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
SMILES
C(C1=NCCN1)C2=CC=CC3=CC=CC=C23
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)
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 |
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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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Simultaneous determination of naphazoline, diphenhydramine and phenylephrine in nasal solutions by capillary electrophoresis. | 2003 Feb 5 |
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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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Actual therapeutic management of allergic and hyperreactive nasal disorders. | 2004 |
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Course and therapy of intoxication with imidazoline derivate naphazoline. | 2004 Jul |
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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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Association between response to decongestion testing and sensitizations and allergic inflammation. | 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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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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Nasal eosinophils and reversibility to the decongestion test in patients with perennial allergic rhinitis. | 2007 May-Jun |
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Intranasal lidocaine plus naphazoline nitrate improves surgical conditions and perioperative analgesia in septorhinoplasty surgery. | 2009 Feb |
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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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Determination of tetrahydrozoline in urine and blood using gas chromatography-mass spectrometry (GC-MS). | 2010 |
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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 |
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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WHO-ATC |
S01GA51
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R01AB02
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WHO-VATC |
QS01GA51
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QR01AB02
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WHO-ATC |
S01GA01
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QS01GA01
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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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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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H231GF11BV
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D009278
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100000084448
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3369
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C61856
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4153
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)