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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

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
Simultaneous determination of naphazoline, diphenhydramine and phenylephrine in nasal solutions by capillary electrophoresis.
2003 Feb 5
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
Actual therapeutic management of allergic and hyperreactive nasal disorders.
2004
Course and therapy of intoxication with imidazoline derivate naphazoline.
2004 Jul
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
Association between response to decongestion testing and sensitizations and allergic inflammation.
2006 Mar
Different mechanisms between thromboxane A2- and leukotriene D4-induced nasal blockage in guinea pigs.
2006 Sep
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
Nasal eosinophils and reversibility to the decongestion test in patients with perennial allergic rhinitis.
2007 May-Jun
Intranasal lidocaine plus naphazoline nitrate improves surgical conditions and perioperative analgesia in septorhinoplasty surgery.
2009 Feb
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
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
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 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
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PRIMARY
WIKIPEDIA
NAPHAZOLINE
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PRIMARY
MERCK INDEX
m7723
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PRIMARY Merck Index
PUBCHEM
4436
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PRIMARY
ECHA (EC/EINECS)
212-641-5
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PRIMARY
DAILYMED
H231GF11BV
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PRIMARY
EPA CompTox
DTXSID3048449
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PRIMARY
MESH
D009278
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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
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PRIMARY