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)
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 |
---|---|---|
Central action of narcotic analgesics. Part IV. Noradrenergic influences on the activity of analgesics in rats. | 1978 Sep-Oct |
|
Treatment of ulcerative endobronchial tuberculosis and bronchial stenosis with aerosolized streptomycin and steroids. | 2001 Aug |
|
[Electron microscopic studies of the rabbit nasal mucosa after short-term application of naphzoline nitrate]. | 2001 Jul |
|
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 |
|
Markedly increased nasal blockage by intranasal leukotriene D4 in an experimental allergic rhinitis model: contribution of dilated mucosal blood vessels. | 2001 Jun |
|
Synthesis of some 1-(2-naphthyl)-2-(imidazole-1-yl)ethanone oxime and oxime ether derivatives and their anticonvulsant and antimicrobial activities. | 2001 May |
|
[Comparative study of the radiation-protective effectiveness of low doses of cysteamine, heparin, and naphtizine in experiments on mice]. | 2001 May-Jun |
|
Prolonged awakening and pulmonary edema after general anesthesia and naphazoline application in an infant. | 2001 Nov |
|
Naphazoline-induced neuroendocrine changes: increases in ANP and cGMP levels, but suppression of NE, 3H-NE, and cAMP levels in rabbit eyes. | 2002 Jul |
|
[Applications of phosphorimetry in pharmaceutical analysis]. | 2002 Jun |
|
[She really loves Mickey...]. | 2002 Jun |
|
Complementary use of partial least-squares and artificial neural networks for the non-linear spectrophotometric analysis of pharmaceutical samples. | 2002 Oct |
|
Bilateral acute angle-closure glaucoma after use of Fenox nasal drops. | 2002 Sep |
|
Transdermal penetration of vasoconstrictors--present understanding and assessment of the human epidermal flux and retention of free bases and ion-pairs. | 2003 Feb |
|
[Naphazoline intoxication: course and therapy]. | 2003 Feb |
|
Simultaneous determination of naphazoline, diphenhydramine and phenylephrine in nasal solutions by capillary electrophoresis. | 2003 Feb 5 |
|
[Studies on the experimental allergic rhinitis induced by Japanese cedar pollen--role of cysteinyl leukotrienes in nasal allergic symptoms]. | 2003 Jan |
|
Determination of prednisolone and the most important associated compounds in ocular and cutaneous pharmaceutical preparations by micellar electrokinetic capillary chromatography. | 2003 Jan 25 |
|
Octopaminergic modulation of synaptic transmission between an identified sensory afferent and flight motoneuron in the locust. | 2003 Jul 14 |
|
Naphazoline intoxication in a child-a clinical and forensic toxicological case. | 2003 Jul 8 |
|
[Cardiac arrest and secondary pulmonary oedema following accidental intramucosal injection of naphazoline in an adult]. | 2003 May |
|
Effects of topical mydriatics and vasoconstrictors on prostaglandin-E2-induced aqueous flare elevation in pigmented rabbits. | 2003 Sep-Oct |
|
[The application of naphcon eye drops during Lasik surgery]. | 2004 Dec |
|
Therapeutic management of endobronchial tuberculosis. | 2004 Jul |
|
Hemorrhagic stroke after naphazoline exposition: case report. | 2004 Sep |
|
Levocetirizine improves nasal symptoms and airflow in patients with persistent allergic rhinitis: a pilot study. | 2005 Jan |
|
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 |
|
Effect of cold BSS vs naphazoline 0.025% on ocular surface temperature. | 2006 Aug |
|
Epstein-barr virus induced cellular changes in nasal mucosa. | 2006 Feb 1 |
|
A rapid derivative spectrophotometric method for simultaneous determination of naphazoline and antazoline in eye drops. | 2006 Jan |
|
Do topical nasal decongestants affect polyps? | 2006 Mar |
|
Fast simultaneous spectrophotometric determination of naphazoline nitrate and methylparaben by sequential injection chromatography. | 2006 Sep 15 |
|
Theoretical assessment of naphazoline redoxchemistry and photochemistry. | 2007 Apr 19 |
|
UV-Vis spectrophotometrical and analytical methodology for the determination of singlet oxygen in new antibacterials drugs. | 2007 Nov 11 |
|
[The influence of different alpha-sympathomimetic drugs and benzalkoniumchlorid on the ciliary beat frequency of in vitro cultured human nasal mucosa cells]. | 2008 Jan |
|
Relationship between rhinitis duration and response to nasal decongestion test. | 2008 Jul |
|
In vitro culturing of porcine tracheal mucosa as an ideal model for investigating the influence of drugs on human respiratory mucosa. | 2008 Sep |
|
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 |
|
Intranasal lidocaine plus naphazoline nitrate improves surgical conditions and perioperative analgesia in septorhinoplasty surgery. | 2009 Feb |
|
A presentation of longstanding toxoplasmosis chorioretinitis. | 2009 Jan |
|
Allergic contact dermatitis from dibucaine hydrochloride, chlorpheniramine maleate, and naphazoline hydrochloride in an over-the-counter topical antiseptic. | 2009 Jul |
|
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 |
|
Determination of tetrahydrozoline in urine and blood using gas chromatography-mass spectrometry (GC-MS). | 2010 |
|
Pharmacological characterization of a Bombyx mori alpha-adrenergic-like octopamine receptor stably expressed in a mammalian cell line. | 2010 Feb |
|
Simultaneous determination of antazoline and naphazoline by the net analyte signal standard addition method and spectrophotometric technique. | 2010 Nov-Dec |
|
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.
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C29709
Created by
admin on Fri Dec 15 15:06:31 GMT 2023 , Edited by admin on Fri Dec 15 15:06:31 GMT 2023
|
||
|
NCI_THESAURUS |
C29578
Created by
admin on Fri Dec 15 15:06:31 GMT 2023 , Edited by admin on Fri Dec 15 15:06:31 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
100000091842
Created by
admin on Fri Dec 15 15:06:31 GMT 2023 , Edited by admin on Fri Dec 15 15:06:31 GMT 2023
|
PRIMARY | |||
|
C98243
Created by
admin on Fri Dec 15 15:06:31 GMT 2023 , Edited by admin on Fri Dec 15 15:06:31 GMT 2023
|
PRIMARY | |||
|
82332
Created by
admin on Fri Dec 15 15:06:31 GMT 2023 , Edited by admin on Fri Dec 15 15:06:31 GMT 2023
|
PRIMARY | |||
|
DBSALT002621
Created by
admin on Fri Dec 15 15:06:31 GMT 2023 , Edited by admin on Fri Dec 15 15:06:31 GMT 2023
|
PRIMARY | |||
|
DTXSID60863496
Created by
admin on Fri Dec 15 15:06:31 GMT 2023 , Edited by admin on Fri Dec 15 15:06:31 GMT 2023
|
PRIMARY | |||
|
SUB03390MIG
Created by
admin on Fri Dec 15 15:06:31 GMT 2023 , Edited by admin on Fri Dec 15 15:06:31 GMT 2023
|
PRIMARY | |||
|
235810
Created by
admin on Fri Dec 15 15:06:31 GMT 2023 , Edited by admin on Fri Dec 15 15:06:31 GMT 2023
|
PRIMARY | RxNorm | ||
|
5144-52-5
Created by
admin on Fri Dec 15 15:06:31 GMT 2023 , Edited by admin on Fri Dec 15 15:06:31 GMT 2023
|
PRIMARY | |||
|
SC99GR1T5S
Created by
admin on Fri Dec 15 15:06:31 GMT 2023 , Edited by admin on Fri Dec 15 15:06:31 GMT 2023
|
PRIMARY | |||
|
CHEMBL761
Created by
admin on Fri Dec 15 15:06:31 GMT 2023 , Edited by admin on Fri Dec 15 15:06:31 GMT 2023
|
PRIMARY | |||
|
225-915-4
Created by
admin on Fri Dec 15 15:06:31 GMT 2023 , Edited by admin on Fri Dec 15 15:06:31 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
SUBSTANCE RECORD