U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C16H24N2O
Molecular Weight 260.3746
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXYMETAZOLINE

SMILES

CC1=C(CC2=NCCN2)C(C)=C(O)C(=C1)C(C)(C)C

InChI

InChIKey=WYWIFABBXFUGLM-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C16H24N2O
Molecular Weight 260.3746
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Oxymetazoline is an adrenergic alpha-agonist, 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. Oxymetazoline is self-medication for temporary relief of nasal congestion associated with the common cold, hay fever, or other upper respiratory allergies. Oxymetazoline is available over-the-counter as a topical decongestant in the form of oxymetazoline hydrochloride in nasal sprays such as Afrin, Operil, Dristan, Dimetapp, oxyspray, Facimin, Nasivin, Nostrilla, Sudafed OM, Vicks Sinex, Zicam, SinuFrin, and Mucinex Full Force. Due to its vasoconstricting properties, oxymetazoline is also used to treat nose bleeds and eye redness.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Renal actions of the alpha2-adrenoceptor agonist, xylazine, in the anaesthetised rat.
2001 Oct
Vasocontractile effects of alpha 2-adrenergic agonists associated with intracellular calcium release.
2002
Contractile responses of the rat vas deferens after epithelium removal.
2002 May 3
Search of antimicrobial activity of selected non-antibiotic drugs.
2002 Nov-Dec
Pharmacological characterization of alpha 2-adrenoceptor-mediated responses in pig nasal mucosa.
2003 Aug
Evidence for nonadrenoceptor responses to imidazoline derivatives in the porcine isolated rectal artery.
2003 Dec
Alpha(2A)-adrenergic versus imidazoline receptor controversy in rilmenidine's action: alpha(2A)-antagonism in humans versus alpha(2A)-agonism in rabbits.
2003 Dec
Effects of acute, repeated and chronic variable stress on in vivo tyrosine hydroxylase activity and on alpha(2)-adrenoceptor sensitivity in the rat brain.
2003 Dec
Transdermal penetration of vasoconstrictors--present understanding and assessment of the human epidermal flux and retention of free bases and ion-pairs.
2003 Feb
5-HT7 receptor-mediated relaxation of the oviduct in nonpregnant proestrus pigs.
2003 Feb 14
Contractile actions of imidazoline alpha-adrenoceptor agonists and effects of noncompetitive alpha1-adrenoceptor antagonists in human vas deferens.
2003 Feb 21
Functional characterisation of alpha(1)-adrenoceptors in denervated rat vas deferens.
2003 Jul
Alpha 2 adrenoceptor-mediated presynaptic inhibition of primary afferent glutamatergic transmission in rat substantia gelatinosa neurons.
2003 Mar
[Tolerance and effectiveness of oxymetazoline and xylometazoline in treatment of acute rhinitis].
2003 Oct
Oxymetazoline nasal spray three times daily for four weeks in normal subjects is not associated with rebound congestion or tachyphylaxis.
2003 Sep
Sympathomimetic drug allergy: cross-reactivity study by patch test.
2004
Bulk is a determinant of oxymetazoline affinity for the alpha1A-adrenergic receptor.
2004
Synthesis and identification of two potential oxidation degradants of oxymetazoline.
2004
Chronic rhinosinusitis: management for optimal outcomes.
2004
Chromatography studies on bio-affinity of nine ligands of alpha1-adrenoceptor to alpha1D subtypes overexpressed in cell membrane.
2004 Aug
Antimuscarinic action of oxymetazoline on human intraocular muscles.
2004 Aug
[Ethyl-3H]RS-79948-197 alpha2-adrenoceptor autoradiography validation in alpha2-adrenoceptor knockout mice.
2004 Aug 30
Behavioral effects of serotonin and serotonin agonists in two crayfish species, Procambarus clarkii and Orconectes rusticus.
2004 Dec
Construction and analytical applications of plastic membrane electrode for oxymetazoline hydrochloride.
2004 Feb
Human alpha1D-adrenoceptor phosphorylation and desensitization.
2004 May 15
The Janus faces of adrenoceptors: factors controlling the coupling of adrenoceptors to multiple signal transduction pathways.
2004 Nov
Controlling bleeding from superficial wounds by the use of topical alpha adrenoreceptor agonists spray. A randomized, masked, controlled study.
2004 Nov
Allosteric modulation of semicarbazide-sensitive amine oxidase activities in vitro by imidazoline receptor ligands.
2004 Oct
Thunderclap headache and reversible segmental cerebral vasoconstriction associated with use of oxymetazoline nasal spray.
2004 Sep 14
Use of mometasone furoate aqueous nasal spray in the treatment of rhinitis medicamentosa: an experimental study.
2005 Apr
Pulmonary edema following phenylephrine intranasal spray administration during the induction of general anesthesia in a child.
2005 Apr 30
Oxymetazoline solutions inhibit middle ear pathogens and are not ototoxic.
2005 Aug
Differential distribution of functional alph}1-adrenergic receptor subtypes along the rat tail artery.
2005 Aug
Characterisation of alpha2-adrenoceptor subtypes involved in gastric emptying, gastric motility and gastric mucosal defence.
2005 Dec 28
Oxymetazoline is equivalent to ciprofloxacin in preventing postoperative otorrhea or tympanostomy tube obstruction.
2005 Feb
Early changes in insulin secretion and action induced by high-fat diet are related to a decreased sympathetic tone.
2005 Jan
An assessment for the presence of bacterial contamination of Venturi principle atomizers in a clinical setting.
2005 Jan-Feb
Is oxymetazoline really safe for middle ear use.
2005 Jul
[Usefulness of fenspiride in the treatment of acute otitis media in children].
2005 Jun
Otic barotrauma from air travel.
2005 May
Clinical images: Afrin-induced central nervous system vasospasm and thunderclap headache.
2005 Oct
[Investigation of the effect of oxymetazoline on the duration of rhinitis].
2005 Oct 13
[Investigation of the effect of oxymetazoline on the duration of rhinitis. results of a placebo-controlled double-blind study in patients with acute rhinitis].
2005 Oct 6
[The observation of the ciliotoxicity of nasal mucosa with nasal decongestant].
2005 Sep
Pharmacological characterization of postjunctional alpha-adrenoceptors in human nasal mucosa.
2005 Sep-Oct
Oxymetazoline inhibits proinflammatory reactions: effect on arachidonic acid-derived metabolites.
2006 Feb
In situ gelling, bioadhesive nasal inserts for extended drug delivery: in vitro characterization of a new nasal dosage form.
2006 Jan
Nasal wall compliance in vasomotor rhinitis.
2006 Jan
Human breast cell lines exhibit functional alpha2-adrenoceptors.
2006 Jul
Simultaneous determination of triamcinolone acetonide and oxymetazoline hydrochloride in nasal spray formulations by HPLC.
2006 Mar 18
Patents

Sample Use Guides

In Vivo Use Guide
Pediatric Patients Nasal Congestion Intranasal For self-medication in children ≥6 years of age: 2 or 3 sprays of a 0.05% nasal solution in each nostril every 10–12 hours (usually in the morning and evening), up to 2 times daily. Conjunctival Congestion Ophthalmic For self-medication in children ≥6 years of age: 1 or 2 drops of a 0.025% ophthalmic solution in the affected eye(s) every 6 hours as needed. Adults Nasal Congestion Intranasal For self-medication: 2 or 3 sprays of a 0.05% nasal solution in each nostril every 10–12 hours (usually in the morning and evening), up to 2 times daily. Conjunctival Congestion Ophthalmic For self-medication: 1 or 2 drops of a 0.025% ophthalmic solution in the affected eye(s) every 6 hours as needed.
Route of Administration: Nasal
In Vitro Use Guide
Oxymetazoline had a concentration-dependent inhibitory effect on cultured human nasal CBF from 0.25 to 2.00 g/L.
Substance Class Chemical
Created
by admin
on Tue Oct 22 06:09:56 UTC 2019
Edited
by admin
on Tue Oct 22 06:09:56 UTC 2019
Record UNII
8VLN5B44ZY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OXYMETAZOLINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
NASACON
Brand Name English
AFRIN
Brand Name English
OXYMETAZOLINE [WHO-DD]
Common Name English
OPERIL
Brand Name English
OXYMETAZOLINE [VANDF]
Common Name English
OXYMETAZOLINE [INN]
Common Name English
PHENOL, 3-((4,5-DIHYDRO-1H-IMIDAZOL-2-YL)METHYL)-6-(1,1-DIMETHYLETHYL)-2,4-DIMETHYL-
Systematic Name English
OXYMETAZOLINE [HSDB]
Common Name English
6-TERT-BUTYL-3-(2-IMIDAZOLIN-2-YLMETHYL)-2,4-DIMETHYLPHENOL
Systematic Name English
OXYMETAZOLINE [MI]
Common Name English
Classification Tree Code System Code
WHO-VATC QR01AA05
Created by admin on Tue Oct 22 06:09:56 UTC 2019 , Edited by admin on Tue Oct 22 06:09:56 UTC 2019
WHO-ATC S01GA04
Created by admin on Tue Oct 22 06:09:56 UTC 2019 , Edited by admin on Tue Oct 22 06:09:56 UTC 2019
WHO-ATC R01AB07
Created by admin on Tue Oct 22 06:09:56 UTC 2019 , Edited by admin on Tue Oct 22 06:09:56 UTC 2019
NDF-RT N0000192562
Created by admin on Tue Oct 22 06:09:56 UTC 2019 , Edited by admin on Tue Oct 22 06:09:56 UTC 2019
WHO-VATC QR01AB07
Created by admin on Tue Oct 22 06:09:56 UTC 2019 , Edited by admin on Tue Oct 22 06:09:56 UTC 2019
NCI_THESAURUS C29709
Created by admin on Tue Oct 22 06:09:56 UTC 2019 , Edited by admin on Tue Oct 22 06:09:56 UTC 2019
WHO-ATC R01AA05
Created by admin on Tue Oct 22 06:09:56 UTC 2019 , Edited by admin on Tue Oct 22 06:09:56 UTC 2019
WHO-VATC QS01GA04
Created by admin on Tue Oct 22 06:09:56 UTC 2019 , Edited by admin on Tue Oct 22 06:09:56 UTC 2019
Code System Code Type Description
ECHA (EC/EINECS)
216-079-1
Created by admin on Tue Oct 22 06:09:56 UTC 2019 , Edited by admin on Tue Oct 22 06:09:56 UTC 2019
PRIMARY
ChEMBL
CHEMBL762
Created by admin on Tue Oct 22 06:09:56 UTC 2019 , Edited by admin on Tue Oct 22 06:09:56 UTC 2019
PRIMARY
NCI_THESAURUS
C61871
Created by admin on Tue Oct 22 06:09:56 UTC 2019 , Edited by admin on Tue Oct 22 06:09:56 UTC 2019
PRIMARY
HSDB
1491-59-4
Created by admin on Tue Oct 22 06:09:56 UTC 2019 , Edited by admin on Tue Oct 22 06:09:56 UTC 2019
PRIMARY
MERCK INDEX
M8335
Created by admin on Tue Oct 22 06:09:56 UTC 2019 , Edited by admin on Tue Oct 22 06:09:56 UTC 2019
PRIMARY Merck Index
MESH
D010109
Created by admin on Tue Oct 22 06:09:56 UTC 2019 , Edited by admin on Tue Oct 22 06:09:56 UTC 2019
PRIMARY
RXCUI
7812
Created by admin on Tue Oct 22 06:09:56 UTC 2019 , Edited by admin on Tue Oct 22 06:09:56 UTC 2019
PRIMARY RxNorm
DRUG BANK
DB00935
Created by admin on Tue Oct 22 06:09:56 UTC 2019 , Edited by admin on Tue Oct 22 06:09:56 UTC 2019
PRIMARY
EPA CompTox
1491-59-4
Created by admin on Tue Oct 22 06:09:56 UTC 2019 , Edited by admin on Tue Oct 22 06:09:56 UTC 2019
PRIMARY
EVMPD
SUB09567MIG
Created by admin on Tue Oct 22 06:09:56 UTC 2019 , Edited by admin on Tue Oct 22 06:09:56 UTC 2019
PRIMARY
IUPHAR
124
Created by admin on Tue Oct 22 06:09:56 UTC 2019 , Edited by admin on Tue Oct 22 06:09:56 UTC 2019
PRIMARY
LactMed
1491-59-4
Created by admin on Tue Oct 22 06:09:56 UTC 2019 , Edited by admin on Tue Oct 22 06:09:56 UTC 2019
PRIMARY
NDF-RT
N0000011304
Created by admin on Tue Oct 22 06:09:56 UTC 2019 , Edited by admin on Tue Oct 22 06:09:56 UTC 2019
PRIMARY Imidazolines [Chemical/Ingredient]
PUBCHEM
4636
Created by admin on Tue Oct 22 06:09:56 UTC 2019 , Edited by admin on Tue Oct 22 06:09:56 UTC 2019
PRIMARY
NDF-RT
N0000009908
Created by admin on Tue Oct 22 06:09:56 UTC 2019 , Edited by admin on Tue Oct 22 06:09:56 UTC 2019
PRIMARY Vasoconstriction [PE]
INN
1400
Created by admin on Tue Oct 22 06:09:56 UTC 2019 , Edited by admin on Tue Oct 22 06:09:56 UTC 2019
PRIMARY
CAS
1491-59-4
Created by admin on Tue Oct 22 06:09:56 UTC 2019 , Edited by admin on Tue Oct 22 06:09:56 UTC 2019
PRIMARY
WIKIPEDIA
OXYMETAZOLINE
Created by admin on Tue Oct 22 06:09:56 UTC 2019 , Edited by admin on Tue Oct 22 06:09:56 UTC 2019
PRIMARY
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