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Details

Stereochemistry ACHIRAL
Molecular Formula C14H14N2
Molecular Weight 210.2744
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NAPHAZOLINE

SMILES

C(C1=NCCN1)C2=CC=CC3=CC=CC=C23

InChI

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

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

1.46275205E11
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
Complementary use of partial least-squares and artificial neural networks for the non-linear spectrophotometric analysis of pharmaceutical samples.
2002 Oct
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
Effects of topical mydriatics and vasoconstrictors on prostaglandin-E2-induced aqueous flare elevation in pigmented rabbits.
2003 Sep-Oct
Actual therapeutic management of allergic and hyperreactive nasal disorders.
2004
[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
Course and therapy of intoxication with imidazoline derivate naphazoline.
2004 Jul
Comparison of three different phosphorescent methodologies in solution for the analysis of naphazoline in pharmaceutical preparations.
2004 May
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
Application of solid-phase microextraction to antidoping analysis: determination of stimulants, narcotics, and other classes of substances excreted free in urine.
2005 May-Jun
[Efficacy of Derinox assessed with one PNIF (Peak Nasal Inspiratory Flow) in patients suffering from common cold].
2005 Nov
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
Antagonism by imidazoline-type drugs of muscarinic and other receptors in the guinea-pig ileum.
2006 Jul
Rhinoplasty - indications and techniques.
2007
Eyelid ptosis from sympathetic nerve dysfunction mistaken as myopathy: a simple test to identify this condition.
2007 Jun
Nasal eosinophils and reversibility to the decongestion test in patients with perennial allergic rhinitis.
2007 May-Jun
Ebastine improves nasal symptoms and airflow and affects response to decongestion test in patients with persistent allergic rhinitis: a pilot study.
2007 Sep-Oct
In vitro culturing of porcine tracheal mucosa as an ideal model for investigating the influence of drugs on human respiratory mucosa.
2008 Sep
Successful endonasal dacryocystorhinostomy in a patient with Wegener's granulomatosis.
2009
Nasal irrigation with lavonase as ancillary treatment of acute rhinosinusitis: a pilot study.
2009 Apr-Jun
Ebastine in the light of CONGA recommendations for the development of third-generation antihistamines.
2009 Aug 31
[Peritopic anesthesia in cataract surgery].
2009 Feb
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
Flow-injection chemiluminescence method for the determination of naphazoline hydrochloride and oxymetazoline hydrochloride.
2009 May-Jun
[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
Pulmonary edema and prolonged awakening after nasal naphazoline application in a transspenoidal hypophysectomy patient.
2010 Jul
Functional and pharmacological characterization of a beta-adrenergic-like octopamine receptor from the silkworm Bombyx mori.
2010 Jun
Structural and functional evolution of the trace amine-associated receptors TAAR3, TAAR4 and TAAR5 in primates.
2010 Jun 15
Simultaneous determination of antazoline and naphazoline by the net analyte signal standard addition method and spectrophotometric technique.
2010 Nov-Dec
Treatment of allergic conjunctivitis: results of a 1-month, single-masked randomized study.
2010 Sep-Oct
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
INN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
1H-IMIDAZOLE, 4,5-DIHYDRO-2-(1-NAPHTHALENYLMETHYL)-
Systematic Name English
NAPHAZOLINE [MART.]
Common Name English
2-(1-NAPHTHYLMETHYL)-2-IMIDAZOLINE
Systematic Name English
naphazoline [INN]
Common Name English
Naphazoline [WHO-DD]
Common Name English
NAPHAZOLINE [MI]
Common Name English
NAFAZOLIN
Brand Name English
NAPHAZOLINE [VANDF]
Common Name English
Classification Tree Code System Code
WHO-ATC S01GA51
Created by admin on Fri Dec 15 15:11:52 UTC 2023 , Edited by admin on Fri Dec 15 15:11:52 UTC 2023
WHO-ATC R01AB02
Created by admin on Fri Dec 15 15:11:52 UTC 2023 , Edited by admin on Fri Dec 15 15:11:52 UTC 2023
WHO-ATC R01AA08
Created by admin on Fri Dec 15 15:11:52 UTC 2023 , Edited by admin on Fri Dec 15 15:11:52 UTC 2023
WHO-VATC QS01GA51
Created by admin on Fri Dec 15 15:11:52 UTC 2023 , Edited by admin on Fri Dec 15 15:11:52 UTC 2023
WHO-VATC QR01AB02
Created by admin on Fri Dec 15 15:11:52 UTC 2023 , Edited by admin on Fri Dec 15 15:11:52 UTC 2023
WHO-ATC S01GA01
Created by admin on Fri Dec 15 15:11:52 UTC 2023 , Edited by admin on Fri Dec 15 15:11:52 UTC 2023
WHO-VATC QS01GA01
Created by admin on Fri Dec 15 15:11:52 UTC 2023 , Edited by admin on Fri Dec 15 15:11:52 UTC 2023
WHO-VATC QR01AA08
Created by admin on Fri Dec 15 15:11:52 UTC 2023 , Edited by admin on Fri Dec 15 15:11:52 UTC 2023
NCI_THESAURUS C29709
Created by admin on Fri Dec 15 15:11:52 UTC 2023 , Edited by admin on Fri Dec 15 15:11:52 UTC 2023
Code System Code Type Description
EVMPD
SUB09154MIG
Created by admin on Fri Dec 15 15:11:52 UTC 2023 , Edited by admin on Fri Dec 15 15:11:52 UTC 2023
PRIMARY
FDA UNII
H231GF11BV
Created by admin on Fri Dec 15 15:11:52 UTC 2023 , Edited by admin on Fri Dec 15 15:11:52 UTC 2023
PRIMARY
ChEMBL
CHEMBL761
Created by admin on Fri Dec 15 15:11:52 UTC 2023 , Edited by admin on Fri Dec 15 15:11:52 UTC 2023
PRIMARY
IUPHAR
5509
Created by admin on Fri Dec 15 15:11:52 UTC 2023 , Edited by admin on Fri Dec 15 15:11:52 UTC 2023
PRIMARY
RXCUI
7247
Created by admin on Fri Dec 15 15:11:52 UTC 2023 , Edited by admin on Fri Dec 15 15:11:52 UTC 2023
PRIMARY RxNorm
DRUG BANK
DB06711
Created by admin on Fri Dec 15 15:11:52 UTC 2023 , Edited by admin on Fri Dec 15 15:11:52 UTC 2023
PRIMARY
CAS
835-31-4
Created by admin on Fri Dec 15 15:11:52 UTC 2023 , Edited by admin on Fri Dec 15 15:11:52 UTC 2023
PRIMARY
WIKIPEDIA
NAPHAZOLINE
Created by admin on Fri Dec 15 15:11:52 UTC 2023 , Edited by admin on Fri Dec 15 15:11:52 UTC 2023
PRIMARY
MERCK INDEX
m7723
Created by admin on Fri Dec 15 15:11:52 UTC 2023 , Edited by admin on Fri Dec 15 15:11:52 UTC 2023
PRIMARY Merck Index
PUBCHEM
4436
Created by admin on Fri Dec 15 15:11:52 UTC 2023 , Edited by admin on Fri Dec 15 15:11:52 UTC 2023
PRIMARY
ECHA (EC/EINECS)
212-641-5
Created by admin on Fri Dec 15 15:11:52 UTC 2023 , Edited by admin on Fri Dec 15 15:11:52 UTC 2023
PRIMARY
DAILYMED
H231GF11BV
Created by admin on Fri Dec 15 15:11:52 UTC 2023 , Edited by admin on Fri Dec 15 15:11:52 UTC 2023
PRIMARY
EPA CompTox
DTXSID3048449
Created by admin on Fri Dec 15 15:11:52 UTC 2023 , Edited by admin on Fri Dec 15 15:11:52 UTC 2023
PRIMARY
MESH
D009278
Created by admin on Fri Dec 15 15:11:52 UTC 2023 , Edited by admin on Fri Dec 15 15:11:52 UTC 2023
PRIMARY
SMS_ID
100000084448
Created by admin on Fri Dec 15 15:11:52 UTC 2023 , Edited by admin on Fri Dec 15 15:11:52 UTC 2023
PRIMARY
DRUG CENTRAL
3369
Created by admin on Fri Dec 15 15:11:52 UTC 2023 , Edited by admin on Fri Dec 15 15:11:52 UTC 2023
PRIMARY
NCI_THESAURUS
C61856
Created by admin on Fri Dec 15 15:11:52 UTC 2023 , Edited by admin on Fri Dec 15 15:11:52 UTC 2023
PRIMARY
INN
4153
Created by admin on Fri Dec 15 15:11:52 UTC 2023 , Edited by admin on Fri Dec 15 15:11:52 UTC 2023
PRIMARY