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Details

Stereochemistry ACHIRAL
Molecular Formula C16H24N2O.ClH
Molecular Weight 296.836
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXYMETAZOLINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=BEEDODBODQVSIM-UHFFFAOYSA-N
InChI=1S/C16H24N2O.ClH/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);1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C16H24N2O
Molecular Weight 260.3746
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/monograph/oxymetazoline-hydrochloride.html

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

Curator's Comment: Oxymetazoline does not cross the blood brain barrier

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Oxymetazoline Hydrochloride

Approved Use

Temporary relief of nasal congestion (due to a cold, hay fever, or other upper respiratory allergies) and sinus congestion/pressure.

Launch Date

1989
Primary
OCUCLEAR

Approved Use

Relief of redness of eye due to minor eye irritations

Launch Date

1986
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
60.5 pg/mL
3 mg single, topical
dose: 3 mg
route of administration: Topical
experiment type: SINGLE
co-administered:
OXYMETAZOLINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1.78 ng/mL
0.3 mg single, nasal
dose: 0.3 mg
route of administration: Nasal
experiment type: SINGLE
co-administered: Tetracaine
OXYMETAZOLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
895 pg × h/mL
3 mg single, topical
dose: 3 mg
route of administration: Topical
experiment type: SINGLE
co-administered:
OXYMETAZOLINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
4.24 ng × h/mL
0.3 mg single, nasal
dose: 0.3 mg
route of administration: Nasal
experiment type: SINGLE
co-administered: Tetracaine
OXYMETAZOLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5.23 h
0.3 mg single, nasal
dose: 0.3 mg
route of administration: Nasal
experiment type: SINGLE
co-administered: Tetracaine
OXYMETAZOLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
0.05 % single, intranasal
Dose: 0.05 %
Route: intranasal
Route: single
Dose: 0.05 %
Sources:
unhealthy, 4 years
Health Status: unhealthy
Age Group: 4 years
Sex: M
Sources:
Other AEs: Hypertensive crisis...
Other AEs:
Hypertensive crisis (1 patient)
Sources:
1 % 1 times / day multiple, topical
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, 53.1 years (range: 19–81 years)
Health Status: unhealthy
Age Group: 53.1 years (range: 19–81 years)
Sex: M+F
Sources:
Disc. AE: Application site dermatitis, Application site erythema...
AEs leading to
discontinuation/dose reduction:
Application site dermatitis (1.4%)
Application site erythema (0.5%)
Application site pain (0.5%)
Application site dryness (0.2%)
Hypoesthesia (0.2%)
Paresthesia (0.2%)
Rash (0.2%)
Urticaria (0.2%)
Photosensitivity reaction (0.2%)
Sources:
1.5 % 2 times / day multiple, topical
Highest studied dose
Dose: 1.5 %, 2 times / day
Route: topical
Route: multiple
Dose: 1.5 %, 2 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
AEs

AEs

AESignificanceDosePopulation
Hypertensive crisis 1 patient
0.05 % single, intranasal
Dose: 0.05 %
Route: intranasal
Route: single
Dose: 0.05 %
Sources:
unhealthy, 4 years
Health Status: unhealthy
Age Group: 4 years
Sex: M
Sources:
Application site dryness 0.2%
Disc. AE
1 % 1 times / day multiple, topical
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, 53.1 years (range: 19–81 years)
Health Status: unhealthy
Age Group: 53.1 years (range: 19–81 years)
Sex: M+F
Sources:
Hypoesthesia 0.2%
Disc. AE
1 % 1 times / day multiple, topical
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, 53.1 years (range: 19–81 years)
Health Status: unhealthy
Age Group: 53.1 years (range: 19–81 years)
Sex: M+F
Sources:
Paresthesia 0.2%
Disc. AE
1 % 1 times / day multiple, topical
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, 53.1 years (range: 19–81 years)
Health Status: unhealthy
Age Group: 53.1 years (range: 19–81 years)
Sex: M+F
Sources:
Photosensitivity reaction 0.2%
Disc. AE
1 % 1 times / day multiple, topical
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, 53.1 years (range: 19–81 years)
Health Status: unhealthy
Age Group: 53.1 years (range: 19–81 years)
Sex: M+F
Sources:
Rash 0.2%
Disc. AE
1 % 1 times / day multiple, topical
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, 53.1 years (range: 19–81 years)
Health Status: unhealthy
Age Group: 53.1 years (range: 19–81 years)
Sex: M+F
Sources:
Urticaria 0.2%
Disc. AE
1 % 1 times / day multiple, topical
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, 53.1 years (range: 19–81 years)
Health Status: unhealthy
Age Group: 53.1 years (range: 19–81 years)
Sex: M+F
Sources:
Application site erythema 0.5%
Disc. AE
1 % 1 times / day multiple, topical
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, 53.1 years (range: 19–81 years)
Health Status: unhealthy
Age Group: 53.1 years (range: 19–81 years)
Sex: M+F
Sources:
Application site pain 0.5%
Disc. AE
1 % 1 times / day multiple, topical
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, 53.1 years (range: 19–81 years)
Health Status: unhealthy
Age Group: 53.1 years (range: 19–81 years)
Sex: M+F
Sources:
Application site dermatitis 1.4%
Disc. AE
1 % 1 times / day multiple, topical
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, 53.1 years (range: 19–81 years)
Health Status: unhealthy
Age Group: 53.1 years (range: 19–81 years)
Sex: M+F
Sources:
OverviewDrug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
yes
yes
no (co-administration study)
Comment: concomitant oral moderate CYP2C19 inhibitors (e.g., esomeprazole, fluoxetine, and omeprazole): the results did not indicate an increase in oxymetazoline exposure associated with coadministration of oral moderate CYP2C19 inhibitors
Page: 7.0
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Hypertonic saline nasal provocation and acoustic rhinometry.
2002 Apr
Increased nasal mucosal swelling in subjects with asthma.
2002 Jan
The stability of oxymetazoline hydrochloride in aqueous solution.
2002 Jan-Feb
Acute exudative inflammation and nasally exhaled nitric oxide are two independent phenomena.
2002 Jan-Feb
Segmental analysis of nasal cavity compliance by acoustic rhinometry.
2002 Jul
Naphazoline-induced neuroendocrine changes: increases in ANP and cGMP levels, but suppression of NE, 3H-NE, and cAMP levels in rabbit eyes.
2002 Jul
Improved strategies and new treatment options for allergic rhinitis.
2002 Jun
Intracellular sodium modulates the state of protein kinase C phosphorylation of rat proximal tubule Na+,K+-ATPase.
2002 Jun
Effects of oxymetazoline on the ventilation of paranasal sinuses in healthy subjects.
2002 Mar-Apr
Desensitization of alpha(2)-adrenoceptors which regulate noradrenaline synthesis and release after chronic treatment with clorgyline in the rat brain.
2002 May
Search of antimicrobial activity of selected non-antibiotic drugs.
2002 Nov-Dec
Topical nasal anesthesia for transnasal fiberoptic laryngoscopy: a prospective, double-blind, cross-over study.
2003 Apr
alpha 2B-Adrenoceptor levels govern agonist and inverse agonist responses in PC12 cells.
2003 Aug 15
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
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
Central serous chorioretinopathy associated with administration of sympathomimetic agents.
2003 Jul
Stroke associated with sympathomimetics contained in over-the-counter cough and cold drugs.
2003 Jul
Alpha 2 adrenoceptor-mediated presynaptic inhibition of primary afferent glutamatergic transmission in rat substantia gelatinosa neurons.
2003 Mar
[The use of oxymetazoline in nasal endoscopic sinus surgery].
2003 May
[Acute exposure to imidazoline derivatives in children].
2003 Nov-Dec
[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
Synthesis and identification of two potential oxidation degradants of oxymetazoline.
2004
Intranasal drug delivery: an alternative to intravenous administration in selected emergency cases.
2004 Apr
Antimuscarinic action of oxymetazoline on human intraocular muscles.
2004 Aug
Behavioral effects of serotonin and serotonin agonists in two crayfish species, Procambarus clarkii and Orconectes rusticus.
2004 Dec
Safety review of benzalkonium chloride used as a preservative in intranasal solutions: an overview of conflicting data and opinions.
2004 Jan
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
Use of mometasone furoate aqueous nasal spray in the treatment of rhinitis medicamentosa: an experimental study.
2005 Apr
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
An assessment for the presence of bacterial contamination of Venturi principle atomizers in a clinical setting.
2005 Jan-Feb
[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
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
Curator's Comment: Ophthalmic use or intranasal: Intranasal Administration Administer nasal solution intranasally as sprays or nasal pumps. Prior to initial use of metered sprays, prime nasal inhaler by depressing the pump firmly several times. Administer nasal spray or pump into each nostril while head is erect. Ophthalmic Administration Administer ophthalmic solution topically to the conjunctiva.
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
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 Mon Mar 31 17:35:56 GMT 2025
Edited
by admin
on Mon Mar 31 17:35:56 GMT 2025
Record UNII
K89MJ0S5VY
Record Status Validated (UNII)
Record Version
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Name Type Language
KOVANAZE COMPONENT OXYMETAZOLINE HYDROCHLORIDE
Preferred Name English
OXYMETAZOLINE HYDROCHLORIDE
EP   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
OXYMETAZOLINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
OXYMETAZOLINE HYDROCHLORIDE [MART.]
Common Name English
NSC-757254
Code English
UPNEEQ
Brand Name English
AGN-199201
Common Name English
OXYMETAZOLINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
OXYMETAZOLINE HYDROCHLORIDE [USP IMPURITY]
Common Name English
OXYMETAZOLINE HYDROCHLORIDE [JAN]
Common Name English
VISINE L.R.
Brand Name English
SCH-9384
Code English
Oxymetazoline hydrochloride [WHO-DD]
Common Name English
OXYMETAZOLINE HYDROCHLORIDE [USAN]
Common Name English
PHENOL, 3-((4,5-DIHYDRO-1H-IMIDAZOL-2-YL)METHYL)-6-(1,1-DIMETHYLETHYL)-2,4-DIMETHYL-, MONOHYDROCHLORIDE
Common Name English
OXYMETAZOLINE HYDROCHLORIDE [VANDF]
Common Name English
OXYMETAZOLINE HYDROCHLORIDE [MI]
Common Name English
6-tert-Butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenol monohydrochloride
Systematic Name English
OCUCLEAR
Brand Name English
OXYMETAZOLINE HCL
Common Name English
SCH 9384
Code English
OXYMETAZOLINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
RHOFADE
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C29709
Created by admin on Mon Mar 31 17:35:56 GMT 2025 , Edited by admin on Mon Mar 31 17:35:56 GMT 2025
CFR 21 CFR 341.20
Created by admin on Mon Mar 31 17:35:56 GMT 2025 , Edited by admin on Mon Mar 31 17:35:56 GMT 2025
EU-Orphan Drug EU/3/17/1892
Created by admin on Mon Mar 31 17:35:56 GMT 2025 , Edited by admin on Mon Mar 31 17:35:56 GMT 2025
Code System Code Type Description
PUBCHEM
66259
Created by admin on Mon Mar 31 17:35:56 GMT 2025 , Edited by admin on Mon Mar 31 17:35:56 GMT 2025
PRIMARY
MERCK INDEX
m8335
Created by admin on Mon Mar 31 17:35:56 GMT 2025 , Edited by admin on Mon Mar 31 17:35:56 GMT 2025
PRIMARY Merck Index
CHEBI
7863
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PRIMARY
EPA CompTox
DTXSID80177729
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PRIMARY
ChEMBL
CHEMBL762
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PRIMARY
DAILYMED
K89MJ0S5VY
Created by admin on Mon Mar 31 17:35:56 GMT 2025 , Edited by admin on Mon Mar 31 17:35:56 GMT 2025
PRIMARY
NSC
757254
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PRIMARY
DRUG BANK
DBSALT000821
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PRIMARY
FDA UNII
K89MJ0S5VY
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PRIMARY
CAS
2315-02-8
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PRIMARY
RXCUI
106101
Created by admin on Mon Mar 31 17:35:56 GMT 2025 , Edited by admin on Mon Mar 31 17:35:56 GMT 2025
PRIMARY RxNorm
ECHA (EC/EINECS)
219-015-0
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PRIMARY
SMS_ID
100000090269
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PRIMARY
NCI_THESAURUS
C29313
Created by admin on Mon Mar 31 17:35:56 GMT 2025 , Edited by admin on Mon Mar 31 17:35:56 GMT 2025
PRIMARY
RS_ITEM_NUM
1486004
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PRIMARY
EVMPD
SUB03589MIG
Created by admin on Mon Mar 31 17:35:56 GMT 2025 , Edited by admin on Mon Mar 31 17:35:56 GMT 2025
PRIMARY
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