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=C3C=CC=CC3=CC=C2

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
Sources:
unhealthy, 35±15
Health Status: unhealthy
Age Group: 35±15
Sex: M+F
Sources:
Disc. AE: Burning sensation...
AEs leading to
discontinuation/dose reduction:
Burning sensation (6.7%)
Sources:
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
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
Sources:
unhealthy, 35±15
Health Status: unhealthy
Age Group: 35±15
Sex: M+F
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Identification and characterization of platelet α2-adrenoceptors and imidazoline receptors in rats, rabbits, cats, dogs, cattle, and horses.
2013-11-15
Spectroscopic analyses on interaction of Naphazoline hydrochloride with bovine serum albumin.
2012-12
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011-07-14
Simultaneous determination of antazoline and naphazoline by the net analyte signal standard addition method and spectrophotometric technique.
2011-02-15
Pulmonary edema and prolonged awakening after nasal naphazoline application in a transspenoidal hypophysectomy patient.
2010-07
Structural and functional evolution of the trace amine-associated receptors TAAR3, TAAR4 and TAAR5 in primates.
2010-06-15
Functional and pharmacological characterization of a beta-adrenergic-like octopamine receptor from the silkworm Bombyx mori.
2010-06
[Microhemocirculation and its correction in duodenal ulcer during period of rehabilitation].
2010-05-12
Synthesis, anticonvulsant and antimicrobial activities of some new 2-acetylnaphthalene derivatives.
2010-04-15
Treatment of allergic conjunctivitis: results of a 1-month, single-masked randomized study.
2010-04-13
Pharmacological characterization of a Bombyx mori alpha-adrenergic-like octopamine receptor stably expressed in a mammalian cell line.
2010-02
Determination of tetrahydrozoline in urine and blood using gas chromatography-mass spectrometry (GC-MS).
2010
Ebastine in the light of CONGA recommendations for the development of third-generation antihistamines.
2009-08-31
A comparative kinetic and mechanistic study between tetrahydrozoline and naphazoline toward photogenerated reactive oxygen species.
2009-08-28
Nasal irrigation with lavonase as ancillary treatment of acute rhinosinusitis: a pilot study.
2009-07-11
Allergic contact dermatitis from dibucaine hydrochloride, chlorpheniramine maleate, and naphazoline hydrochloride in an over-the-counter topical antiseptic.
2009-07
Effect of subconjunctival bevacizumab on primary pterygium.
2009-05
Influence of the ageing phenomenon on the low-frequency electrical impedance behavior of naphazoline hydrochloride solutions and paracetamol syrup.
2009-05
Flow-injection chemiluminescence method for the determination of naphazoline hydrochloride and oxymetazoline hydrochloride.
2009-03-03
[Peritopic anesthesia in cataract surgery].
2009-02
Intranasal lidocaine plus naphazoline nitrate improves surgical conditions and perioperative analgesia in septorhinoplasty surgery.
2009-02
A presentation of longstanding toxoplasmosis chorioretinitis.
2009-01
Successful endonasal dacryocystorhinostomy in a patient with Wegener's granulomatosis.
2009
Simultaneous determination of dibucaine and naphazoline in human serum by monolithic silica spin column extraction and liquid chromatography-mass spectrometry.
2008-09-01
In vitro culturing of porcine tracheal mucosa as an ideal model for investigating the influence of drugs on human respiratory mucosa.
2008-09
Relationship between rhinitis duration and response to nasal decongestion test.
2008-07
Acute pulmonary edema associated with naphazoline ingestion.
2008-03
[The influence of different alpha-sympathomimetic drugs and benzalkoniumchlorid on the ciliary beat frequency of in vitro cultured human nasal mucosa cells].
2008-01
UV-Vis spectrophotometrical and analytical methodology for the determination of singlet oxygen in new antibacterials drugs.
2007-11-11
Ischemic stroke in a man with naphazoline abuse history.
2007-10
Ebastine improves nasal symptoms and airflow and affects response to decongestion test in patients with persistent allergic rhinitis: a pilot study.
2007-09-22
The pK(a) Distribution of Drugs: Application to Drug Discovery.
2007-09-17
Nasal eosinophils and reversibility to the decongestion test in patients with perennial allergic rhinitis.
2007-07-11
Eyelid ptosis from sympathetic nerve dysfunction mistaken as myopathy: a simple test to identify this condition.
2007-06
Theoretical assessment of naphazoline redoxchemistry and photochemistry.
2007-04-19
Rhinoplasty - indications and techniques.
2007
Naphazoline intoxication in children.
2006-11
Fast simultaneous spectrophotometric determination of naphazoline nitrate and methylparaben by sequential injection chromatography.
2006-09-15
Different mechanisms between thromboxane A2- and leukotriene D4-induced nasal blockage in guinea pigs.
2006-09
Antagonism by imidazoline-type drugs of muscarinic and other receptors in the guinea-pig ileum.
2006-07
Do topical nasal decongestants affect polyps?
2006-03
Association between response to decongestion testing and sensitizations and allergic inflammation.
2006-03
Evaluation, in vitro, of the radioprotection of DNA from gamma-rays by naphazoline.
2006-03
Net analyte signal-based simultaneous determination of antazoline and naphazoline using wavelength region selection by experimental design-neural networks.
2006-02-15
The thermodynamic dissociation constants of ambroxol, antazoline, naphazoline, oxymetazoline and ranitidine by the regression analysis of spectrophotometric data.
2004-02-27
Actual therapeutic management of allergic and hyperreactive nasal disorders.
2004
Radioprotective Activity and Synthesis of Siladithioacetals and Germadithioacetals Derived from N-substituted Naphthylethylimidazoline.
2001
Selective inhibition of alpha1B-adrenergic receptor expression and function using a phosphorothioate antisense oligodeoxynucleotide.
1998-06
The influence of alpha-adrenergic drugs on catalepsy induced by haloperidol or fluphenazine in rats.
1978-09-01
Central action of narcotic analgesics. Part IV. Noradrenergic influences on the activity of analgesics in rats.
1978-09-01
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 Mon Mar 31 17:49:51 GMT 2025
Edited
by admin
on Mon Mar 31 17:49:51 GMT 2025
Record UNII
H231GF11BV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NAPHAZOLINE
INN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
NAFAZOLIN
Preferred 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
NAPHAZOLINE [VANDF]
Common Name English
Classification Tree Code System Code
WHO-ATC S01GA51
Created by admin on Mon Mar 31 17:49:51 GMT 2025 , Edited by admin on Mon Mar 31 17:49:51 GMT 2025
WHO-ATC R01AB02
Created by admin on Mon Mar 31 17:49:51 GMT 2025 , Edited by admin on Mon Mar 31 17:49:51 GMT 2025
WHO-ATC R01AA08
Created by admin on Mon Mar 31 17:49:51 GMT 2025 , Edited by admin on Mon Mar 31 17:49:51 GMT 2025
WHO-VATC QS01GA51
Created by admin on Mon Mar 31 17:49:51 GMT 2025 , Edited by admin on Mon Mar 31 17:49:51 GMT 2025
WHO-VATC QR01AB02
Created by admin on Mon Mar 31 17:49:51 GMT 2025 , Edited by admin on Mon Mar 31 17:49:51 GMT 2025
WHO-ATC S01GA01
Created by admin on Mon Mar 31 17:49:51 GMT 2025 , Edited by admin on Mon Mar 31 17:49:51 GMT 2025
WHO-VATC QS01GA01
Created by admin on Mon Mar 31 17:49:51 GMT 2025 , Edited by admin on Mon Mar 31 17:49:51 GMT 2025
WHO-VATC QR01AA08
Created by admin on Mon Mar 31 17:49:51 GMT 2025 , Edited by admin on Mon Mar 31 17:49:51 GMT 2025
NCI_THESAURUS C29709
Created by admin on Mon Mar 31 17:49:51 GMT 2025 , Edited by admin on Mon Mar 31 17:49:51 GMT 2025
Code System Code Type Description
EVMPD
SUB09154MIG
Created by admin on Mon Mar 31 17:49:51 GMT 2025 , Edited by admin on Mon Mar 31 17:49:51 GMT 2025
PRIMARY
FDA UNII
H231GF11BV
Created by admin on Mon Mar 31 17:49:51 GMT 2025 , Edited by admin on Mon Mar 31 17:49:51 GMT 2025
PRIMARY
ChEMBL
CHEMBL761
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PRIMARY
IUPHAR
5509
Created by admin on Mon Mar 31 17:49:51 GMT 2025 , Edited by admin on Mon Mar 31 17:49:51 GMT 2025
PRIMARY
RXCUI
7247
Created by admin on Mon Mar 31 17:49:51 GMT 2025 , Edited by admin on Mon Mar 31 17:49:51 GMT 2025
PRIMARY RxNorm
DRUG BANK
DB06711
Created by admin on Mon Mar 31 17:49:51 GMT 2025 , Edited by admin on Mon Mar 31 17:49:51 GMT 2025
PRIMARY
CAS
835-31-4
Created by admin on Mon Mar 31 17:49:51 GMT 2025 , Edited by admin on Mon Mar 31 17:49:51 GMT 2025
PRIMARY
WIKIPEDIA
NAPHAZOLINE
Created by admin on Mon Mar 31 17:49:51 GMT 2025 , Edited by admin on Mon Mar 31 17:49:51 GMT 2025
PRIMARY
MERCK INDEX
m7723
Created by admin on Mon Mar 31 17:49:51 GMT 2025 , Edited by admin on Mon Mar 31 17:49:51 GMT 2025
PRIMARY Merck Index
PUBCHEM
4436
Created by admin on Mon Mar 31 17:49:51 GMT 2025 , Edited by admin on Mon Mar 31 17:49:51 GMT 2025
PRIMARY
ECHA (EC/EINECS)
212-641-5
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PRIMARY
DAILYMED
H231GF11BV
Created by admin on Mon Mar 31 17:49:51 GMT 2025 , Edited by admin on Mon Mar 31 17:49:51 GMT 2025
PRIMARY
EPA CompTox
DTXSID3048449
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PRIMARY
MESH
D009278
Created by admin on Mon Mar 31 17:49:51 GMT 2025 , Edited by admin on Mon Mar 31 17:49:51 GMT 2025
PRIMARY
SMS_ID
100000084448
Created by admin on Mon Mar 31 17:49:51 GMT 2025 , Edited by admin on Mon Mar 31 17:49:51 GMT 2025
PRIMARY
DRUG CENTRAL
3369
Created by admin on Mon Mar 31 17:49:51 GMT 2025 , Edited by admin on Mon Mar 31 17:49:51 GMT 2025
PRIMARY
NCI_THESAURUS
C61856
Created by admin on Mon Mar 31 17:49:51 GMT 2025 , Edited by admin on Mon Mar 31 17:49:51 GMT 2025
PRIMARY
INN
4153
Created by admin on Mon Mar 31 17:49:51 GMT 2025 , Edited by admin on Mon Mar 31 17:49:51 GMT 2025
PRIMARY
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TARGET -> AGONIST
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ACTIVE MOIETY