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targets (2)
for drugs
Identification
Name Naphazoline
Accession Number DB06711
Type small molecule
Groups approved
Description

Naphazoline is a rapid acting sympathomimetic vasoconstrictor of occular artierioles. It acts to decrease congestion of the conjunctiva and is found in many over-the-counter eye drops.
Structure Thumb
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Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts
  • Naphazoline hydrochloride
Brand names
Name Company
Albalon
Brand mixtures
Brand Name Ingredients
Naphcon-A Naphazoline hydrochloride + pheniramine maleate
Categories
  • Adrenergic alpha-Agonists
  • Sympathomimetic
CAS number 835-31-4
Weight Average: 210.2744
Monoisotopic: 210.115698458
Chemical Formula C14H14N2
InChI Key InChIKey=CNIIGCLFLJGOGP-UHFFFAOYSA-N
InChI
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)
Plain Text
IUPAC Name
2-(naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazole
SMILES
C(C1=NCCN1)C1=CC=CC2=CC=CC=C12
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Naphthalenes
  • Phenethylamines
Substructures
  • Imidazolines
  • Carboxylic Acids and Derivatives
  • Naphthalenes
  • Benzene and Derivatives
  • Imidazoles
  • Phenethylamines
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamidines
  • Imines
Pharmacology
Indication 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
Pharmacodynamics 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.
Mechanism of action 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.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Not Available
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Extended usage of Naphazoline can result in decreased effectiveness or a build up of tolerance against the drug. The number of receptors decreases, and when the administration of the drug is ceased, chronic congestion can occur; this is called rhinitis medicamentosa, commonly referred to as rebound congestion. Moreover long-term overdosing can cause degenerative changes in nasal mucous membranes that pose another health problem.
Affected organisms Not Available
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Allergan inc
  • Bausch and lomb pharmaceuticals inc
  • Pharmafair inc
  • Taylor pharmaceuticals
  • Alcon laboratories inc
  • Novartis pharmaceuticals corp
Packagers Not Available
Dosage forms
Form Route Strength
Solution / drops Ophthalmic 0.1%
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties Not Available
Predicted Properties
Property Value Source
water solubility 3.81e-02 g/l ALOGPS
logP 3.44 ALOGPS
logP 2.19 ChemAxon
logS -3.7 ALOGPS
pKa (strongest basic) 10.19 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 24.39 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 65.52 ChemAxon
polarizability 23.77 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D08253 Link_out
PubChem Compound 4436 Link_out
PubChem Substance 99443263 Link_out
BindingDB 50027061 Link_out
PharmGKB PA165958384 Link_out
Wikipedia http://en.wikipedia.org/wiki/Naphazoline Link_out
ATC Codes
  • R01AA08
  • S01GA01
  • R01AB02
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Alpha-1A adrenergic receptor

Pharmacological action: yes
Actions: agonist

This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins

Organism class: human
UniProt ID: P35348 Link_out
Gene: ADRA1A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Bogacka E: [Decongestants in treatment of nasal obstruction]. Otolaryngol Pol. 1999;53(3):347-52. Pubmed
  2. Leonardi A: Emerging drugs for ocular allergy. Expert Opin Emerg Drugs. 2005 Aug;10(3):505-20. Pubmed
  3. Piletz JE, Zhu H, Chikkala DN: Comparison of ligand binding affinities at human I1-imidazoline binding sites and the high affinity state of alpha-2 adrenoceptor subtypes. J Pharmacol Exp Ther. 1996 Nov;279(2):694-702. Pubmed
  4. Hrometz SL, Edelmann SE, McCune DF, Olges JR, Hadley RW, Perez DM, Piascik MT: Expression of multiple alpha1-adrenoceptors on vascular smooth muscle: correlation with the regulation of contraction. J Pharmacol Exp Ther. 1999 Jul;290(1):452-63. Pubmed
  5. Kai T: [Effects of topical alpha 1- and beta 2-adrenoceptor stimulants on nasal nitric oxide level]. Nippon Jibiinkoka Gakkai Kaiho. 1999 Jul;102(7):898-906. Pubmed
  6. Ogidigben MJ, Chu TC, Potter DE: Naphazoline-induced suppression of aqueous humor pressure and flow: involvement of central and peripheral alpha(2)/I(1) receptors. Exp Eye Res. 2001 Mar;72(3):331-9. Pubmed

2. Alpha-2A adrenergic receptor

Pharmacological action: yes
Actions: agonist

Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol

Organism class: human
UniProt ID: P08913 Link_out
Gene: ADRA2A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Piletz JE, Zhu H, Chikkala DN: Comparison of ligand binding affinities at human I1-imidazoline binding sites and the high affinity state of alpha-2 adrenoceptor subtypes. J Pharmacol Exp Ther. 1996 Nov;279(2):694-702. Pubmed
  2. Fukushima H, Norimoto K, Seki T, Nishiguchi T, Nakamura T, Konobu T, Nishio K, Okuchi K: Acute pulmonary edema associated with naphazoline ingestion. Clin Toxicol (Phila). 2008 Mar;46(3):254-6. Pubmed
  3. Ogidigben MJ, Chu TC, Potter DE: Naphazoline-induced suppression of aqueous humor pressure and flow: involvement of central and peripheral alpha(2)/I(1) receptors. Exp Eye Res. 2001 Mar;72(3):331-9. Pubmed
Comments
Drug created on May 16, 2010 11:05 / Updated on February 08, 2013 16:24