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

Details

Stereochemistry ACHIRAL
Molecular Formula C14H14N2.ClH
Molecular Weight 246.735
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NAPHAZOLINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=DJDFFEBSKJCGHC-UHFFFAOYSA-N
InChI=1S/C14H14N2.ClH/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);1H

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
Selective inhibition of alpha1B-adrenergic receptor expression and function using a phosphorothioate antisense oligodeoxynucleotide.
1998 Jun
Expression of multiple alpha1-adrenoceptors on vascular smooth muscle: correlation with the regulation of contraction.
1999 Jul
Markedly increased nasal blockage by intranasal leukotriene D4 in an experimental allergic rhinitis model: contribution of dilated mucosal blood vessels.
2001 Jun
[Comparative study of the radiation-protective effectiveness of low doses of cysteamine, heparin, and naphtizine in experiments on mice].
2001 May-Jun
Transdermal penetration of vasoconstrictors--present understanding and assessment of the human epidermal flux and retention of free bases and ion-pairs.
2003 Feb
[Studies on the experimental allergic rhinitis induced by Japanese cedar pollen--role of cysteinyl leukotrienes in nasal allergic symptoms].
2003 Jan
[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
[The tolerability of nasal drugs with special regard to preservatives and physico-chemical parameters].
2003 Nov
[Acute exposure to imidazoline derivatives in children].
2003 Nov-Dec
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
Course and therapy of intoxication with imidazoline derivate naphazoline.
2004 Jul
Hemorrhagic stroke after naphazoline exposition: case report.
2004 Sep
Early bronchial airflow impairment in patients with persistent allergic rhinitis and bronchial hyperreactivity.
2005 Dec
Levocetirizine improves nasal symptoms and airflow in patients with persistent allergic rhinitis: a pilot study.
2005 Jan
Epstein-barr virus induced cellular changes in nasal mucosa.
2006 Feb 1
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
Different mechanisms between thromboxane A2- and leukotriene D4-induced nasal blockage in guinea pigs.
2006 Sep
Rhinoplasty - indications and techniques.
2007
Theoretical assessment of naphazoline redoxchemistry and photochemistry.
2007 Apr 19
Eyelid ptosis from sympathetic nerve dysfunction mistaken as myopathy: a simple test to identify this condition.
2007 Jun
Relationship between rhinitis duration and response to nasal decongestion test.
2008 Jul
[Peritopic anesthesia in cataract surgery].
2009 Feb
Intranasal lidocaine plus naphazoline nitrate improves surgical conditions and perioperative analgesia in septorhinoplasty surgery.
2009 Feb
A presentation of longstanding toxoplasmosis chorioretinitis.
2009 Jan
Determination of tetrahydrozoline in urine and blood using gas chromatography-mass spectrometry (GC-MS).
2010
A comparative kinetic and mechanistic study between tetrahydrozoline and naphazoline toward photogenerated reactive oxygen species.
2010 Jan-Feb
Structural and functional evolution of the trace amine-associated receptors TAAR3, TAAR4 and TAAR5 in primates.
2010 Jun 15
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 HYDROCHLORIDE
EP   HSDB   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common Name English
NAPHAZOLINE HCL
INCI  
INCI  
Official Name English
OPCON-A COMPONENT NAPHAZOLINE HYDROCHLORIDE
Common Name English
2-(1-Naphthylmethyl)-2-imidazoline monohydrochloride
Systematic Name English
NAPHAZOLINE HYDROCHLORIDE COMPONENT OF NAPHCON-A
Common Name English
VISINE-A COMPONENT NAPHAZOLINE HYDROCHLORIDE
Common Name English
NAFAZAIR
Brand Name English
NAPHAZOLINE HYDROCHLORIDE COMPONENT OF VASOCON-A
Common Name English
Naphazoline hydrochloride [WHO-DD]
Common Name English
NAPHAZOLINE HYDROCHLORIDE [EP IMPURITY]
Common Name English
NAPHAZOLINE HYDROCHLORIDE [MART.]
Common Name English
NAPHCON-A COMPONENT NAPHAZOLINE HYDROCHLORIDE
Common Name English
ALBALON
Brand Name English
NAPHAZOLINE HYDROCHLORIDE [MI]
Common Name English
NAPHAZOLINE HYDROCHLORIDE COMPONENT OF VISINE-A
Common Name English
VASOCON
Brand Name English
1H-IMIDAZOLE, 4,5-DIHYDRO-2-(1-NAPHTHALENYLMETHYL)-, MONOHYDROCHLORIDE
Common Name English
NAPHAZOLINE HCL [INCI]
Common Name English
NAPHAZOLINE HYDROCHLORIDE [HSDB]
Common Name English
NAPHAZOLINE HYDROCHLORIDE [VANDF]
Common Name English
VASOCON-A COMPONENT NAPHAZOLINE HYDROCHLORIDE
Common Name English
NAPHAZOLINE HYDROCHLORIDE COMPONENT OF OPCON-A
Common Name English
NAPHAZOLINE HYDROCHLORIDE [USP-RS]
Common Name English
NSC-35711
Code English
NAPHAZOLINE HYDROCHLORIDE [JAN]
Common Name English
NAPHAZOLINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
NAPHAZOLINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
NAPHAZOLINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
NAPHCON FORTE
Brand Name English
OPCON
Brand Name English
Classification Tree Code System Code
CFR 21 CFR 349.18
Created by admin on Fri Dec 15 15:10:15 GMT 2023 , Edited by admin on Fri Dec 15 15:10:15 GMT 2023
CFR 21 CFR 341.20
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NCI_THESAURUS C29709
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Code System Code Type Description
RXCUI
82054
Created by admin on Fri Dec 15 15:10:15 GMT 2023 , Edited by admin on Fri Dec 15 15:10:15 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID7045788
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PRIMARY
DRUG BANK
DBSALT000127
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PRIMARY
SMS_ID
100000090391
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PRIMARY
HSDB
2174
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PRIMARY
ECHA (EC/EINECS)
208-989-2
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PRIMARY
MERCK INDEX
m7723
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PRIMARY Merck Index
NCI_THESAURUS
C47632
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PRIMARY
RS_ITEM_NUM
1457006
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PRIMARY
EVMPD
SUB03389MIG
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PRIMARY
CAS
550-99-2
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PRIMARY
FDA UNII
MZ1131787D
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PRIMARY
NSC
35711
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PRIMARY
PUBCHEM
11079
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PRIMARY
ChEMBL
CHEMBL761
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PRIMARY
DAILYMED
MZ1131787D
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PRIMARY