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

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 C14H14N2
Molecular Weight 210.2744
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
Expression of multiple alpha1-adrenoceptors on vascular smooth muscle: correlation with the regulation of contraction.
1999 Jul
[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
Involvement of nitric oxide in pollen-induced biphasic nasal blockage in sensitised guinea pigs.
2001 Jun 29
Treatment of rhinitis medicamentosa with fluticasone propionate--an experimental study.
2001 Mar
Naphazoline-induced suppression of aqueous humor pressure and flow: involvement of central and peripheral alpha(2)/I(1) receptors.
2001 Mar
Synthesis of some 1-(2-naphthyl)-2-(imidazole-1-yl)ethanone oxime and oxime ether derivatives and their anticonvulsant and antimicrobial activities.
2001 May
Prolonged awakening and pulmonary edema after general anesthesia and naphazoline application in an infant.
2001 Nov
[Applications of phosphorimetry in pharmaceutical analysis].
2002 Jun
Complementary use of partial least-squares and artificial neural networks for the non-linear spectrophotometric analysis of pharmaceutical samples.
2002 Oct
Actual therapeutic management of allergic and hyperreactive nasal disorders.
2004
[Pharmacological correction of cochleovestibular impairments].
2004
A rapid derivative spectrophotometric method for simultaneous determination of naphazoline and antazoline in eye drops.
2006 Jan
Naphazoline intoxication in children.
2006 Nov
Rhinoplasty - indications and techniques.
2007
Ischemic stroke in a man with naphazoline abuse history.
2007 Oct
The pK(a) Distribution of Drugs: Application to Drug Discovery.
2007 Sep 17
Ebastine improves nasal symptoms and airflow and affects response to decongestion test in patients with persistent allergic rhinitis: a pilot study.
2007 Sep-Oct
[The influence of different alpha-sympathomimetic drugs and benzalkoniumchlorid on the ciliary beat frequency of in vitro cultured human nasal mucosa cells].
2008 Jan
Successful endonasal dacryocystorhinostomy in a patient with Wegener's granulomatosis.
2009
Ebastine in the light of CONGA recommendations for the development of third-generation antihistamines.
2009 Aug 31
[Peritopic anesthesia in cataract surgery].
2009 Feb
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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:10:15 GMT 2023
Edited
by admin
on Fri Dec 15 15:10:15 GMT 2023
Record UNII
MZ1131787D
Record Status Validated (UNII)
Record Version
  • Download
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
Created by admin on Fri Dec 15 15:10:15 GMT 2023 , Edited by admin on Fri Dec 15 15:10:15 GMT 2023
NCI_THESAURUS C29709
Created by admin on Fri Dec 15 15:10:15 GMT 2023 , Edited by admin on Fri Dec 15 15:10:15 GMT 2023
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
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
SMS_ID
100000090391
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
HSDB
2174
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
ECHA (EC/EINECS)
208-989-2
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PRIMARY
MERCK INDEX
m7723
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 Merck Index
NCI_THESAURUS
C47632
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PRIMARY
RS_ITEM_NUM
1457006
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PRIMARY
EVMPD
SUB03389MIG
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
CAS
550-99-2
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
FDA UNII
MZ1131787D
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
NSC
35711
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
PUBCHEM
11079
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
ChEMBL
CHEMBL761
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
DAILYMED
MZ1131787D
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
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