Details
Stereochemistry | ACHIRAL |
Molecular Formula | C14H14N2 |
Molecular Weight | 210.2749 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
c1ccc2c(c1)cccc2CC3=NCCN3
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)
Molecular Formula | C14H14N2 |
Molecular Weight | 210.2749 |
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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Selective inhibition of alpha1B-adrenergic receptor expression and function using a phosphorothioate antisense oligodeoxynucleotide. | 1998 Jun |
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Radioprotective Activity and Synthesis of Siladithioacetals and Germadithioacetals Derived from N-substituted Naphthylethylimidazoline. | 2001 |
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Actual therapeutic management of allergic and hyperreactive nasal disorders. | 2004 |
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The thermodynamic dissociation constants of ambroxol, antazoline, naphazoline, oxymetazoline and ranitidine by the regression analysis of spectrophotometric data. | 2004 Feb 27 |
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Early bronchial airflow impairment in patients with persistent allergic rhinitis and bronchial hyperreactivity. | 2005 Dec |
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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 |
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[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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Epstein-barr virus induced cellular changes in nasal mucosa. | 2006 Feb 1 |
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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 |
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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 |
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Association between response to decongestion testing and sensitizations and allergic inflammation. | 2006 Mar |
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Evaluation, in vitro, of the radioprotection of DNA from gamma-rays by naphazoline. | 2006 Mar |
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Naphazoline intoxication in children. | 2006 Nov |
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Different mechanisms between thromboxane A2- and leukotriene D4-induced nasal blockage in guinea pigs. | 2006 Sep |
|
Fast simultaneous spectrophotometric determination of naphazoline nitrate and methylparaben by sequential injection chromatography. | 2006 Sep 15 |
|
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 |
|
Ischemic stroke in a man with naphazoline abuse history. | 2007 Oct |
|
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 |
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Relationship between rhinitis duration and response to nasal decongestion test. | 2008 Jul |
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Acute pulmonary edema associated with naphazoline ingestion. | 2008 Mar |
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In vitro culturing of porcine tracheal mucosa as an ideal model for investigating the influence of drugs on human respiratory mucosa. | 2008 Sep |
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Simultaneous determination of dibucaine and naphazoline in human serum by monolithic silica spin column extraction and liquid chromatography-mass spectrometry. | 2008 Sep 1 |
|
Successful endonasal dacryocystorhinostomy in a patient with Wegener's granulomatosis. | 2009 |
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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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[Peritopic anesthesia in cataract surgery]. | 2009 Feb |
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Intranasal lidocaine plus naphazoline nitrate improves surgical conditions and perioperative analgesia in septorhinoplasty surgery. | 2009 Feb |
|
A presentation of longstanding toxoplasmosis chorioretinitis. | 2009 Jan |
|
Effect of subconjunctival bevacizumab on primary pterygium. | 2009 May |
|
Influence of the ageing phenomenon on the low-frequency electrical impedance behavior of naphazoline hydrochloride solutions and paracetamol syrup. | 2009 May |
|
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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Determination of tetrahydrozoline in urine and blood using gas chromatography-mass spectrometry (GC-MS). | 2010 |
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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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Pulmonary edema and prolonged awakening after nasal naphazoline application in a transspenoidal hypophysectomy patient. | 2010 Jul |
|
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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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
by
admin
on
Edited
Sat Jun 26 14:53:06 UTC 2021
by
admin
on
Sat Jun 26 14:53:06 UTC 2021
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Record UNII |
H231GF11BV
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Record Status |
Validated (UNII)
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Record Version |
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S01GA51
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R01AB02
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R01AA08
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QS01GA51
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WHO-VATC |
QR01AB02
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WHO-ATC |
S01GA01
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WHO-VATC |
QS01GA01
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WHO-VATC |
QR01AA08
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NCI_THESAURUS |
C29709
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SUB09154MIG
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H231GF11BV
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CHEMBL761
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5509
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7247
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DB06711
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835-31-4
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NAPHAZOLINE
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M7723
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4436
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212-641-5
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835-31-4
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D009278
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3369
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C61856
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4153
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> AGONIST |
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ACTIVE MOIETY |