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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

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
Central action of narcotic analgesics. Part IV. Noradrenergic influences on the activity of analgesics in rats.
1978 Sep-Oct
Treatment of ulcerative endobronchial tuberculosis and bronchial stenosis with aerosolized streptomycin and steroids.
2001 Aug
[Electron microscopic studies of the rabbit nasal mucosa after short-term application of naphzoline nitrate].
2001 Jul
Sustained prediction ability of net analyte preprocessing methods using reduced calibration sets. Theoretical and experimental study involving the spectrophotometric analysis of multicomponent mixtures.
2001 Jul
Markedly increased nasal blockage by intranasal leukotriene D4 in an experimental allergic rhinitis model: contribution of dilated mucosal blood vessels.
2001 Jun
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
Prolonged awakening and pulmonary edema after general anesthesia and naphazoline application in an infant.
2001 Nov
Naphazoline-induced neuroendocrine changes: increases in ANP and cGMP levels, but suppression of NE, 3H-NE, and cAMP levels in rabbit eyes.
2002 Jul
[Applications of phosphorimetry in pharmaceutical analysis].
2002 Jun
[She really loves Mickey...].
2002 Jun
Complementary use of partial least-squares and artificial neural networks for the non-linear spectrophotometric analysis of pharmaceutical samples.
2002 Oct
Bilateral acute angle-closure glaucoma after use of Fenox nasal drops.
2002 Sep
Transdermal penetration of vasoconstrictors--present understanding and assessment of the human epidermal flux and retention of free bases and ion-pairs.
2003 Feb
[Naphazoline intoxication: course and therapy].
2003 Feb
Simultaneous determination of naphazoline, diphenhydramine and phenylephrine in nasal solutions by capillary electrophoresis.
2003 Feb 5
[Studies on the experimental allergic rhinitis induced by Japanese cedar pollen--role of cysteinyl leukotrienes in nasal allergic symptoms].
2003 Jan
Determination of prednisolone and the most important associated compounds in ocular and cutaneous pharmaceutical preparations by micellar electrokinetic capillary chromatography.
2003 Jan 25
Octopaminergic modulation of synaptic transmission between an identified sensory afferent and flight motoneuron in the locust.
2003 Jul 14
Naphazoline intoxication in a child-a clinical and forensic toxicological case.
2003 Jul 8
[Cardiac arrest and secondary pulmonary oedema following accidental intramucosal injection of naphazoline in an adult].
2003 May
Effects of topical mydriatics and vasoconstrictors on prostaglandin-E2-induced aqueous flare elevation in pigmented rabbits.
2003 Sep-Oct
[The application of naphcon eye drops during Lasik surgery].
2004 Dec
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 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
Effect of cold BSS vs naphazoline 0.025% on ocular surface temperature.
2006 Aug
Epstein-barr virus induced cellular changes in nasal mucosa.
2006 Feb 1
A rapid derivative spectrophotometric method for simultaneous determination of naphazoline and antazoline in eye drops.
2006 Jan
Do topical nasal decongestants affect polyps?
2006 Mar
Fast simultaneous spectrophotometric determination of naphazoline nitrate and methylparaben by sequential injection chromatography.
2006 Sep 15
Theoretical assessment of naphazoline redoxchemistry and photochemistry.
2007 Apr 19
UV-Vis spectrophotometrical and analytical methodology for the determination of singlet oxygen in new antibacterials drugs.
2007 Nov 11
[The influence of different alpha-sympathomimetic drugs and benzalkoniumchlorid on the ciliary beat frequency of in vitro cultured human nasal mucosa cells].
2008 Jan
Relationship between rhinitis duration and response to nasal decongestion test.
2008 Jul
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
Successful endonasal dacryocystorhinostomy in a patient with Wegener's granulomatosis.
2009
Intranasal lidocaine plus naphazoline nitrate improves surgical conditions and perioperative analgesia in septorhinoplasty surgery.
2009 Feb
A presentation of longstanding toxoplasmosis chorioretinitis.
2009 Jan
Allergic contact dermatitis from dibucaine hydrochloride, chlorpheniramine maleate, and naphazoline hydrochloride in an over-the-counter topical antiseptic.
2009 Jul
Effect of subconjunctival bevacizumab on primary pterygium.
2009 May
Influence of the ageing phenomenon on the low-frequency electrical impedance behavior of naphazoline hydrochloride solutions and paracetamol syrup.
2009 May
Determination of tetrahydrozoline in urine and blood using gas chromatography-mass spectrometry (GC-MS).
2010
Pharmacological characterization of a Bombyx mori alpha-adrenergic-like octopamine receptor stably expressed in a mammalian cell line.
2010 Feb
Simultaneous determination of antazoline and naphazoline by the net analyte signal standard addition method and spectrophotometric technique.
2010 Nov-Dec
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Spectroscopic analyses on interaction of Naphazoline hydrochloride with bovine serum albumin.
2012 Dec
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.
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