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
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
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 |
---|---|---|
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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Expression of multiple alpha1-adrenoceptors on vascular smooth muscle: correlation with the regulation of contraction. | 1999 Jul |
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[Electron microscopic studies of the rabbit nasal mucosa after short-term application of naphzoline nitrate]. | 2001 Jul |
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Sustained prediction ability of net analyte preprocessing methods using reduced calibration sets. Theoretical and experimental study involving the spectrophotometric analysis of multicomponent mixtures. | 2001 Jul |
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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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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 |
|
Actual therapeutic management of allergic and hyperreactive nasal disorders. | 2004 |
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[Pharmacological correction of cochleovestibular impairments]. | 2004 |
|
A rapid derivative spectrophotometric method for simultaneous determination of naphazoline and antazoline in eye drops. | 2006 Jan |
|
Naphazoline intoxication in children. | 2006 Nov |
|
Rhinoplasty - indications and techniques. | 2007 |
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Ischemic stroke in a man with naphazoline abuse history. | 2007 Oct |
|
The pK(a) Distribution of Drugs: Application to Drug Discovery. | 2007 Sep 17 |
|
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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Successful endonasal dacryocystorhinostomy in a patient with Wegener's granulomatosis. | 2009 |
|
Ebastine in the light of CONGA recommendations for the development of third-generation antihistamines. | 2009 Aug 31 |
|
[Peritopic anesthesia in cataract surgery]. | 2009 Feb |
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Determination of tetrahydrozoline in urine and blood using gas chromatography-mass spectrometry (GC-MS). | 2010 |
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Synthesis, anticonvulsant and antimicrobial activities of some new 2-acetylnaphthalene derivatives. | 2010 Apr 15 |
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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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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 |
|
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
|
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
Fri Dec 15 15:10:15 GMT 2023
by
admin
on
Fri Dec 15 15:10:15 GMT 2023
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Record UNII |
MZ1131787D
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Record Status |
Validated (UNII)
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Record Version |
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CFR |
21 CFR 349.18
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CFR |
21 CFR 341.20
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C29709
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82054
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DBSALT000127
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m7723
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C47632
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1457006
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35711
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11079
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CHEMBL761
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