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Details

Stereochemistry ACHIRAL
Molecular Formula C14H14N2.HNO3
Molecular Weight 273.2872
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NAPHAZOLINE NITRATE

SMILES

O[N+]([O-])=O.C(C1=NCCN1)C2=CC=CC3=CC=CC=C23

InChI

InChIKey=ZAHXYMFVNNUHCP-UHFFFAOYSA-N
InChI=1S/C14H14N2.HNO3/c1-2-7-13-11(4-1)5-3-6-12(13)10-14-15-8-9-16-14;2-1(3)4/h1-7H,8-10H2,(H,15,16);(H,2,3,4)

HIDE SMILES / InChI

Molecular Formula C14H14N2
Molecular Weight 210.2744
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula HNO3
Molecular Weight 63.0128
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/pro/naphazoline.html

Naphazoline is a direct acting sympathomimetic adrenergic alpha-agonist used to induce systemic vasoconstriction, thereby decreasing nasal congestion and inducing constriction around the conjunctiva. The sympathomimetic action of Naphazoline constricts the smaller arterioles of the nasal passages, producing a decongesting effect. Naphazoline ophthalmic causes constriction of blood vessels in the eyes. It also decreases itching and irritation of the eyes. aphazoline constricts the vascular system of the conjunctiva. It is presumed that this effect is due to direct stimulation action of the drug upon the alpha adrenergic receptors in the arterioles of the conjunctiva resulting in decreased conjunctival congestion. Naphazoline belongs to the imidazoline class of sympathomimetics. Naphazoline is a direct acting sympathomimetic drug, which acts on alpha-adrenergic receptors in the arterioles of the nasal mucosa. This activates the adrenal system to yield systemic vasoconstrction. In producing vasoconstriction, the result is a decrease in blood flow in the nasal passages and consequently decreased nasal congestion. The vasoconstriction means that there is less pressure in the capillaries and less water can filter out, thus less discharge is made. Naphazoline is primarily indicated in conditions like Corneal vascularity, Hyperaemia, Itching, Nasal congestion, and can also be given in adjunctive therapy as an alternative drug of choice in Sinusitis.

CNS Activity

Curator's Comment: poorly crosses the blood-brain barrier

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
63.1 nM [EC50]
5.0 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Naphazoline Hydrochloride

Approved Use

Naphazoline Hydrochloride Ophthalmic Solution is indicated for use as a topical ocular vasoconstrictor.

Launch Date

1974
Doses

Doses

DosePopulationAdverse events​
0.25 mg/mL 2 times / day multiple, topical
Recommended
Dose: 0.25 mg/mL, 2 times / day
Route: topical
Route: multiple
Dose: 0.25 mg/mL, 2 times / day
Co-administed with::
antazoline(5 mg/ml topical)
Sources: Page: p.814
unhealthy, 35±15
n = 30
Health Status: unhealthy
Condition: Allergic conjunctivitis
Age Group: 35±15
Sex: M+F
Population Size: 30
Sources: Page: p.814
Disc. AE: Burning sensation...
AEs leading to
discontinuation/dose reduction:
Burning sensation (6.7%)
Sources: Page: p.814
2 drop 8 times / day multiple, topical
Highest studied dose
Dose: 2 drop, 8 times / day
Route: topical
Route: multiple
Dose: 2 drop, 8 times / day
Sources:
healthy
Health Status: healthy
Condition: Eye redness
Sources:
AEs

AEs

AESignificanceDosePopulation
Burning sensation 6.7%
Disc. AE
0.25 mg/mL 2 times / day multiple, topical
Recommended
Dose: 0.25 mg/mL, 2 times / day
Route: topical
Route: multiple
Dose: 0.25 mg/mL, 2 times / day
Co-administed with::
antazoline(5 mg/ml topical)
Sources: Page: p.814
unhealthy, 35±15
n = 30
Health Status: unhealthy
Condition: Allergic conjunctivitis
Age Group: 35±15
Sex: M+F
Population Size: 30
Sources: Page: p.814
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
The influence of alpha-adrenergic drugs on catalepsy induced by haloperidol or fluphenazine in rats.
1978 Sep-Oct
Central action of narcotic analgesics. Part IV. Noradrenergic influences on the activity of analgesics in rats.
1978 Sep-Oct
Selective inhibition of alpha1B-adrenergic receptor expression and function using a phosphorothioate antisense oligodeoxynucleotide.
1998 Jun
Radioprotective Activity and Synthesis of Siladithioacetals and Germadithioacetals Derived from N-substituted Naphthylethylimidazoline.
2001
Treatment of ulcerative endobronchial tuberculosis and bronchial stenosis with aerosolized streptomycin and steroids.
2001 Aug
Synthesis of some 1-(2-naphthyl)-2-(imidazole-1-yl)ethanone oxime and oxime ether derivatives and their anticonvulsant and antimicrobial activities.
2001 May
[Comparative study of the radiation-protective effectiveness of low doses of cysteamine, heparin, and naphtizine in experiments on mice].
2001 May-Jun
[She really loves Mickey...].
2002 Jun
[Naphazoline intoxication: course and therapy].
2003 Feb
[Adult cases of naphazoline-containing antiseptic first aid liquid poisoning].
2003 Jul
Octopaminergic modulation of synaptic transmission between an identified sensory afferent and flight motoneuron in the locust.
2003 Jul 14
[Cardiac arrest and secondary pulmonary oedema following accidental intramucosal injection of naphazoline in an adult].
2003 May
[Acute exposure to imidazoline derivatives in children].
2003 Nov-Dec
[Pharmacological correction of cochleovestibular impairments].
2004
[The application of naphcon eye drops during Lasik surgery].
2004 Dec
The thermodynamic dissociation constants of ambroxol, antazoline, naphazoline, oxymetazoline and ranitidine by the regression analysis of spectrophotometric data.
2004 Feb 27
Therapeutic management of endobronchial tuberculosis.
2004 Jul
Hemorrhagic stroke after naphazoline exposition: case report.
2004 Sep
Levocetirizine improves nasal symptoms and airflow in patients with persistent allergic rhinitis: a pilot study.
2005 Jan
A fluorescence optosensor for analyzing naphazoline in pharmaceutical preparations. Comparison with other sensors.
2005 Jul 15
A comparison of the clinical efficacy of pheniramine maleate/naphazoline hydrochloride ophthalmic solution and olopatadine hydrochloride ophthalmic solution in the conjunctival allergen challenge model.
2005 May
[Efficacy of Derinox assessed with one PNIF (Peak Nasal Inspiratory Flow) in patients suffering from common cold].
2005 Nov
Epstein-barr virus induced cellular changes in nasal mucosa.
2006 Feb 1
Net analyte signal-based simultaneous determination of antazoline and naphazoline using wavelength region selection by experimental design-neural networks.
2006 Feb 15
Antagonism by imidazoline-type drugs of muscarinic and other receptors in the guinea-pig ileum.
2006 Jul
Do topical nasal decongestants affect polyps?
2006 Mar
Association between response to decongestion testing and sensitizations and allergic inflammation.
2006 Mar
Evaluation, in vitro, of the radioprotection of DNA from gamma-rays by naphazoline.
2006 Mar
Naphazoline intoxication in children.
2006 Nov
Different mechanisms between thromboxane A2- and leukotriene D4-induced nasal blockage in guinea pigs.
2006 Sep
Ischemic stroke in a man with naphazoline abuse history.
2007 Oct
Relationship between rhinitis duration and response to nasal decongestion test.
2008 Jul
Acute pulmonary edema associated with naphazoline ingestion.
2008 Mar
In vitro culturing of porcine tracheal mucosa as an ideal model for investigating the influence of drugs on human respiratory mucosa.
2008 Sep
Simultaneous determination of dibucaine and naphazoline in human serum by monolithic silica spin column extraction and liquid chromatography-mass spectrometry.
2008 Sep 1
Ebastine in the light of CONGA recommendations for the development of third-generation antihistamines.
2009 Aug 31
[Peritopic anesthesia in cataract surgery].
2009 Feb
Influence of the ageing phenomenon on the low-frequency electrical impedance behavior of naphazoline hydrochloride solutions and paracetamol syrup.
2009 May
[Microhemocirculation and its correction in duodenal ulcer during period of rehabilitation].
2009 Oct-Dec
Determination of tetrahydrozoline in urine and blood using gas chromatography-mass spectrometry (GC-MS).
2010
Synthesis, anticonvulsant and antimicrobial activities of some new 2-acetylnaphthalene derivatives.
2010 Apr 15
Pharmacological characterization of a Bombyx mori alpha-adrenergic-like octopamine receptor stably expressed in a mammalian cell line.
2010 Feb
A comparative kinetic and mechanistic study between tetrahydrozoline and naphazoline toward photogenerated reactive oxygen species.
2010 Jan-Feb
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Identification and characterization of platelet α2-adrenoceptors and imidazoline receptors in rats, rabbits, cats, dogs, cattle, and horses.
2013 Nov 15
Patents

Sample Use Guides

In Vivo Use Guide
Instill one or two drops in the conjunctival sac(s) every three to four hours as needed.
Route of Administration: Other
Naphazoline (1, 10, and 100 umol/l) caused a dose-related inhibition of NE release from ICBs (iris-ciliary body) of the rabbit eye: 25, 45, and 80%, respectively.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:06:31 GMT 2023
Edited
by admin
on Fri Dec 15 15:06:31 GMT 2023
Record UNII
SC99GR1T5S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NAPHAZOLINE NITRATE
EP   MART.   WHO-DD  
Common Name English
NAPHAZOLINE NITRATE [MART.]
Common Name English
NAPHAZOLINE NITRATE [JAN]
Common Name English
2-(1-NAPHTHYLMETHYL)-2-IMIDAZOLINE NITRATE
Systematic Name English
2-(NAPHTHALEN-1-YLMETHYL)-4,5-DIHYDRO-1H-IMIDAZOLE MONONITRATE
Systematic Name English
Naphazoline nitrate [WHO-DD]
Common Name English
NAPHAZOLINE NITRATE [EP IMPURITY]
Common Name English
NAPHAZOLINE NITRATE [EP MONOGRAPH]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29709
Created by admin on Fri Dec 15 15:06:31 GMT 2023 , Edited by admin on Fri Dec 15 15:06:31 GMT 2023
NCI_THESAURUS C29578
Created by admin on Fri Dec 15 15:06:31 GMT 2023 , Edited by admin on Fri Dec 15 15:06:31 GMT 2023
Code System Code Type Description
SMS_ID
100000091842
Created by admin on Fri Dec 15 15:06:31 GMT 2023 , Edited by admin on Fri Dec 15 15:06:31 GMT 2023
PRIMARY
NCI_THESAURUS
C98243
Created by admin on Fri Dec 15 15:06:31 GMT 2023 , Edited by admin on Fri Dec 15 15:06:31 GMT 2023
PRIMARY
PUBCHEM
82332
Created by admin on Fri Dec 15 15:06:31 GMT 2023 , Edited by admin on Fri Dec 15 15:06:31 GMT 2023
PRIMARY
DRUG BANK
DBSALT002621
Created by admin on Fri Dec 15 15:06:31 GMT 2023 , Edited by admin on Fri Dec 15 15:06:31 GMT 2023
PRIMARY
EPA CompTox
DTXSID60863496
Created by admin on Fri Dec 15 15:06:31 GMT 2023 , Edited by admin on Fri Dec 15 15:06:31 GMT 2023
PRIMARY
EVMPD
SUB03390MIG
Created by admin on Fri Dec 15 15:06:31 GMT 2023 , Edited by admin on Fri Dec 15 15:06:31 GMT 2023
PRIMARY
RXCUI
235810
Created by admin on Fri Dec 15 15:06:31 GMT 2023 , Edited by admin on Fri Dec 15 15:06:31 GMT 2023
PRIMARY RxNorm
CAS
5144-52-5
Created by admin on Fri Dec 15 15:06:31 GMT 2023 , Edited by admin on Fri Dec 15 15:06:31 GMT 2023
PRIMARY
FDA UNII
SC99GR1T5S
Created by admin on Fri Dec 15 15:06:31 GMT 2023 , Edited by admin on Fri Dec 15 15:06:31 GMT 2023
PRIMARY
ChEMBL
CHEMBL761
Created by admin on Fri Dec 15 15:06:31 GMT 2023 , Edited by admin on Fri Dec 15 15:06:31 GMT 2023
PRIMARY
ECHA (EC/EINECS)
225-915-4
Created by admin on Fri Dec 15 15:06:31 GMT 2023 , Edited by admin on Fri Dec 15 15:06:31 GMT 2023
PRIMARY
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