Details
Stereochemistry | ACHIRAL |
Molecular Formula | C14H14N2.ClH |
Molecular Weight | 246.735 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.C(C1=NCCN1)C2=CC=CC3=CC=CC=C23
InChI
InChIKey=DJDFFEBSKJCGHC-UHFFFAOYSA-N
InChI=1S/C14H14N2.ClH/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);1H
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 |
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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 |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
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Sources: https://pubmed.ncbi.nlm.nih.gov/18493746/ |
no |
PubMed
Title | Date | PubMed |
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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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Expression of multiple alpha1-adrenoceptors on vascular smooth muscle: correlation with the regulation of contraction. | 1999 Jul |
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Markedly increased nasal blockage by intranasal leukotriene D4 in an experimental allergic rhinitis model: contribution of dilated mucosal blood vessels. | 2001 Jun |
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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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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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[Studies on the experimental allergic rhinitis induced by Japanese cedar pollen--role of cysteinyl leukotrienes in nasal allergic symptoms]. | 2003 Jan |
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[Adult cases of naphazoline-containing antiseptic first aid liquid poisoning]. | 2003 Jul |
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Octopaminergic modulation of synaptic transmission between an identified sensory afferent and flight motoneuron in the locust. | 2003 Jul 14 |
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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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Actual therapeutic management of allergic and hyperreactive nasal disorders. | 2004 |
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[Pharmacological correction of cochleovestibular impairments]. | 2004 |
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[The application of naphcon eye drops during Lasik surgery]. | 2004 Dec |
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Course and therapy of intoxication with imidazoline derivate naphazoline. | 2004 Jul |
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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 |
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Levocetirizine improves nasal symptoms and airflow in patients with persistent allergic rhinitis: a pilot study. | 2005 Jan |
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Epstein-barr virus induced cellular changes in nasal mucosa. | 2006 Feb 1 |
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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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Different mechanisms between thromboxane A2- and leukotriene D4-induced nasal blockage in guinea pigs. | 2006 Sep |
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Rhinoplasty - indications and techniques. | 2007 |
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Theoretical assessment of naphazoline redoxchemistry and photochemistry. | 2007 Apr 19 |
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Eyelid ptosis from sympathetic nerve dysfunction mistaken as myopathy: a simple test to identify this condition. | 2007 Jun |
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Relationship between rhinitis duration and response to nasal decongestion test. | 2008 Jul |
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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 |
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A presentation of longstanding toxoplasmosis chorioretinitis. | 2009 Jan |
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Determination of tetrahydrozoline in urine and blood using gas chromatography-mass spectrometry (GC-MS). | 2010 |
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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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Structural and functional evolution of the trace amine-associated receptors TAAR3, TAAR4 and TAAR5 in primates. | 2010 Jun 15 |
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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 |
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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.
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Classification Tree | Code System | Code | ||
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CFR |
21 CFR 349.18
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CFR |
21 CFR 341.20
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NCI_THESAURUS |
C29709
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82054
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DTXSID7045788
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DBSALT000127
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100000090391
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2174
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208-989-2
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m7723
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C47632
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1457006
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SUB03389MIG
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550-99-2
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MZ1131787D
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35711
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11079
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CHEMBL761
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MZ1131787D
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ACTIVE MOIETY
SUBSTANCE RECORD