spray	.005 g/100mL	Nasal	Win Co Foods, Llc,	2014-11-26	Not applicable	US
Winco Foods Original Nasal	Spray	.05 g/100mL	Nasal	Win Co Foods, Llc,	2014-11-26	Not applicable	US
Winco Foods Severe Congestion Nasal Relief	Spray	.05 g/100mL	Nasal	Win Co Foods, Llc,	2014-12-01	Not applicable	US
Zicam	Spray	.5 mg/mL	Nasal	Matrixx Initiatives, Inc.	2002-05-29	Not applicable	US
Zicam	Spray	.5 mg/mL	Nasal	Matrixx Initiatives, Inc.	2002-05-20	Not applicable	US
Zicam Congestion Relief	Solution	0.05 %	Nasal	Zicam Llc	2008-11-27	2009-11-20	Canada
Zicam Sinus Relief	Solution	0.05 %	Nasal	Zicam Llc	2008-11-27	2009-11-20	Canada

Unapproved/Other Products

Not Available

International Brands

Name	Company
Afrin	Not Available
Dristan 12-Hour	Not Available
Duramist Plus	Not Available
Genasal Nasal Spray Up to 12 Hour Relief	Not Available
Iliadin	Not Available
Neo-Synephrine 12 Hour Spray	Not Available
Nezeril	Not Available
Nostrilla 12 Hour Nasal Decongestant	Not Available
OcuClear	Not Available
Vicks Sinex 12 Hour Nasal Spray	Not Available
Vicks Sinex 12 Hour Ultra Fine Mist for Sinus Relief	Not Available

Brand mixtures

Not Available

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	Kind	Pharmacological action	Actions	Organism	UniProt ID
Alpha-1A adrenergic receptor	Protein	yes	agonist	Human	P35348	details
Alpha-2A adrenergic receptor	Protein	yes	agonist	Human	P08913	details
Alpha-2C adrenergic receptor	Protein	unknown	agonist	Human	P18825	details
Alpha-2B adrenergic receptor	Protein	unknown	binder	Human	P18089	details
Alpha-1B adrenergic receptor	Protein	unknown	agonist	Human	P35368	details
Alpha-1D adrenergic receptor	Protein	unknown	agonist	Human	P25100	details

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
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
Amphetamine	The risk or severity of adverse effects can be increased when Amphetamine is combined with Oxymetazoline.	Approved, Illicit
Arotinolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Arotinolol.	Approved
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
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 activities of Oxymetazoline.	Approved, Investigational
Bufuralol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Bufuralol.	Experimental, Investigational
Bupranolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Bupranolol.	Approved
Cabergoline	Cabergoline may increase the hypertensive 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, Vet Approved
Clomipramine	Clomipramine may decrease the antihypertensive activities of Oxymetazoline.	Approved, Vet Approved
Cyclobenzaprine	Cyclobenzaprine may decrease the antihypertensive activities of Oxymetazoline.	Approved
Desipramine	Desipramine may decrease the antihypertensive activities of Oxymetazoline.	Approved
Desvenlafaxine	Desvenlafaxine may increase the tachycardic activities of Oxymetazoline.	Approved
Dihydroergotamine	Dihydroergotamine may increase the hypertensive activities of Oxymetazoline.	Approved
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
Doxofylline	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Doxofylline.	Approved
Dronabinol	Dronabinol may increase the tachycardic activities of Oxymetazoline.	Approved, Illicit
Duloxetine	Duloxetine may increase the tachycardic activities of Oxymetazoline.	Approved
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 activities of Oxymetazoline.	Approved
Ergonovine	Ergonovine may increase the hypertensive activities of Oxymetazoline.	Approved
Ergotamine	Ergotamine may increase the hypertensive 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
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 hydrobromide.	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
Isoprenaline	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Isoprenaline.	Approved
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
Levomilnacipran	Levomilnacipran may increase the tachycardic activities of Oxymetazoline.	Approved
Linezolid	Linezolid may increase the hypertensive activities of Oxymetazoline.	Approved, Investigational
Mephentermine	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Mephentermine.	Approved
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
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
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
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
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
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
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
Practolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Practolol.	Approved
Prazosin	Prazosin may decrease the vasoconstricting activities of Oxymetazoline.	Approved
Procaterol	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Procaterol.	Approved
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
Ritodrine	The risk or severity of adverse effects can be increased when Ritodrine is combined with Oxymetazoline.	Approved
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
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
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
Timolol	Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Timolol.	Approved
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
Venlafaxine	Venlafaxine may increase the tachycardic activities of Oxymetazoline.	Approved

Food Interactions

Not Available

References

Synthesis Reference

Not Available

General References

Not Available

External Links

Resource	Link
Human Metabolome Database (HMDB)	HMDB15070
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	124
Drug Product Database	10195
Drugs.com	http://www.drugs.com/cdi/oxymetazoline-solution.html
Wikipedia	Oxymetazoline

ATC Codes

R01AA05

S01GA04

R01AB07

AHFS Codes

52:32.00

PDB Entries

Not Available

FDA label

Not Available

MSDS

Download (74.6 KB)

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	Not Yet Recruiting	Treatment	Rhinitis	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	Treatment	Chronic Nasal Congestion / Sleep Apnea Syndrome	1
4	Withdrawn	Treatment	Allergic Rhinitis (AR) / Rhinitis Medicamentosa / Tachyphylaxis	1
Not Available	Completed	Treatment	Nasal Obstruction	1
Not Available	Enrolling by Invitation	Treatment	Adenoidectomy / Functional Endoscopic Sinus Surgery (FESS) / Turbinate Surgery	1
Not Available	Recruiting	Basic Science	Middle Ear Disease / Nasal Allergies	1
Not Available	Recruiting	Treatment	Blood Pressures / Nasal Bleeding	1
Not Available	Terminated	Treatment	Chronic Rhinitis	1

Pharmacoeconomics

Manufacturers

Schering plough healthcare products inc
Johnson and johnson group consumer companies

Packagers

Dosage forms

Form	Route	Strength
Liquid	Nasal	50 mg/100mL
Spray	Nasal	.05 g/mL
Spray	Nasal	0.05 mg
Spray, metered	Nasal	.05 mg/mL
Spray, metered	Nasal	.05 g/100mL
Spray	Nasal	.05 mg/100mL
Spray	Nasal	.2 mg/.4mL
Spray	Nasal	0.5 %
Spray	Nasal	.0005 g/mL
Solution	Nasal	0.05 %
Spray	Nasal	.05 g/100mL
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	Nasal	.5 mg/mL
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 %
Liquid	Ophthalmic	.25 mg/mL
Liquid	Ophthalmic	.025 %
Solution / drops	Ophthalmic	0.025 %
Spray	Nasal	.005 g/100mL

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

Not Available

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	Yes	ChemAxon
MDDR-like Rule	Yes	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)

Download (10.5 KB)

Spectra

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	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

Substituents

Xylenol / Phenylpropane / M-xylene / O-cresol / P-cresol / Phenol / Imidolactam / 2-imidazoline / Amidine / Carboxylic acid amidine

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

phenols, carboxamidine, imidazolines (CHEBI:7862 )

Targets

Details

1. 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) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine(PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:: ADRA1A
Uniprot ID:: P35348
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 ]

Details

2. 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 oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianser...
Gene Name:: ADRA2A
Uniprot ID:: P08913
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 ]

Details

3. 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
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 ]

Details

4. 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 > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phent...
Gene Name:: ADRA2B
Uniprot ID:: P18089
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 ]

Details

5. 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) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine (PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:: ADRA1B
Uniprot ID:: P35368
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 ]

Details

6. 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
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 June 11, 2017 15:45

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Structure for DB00935 (Oxymetazoline)

Targets

References

References

References

References

References

References