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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 Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Oximetazolinum
oxymetazoline hydrochloride crystalline
Oxymethazoline
Oxymetozoline
Salts Not Available
Brand names
Name Company
Afrin
Afrin Cherry 12 Hour Nasal Spray
Afrin Extra Moisturizing 12 Hour Nasal Spray
Afrin Original 12 Hour Nasal Spray
Afrin Original 12 Hour Nose Drops
Afrin Original 12 Hour Pump Mist
Afrin Sinus 12 Hour Nasal Spray
Dristan Long Lasting Mentholated Nasal Spray
Dristan Long Lasting Nasal Mist
Drixoral Nasal Solution
Duramist Plus Up To 12 Hour Nasal Decongestant Spray
Duration 12 Hour Nasal Spray
Genasal Nasal Spray Up to 12 Hour Relief
Hazol
Iliadin
Nafrine
Nasal Relief 12 Hour Nasal Spray
Nasivine
Navasin
Navisin
Neo-Synephrine 12 Hour Spray
Nezeril
Nostrilla 12 Hour Nasal Decongestant
OcuClear
Oxylazine
Rhinofrenol
Rhinolitan
Sinerol
Vicks Sinex 12 Hour Nasal Spray
Vicks Sinex 12 Hour Ultra Fine Mist for Sinus Relief
Visine L.R
Visine L.R.
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Brand mixtures Not Available
Categories
  • Sympathomimetics
  • Adrenergic alpha-Agonists
  • Nasal Decongestants
CAS number 1491-59-4
Weight Average: 260.3746
Monoisotopic: 260.1888634
Chemical Formula C16H24N2O
InChI Key InChIKey=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)
Plain Text
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
Plain Text
Mass Spec show (10.5 KB)
Taxonomy
Kingdom Organic
Classes
  • Phenols and Derivatives
  • Cumenes and Derivatives
  • Phenethylamines
Substructures
  • Hydroxy Compounds
  • Imidazolines
  • Carboxylic Acids and Derivatives
  • Phenols and Derivatives
  • Benzene and Derivatives
  • Cumenes and Derivatives
  • Imidazoles
  • Phenethylamines
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamidines
  • Imines
  • Phenyl Esters
Pharmacology
Indication For treatment of nasal congestion and redness associated with minor irritations of the eye
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.
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
Pharmacoeconomics
Manufacturers
  • Schering plough healthcare products inc
  • Johnson and johnson group consumer companies
Packagers
Dosage forms
Form Route Strength
Liquid Nasal
Solution Nasal
Solution Respiratory (inhalation)
Solution / drops Ophthalmic
Spray Nasal
Prices
Unit description Cost Unit
Oxymetazoline hcl powder 84.42 USD g
Afrin 0.05% nose spray 0.62 USD ml
Drixoral cold & allergy tablet sa 0.4 USD tablet
Afrin no drip sinus pump mist 0.38 USD ml
Oxymetazoline 0.05% spray 0.38 USD ml
Anefrin 0.05% nasal spray 0.37 USD ml
Afrin sinus spray 0.33 USD ml
Dristan long lasting mist 0.32 USD ml
Neo-synephrine 12 hour spray 0.28 USD ml
Visine long lasting eye drops 0.27 USD ml
12 hour nasal relief spray 0.24 USD ml
Dristan cold multi-symp tablet 0.23 USD tablet
Ocuclear eye drops 0.23 USD ml
CVS Pharmacy nasal spray 0.05% 0.22 USD ml
No drip 0.05% nasal spray 0.13 USD ml
Nasal spray 0.05% 0.06 USD ml
Sinus nasal spray 0.06 USD ml
Nasal decongestant 0.05% spray 0.03 USD ml
Pv nasal spray 0.05% 0.03 USD ml
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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 182 °C PhysProp
logP 3.4 Not Available
Predicted Properties
Property Value Source
water solubility 5.15e-02 g/l 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 ChemAxon
rotatable bond count 3 ChemAxon
refractivity 79.8 ChemAxon
polarizability 30.64 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C07363 Link_out
PubChem Compound 4636 Link_out
PubChem Substance 46505622 Link_out
ChemSpider 4475 Link_out
BindingDB 50027075 Link_out
Therapeutic Targets Database DAP000235 Link_out
PharmGKB PA164748840 Link_out
IUPHAR 124 Link_out
Guide to Pharmacology 124 Link_out
Drug Product Database 2245578 Link_out
Drugs.com http://www.drugs.com/cdi/oxymetazoline-solution.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Oxymetazoline Link_out
ATC Codes
  • R01AA05
  • R01AB07
  • S01GA04
AHFS Codes
  • 52:32.00
PDB Entries Not Available
FDA label Not Available
MSDS show (74.6 KB)
Interactions
Drug Interactions
Drug Interaction
Tranylcypromine The MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the alpha1-agonist, Oxymetazoline. Concomitant therapy should be avoided.
Food Interactions Not Available
Targets

1. Alpha-1A adrenergic receptor

Pharmacological action: yes
Actions: agonist

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

Organism class: human
UniProt ID: P35348 Link_out
Gene: ADRA1A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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
  2. 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
  3. Shibata K, Taketani K: [Excitatory effect of noradrenaline on rat airway parasympathetic ganglion neurons] Fukuoka Igaku Zasshi. 2001 Nov;92(11):377-83. Pubmed
  4. 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
  5. 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

2. Alpha-2A adrenergic receptor

Pharmacological action: yes
Actions: agonist

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 = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol

Organism class: human
UniProt ID: P08913 Link_out
Gene: ADRA2A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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
  2. 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
  3. 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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19