Naphazoline

Identification

Summary

Naphazoline is a sympathomimetic vasoconstrictor used for the symptomatic relief of redness and itching of the eye, and nasal congestion.

Brand Names
Advanced Eye Relief Redness Instant Relief, Ak-con, Clear Eyes Complete, Clear Eyes Cooling Comfort, Clear Eyes Redness Relief Reformulated Nov 2011, Naphcon, Naphcon A, Opcon-A, Privine, Vasocon, Visine-A
Generic Name
Naphazoline
DrugBank Accession Number
DB06711
Background

Naphazoline is a rapid acting imidazoline sympathomimetic vasoconstrictor of ocular or nasal artierioles6,7. It acts to decrease congestion and is found in many over the counter (OTC) eye drops and nasal preparations6,7.

Naphazoline was first developed in 1942 as a nasal formulation for congestion4.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 210.2744
Monoisotopic: 210.115698458
Chemical Formula
C14H14N2
Synonyms
  • Nafazolin
  • Nafazolina
  • Naphazoline

Pharmacology

Indication

Naphazoline is indicated for use as OTC eyedrops for ocular vasoconstriction or as a nasal preparation for nasal congestion1,6,7.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatBacterial conjunctivitisCombination Product in combination with: Tetracycline (DB00759), Betamethasone (DB00443)••••••••••••••••••• ••• ••••••••• ••••••••• •••••••• • •••••
Used in combination to treatBlepharoconjunctivitisCombination Product in combination with: Betamethasone (DB00443), Tetracycline (DB00759)••••••••••••••••••• ••• ••••••••• ••••••••• •••••••• • •••••
Used in combination to treatConjunctivitisCombination Product in combination with: Pheniramine (DB01620)••••••••••••••••••••
Used in combination for symptomatic treatment ofConjunctivitisCombination Product in combination with: Zinc sulfate (DB09322)•••••••••••••••••••• • •••••
Used in combination for symptomatic treatment ofConjunctivitisCombination Product in combination with: Dexamethasone (DB01234)••••••••••••••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Naphazoline is a sympathomimetic alpha adrenergic agonist that acts to vasoconstrict nasal or ocular arterioles, resulting in reduced congestion at the site of administration6,7.

Mechanism of action

Naphazoline is a vasoconstrictor that functions by stimulating alpha adrenergic receptors in arterioles leading to decreased congestion at the site of administration6.

Naphazoline causes the release of norepinephrine in sympathetic nerves3. Norepinephrine binds to alpha adrenergic receptors and causes vasoconstriction3. Naphazoline is also a mild beta adrenergic receptor agonist, which can cause rebound vasodilation after the alpha adrenergic stimulation has ended3. Naphazoline's release of norepinephrine also triggers a negative feedback loop which decreases production of norepinephrine, which can lead to rhinitis medicamentosa after long term use when naphazoline is stopped3.

TargetActionsOrganism
AAlpha-2A adrenergic receptor
agonist
Humans
AAlpha-1A adrenergic receptor
agonist
Humans
Absorption

Absorption data for naphazoline are scarce but imidazoline compounds in general are weakly basic and lipophilic, with high bioavailability from the gastrointestinal tract5.

Volume of distribution

Distribution data for naphazoline are scarce but imidazoline compounds are distributed throughout the body, and can cross the blood-brain barrier5.

Protein binding

Protein binding data for naphazoline is unavailable12.

Metabolism

Metabolism data for naphazoline are scarce. Imidazoline compounds undergo some hepatic metabolism but a large fraction of the dose may be excreted unchanged in the urine5.

Route of elimination

Imidazoline compounds undergo some hepatic metabolism but a large fraction of the dose may be excreted unchanged in the urine5. Urinary excretion is higher with more acidic urine5.

Half-life

Half life has not been determined but effects last for 4 to 8 hours7. Other imidazoline compounds have half lives varying from 2 to 12 hours5.

Clearance

Clearance data for naphazoline is unavailable12.

Adverse Effects
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Toxicity

In high doses or when ingested, naphazoline can lead to central nervous system depression (which can progress to coma and death), hypothermia, bradycardia, and death1. This effect is especially pronounced in children under 6 years1,2.

Long term use of naphazoline can lead to rhinitis medicamentosa once naphazoline is stopped3. This condition is a result of norepinephrine release by naphazoline triggering a negative feedback loop3.

Safety and effectiveness in children under 12 has not been established12. Studies in elderly patients have yet to be performed12. Risk in pregnancy, breast feeding, and on overall fertility have not been established, though pregnant and breast feeding patients should consider the risk and benefit before starting naphazoline treatment12.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcebutololThe therapeutic efficacy of Naphazoline can be decreased when used in combination with Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Naphazoline is combined with Aceclofenac.
AcemetacinThe risk or severity of hypertension can be increased when Naphazoline is combined with Acemetacin.
AcetyldigitoxinThe risk or severity of Cardiac Arrhythmia can be increased when Naphazoline is combined with Acetyldigitoxin.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Naphazoline.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Naphazoline hydrochlorideMZ1131787D550-99-2DJDFFEBSKJCGHC-UHFFFAOYSA-N
Naphazoline nitrateSC99GR1T5S5144-52-5ZAHXYMFVNNUHCP-UHFFFAOYSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
NaphconSolution1 mg/1mLOphthalmicAlcon2006-09-26Not applicableUS flag
VasoconSolution1 mg/1mLOphthalmicCiba Vision2006-08-31Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AK-ConSolution1 mg/1mLOphthalmicRebel Distributors1974-08-22Not applicableUS flag
AK-ConSolution / drops1 mg/1mLOphthalmicPhysicians Total Care, Inc.2000-07-282012-06-30US flag
AK-ConSolution / drops1 mg/1mLOphthalmicPreferreed Pharmaceuticals Inc.2005-03-242018-01-23US flag
AlbalonSolution1 mg/1mLOphthalmicAllergan Inc.1984-11-012008-10-21US flag
NaphazolineSolution / drops1 mg/1mLOphthalmicA S Medication Solutions1995-12-19Not applicableUS flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AlbalonSolution / drops.1 %OphthalmicAbbvie1970-12-31Not applicableCanada flag
Clear EyesLiquid.012 %OphthalmicPrestige Brands Inc2004-03-24Not applicableCanada flag
Clear Eyes By Murine Eye DpsLiquid.012 %OphthalmicAbbott1970-12-312003-10-10Canada flag
Diopticon Liq 0.1%Solution0.1 %OphthalmicPharma Stulln Inc.1994-12-31Not applicableCanada flag
NafasolinaSolution / drops0.376 mg/100mgNasalDUY DRUGS, INC2021-02-15Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
7 Select Redness ReliefNaphazoline hydrochloride (0.00012 mg/1mL) + Glycerin (0.0025 mg/1mL)Solution / dropsOphthalmic7-Select, Inc2017-03-28Not applicableUS flag
Advanced Eye Relief/ Redness Instant ReliefNaphazoline hydrochloride (0.1 mg/1mL) + Polyethylene glycol 300 (2 mg/1mL)Solution / dropsOphthalmicBausch & Lomb Incorporated2010-09-13Not applicableUS flag
Advanced Eye Relief/ Redness Maximum ReliefNaphazoline hydrochloride (0.3 mg/1mL) + Hypromellose (5 mg/1mL)Solution / dropsOphthalmicBausch & Lomb Incorporated2010-09-02Not applicableUS flag
Advanced Eye Relief/ Redness Maximum ReliefNaphazoline hydrochloride (0.3 mg/1mL) + Hypromellose (5 mg/1mL)Solution / dropsOphthalmicPreferreed Pharmaceuticals Inc.2010-09-02Not applicableUS flag
Albalon ANaphazoline hydrochloride (.05 %) + Antazoline phosphate (.5 %)LiquidOphthalmicAllergan1978-12-312017-07-26Canada flag

Categories

ATC Codes
R01AB02 — NaphazolineS01GA01 — NaphazolineS01GA51 — Naphazoline, combinationsR01AA08 — Naphazoline
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Naphthalenes
Sub Class
Not Available
Direct Parent
Naphthalenes
Alternative Parents
Imidolactams / Imidazolines / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Carboxamidines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
2-imidazoline / Amidine / Aromatic heteropolycyclic compound / Azacycle / Carboximidamide / Carboxylic acid amidine / Hydrocarbon derivative / Imidolactam / Naphthalene / Organic 1,3-dipolar compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
H231GF11BV
CAS number
835-31-4
InChI Key
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-yl)methyl]-4,5-dihydro-1H-imidazole
SMILES
C(C1=NCCN1)C1=CC=CC2=CC=CC=C12

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 References
  1. Vitezic D, Rozmanic V, Franulovic J, Ahel V, Matesic D: Naphazoline nasal drops intoxication in children. Arh Hig Rada Toksikol. 1994 Mar;45(1):25-9. [Article]
  2. Mahieu LM, Rooman RP, Goossens E: Imidazoline intoxication in children. Eur J Pediatr. 1993 Nov;152(11):944-6. [Article]
  3. Ramey JT, Bailen E, Lockey RF: Rhinitis medicamentosa. J Investig Allergol Clin Immunol. 2006;16(3):148-55. [Article]
  4. HAINSWORTH WC: Accidental poisoning with naphazoline (privine) hydrochloride. Am J Dis Child. 1948 Jan;75(1):76-80. [Article]
  5. Dalefield, Rosalind (2015). 12. In Veterinary Toxicology for Australia and New Zealand (pp. 170-171). Elsevier. [ISBN:978-0-12-420227-6]
  6. Naphazoline Hydrochloride Solution/Drops [Link]
  7. Toxnet: Naphazoline Hydrochloride [Link]
  8. INVIMA Product Authorization: Osmocrom-N (sodium cromoglycate/naphazoline hydrochloride) ophthalmic drops [Link]
  9. INVIMA Product Authorization: Ocunid (dexamethasone/naphazoline) ophthalmic solution [Link]
  10. BASG Product Information: Coldistan (diphenhydramine hydrochloride/naphazoline hydrochloride) nasal drops [Link]
  11. BASG Product Information: Coldistan (diphenhydramine hydrochloride/naphazoline hydrochloride) ophthalmic drops [Link]
  12. New Zealand Data Sheet: Naphcon-A Eye Drops [File]
Human Metabolome Database
HMDB0015656
KEGG Drug
D08253
PubChem Compound
4436
PubChem Substance
99443263
ChemSpider
4283
BindingDB
50001922
RxNav
7247
ChEBI
93363
ChEMBL
CHEMBL761
ZINC
ZINC000000119717
PharmGKB
PA165958384
Wikipedia
Naphazoline
MSDS
Download (115 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Unknown StatusTreatmentAllergic Conjunctivitis (AC)1
3CompletedTreatmentAllergic Conjunctivitis (AC)2
3CompletedTreatmentAllergic Disorder of Respiratory System / Cold / Flu caused by Influenza1
3CompletedTreatmentNasal Congestion1
1CompletedTreatmentHyperemia Eye1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionNasal1.000 mg
SolutionOphthalmic0.100 g
SolutionConjunctival; Ophthalmic100000 mg
SolutionOphthalmic0.012 %
Solution / dropsNasal0.2 %
Solution / dropsOphthalmic0.1 %
SprayNasal0.2 %
SolutionOphthalmic0.500 mg
LiquidOphthalmic.012 %
LiquidOphthalmic
Solution / dropsOphthalmic1 mg/ml
Solution / dropsNasal1 mg/ml
SprayNasal1 mg/ml
Solution / drops; suspension / dropsNasal
Solution / dropsOphthalmic0.2 mg/ml
SolutionConjunctival; Ophthalmic; Topical
SprayNasal
Solution / drops; suspension / dropsOphthalmic0.6 mg/m0.6mL
SolutionNasal0.01 g/10ml
SolutionConjunctival; Ophthalmic1 mg
SolutionOphthalmic1.0000 mg
Solution / dropsOphthalmic
SprayNasal3 mg/ml
Solution / dropsTopical
Solution / dropsConjunctival
SolutionOphthalmic0.001 g
SolutionConjunctival; Ophthalmic0.001 g
Solution / dropsNasal0.376 mg/100mg
SolutionOphthalmic
SprayNasal
SolutionOphthalmic1 mg
Solution / dropsOphthalmic1 mg/1mL
SolutionOphthalmic0.25 mg/ml
LiquidNasal50 mg/100mL
SolutionOphthalmic1.0000 mg
Solution / dropsOphthalmic0.2 mg/1mL
SolutionOphthalmic.1 %
SolutionOphthalmic1.000 mg
Solution / dropsOphthalmic.1 %
SolutionOphthalmic0.1 % w/v
SolutionConjunctival; Ophthalmic0.1 mg
SolutionConjunctival; Ophthalmic0.5 mg
SolutionConjunctival; Ophthalmic
Solution / dropsOphthalmic1 mg/1
Solution / dropsNasal1 mg/1
SprayNasal0.1 mL/20mL
Suspension / dropsNasal0.125 mL/25mL
LiquidOphthalmic.1 %
SolutionOphthalmic0.1 %
LiquidNasal
Solution / drops; suspension / dropsNasal1 mg/ml
Solution / drops; suspension / dropsNasal1.05 mg/ml
CreamNasal25 MG/100G
Solution / dropsNasal
Solution / dropsOphthalmic
Solution / dropsOphthalmic12 mg/100mL
SolutionConjunctival; Ophthalmic0.125 mg
Solution / dropsOphthalmic0.012 % w/v
Solution / drops; suspension / dropsOphthalmic1 mg/mL
SolutionOphthalmic1 mg/1mL
Solution / dropsOphthalmic1 mg / mL
SolutionOphthalmic
SprayNasal100 mg/100ml
LiquidOphthalmic1 mg/1ml
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
boiling point (°C)440.466http://www.chemspider.com/Chemical-Structure.4283.html
logP3.881http://www.chemspider.com/Chemical-Structure.4283.html
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
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0006-2900000000-026b23156746d2a4a1de
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-0390000000-bf587920984867425a82
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0090000000-1c107f398be7a385f9a6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0190000000-cf01fd9977227e9501c5
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0190000000-7a212f685044c93cb2d2
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0910000000-e3a065b6d6b68ac5d2b3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-002f-0900000000-cb3f5d69c3e5193dac7e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-1910000000-5f3ccb1a52058229a011
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-154.3603249
predicted
DarkChem Lite v0.1.0
[M-H]-154.2499249
predicted
DarkChem Lite v0.1.0
[M-H]-141.58623
predicted
DeepCCS 1.0 (2019)
[M+H]+155.3885249
predicted
DarkChem Lite v0.1.0
[M+H]+154.9620249
predicted
DarkChem Lite v0.1.0
[M+H]+143.94421
predicted
DeepCCS 1.0 (2019)
[M+Na]+154.2022249
predicted
DarkChem Lite v0.1.0
[M+Na]+154.2102249
predicted
DarkChem Lite v0.1.0
[M+Na]+150.81941
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
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 oxymetazo...
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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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) prot...
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. [Article]
  2. Leonardi A: Emerging drugs for ocular allergy. Expert Opin Emerg Drugs. 2005 Aug;10(3):505-20. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]

Drug created at May 16, 2010 17:05 / Updated at April 19, 2024 20:55