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Identification
NameNaphazoline
Accession NumberDB06711
TypeSmall Molecule
GroupsApproved
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
Synonyms
SynonymLanguageCode
NafazolinNot AvailableNot Available
Salts
Name/CAS Structure Properties
Naphazoline hydrochloride
Thumb
  • InChI Key: DJDFFEBSKJCGHC-UHFFFAOYSA-N
  • Monoisotopic Mass: 246.092376197
  • Average Mass: 246.735
DBSALT000127
Brand names
NameCompany
AK-ConNot Available
AlbalonNot Available
Brand mixtures
Brand NameIngredients
Naphcon-ANaphazoline hydrochloride + pheniramine maleate
Categories
CAS number835-31-4
WeightAverage: 210.2744
Monoisotopic: 210.115698458
Chemical FormulaC14H14N2
InChI KeyCNIIGCLFLJGOGP-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)
IUPAC Name
2-(naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazole
SMILES
C(C1=NCCN1)C1=CC=CC2=CC=CC=C12
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassAcenes and Derivatives
SubclassNaphthalenes
Direct parentNaphthalenes
Alternative parentsBenzene and Substituted Derivatives; Carboxamidines; Polyamines
Substituentsbenzene; amidine; carboxylic acid amidine; polyamine; organonitrogen compound
Classification descriptionThis compound belongs to the naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
Pharmacology
IndicationNaphazoline 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
PharmacodynamicsNaphazoline 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 actionNaphazoline 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityExtended 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 organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9936
Blood Brain Barrier + 0.9693
Caco-2 permeable - 0.6307
P-glycoprotein substrate Substrate 0.7448
P-glycoprotein inhibitor I Non-inhibitor 0.8385
P-glycoprotein inhibitor II Non-inhibitor 0.6449
Renal organic cation transporter Inhibitor 0.8506
CYP450 2C9 substrate Non-substrate 0.8202
CYP450 2D6 substrate Substrate 0.7094
CYP450 3A4 substrate Non-substrate 0.7297
CYP450 1A2 substrate Non-inhibitor 0.9046
CYP450 2C9 substrate Non-inhibitor 0.92
CYP450 2D6 substrate Inhibitor 0.8931
CYP450 2C19 substrate Non-inhibitor 0.9479
CYP450 3A4 substrate Non-inhibitor 0.9206
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.889
Ames test Non AMES toxic 0.8156
Carcinogenicity Non-carcinogens 0.9476
Biodegradation Not ready biodegradable 0.9961
Rat acute toxicity 2.6904 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.7043
hERG inhibition (predictor II) Non-inhibitor 0.5354
Pharmacoeconomics
Manufacturers
  • Allergan inc
  • Bausch and lomb pharmaceuticals inc
  • Pharmafair inc
  • Taylor pharmaceuticals
  • Alcon laboratories inc
  • Novartis pharmaceuticals corp
PackagersNot Available
Dosage forms
FormRouteStrength
Solution / dropsOphthalmic0.1%
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0381ALOGPS
logP3.44ALOGPS
logP2.19ChemAxon
logS-3.7ALOGPS
pKa (Strongest Basic)10.19ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area24.39 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity65.52 m3·mol-1ChemAxon
Polarizability23.77 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Roy W. Bryant, Ravi Parihar, Thomas Rowe, Susan Caballa, “Methods of Making and Using Stable Pharmaceutical Compositions Comprising Ketotifen and Naphazoline.” U.S. Patent US20110312998, issued December 22, 2011.

US20110312998
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD08253
PubChem Compound4436
PubChem Substance99443263
BindingDB50027061
PharmGKBPA165958384
WikipediaNaphazoline
ATC CodesR01AA08S01GA01R01AB02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Alpha-1A adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Alpha-1A adrenergic receptor P35348 Details

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

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Alpha-2A adrenergic receptor P08913 Details

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

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Drug created on May 16, 2010 11:05 / Updated on September 16, 2013 18:04