Details
Stereochemistry | ACHIRAL |
Molecular Formula | C14H14N2.HNO3 |
Molecular Weight | 273.2872 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O[N+]([O-])=O.C(C1=NCCN1)C2=CC=CC3=CC=CC=C23
InChI
InChIKey=ZAHXYMFVNNUHCP-UHFFFAOYSA-N
InChI=1S/C14H14N2.HNO3/c1-2-7-13-11(4-1)5-3-6-12(13)10-14-15-8-9-16-14;2-1(3)4/h1-7H,8-10H2,(H,15,16);(H,2,3,4)
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 |
Molecular Formula | HNO3 |
Molecular Weight | 63.0128 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB06711Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/naphazoline.html
Sources: http://www.drugbank.ca/drugs/DB06711
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3021557
Curator's Comment: poorly crosses the blood-brain barrier
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11597419 |
63.1 nM [EC50] | ||
Target ID: CHEMBL232 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11597419 |
5.0 µM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Naphazoline Hydrochloride Approved UseNaphazoline Hydrochloride Ophthalmic Solution is indicated for use as a topical ocular vasoconstrictor. Launch Date1.46275205E11 |
Doses
Dose | Population | Adverse 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
AE | Significance | Dose | Population |
---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/18493746/ |
no |
PubMed
Title | Date | PubMed |
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The influence of alpha-adrenergic drugs on catalepsy induced by haloperidol or fluphenazine in rats. | 1978 Sep-Oct |
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Central action of narcotic analgesics. Part IV. Noradrenergic influences on the activity of analgesics in rats. | 1978 Sep-Oct |
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Involvement of nitric oxide in pollen-induced biphasic nasal blockage in sensitised guinea pigs. | 2001 Jun 29 |
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Treatment of rhinitis medicamentosa with fluticasone propionate--an experimental study. | 2001 Mar |
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Naphazoline-induced suppression of aqueous humor pressure and flow: involvement of central and peripheral alpha(2)/I(1) receptors. | 2001 Mar |
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Synthesis of some 1-(2-naphthyl)-2-(imidazole-1-yl)ethanone oxime and oxime ether derivatives and their anticonvulsant and antimicrobial activities. | 2001 May |
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[Comparative study of the radiation-protective effectiveness of low doses of cysteamine, heparin, and naphtizine in experiments on mice]. | 2001 May-Jun |
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Prolonged awakening and pulmonary edema after general anesthesia and naphazoline application in an infant. | 2001 Nov |
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[Applications of phosphorimetry in pharmaceutical analysis]. | 2002 Jun |
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Complementary use of partial least-squares and artificial neural networks for the non-linear spectrophotometric analysis of pharmaceutical samples. | 2002 Oct |
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Determination of prednisolone and the most important associated compounds in ocular and cutaneous pharmaceutical preparations by micellar electrokinetic capillary chromatography. | 2003 Jan 25 |
|
Octopaminergic modulation of synaptic transmission between an identified sensory afferent and flight motoneuron in the locust. | 2003 Jul 14 |
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[Cardiac arrest and secondary pulmonary oedema following accidental intramucosal injection of naphazoline in an adult]. | 2003 May |
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Effects of topical mydriatics and vasoconstrictors on prostaglandin-E2-induced aqueous flare elevation in pigmented rabbits. | 2003 Sep-Oct |
|
Actual therapeutic management of allergic and hyperreactive nasal disorders. | 2004 |
|
The thermodynamic dissociation constants of ambroxol, antazoline, naphazoline, oxymetazoline and ranitidine by the regression analysis of spectrophotometric data. | 2004 Feb 27 |
|
Hemorrhagic stroke after naphazoline exposition: case report. | 2004 Sep |
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Levocetirizine improves nasal symptoms and airflow in patients with persistent allergic rhinitis: a pilot study. | 2005 Jan |
|
A fluorescence optosensor for analyzing naphazoline in pharmaceutical preparations. Comparison with other sensors. | 2005 Jul 15 |
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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 |
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Application of solid-phase microextraction to antidoping analysis: determination of stimulants, narcotics, and other classes of substances excreted free in urine. | 2005 May-Jun |
|
[Efficacy of Derinox assessed with one PNIF (Peak Nasal Inspiratory Flow) in patients suffering from common cold]. | 2005 Nov |
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Effect of cold BSS vs naphazoline 0.025% on ocular surface temperature. | 2006 Aug |
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Net analyte signal-based simultaneous determination of antazoline and naphazoline using wavelength region selection by experimental design-neural networks. | 2006 Feb 15 |
|
Antagonism by imidazoline-type drugs of muscarinic and other receptors in the guinea-pig ileum. | 2006 Jul |
|
Evaluation, in vitro, of the radioprotection of DNA from gamma-rays by naphazoline. | 2006 Mar |
|
Fast simultaneous spectrophotometric determination of naphazoline nitrate and methylparaben by sequential injection chromatography. | 2006 Sep 15 |
|
Ischemic stroke in a man with naphazoline abuse history. | 2007 Oct |
|
A presentation of longstanding toxoplasmosis chorioretinitis. | 2009 Jan |
|
Determination of tetrahydrozoline in urine and blood using gas chromatography-mass spectrometry (GC-MS). | 2010 |
|
Pharmacological characterization of a Bombyx mori alpha-adrenergic-like octopamine receptor stably expressed in a mammalian cell line. | 2010 Feb |
|
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/naphazoline.html
Instill one or two drops in the conjunctival sac(s) every three to four hours as needed.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12037379
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
Edited
Fri Dec 15 15:06:31 UTC 2023
by
admin
on
Fri Dec 15 15:06:31 UTC 2023
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Record UNII |
SC99GR1T5S
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C29709
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NCI_THESAURUS |
C29578
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100000091842
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C98243
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82332
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DBSALT002621
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SUB03390MIG
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235810
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5144-52-5
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SC99GR1T5S
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CHEMBL761
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225-915-4
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