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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyOxymetazoline
Identification
- Name
- Oxymetazoline
- Accession Number
- DB00935 (APRD01158)
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Description
A direct acting sympathomimetic used as a vasoconstrictor to relieve nasal congestion. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1251)
- Structure
Structure for DB00935 (Oxymetazoline)
- 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
- 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 Canada 
Rhofade Cream 10 mg/g Topical Allergan 2017-01-18 Not applicable US 
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End 12 Hour Nasal Spray .05 g/100mL Nasal Meijer Distribution 2015-05-06 Not applicable US 12 Hour Nasal Spray .05 g/100mL Nasal Healthlife of Usa 2018-01-02 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 Altaire Pharmaceuticals Inc. 2001-06-01 Not applicable US 12 Hour Original Nasal Decongestant Liquid 50 mg/100mL Nasal Faria Llc Dba Sheffield Pharmaceutcials 2014-05-30 Not applicable US 12 Hour Original Nasal Decongestant Liquid 50 mg/100mL Nasal Preferreed Pharmaceuticals Inc. 2018-01-02 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 Spray .5 mg/mL Topical Navajo Manuracturing Company 2017-12-04 Not applicable US Afrin Cold Spray 0.05 mg Nasal Schering Plough 2002-09-28 2006-08-01 Canada - 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 US - 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
- Adrenergic Agents
- Adrenergic Agonists
- Adrenergic alpha-1 Receptor Agonists
- Adrenergic alpha-2 Receptor Agonists
- Adrenergic alpha-Agonists
- Autonomic Agents
- Cardiovascular Agents
- Decongestants and Antiallergics
- Imidazoles
- Nasal Decongestants
- Nasal Preparations
- Neurotransmitter Agents
- Ophthalmologicals
- Peripheral Nervous System Agents
- Respiratory System Agents
- Sensory Organs
- Sympathomimetics
- Sympathomimetics Used as Decongestants
- Sympathomimetics, Plain
- Vasoconstrictor Agents
- 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
- Associated Conditions
- 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 agonistHuman AAlpha-2A adrenergic receptor agonistpartial agonistHuman UAlpha-2C adrenergic receptor agonistHuman UAlpha-2B adrenergic receptor binderHuman UAlpha-1B adrenergic receptor agonistHuman UAlpha-1D adrenergic receptor agonistHuman - 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 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypertensive activities of Oxymetazoline. Experimental Acebutolol Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Acebutolol. Approved, Investigational Acepromazine Acepromazine may decrease the vasoconstricting activities of Oxymetazoline. Approved, Vet 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 Amiodarone Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Amiodarone. Approved, Investigational Amitriptyline Amitriptyline may decrease the antihypertensive activities of Oxymetazoline. Approved Amitriptylinoxide Amitriptylinoxide may decrease the antihypertensive activities of Oxymetazoline. Approved, Investigational Amoxapine Amoxapine may decrease the antihypertensive activities of Oxymetazoline. Approved Amphetamine Amphetamine may increase the hypertensive activities of Oxymetazoline. Approved, Illicit, Investigational Aripiprazole Aripiprazole may decrease the vasoconstricting activities of Oxymetazoline. Approved, Investigational Arotinolol Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Arotinolol. Investigational Asenapine Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Asenapine. 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 Benmoxin Benmoxin may increase the hypertensive activities of Oxymetazoline. Withdrawn 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 Brexpiprazole Brexpiprazole may decrease the vasoconstricting activities of Oxymetazoline. Approved, Investigational Brofaromine Brofaromine may increase the hypertensive activities of Oxymetazoline. Experimental 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 Butriptyline Butriptyline may decrease the antihypertensive activities of Oxymetazoline. Approved Cabergoline Cabergoline may increase the hypertensive and vasoconstricting activities of Oxymetazoline. Approved Caroxazone Caroxazone may increase the hypertensive activities of Oxymetazoline. Withdrawn 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 Chlorpromazine Chlorpromazine may decrease the vasoconstricting activities of Oxymetazoline. Approved, Investigational, Vet Approved 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 Clozapine Clozapine may decrease the vasoconstricting activities of Oxymetazoline. Approved Dapiprazole Dapiprazole may decrease the vasoconstricting 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 Dextroamphetamine Dextroamphetamine may decrease the vasoconstricting activities of Oxymetazoline. Approved, Illicit Dibenzepin Dibenzepin may decrease the antihypertensive activities of Oxymetazoline. Experimental Dihydroergocornine Dihydroergocornine may increase the hypertensive activities of Oxymetazoline. Approved Dihydroergocristine Dihydroergocristine may increase the hypertensive activities of Oxymetazoline. Approved, Experimental Dihydroergocryptine Dihydroergocryptine may increase the hypertensive activities of Oxymetazoline. Experimental Dihydroergotamine Dihydroergotamine may increase the hypertensive and vasoconstricting activities of Oxymetazoline. Approved, Investigational Dimetacrine Dimetacrine may decrease the antihypertensive activities of Oxymetazoline. Approved, Withdrawn 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 Dronedarone Dronedarone may decrease the vasoconstricting activities of Oxymetazoline. Approved Droperidol Droperidol may decrease the vasoconstricting activities of Oxymetazoline. Approved, Vet Approved 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 Esatenolol Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Esatenolol. Experimental Escitalopram Escitalopram may decrease the vasoconstricting activities of Oxymetazoline. Approved, 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 Fentanyl The serum concentration of Fentanyl can be decreased when it is combined with Oxymetazoline. Approved, Illicit, Investigational, Vet Approved Flupentixol Flupentixol may decrease the vasoconstricting activities of Oxymetazoline. Approved, Investigational, Withdrawn Furazolidone Furazolidone may increase the hypertensive activities of Oxymetazoline. Approved, Investigational, Vet Approved Harmaline Harmaline may increase the hypertensive activities of Oxymetazoline. Experimental Hyaluronidase Hyaluronidase may increase the vasoconstricting activities of Oxymetazoline. Approved, Investigational Hydracarbazine Hydracarbazine may increase the hypertensive activities of Oxymetazoline. Experimental Hydroxyamphetamine The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Hydroxyamphetamine. Approved Iloperidone Iloperidone may decrease the vasoconstricting activities of Oxymetazoline. 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 Iproclozide Iproclozide may increase the hypertensive activities of Oxymetazoline. Withdrawn Iproniazid Iproniazid may increase the hypertensive activities of Oxymetazoline. Withdrawn Isocarboxazid Isocarboxazid may increase the hypertensive activities of Oxymetazoline. Approved 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 Levobetaxolol Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Levobetaxolol. Approved, Investigational Levomilnacipran Levomilnacipran may increase the tachycardic activities of Oxymetazoline. Approved, Investigational Linezolid Linezolid may increase the hypertensive activities of Oxymetazoline. Approved, Investigational Lisdexamfetamine Lisdexamfetamine may decrease the vasoconstricting activities of Oxymetazoline. Approved, Investigational Lisuride Lisuride may increase the hypertensive activities of Oxymetazoline. Approved, Investigational Lofepramine Lofepramine may decrease the antihypertensive activities of Oxymetazoline. Experimental Lysergic Acid Diethylamide Lysergic Acid Diethylamide may increase the hypertensive activities of Oxymetazoline. Illicit, Investigational, Withdrawn Mebanazine Mebanazine may increase the hypertensive activities of Oxymetazoline. Withdrawn Mefenorex The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Mefenorex. Experimental Melitracen Melitracen may decrease the antihypertensive activities of Oxymetazoline. Experimental, Investigational 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 Metergoline Metergoline may increase the hypertensive activities of Oxymetazoline. Experimental Methamphetamine The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Methamphetamine. Approved, Illicit Methotrimeprazine Methotrimeprazine may decrease the vasoconstricting activities of Oxymetazoline. Approved, Investigational Methoxamine The risk or severity of adverse effects can be increased when Methoxamine is combined with Oxymetazoline. Approved, Investigational Methylene blue Methylene blue may increase the hypertensive activities of Oxymetazoline. Approved, Investigational Methylergometrine Methylergometrine may increase the hypertensive and vasoconstricting activities of Oxymetazoline. Approved Methysergide Methysergide may increase the hypertensive 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 Minaprine Minaprine may increase the hypertensive activities of Oxymetazoline. Approved Mirtazapine Mirtazapine may decrease the antihypertensive activities of Oxymetazoline. Approved Moclobemide Moclobemide may increase the hypertensive activities of Oxymetazoline. Approved, Investigational 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 Nefazodone Nefazodone may decrease the vasoconstricting activities of Oxymetazoline. Approved, Withdrawn Nialamide Nialamide may increase the hypertensive activities of Oxymetazoline. Withdrawn Nicardipine Nicardipine may decrease the vasoconstricting activities of Oxymetazoline. Approved, Investigational Nicergoline Nicergoline may increase the hypertensive activities of Oxymetazoline. Approved, Investigational Niguldipine Niguldipine may decrease the vasoconstricting activities of Oxymetazoline. Experimental 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 Octamoxin Octamoxin may increase the hypertensive activities of Oxymetazoline. Withdrawn Olanzapine Olanzapine may decrease the vasoconstricting activities of Oxymetazoline. Approved, Investigational 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 Paliperidone Paliperidone may decrease the vasoconstricting activities of Oxymetazoline. Approved Pargyline Pargyline may increase the hypertensive activities of Oxymetazoline. 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 Pergolide Pergolide may increase the hypertensive activities of Oxymetazoline. Approved, Investigational, Vet Approved, Withdrawn Phenelzine Phenelzine may increase the hypertensive activities of Oxymetazoline. Approved Pheniprazine Pheniprazine may increase the hypertensive activities of Oxymetazoline. Withdrawn Phenmetrazine The risk or severity of adverse effects can be increased when Phenmetrazine is combined with Oxymetazoline. Approved, Illicit Phenoxybenzamine Phenoxybenzamine may decrease the vasoconstricting activities of Oxymetazoline. Approved Phenoxypropazine Phenoxypropazine may increase the hypertensive activities of Oxymetazoline. Withdrawn Phentermine The risk or severity of adverse effects can be increased when Phentermine is combined with Oxymetazoline. Approved, Illicit Phentolamine Phentolamine may decrease the vasoconstricting activities of Oxymetazoline. Approved 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 Pirlindole Pirlindole may increase the hypertensive activities of Oxymetazoline. Approved Pivhydrazine Pivhydrazine may increase the hypertensive activities of Oxymetazoline. Withdrawn Pizotifen Pizotifen may decrease the vasoconstricting activities of Oxymetazoline. Approved 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 Procaine Procaine may increase the hypertensive activities of Oxymetazoline. Approved, Investigational, Vet Approved Procarbazine Procarbazine may increase the hypertensive activities of Oxymetazoline. Approved, Investigational Procaterol The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Procaterol. Approved, Investigational Promazine Promazine may decrease the vasoconstricting activities of Oxymetazoline. Approved, Vet Approved Propafenone Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Propafenone. Approved Propericiazine Propericiazine may decrease the vasoconstricting activities of Oxymetazoline. Approved, Investigational Propiomazine Propiomazine may decrease the vasoconstricting activities of Oxymetazoline. Approved Propiverine Propiverine may decrease the vasoconstricting activities of Oxymetazoline. 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 Quetiapine Quetiapine may decrease the vasoconstricting activities of Oxymetazoline. Approved Quinidine Quinidine may decrease the vasoconstricting activities of Oxymetazoline. Approved, Investigational Racepinephrine The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Racepinephrine. Approved Rasagiline Rasagiline may increase the hypertensive activities of Oxymetazoline. Approved Risperidone Risperidone may decrease the vasoconstricting activities of Oxymetazoline. Approved, Investigational Ritodrine The risk or severity of adverse effects can be increased when Ritodrine is combined with Oxymetazoline. Approved, Investigational Safrazine Safrazine may increase the hypertensive activities of Oxymetazoline. Withdrawn Selegiline Selegiline may increase the hypertensive activities of Oxymetazoline. Approved, Investigational, Vet 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 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 Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Terbutaline. Approved Terguride Terguride may increase the hypertensive activities of Oxymetazoline. Experimental 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 Thioproperazine Thioproperazine may decrease the vasoconstricting activities of Oxymetazoline. Approved Thioridazine Thioridazine may decrease the vasoconstricting activities of Oxymetazoline. Approved, Withdrawn Tianeptine Tianeptine may decrease the antihypertensive activities of Oxymetazoline. Approved, Investigational Timolol Oxymetazoline may increase the atrioventricular blocking (AV block) activities of Timolol. Approved Tolazoline Tolazoline may decrease the vasoconstricting activities of Oxymetazoline. Approved, Vet Approved Toloxatone Toloxatone may increase the hypertensive activities of Oxymetazoline. Approved Tramazoline The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Tramazoline. Investigational Tranylcypromine Tranylcypromine may increase the hypertensive activities of Oxymetazoline. Approved, Investigational Trazodone Trazodone may decrease the vasoconstricting activities of Oxymetazoline. Approved, Investigational Tretoquinol The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Tretoquinol. Experimental Trifluoperazine Trifluoperazine may decrease the vasoconstricting activities of Oxymetazoline. Approved, Investigational 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 Verapamil Verapamil may decrease the vasoconstricting activities of Oxymetazoline. Approved Ziprasidone Ziprasidone may decrease the vasoconstricting activities of Oxymetazoline. Approved Zuclopenthixol Zuclopenthixol may decrease the vasoconstricting activities of Oxymetazoline. Approved, Investigational - Food Interactions
- Not Available
References
- General References
- Not Available
- External Links
- Human Metabolome Database
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- KEGG Compound
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- Oxymetazoline
- ATC Codes
- R01AA05 — Oxymetazoline
- R01AA — Sympathomimetics, plain
- R01A — DECONGESTANTS AND OTHER NASAL PREPARATIONS FOR TOPICAL USE
- R01 — NASAL PREPARATIONS
- R — RESPIRATORY SYSTEM
- R01AB — Sympathomimetics, combinations excl. corticosteroids
- R01A — DECONGESTANTS AND OTHER NASAL PREPARATIONS FOR TOPICAL USE
- R01 — NASAL PREPARATIONS
- R — RESPIRATORY SYSTEM
- AHFS Codes
- 52:32.00 — Vasoconstrictors
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- 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 Nasal .05 g/mL 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 .2 mg/.4mL Spray Nasal 0.5 % Spray Nasal .0005 g/mL Spray Nasal .5 mg/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 .05 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 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 US US6413499 No 2000-03-20 2020-03-20 US US9308191 No 2010-04-02 2030-04-02 US US8883838 No 2011-12-01 2031-12-01 US US7812049 No 2008-05-02 2028-05-02 US US8420688 No 2004-08-02 2024-08-02 US
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
Spectra
- Mass Spec (NIST)
- Download (10.5 KB)
- 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
- 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]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Yes
- Actions
- AgonistPartial 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]
- 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]
- 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]
- 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]
- 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 June 24, 2018 20:22