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 Date1974 |
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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Selective inhibition of alpha1B-adrenergic receptor expression and function using a phosphorothioate antisense oligodeoxynucleotide. | 1998 Jun |
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[Applications of phosphorimetry in pharmaceutical analysis]. | 2002 Jun |
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Transdermal penetration of vasoconstrictors--present understanding and assessment of the human epidermal flux and retention of free bases and ion-pairs. | 2003 Feb |
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[Naphazoline intoxication: course and therapy]. | 2003 Feb |
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[Adult cases of naphazoline-containing antiseptic first aid liquid poisoning]. | 2003 Jul |
|
Octopaminergic modulation of synaptic transmission between an identified sensory afferent and flight motoneuron in the locust. | 2003 Jul 14 |
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Naphazoline intoxication in a child-a clinical and forensic toxicological case. | 2003 Jul 8 |
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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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[The tolerability of nasal drugs with special regard to preservatives and physico-chemical parameters]. | 2003 Nov |
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[Acute exposure to imidazoline derivatives in children]. | 2003 Nov-Dec |
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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 |
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Therapeutic management of endobronchial tuberculosis. | 2004 Jul |
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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 |
|
Hemorrhagic stroke after naphazoline exposition: case report. | 2004 Sep |
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Early bronchial airflow impairment in patients with persistent allergic rhinitis and bronchial hyperreactivity. | 2005 Dec |
|
A fluorescence optosensor for analyzing naphazoline in pharmaceutical preparations. Comparison with other sensors. | 2005 Jul 15 |
|
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 |
|
A rapid derivative spectrophotometric method for simultaneous determination of naphazoline and antazoline in eye drops. | 2006 Jan |
|
Antagonism by imidazoline-type drugs of muscarinic and other receptors in the guinea-pig ileum. | 2006 Jul |
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Do topical nasal decongestants affect polyps? | 2006 Mar |
|
Association between response to decongestion testing and sensitizations and allergic inflammation. | 2006 Mar |
|
Naphazoline intoxication in children. | 2006 Nov |
|
Different mechanisms between thromboxane A2- and leukotriene D4-induced nasal blockage in guinea pigs. | 2006 Sep |
|
Rhinoplasty - indications and techniques. | 2007 |
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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 |
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Nasal eosinophils and reversibility to the decongestion test in patients with perennial allergic rhinitis. | 2007 May-Jun |
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UV-Vis spectrophotometrical and analytical methodology for the determination of singlet oxygen in new antibacterials drugs. | 2007 Nov 11 |
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Nasal irrigation with lavonase as ancillary treatment of acute rhinosinusitis: a pilot study. | 2009 Apr-Jun |
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Ebastine in the light of CONGA recommendations for the development of third-generation antihistamines. | 2009 Aug 31 |
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A presentation of longstanding toxoplasmosis chorioretinitis. | 2009 Jan |
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Effect of subconjunctival bevacizumab on primary pterygium. | 2009 May |
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Influence of the ageing phenomenon on the low-frequency electrical impedance behavior of naphazoline hydrochloride solutions and paracetamol syrup. | 2009 May |
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Flow-injection chemiluminescence method for the determination of naphazoline hydrochloride and oxymetazoline hydrochloride. | 2009 May-Jun |
|
[Microhemocirculation and its correction in duodenal ulcer during period of rehabilitation]. | 2009 Oct-Dec |
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Pharmacological characterization of a Bombyx mori alpha-adrenergic-like octopamine receptor stably expressed in a mammalian cell line. | 2010 Feb |
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A comparative kinetic and mechanistic study between tetrahydrozoline and naphazoline toward photogenerated reactive oxygen species. | 2010 Jan-Feb |
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Pulmonary edema and prolonged awakening after nasal naphazoline application in a transspenoidal hypophysectomy patient. | 2010 Jul |
|
Functional and pharmacological characterization of a beta-adrenergic-like octopamine receptor from the silkworm Bombyx mori. | 2010 Jun |
|
Structural and functional evolution of the trace amine-associated receptors TAAR3, TAAR4 and TAAR5 in primates. | 2010 Jun 15 |
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Simultaneous determination of antazoline and naphazoline by the net analyte signal standard addition method and spectrophotometric technique. | 2010 Nov-Dec |
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Treatment of allergic conjunctivitis: results of a 1-month, single-masked randomized study. | 2010 Sep-Oct |
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Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
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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 |
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
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admin
on
Edited
Fri Dec 15 15:06:31 GMT 2023
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on
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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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C29709
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C29578
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C98243
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