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
Nafazolin
External IDs Not Available
Product Ingredients
IngredientUNIICASInChI KeyDetails
Naphazoline hydrochlorideMZ1131787D 550-99-2DJDFFEBSKJCGHC-UHFFFAOYSA-NDetails
Approved Prescription ProductsNot Available
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ak-conSolution / drops1 mg/mLOphthalmicPreferreed Pharmaceuticals Inc.2005-03-24Not applicableUs
Ak-conSolution1 mg/mLOphthalmicRebel Distributors1974-08-22Not applicableUs
NaphazolineSolution / drops1 mg/mLOphthalmicAkorn1995-12-19Not applicableUs
NaphazolineSolution / drops1 mg/mLOphthalmicProficient Rx LP1995-12-19Not applicableUs
NaphazolineSolution / drops1 mg/mLOphthalmicA S Medication Solutions1995-12-192017-06-20Us
NaphazolineSolution / drops1 mg/mLOphthalmicA S Medication Solutions1995-12-192017-06-20Us
NaphazolineSolution / drops1 mg/mLOphthalmicPreferreed Pharmaceuticals Inc.2013-04-22Not applicableUs
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AlbalonSolution / drops.1 %OphthalmicAllergan1970-12-31Not applicableCanada
Clear EyesLiquid.012 %OphthalmicPrestige Brands Inc2004-03-24Not applicableCanada
Clear Eyes By Murine Eye DpsLiquid.012 %OphthalmicAbbott1970-12-312003-10-10Canada
Diopticon Liq 0.1%Solution.1 %OphthalmicDioptic Pharmaceuticals Inc1994-12-31Not applicableCanada
Naphcon ForteSolution0.1 %OphthalmicAlcon, Inc.1977-12-31Not applicableCanada
NazalLiquid50 mg/100mLNasalSato Pharmaceutical1990-06-11Not applicableUs
Odan-naphazolineSolution.1 %OphthalmicOdan Laboratories Ltd1986-12-31Not applicableCanada
Opcon Oph Soln 0.1%Solution / drops.1 %OphthalmicBausch & Lomb Inc1987-12-311996-09-09Canada
Opti-tears Red EyeSolution0.1 %OphthalmicAlcon, Inc.2017-04-04Not applicableCanada
Pi Yen ChinSolution / drops1 mg/1OphthalmicInternational Nature Nutraceuticals1985-07-01Not applicableUs
PrivineSuspension / drops.125 mL/25mLNasalInsight Pharmaceuticals2009-07-16Not applicableUs
PrivineSpray.1 mL/20mLNasalInsight Pharmaceuticals2009-07-16Not applicableUs
R.O.-naphzLiquid.1 %OphthalmicRichmond Pharmaceuticals1992-12-311997-08-11Canada
Red AwayLiquid.1 %OphthalmicRivex Ophthalmics Inc.1997-08-112003-07-28Canada
Redness Eye DropsSolution / drops0.012 %OphthalmicBausch & Lomb Inc2013-02-19Not applicableCanada
Refresh Redness ReliefSolution0.1 %OphthalmicAllergan2009-02-09Not applicableCanada
Sato ClearSolution / drops12 mg/100mLOphthalmicSato Pharmaceutical1989-05-31Not applicableUs
Soothe RednessSolution / drops0.012 %OphthalmicBausch & Lomb Inc1988-12-31Not applicableCanada
Vasocon Eye DropsSolution / drops1 mgOphthalmicNovartis Ophthalmics Novartis Pharmaceuticals (Canada) Inc1996-09-032006-08-01Canada
Vasocon Oph Soln 0.1%Solution / drops.1 %OphthalmicIolab Pharmaceuticals1988-12-311996-09-09Canada
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
7 Select Redness ReliefSolution / dropsOphthalmic7 Select, Inc2017-03-28Not applicableUs
Advanced Eye Relief/ Redness Instant ReliefSolution / dropsOphthalmicBauch & Lomb Incorporated2010-09-13Not applicableUs
Advanced Eye Relief/ Redness Maximum ReliefSolution / dropsOphthalmicBauch & Lomb Incorporated2010-09-02Not applicableUs
Albalon ALiquidOphthalmicAllergan1978-12-31Not applicableCanada
Allergy Eye DropsSolution / dropsOphthalmicCvs Health2013-01-25Not applicableUs
Blue CollyriumLiquidOphthalmicSandoz Canada Incorporated1997-05-13Not applicableCanada
Careone Maximum Strength Redness ReliefSolution / dropsOphthalmicFoodhold U.S.A.2017-05-18Not applicableUs
Clear Eyes Acr By MurineLiquidOphthalmicAbbott1998-09-022003-10-10Canada
Clear Eyes AllergyLiquidOphthalmicPrestige Brands Inc2004-03-24Not applicableCanada
Clear Eyes Complete 7 Symptom ReliefLiquidOphthalmicPrestige Brands Holdings, Inc.2010-03-01Not applicableUs
Clear Eyes Complete 7 Sympton ReliefLiquidOphthalmicPrestige Brands Holdings, Inc.2013-06-12Not applicableUs
Clear Eyes Cooling Itchy Eye ReliefLiquidOphthalmicPrestige Brands Holdings, Inc.2011-02-15Not applicableUs
Clear Eyes Cooling Redness ReliefLiquidOphthalmicPrestige Brands Holdings, Inc.2011-02-15Not applicableUs
Clear Eyes Extra Strength Redness ReliefSolutionOphthalmicPrestige Brands Inc2011-04-27Not applicableCanada
Clear Eyes for Dry Eyes Plus Redness ReliefSolutionOphthalmicPrestige Brands Inc2008-03-262014-03-20Canada
Clear Eyes Maximum Itchy Eye ReliefLiquidOphthalmicPrestige Brands Holdings, Inc.2011-03-15Not applicableUs
Clear Eyes Maximum Redness ReliefLiquidOphthalmicPrestige Brands Holdings, Inc.2010-09-01Not applicableUs
Clear Eyes Redness ReliefLiquidOphthalmicPrestige Brands Holdings, Inc.2011-04-27Not applicableUs
Clear Eyes Redness Relief Handy Pocket PalLiquidOphthalmicPrestige Brands Holdings, Inc.2012-11-01Not applicableUs
Collyre BleuSolution / dropsOphthalmicSabex Inc1991-12-311997-11-26Canada
Cooper A.R.Solution / dropsOphthalmicCoopervision, Inc.1996-08-141998-03-12Canada
Dg Health Maximum Redness ReliefSolution / dropsOphthalmicDolgencorp2014-11-24Not applicableUs
Diopticon A LiqSolutionOphthalmicDioptic Pharmaceuticals Inc1994-12-31Not applicableCanada
Eye Allergy ReliefSolution / dropsOphthalmicWalgreen2010-08-31Not applicableUs
Eye Drops Redness and Dry Eye ReliefSolution / dropsOphthalmicKc Pharmaceuticals, Inc.2007-10-22Not applicableUs
Floril Redness ReliefSolution / dropsOphthalmicVitaline S.A.C.2005-11-10Not applicableUs
Good Neighbor Pharmacy Redness ReliefSolution / dropsOphthalmicAmerisource Bergen2017-03-24Not applicableUs
Goodsense Maximum Strength Redness Relief PlusSolution / dropsOphthalmicGood Sense (Geiss, Destin & Dunn, Inc.)2016-01-05Not applicableUs
Health Mart Redness ReliefLiquidOphthalmicMc Kesson2015-07-01Not applicableUs
Lidl Redness ReliefSolution / dropsOphthalmicLidl Us, Llc2017-03-10Not applicableUs
Lubricant / Redness RelieverSolution / dropsOphthalmicRite Aid2010-09-02Not applicableUs
Lubricant and Redness RelieverSolution / dropsOphthalmicTarget Corporation.2010-09-13Not applicableUs
Maximum Redness Relief EyeSolution / dropsOphthalmicWin Co Foods, Llc,2015-01-09Not applicableUs
Naphazoline Hci and Pheniramine MaleateSolution / dropsOphthalmicAltaire Pharmaceuticals Inc.2010-10-06Not applicableUs
Naphazoline Hydrochloride and Pheniramine MaleateSolution / dropsOphthalmicWalgreens2013-04-23Not applicableUs
Naphcon ASolution / dropsOphthalmicAlcon, Inc.1994-06-08Not applicableUs
Opcon-ASolution / dropsOphthalmicBauch & Lomb Incorporated1994-06-08Not applicableUs
Opti-tears AllergySolutionOphthalmicAlcon, Inc.2017-04-04Not applicableCanada
Optic SplashSolution / dropsOphthalmicSato Pharmaceutical2008-01-22Not applicableUs
Original Redness RelieverSolution / dropsOphthalmicRite Aid2010-09-13Not applicableUs
Pure Eyes Sterile EyesSolution / dropsOphthalmicSamson Pharmaceutical2015-01-01Not applicableUs
Reactine Eye DropsSolution / dropsOphthalmicMcneil Consumer Healthcare Division Of Johnson & Johnson IncNot applicableNot applicableCanada
Red Eye ReliefSolution / dropsOphthalmicTarget Corporation.2015-03-04Not applicableUs
Refresh Eye Allergy ReliefSolutionOphthalmicAllergan2009-02-09Not applicableCanada
Rhino MexLiquidNasalLaboratoires Charton Laboratories1978-12-311999-09-17Canada
Rohto CoolLiquidOphthalmicThe Mentholatum Company2001-08-21Not applicableUs
Rohto Cool MaxLiquidOphthalmicThe Mentholatum Company2014-05-05Not applicableUs
Soothe AllergySolution / dropsOphthalmicBausch & Lomb Inc1987-12-31Not applicableCanada
Steritears ArSolution / dropsOphthalmicLaboratoires Sterigen IncNot applicableNot applicableCanada
Sunmark Redness ReliefLiquidOphthalmicMc Kesson2009-10-01Not applicableUs
Vasocon A Eye DropsSolution / dropsOphthalmicNovartis Ophthalmics Novartis Pharmaceuticals (Canada) Inc1996-12-312005-03-01Canada
Vasocon A Oph SolnSolution / dropsOphthalmicIolab Pharmaceuticals1988-12-311996-09-09Canada
Visine A Multi-action Eye Allergy ReliefSolution / dropsOphthalmicJohnson & Johnson2010-12-15Not applicableUs
Visine for Allergy With AntihistamineSolution / dropsOphthalmicJohnson & Johnson2003-12-29Not applicableCanada
Walgreens Maximum Redness ReliefSolutionOphthalmicWalgreen2014-11-25Not applicableUs
Zincfrin ASolution / dropsOphthalmicAlcon, Inc.1969-12-312009-04-24Canada
Categories
UNIIH231GF11BV
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
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

Structured Indications
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.

TargetKindPharmacological actionActionsOrganismUniProt ID
Alpha-1A adrenergic receptorProteinyes
agonist
HumanP35348 details
Alpha-2A adrenergic receptorProteinyes
agonist
HumanP08913 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot 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 organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcebutololNaphazoline may increase the atrioventricular blocking (AV block) activities of Acebutolol.Approved
AlfuzosinAlfuzosin may decrease the vasoconstricting activities of Naphazoline.Approved, Investigational
AlprenololNaphazoline may increase the atrioventricular blocking (AV block) activities of Alprenolol.Approved, Withdrawn
AmineptineAmineptine may decrease the antihypertensive activities of Naphazoline.Illicit, Withdrawn
AmitriptylineAmitriptyline may decrease the antihypertensive activities of Naphazoline.Approved
ArotinololNaphazoline may increase the atrioventricular blocking (AV block) activities of Arotinolol.Approved
AtenololNaphazoline may increase the atrioventricular blocking (AV block) activities of Atenolol.Approved
BefunololNaphazoline may increase the atrioventricular blocking (AV block) activities of Befunolol.Experimental
Benzylpenicilloyl PolylysineNaphazoline may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BetaxololNaphazoline may increase the atrioventricular blocking (AV block) activities of Betaxolol.Approved
BevantololNaphazoline may increase the atrioventricular blocking (AV block) activities of Bevantolol.Approved
BisoprololNaphazoline may increase the atrioventricular blocking (AV block) activities of Bisoprolol.Approved
BopindololNaphazoline may increase the atrioventricular blocking (AV block) activities of Bopindolol.Approved
BromocriptineBromocriptine may increase the hypertensive activities of Naphazoline.Approved, Investigational
BucindololNaphazoline may increase the atrioventricular blocking (AV block) activities of Bucindolol.Investigational
BufuralolNaphazoline may increase the atrioventricular blocking (AV block) activities of Bufuralol.Experimental, Investigational
BupranololNaphazoline may increase the atrioventricular blocking (AV block) activities of Bupranolol.Approved
CabergolineCabergoline may increase the hypertensive activities of Naphazoline.Approved
CarteololNaphazoline may increase the atrioventricular blocking (AV block) activities of Carteolol.Approved
CarvedilolNaphazoline may increase the atrioventricular blocking (AV block) activities of Carvedilol.Approved, Investigational
CeliprololNaphazoline may increase the atrioventricular blocking (AV block) activities of Celiprolol.Approved, Investigational
ClomipramineClomipramine may decrease the antihypertensive activities of Naphazoline.Approved, Vet Approved
CyclobenzaprineCyclobenzaprine may decrease the antihypertensive activities of Naphazoline.Approved
DesipramineDesipramine may decrease the antihypertensive activities of Naphazoline.Approved
DesvenlafaxineDesvenlafaxine may increase the tachycardic activities of Naphazoline.Approved
DihydroergotamineDihydroergotamine may increase the hypertensive activities of Naphazoline.Approved
DosulepinDosulepin may decrease the antihypertensive activities of Naphazoline.Approved
DoxazosinDoxazosin may decrease the vasoconstricting activities of Naphazoline.Approved
DoxepinDoxepin may decrease the antihypertensive activities of Naphazoline.Approved
DuloxetineDuloxetine may increase the tachycardic activities of Naphazoline.Approved
Ergoloid mesylateErgoloid mesylate may increase the hypertensive activities of Naphazoline.Approved
ErgonovineErgonovine may increase the hypertensive activities of Naphazoline.Approved
ErgotamineErgotamine may increase the hypertensive activities of Naphazoline.Approved
EsmirtazapineEsmirtazapine may decrease the antihypertensive activities of Naphazoline.Investigational
EsmololNaphazoline may increase the atrioventricular blocking (AV block) activities of Esmolol.Approved
HyaluronidaseHyaluronidase may increase the vasoconstricting activities of Naphazoline.Approved, Investigational
ImipramineImipramine may decrease the antihypertensive activities of Naphazoline.Approved
IndenololNaphazoline may increase the atrioventricular blocking (AV block) activities of Indenolol.Withdrawn
IndoraminIndoramin may decrease the vasoconstricting activities of Naphazoline.Withdrawn
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Naphazoline.Approved
LabetalolNaphazoline may increase the atrioventricular blocking (AV block) activities of Labetalol.Approved
LandiololNaphazoline may increase the atrioventricular blocking (AV block) activities of Aop200704.Investigational
LevomilnacipranLevomilnacipran may increase the tachycardic activities of Naphazoline.Approved
MetoprololNaphazoline may increase the atrioventricular blocking (AV block) activities of Metoprolol.Approved, Investigational
MianserinThe therapeutic efficacy of Naphazoline can be decreased when used in combination with Mianserin.Approved
MilnacipranMilnacipran may increase the tachycardic activities of Naphazoline.Approved
MirtazapineMirtazapine may decrease the antihypertensive activities of Naphazoline.Approved
NadololNaphazoline may increase the atrioventricular blocking (AV block) activities of Nadolol.Approved
NortriptylineNortriptyline may decrease the antihypertensive activities of Naphazoline.Approved
OpipramolOpipramol may decrease the antihypertensive activities of Naphazoline.Investigational
OxprenololNaphazoline may increase the atrioventricular blocking (AV block) activities of Oxprenolol.Approved
PenbutololNaphazoline may increase the atrioventricular blocking (AV block) activities of Penbutolol.Approved, Investigational
PindololNaphazoline may increase the atrioventricular blocking (AV block) activities of Pindolol.Approved
PractololNaphazoline may increase the atrioventricular blocking (AV block) activities of Practolol.Approved
PrazosinPrazosin may decrease the vasoconstricting activities of Naphazoline.Approved
PropranololNaphazoline may increase the atrioventricular blocking (AV block) activities of Propranolol.Approved, Investigational
ProtriptylineProtriptyline may decrease the antihypertensive activities of Naphazoline.Approved
SilodosinSilodosin may decrease the vasoconstricting activities of Naphazoline.Approved
SotalolNaphazoline may increase the atrioventricular blocking (AV block) activities of Sotalol.Approved
SpironolactoneSpironolactone may decrease the vasoconstricting activities of Naphazoline.Approved
TamsulosinTamsulosin may decrease the vasoconstricting activities of Naphazoline.Approved, Investigational
TerazosinTerazosin may decrease the vasoconstricting activities of Naphazoline.Approved
TianeptineTianeptine may decrease the antihypertensive activities of Naphazoline.Approved
TimololNaphazoline may increase the atrioventricular blocking (AV block) activities of Timolol.Approved
TrimazosinTrimazosin may decrease the vasoconstricting activities of Naphazoline.Experimental
TrimipramineTrimipramine may decrease the antihypertensive activities of Naphazoline.Approved
VenlafaxineVenlafaxine may increase the tachycardic activities of Naphazoline.Approved
Food InteractionsNot 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 CodesR01AB02 — NaphazolineS01GA51 — Naphazoline, combinationsR01AA08 — NaphazolineS01GA01 — Naphazoline
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentConjunctivitis, Seasonal Allergic2
3Not Yet RecruitingTreatmentRhinitis1
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
SolutionOphthalmic1 mg/mL
LiquidOphthalmic.012 %
Solution / dropsOphthalmic1 mg/mL
Solution / dropsOphthalmic
LiquidNasal50 mg/100mL
SolutionOphthalmic.1 %
Solution / dropsOphthalmic.1 %
Solution / dropsOphthalmic1 mg/1
SprayNasal.1 mL/20mL
Suspension / dropsNasal.125 mL/25mL
LiquidOphthalmic.1 %
Solution / dropsOphthalmic0.012 %
SolutionOphthalmic0.1 %
LiquidNasal
LiquidOphthalmic
Solution / dropsOphthalmic12 mg/100mL
Solution / 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 RuleNoChemAxon
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 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassNaphthalenes
Direct ParentNaphthalenes
Alternative ParentsImidolactams / Imidazolines / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Carboxamidines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
SubstituentsNaphthalene / Imidolactam / 2-imidazoline / Azacycle / Organoheterocyclic compound / Organic 1,3-dipolar compound / Propargyl-type 1,3-dipolar organic compound / Carboximidamide / Carboxylic acid amidine / Amidine
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot 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
Uniprot Name:
Alpha-1A adrenergic receptor
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
Uniprot Name:
Alpha-2A adrenergic receptor
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 ]
Drug created on May 16, 2010 11:05 / Updated on August 02, 2017 17:10