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Identification
NameNaphazoline
Accession NumberDB06711
TypeSmall Molecule
GroupsApproved
DescriptionNaphazoline 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
Nafazolin
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ak-consolution/ drops1 mg/mLophthalmicPreferred Pharmaceuticals, Inc.2005-03-24Not applicableUs
Ak-consolution1 mg/mLophthalmicRebel Distributors Corp.1974-08-22Not applicableUs
Naphazolinesolution/ drops1 mg/mLophthalmicAkorn, Inc.1995-12-19Not applicableUs
Naphazolinesolution/ drops1 mg/mLophthalmicPreferred Pharmaceuticals, Inc.2013-04-22Not applicableUs
Naphazolinesolution/ drops1 mg/mLophthalmicA S Medication Solutions Llc1995-12-19Not applicableUs
Naphazolinesolution/ drops1 mg/mLophthalmicProficient Rx LP1995-12-19Not applicableUs
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Albalondrops.1 %ophthalmicAllergan Inc1970-12-31Not applicableCanada
Clear Eyesliquid.012 %ophthalmicPrestige Brands Inc2004-03-24Not applicableCanada
Clear Eyes By Murine Eye Dpsliquid.012 %ophthalmicAbbott Laboratories, Limited1970-12-312003-10-10Canada
Diopticon Liq 0.1%liquid.1 %ophthalmicDioptic Pharmaceuticals Inc1994-12-31Not applicableCanada
Naphcon Fortesolution0.1 %ophthalmicAlcon Canada Inc1977-12-31Not applicableCanada
Nazalliquid50 mg/100mLnasalSato Pharmaceutical Co., Ltd.1990-06-11Not applicableUs
Odan-naphazolinesolution.1 %ophthalmicOdan Laboratories Ltd1986-12-31Not applicableCanada
Opcon Oph Soln 0.1%drops.1 %ophthalmicBausch & Lomb Canada Inc.1987-12-311996-09-09Canada
Opti-tears Red Eyesolution0.1 %ophthalmicAlcon Canada IncNot applicableNot applicableCanada
Pi Yen Chinsolution/ drops1 mg/1ophthalmicInternational Nature Nutraceuticals1985-07-01Not applicableUs
Privinesuspension/ drops.125 mL/25mLnasalInsight Pharmaceuticals LLC2009-07-16Not applicableUs
Privinespray.1 mL/20mLnasalInsight Pharmaceuticals2009-07-16Not applicableUs
R.O.-naphzliquid.1 %ophthalmicRichmond Pharmaceuticals Inc.1992-12-311997-08-11Canada
Red Awayliquid.1 %ophthalmicRivex Ophthalmics Inc.1997-08-112003-07-28Canada
Redness Eye Dropsdrops0.012 %ophthalmicBausch & Lomb Inc2013-02-19Not applicableCanada
Refresh Redness Reliefsolution0.1 %ophthalmicAllergan Inc2009-02-09Not applicableCanada
Sato Clearsolution/ drops12 mg/100mLophthalmicSato Pharmaceutical Co., Ltd.1989-05-31Not applicableUs
Soothe Rednessdrops0.012 %ophthalmicBausch & Lomb Inc1988-12-31Not applicableCanada
Vasocon Eye Dropsdrops1 mgophthalmicNovartis Ophthalmics Novartis Pharmaceuticals (Canada) Inc1996-09-032006-08-01Canada
Vasocon Oph Soln 0.1%drops.1 %ophthalmicIolab Pharmaceuticals1988-12-311996-09-09Canada
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
Advanced Eye Relief/ Redness Instant ReliefBausch & Lomb Incorporated
Advanced Eye Relief/ Redness Maximum ReliefBausch & Lomb Incorporated
Albalon AAllergan Inc
Allergy Eye DropsCVS Pharmacy
Blue CollyriumSandoz Canada Incorporated
Clear Eyes Acr By MurineAbbott Laboratories, Limited
Clear Eyes AllergyPrestige Brands Inc
Clear Eyes Complete 7 Symptom ReliefPrestige Brands Holdings, Inc.
Clear Eyes Complete 7 Sympton ReliefPrestige Brands Holdings, Inc.
Clear Eyes Cooling Itchy Eye ReliefPrestige Brands Holdings, Inc.
Clear Eyes Cooling Redness ReliefPrestige Brands Holdings, Inc.
Clear Eyes Extra Strength Redness ReliefPrestige Brands Inc
Clear Eyes for Dry Eyes Plus Redness ReliefPrestige Brands Inc
Clear Eyes Maximum Itchy Eye ReliefPrestige Brands Holdings, Inc.
Clear Eyes Maximum Redness ReliefPrestige Brands Holdings, Inc.
Clear Eyes Redness ReliefPrestige Brands Holdings, Inc.
Clear Eyes Redness Relief Handy Pocket PalPrestige Brands Holdings, Inc.
Collyre BleuSabex Inc
Cooper A.R.Coopervision Inc.
Dg Health Maximum Redness ReliefDolgencorp Inc
Diopticon A LiqDioptic Pharmaceuticals Inc
Eye Allergy ReliefWalgreen Company
Eye Drops Redness and Dry Eye ReliefKc Pharmaceuticals, Inc.
Floril Redness ReliefVitaline S.A.C.
Goodsense Maximum Strength Redness Relief PlusGood Sense (Geiss, Destin & Dunn, Inc.)
Lubricant / Redness RelieverRite Aid Corporation
Lubricant and Redness RelieverTarget Corporation
Maximum Redness Relief EyeWin Co Foods, Llc
Naphazoline Hci and Pheniramine MaleateAltaire Pharmaceuticals Inc.
Naphazoline Hydrochloride and Pheniramine MaleateWalgreens
Naphcon AAlcon Laboratories, Inc.
Opcon-ABausch & Lomb Incorporated
Opti-tears AllergyAlcon Canada Inc
Optic SplashSato Pharmaceutical, Co., Ltd.
Original Redness RelieverRite Aid Corporation
Pure Eyes Sterile EyesSamson Pharmaceutical
Reactine Eye DropsMcneil Consumer Healthcare Division Of Johnson & Johnson Inc
Red Eye ReliefTarget Corporation
Refresh Eye Allergy ReliefAllergan Inc
Rhino MexLaboratoires Charton Laboratories
Rohto CoolThe Mentholatum Company
Rohto Cool MaxThe Mentholatum Company
Soothe AllergyBausch & Lomb Inc
Steritears ArLaboratoires Sterigen Inc
Vasocon A Eye DropsNovartis Ophthalmics Novartis Pharmaceuticals (Canada) Inc
Vasocon A Oph SolnIolab Pharmaceuticals
Visine A Multi-action Eye Allergy ReliefJohnson & Johnson Consumer Inc.
Visine for Allergy With AntihistamineJohnson & Johnson Inc
Walgreens Maximum Redness ReliefWalgreen Company
Zincfrin AAlcon Canada Inc
Salts
Name/CASStructureProperties
Naphazoline hydrochloride
Thumb
  • InChI Key: DJDFFEBSKJCGHC-UHFFFAOYSA-N
  • Monoisotopic Mass: 246.092376197
  • Average Mass: 246.735
DBSALT000127
Categories
UNIIH231GF11BV
CAS number835-31-4
WeightAverage: 210.2744
Monoisotopic: 210.115698458
Chemical FormulaC14H14N2
InChI KeyInChIKey=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)
IUPAC Name
2-(naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazole
SMILES
C(C1=NCCN1)C1=CC=CC2=CC=CC=C12
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNot Available
Direct ParentNaphthalenes
Alternative Parents
Substituents
  • Naphthalene
  • Imidolactam
  • 2-imidazoline
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Carboxylic acid amidine
  • Amidine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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
PropertyValueProbability
Human Intestinal Absorption+0.9936
Blood Brain Barrier+0.9693
Caco-2 permeable-0.6307
P-glycoprotein substrateSubstrate0.7448
P-glycoprotein inhibitor INon-inhibitor0.8385
P-glycoprotein inhibitor IINon-inhibitor0.6449
Renal organic cation transporterInhibitor0.8506
CYP450 2C9 substrateNon-substrate0.8202
CYP450 2D6 substrateSubstrate0.7094
CYP450 3A4 substrateNon-substrate0.7297
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.92
CYP450 2D6 inhibitorInhibitor0.8931
CYP450 2C19 inhibitorNon-inhibitor0.9479
CYP450 3A4 inhibitorNon-inhibitor0.9206
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.889
Ames testNon AMES toxic0.8156
CarcinogenicityNon-carcinogens0.9476
BiodegradationNot ready biodegradable0.9961
Rat acute toxicity2.6904 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7043
hERG inhibition (predictor II)Non-inhibitor0.5354
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Solutionophthalmic1 mg/mL
Liquidophthalmic.012 %
Dropsophthalmic
Solution/ dropsophthalmic1 mg/mL
Solution/ dropsophthalmic
Liquidnasal50 mg/100mL
Solutionophthalmic.1 %
Dropsophthalmic.1 %
Solution/ dropsophthalmic1 mg/1
Spraynasal.1 mL/20mL
Suspension/ dropsnasal.125 mL/25mL
Liquidophthalmic.1 %
Dropsophthalmic0.012 %
Solutionophthalmic0.1 %
Liquidnasal
Liquidophthalmic
Solution/ dropsophthalmic12 mg/100mL
Dropsophthalmic1 mg
Solutionophthalmic
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0381 mg/mLALOGPS
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 RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
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 ReferencesNot Available
External Links
ATC CodesR01AB02S01GA01R01AA08S01GA51
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcebutololNaphazoline may increase the atrioventricular blocking (AV block) activities of Acebutolol.
AlprenololNaphazoline may increase the atrioventricular blocking (AV block) activities of Alprenolol.
AmineptineThe therapeutic efficacy of Naphazoline can be decreased when used in combination with Amineptine.
AmitriptylineThe therapeutic efficacy of Naphazoline can be decreased when used in combination with Amitriptyline.
ArotinololNaphazoline may increase the atrioventricular blocking (AV block) activities of Arotinolol.
AtenololNaphazoline may increase the atrioventricular blocking (AV block) activities of Atenolol.
BefunololNaphazoline may increase the atrioventricular blocking (AV block) activities of Befunolol.
BetaxololNaphazoline may increase the atrioventricular blocking (AV block) activities of Betaxolol.
BevantololNaphazoline may increase the atrioventricular blocking (AV block) activities of Bevantolol.
BisoprololNaphazoline may increase the atrioventricular blocking (AV block) activities of Bisoprolol.
BopindololNaphazoline may increase the atrioventricular blocking (AV block) activities of Bopindolol.
BufuralolNaphazoline may increase the atrioventricular blocking (AV block) activities of Bufuralol.
BupranololNaphazoline may increase the atrioventricular blocking (AV block) activities of Bupranolol.
CarteololNaphazoline may increase the atrioventricular blocking (AV block) activities of Carteolol.
CarvedilolNaphazoline may increase the atrioventricular blocking (AV block) activities of Carvedilol.
CeliprololNaphazoline may increase the atrioventricular blocking (AV block) activities of Celiprolol.
ClomipramineThe therapeutic efficacy of Naphazoline can be decreased when used in combination with Clomipramine.
CyclobenzaprineThe therapeutic efficacy of Naphazoline can be decreased when used in combination with Cyclobenzaprine.
DesipramineThe therapeutic efficacy of Naphazoline can be decreased when used in combination with Desipramine.
DesvenlafaxineDesvenlafaxine may decrease the antihypertensive activities of Naphazoline.
DosulepinThe therapeutic efficacy of Naphazoline can be decreased when used in combination with Dosulepin.
DoxepinThe therapeutic efficacy of Naphazoline can be decreased when used in combination with Doxepin.
DuloxetineDuloxetine may decrease the antihypertensive activities of Naphazoline.
EsmirtazapineThe therapeutic efficacy of Naphazoline can be decreased when used in combination with Esmirtazapine.
EsmololNaphazoline may increase the atrioventricular blocking (AV block) activities of Esmolol.
ImipramineThe therapeutic efficacy of Naphazoline can be decreased when used in combination with Imipramine.
IndenololNaphazoline may increase the atrioventricular blocking (AV block) activities of Indenolol.
LabetalolNaphazoline may increase the atrioventricular blocking (AV block) activities of Labetalol.
LevomilnacipranLevomilnacipran may decrease the antihypertensive activities of Naphazoline.
MetoprololNaphazoline may increase the atrioventricular blocking (AV block) activities of Metoprolol.
MianserinThe therapeutic efficacy of Naphazoline can be decreased when used in combination with Mianserin.
MilnacipranMilnacipran may decrease the antihypertensive activities of Naphazoline.
MirtazapineThe therapeutic efficacy of Naphazoline can be decreased when used in combination with Mirtazapine.
NadololNaphazoline may increase the atrioventricular blocking (AV block) activities of Nadolol.
NortriptylineThe therapeutic efficacy of Naphazoline can be decreased when used in combination with Nortriptyline.
OxprenololNaphazoline may increase the atrioventricular blocking (AV block) activities of Oxprenolol.
PenbutololNaphazoline may increase the atrioventricular blocking (AV block) activities of Penbutolol.
PindololNaphazoline may increase the atrioventricular blocking (AV block) activities of Pindolol.
PractololNaphazoline may increase the atrioventricular blocking (AV block) activities of Practolol.
PropranololNaphazoline may increase the atrioventricular blocking (AV block) activities of Propranolol.
ProtriptylineThe therapeutic efficacy of Naphazoline can be decreased when used in combination with Protriptyline.
SotalolNaphazoline may increase the atrioventricular blocking (AV block) activities of Sotalol.
TianeptineThe therapeutic efficacy of Naphazoline can be decreased when used in combination with Tianeptine.
TimololNaphazoline may increase the atrioventricular blocking (AV block) activities of Timolol.
TrimipramineThe therapeutic efficacy of Naphazoline can be decreased when used in combination with Trimipramine.
VenlafaxineVenlafaxine may decrease the antihypertensive activities of Naphazoline.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Protein heterodimerization activity
Specific Function:
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. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine(PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular Weight:
51486.005 Da
References
  1. Bogacka E: [Decongestants in treatment of nasal obstruction]. Otolaryngol Pol. 1999;53(3):347-52. [PubMed:10481510 ]
  2. Leonardi A: Emerging drugs for ocular allergy. Expert Opin Emerg Drugs. 2005 Aug;10(3):505-20. [PubMed:16083326 ]
  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:8930173 ]
  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:10381812 ]
  5. Kai T: [Effects of topical alpha 1- and beta 2-adrenoceptor stimulants on nasal nitric oxide level]. Nihon Jibiinkoka Gakkai Kaiho. 1999 Jul;102(7):898-906. [PubMed:10459292 ]
  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:11180982 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Thioesterase binding
Specific Function:
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 = mianser...
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular Weight:
48956.275 Da
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:8930173 ]
  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:17852165 ]
  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:11180982 ]
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Drug created on May 16, 2010 11:05 / Updated on August 17, 2016 12:24