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

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

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
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
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
[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
Actual therapeutic management of allergic and hyperreactive nasal disorders.
2004
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
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
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
Theoretical assessment of naphazoline redoxchemistry and photochemistry.
2007 Apr 19
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
Effect of subconjunctival bevacizumab on primary pterygium.
2009 May
[Microhemocirculation and its correction in duodenal ulcer during period of rehabilitation].
2009 Oct-Dec
A comparative kinetic and mechanistic study between tetrahydrozoline and naphazoline toward photogenerated reactive oxygen species.
2010 Jan-Feb
Functional and pharmacological characterization of a beta-adrenergic-like octopamine receptor from the silkworm Bombyx mori.
2010 Jun
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 15:11:52 GMT 2023
Edited
by admin
on Fri Dec 15 15:11:52 GMT 2023
Record UNII
H231GF11BV
Record Status Validated (UNII)
Record Version
  • Download
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 GMT 2023 , Edited by admin on Fri Dec 15 15:11:52 GMT 2023
WHO-ATC R01AB02
Created by admin on Fri Dec 15 15:11:52 GMT 2023 , Edited by admin on Fri Dec 15 15:11:52 GMT 2023
WHO-ATC R01AA08
Created by admin on Fri Dec 15 15:11:52 GMT 2023 , Edited by admin on Fri Dec 15 15:11:52 GMT 2023
WHO-VATC QS01GA51
Created by admin on Fri Dec 15 15:11:52 GMT 2023 , Edited by admin on Fri Dec 15 15:11:52 GMT 2023
WHO-VATC QR01AB02
Created by admin on Fri Dec 15 15:11:52 GMT 2023 , Edited by admin on Fri Dec 15 15:11:52 GMT 2023
WHO-ATC S01GA01
Created by admin on Fri Dec 15 15:11:52 GMT 2023 , Edited by admin on Fri Dec 15 15:11:52 GMT 2023
WHO-VATC QS01GA01
Created by admin on Fri Dec 15 15:11:52 GMT 2023 , Edited by admin on Fri Dec 15 15:11:52 GMT 2023
WHO-VATC QR01AA08
Created by admin on Fri Dec 15 15:11:52 GMT 2023 , Edited by admin on Fri Dec 15 15:11:52 GMT 2023
NCI_THESAURUS C29709
Created by admin on Fri Dec 15 15:11:52 GMT 2023 , Edited by admin on Fri Dec 15 15:11:52 GMT 2023
Code System Code Type Description
EVMPD
SUB09154MIG
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PRIMARY
FDA UNII
H231GF11BV
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PRIMARY
ChEMBL
CHEMBL761
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PRIMARY
IUPHAR
5509
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PRIMARY
RXCUI
7247
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PRIMARY RxNorm
DRUG BANK
DB06711
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PRIMARY
CAS
835-31-4
Created by admin on Fri Dec 15 15:11:52 GMT 2023 , Edited by admin on Fri Dec 15 15:11:52 GMT 2023
PRIMARY
WIKIPEDIA
NAPHAZOLINE
Created by admin on Fri Dec 15 15:11:52 GMT 2023 , Edited by admin on Fri Dec 15 15:11:52 GMT 2023
PRIMARY
MERCK INDEX
m7723
Created by admin on Fri Dec 15 15:11:52 GMT 2023 , Edited by admin on Fri Dec 15 15:11:52 GMT 2023
PRIMARY Merck Index
PUBCHEM
4436
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PRIMARY
ECHA (EC/EINECS)
212-641-5
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PRIMARY
DAILYMED
H231GF11BV
Created by admin on Fri Dec 15 15:11:52 GMT 2023 , Edited by admin on Fri Dec 15 15:11:52 GMT 2023
PRIMARY
EPA CompTox
DTXSID3048449
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PRIMARY
MESH
D009278
Created by admin on Fri Dec 15 15:11:52 GMT 2023 , Edited by admin on Fri Dec 15 15:11:52 GMT 2023
PRIMARY
SMS_ID
100000084448
Created by admin on Fri Dec 15 15:11:52 GMT 2023 , Edited by admin on Fri Dec 15 15:11:52 GMT 2023
PRIMARY
DRUG CENTRAL
3369
Created by admin on Fri Dec 15 15:11:52 GMT 2023 , Edited by admin on Fri Dec 15 15:11:52 GMT 2023
PRIMARY
NCI_THESAURUS
C61856
Created by admin on Fri Dec 15 15:11:52 GMT 2023 , Edited by admin on Fri Dec 15 15:11:52 GMT 2023
PRIMARY
INN
4153
Created by admin on Fri Dec 15 15:11:52 GMT 2023 , Edited by admin on Fri Dec 15 15:11:52 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY