Tetryzoline

Identification

Name
Tetryzoline
Accession Number
DB06764
Description

Tetryzoline (also known as Tetrahydrozoline), a derivative of imidazoline, is found in over-the-counter eye drops and nasal sprays. Other derivatives include naphazoline, oxymetazoline, and xylometazoline. Johnson and Johnson manufactures tetryzoline eye drops under the brand Visine ®.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 200.285
Monoisotopic: 200.131348523
Chemical Formula
C13H16N2
Synonyms
  • (RS)-2-(1,2,3,4-tetrahydronaphthalen-1-yl)-4,5-dihydro-1H-imidazole
  • 2-(1,2,3,4-Tetrahydro-1-naphthyl)-2-imidazoline
  • 2-Tetralin-1-yl-4,5-dihydro-1H-imidazole
  • 4,5-dihydro-2-(1,2,3,4-tetrahydro-1-naphthalenyl)-1H-imidazole
  • Tetrahydrozoline
  • Tetrizolina
  • Tetryzolin
  • Tetryzolina
  • Tétryzoline
  • Tetryzoline
  • Tetryzolinum

Pharmacology

Pharmacology
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Indication

For temporary relief of discomfort and redness of the eye due to minor eye irritations.

Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Contraindications
Contraindications & Blackbox Warnings
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Pharmacodynamics
Not Available
Mechanism of action

Tetryzoline is an alpha-adrenergic agonist. Its primary action is the constriction of conjunctival blood vessels, which serves to decrease eye redness caused by minor ocular irritants.

TargetActionsOrganism
AAlpha-1A adrenergic receptor
agonist
Humans
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
Adverse Effects
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Toxicity

Reports of prolonged cardiovascular effects after unintentional ingestion of tetrahydrozoline are noted in the literature.

Affected organisms
  • Humans and other mammals
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
AbaloparatideThe risk or severity of adverse effects can be increased when Tetryzoline is combined with Abaloparatide.
AcebutololThe therapeutic efficacy of Tetryzoline can be decreased when used in combination with Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Aceclofenac is combined with Tetryzoline.
AcemetacinThe risk or severity of hypertension can be increased when Tetryzoline is combined with Acemetacin.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Tetryzoline.
AclidiniumThe risk or severity of Tachycardia can be increased when Tetryzoline is combined with Aclidinium.
AdenosineThe risk or severity of Tachycardia can be increased when Adenosine is combined with Tetryzoline.
AlclofenacThe risk or severity of hypertension can be increased when Tetryzoline is combined with Alclofenac.
AlfentanilThe risk or severity of hypertension can be increased when Alfentanil is combined with Tetryzoline.
AlfuzosinThe therapeutic efficacy of Tetryzoline can be decreased when used in combination with Alfuzosin.
Interactions
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Food Interactions
No interactions found.

Products

Products
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Product Ingredients
IngredientUNIICASInChI Key
Tetrahydrozoline hydrochloride0YZT43HS7D522-48-5BJORNXNYWNIWEY-UHFFFAOYSA-N
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
TyzineSolution1 mg/1mLNasalPharma Derm, A Division Of Fougera Pharmaceuticals Inc.1979-11-302017-01-31US flag
TyzineSolution1 mg/1mLNasalFougera Pharmaceuticals Inc.1979-11-302013-12-31US flag
Tyzine PediatricSolution0.5 mg/1mLNasalFougera Pharmaceuticals Inc.1979-11-302014-12-31US flag
Tyzine PediatricSolution0.5 mg/1mLNasalPharma Derm, A Division Of Fougera Pharmaceuticals Inc.1979-11-302017-01-31US flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Assured Original Relief EyeSolution0.5 mg/1mLOphthalmicGreenbrier International, Inc.2013-02-28Not applicableUS flag
CAREALL Eyedrops OriginalSolution / drops0.05 mg/1mLOphthalmicNew World Imports, Inc2014-06-01Not applicableUS flag
Circle K Eye Drops Redness RelieverSolution / drops0.5 mg/1mLTopicalLil' Drug Store Products, Inc.2016-05-04Not applicableUS flag
CVS Redness Relief OriginalSolution / drops0.5 mg/1mLOphthalmicCVS Health2014-03-06Not applicableUS flag
Dg Health OriginalSolution0.5 mg/1mLOphthalmicHANLIM PHARM. CO., LTD.2010-08-12Not applicableUS flag
DG Health Sterile Redness ReliefSolution0.5 mg/1mLOphthalmicDolgencorp2014-11-25Not applicableUS flag
DG Original Eye DropsSolution0.05 g/100mLOphthalmicDolgencorp LLC2020-01-27Not applicableUS flag
Equate Eye DropsLiquid0.5 mg/1mLOphthalmicPrestige Brands Holdings, Inc.2013-02-11Not applicableUS flag
Equate Eye DropsLiquid0.5 mg/1mLOphthalmicAspen SVP (Pty) Ltd.2013-02-11Not applicableUS flag
Equate Eye DropsLiquid0.5 mg/1mLOphthalmicPrestige Brands Holdings, Inc.2013-02-11Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
4248 First Aid KitTetrahydrozoline hydrochloride (0.05 g/100mL) + Acetaminophen (325 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Benzethonium chloride (0.2 g/100g) + Benzethonium chloride (0.2 g/100g) + Benzocaine (10 g/100g) + Benzocaine (10 g/100g) + Caffeine (32.4 mg/1) + Calcium carbonate (420 mg/1) + Ethanol (0.5 mL/1mL) + Hydrocortisone acetate (1 g/100g) + Hydrocortisone acetate (1 g/100g) + Isopropyl alcohol (0.7 mL/1mL) + Levomenthol (0.33 g/100g) + Lidocaine hydrochloride (20 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Phenylephrine hydrochloride (5 mg/1) + Polymyxin B sulfate (5000 [iU]/1g) + Salicylamide (152 mg/1) + Water (98.6 mL/100mL)KitOphthalmic; Oral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
8-symptom ReliefTetrahydrozoline hydrochloride (0.05 %) + Zinc sulfate (0.25 %)SolutionOphthalmicTEVA Canada Limited2016-07-22Not applicableCanada flag
Advance Relief Eye DropsTetrahydrozoline hydrochloride (50 mg/100mL) + Dextran 70 (100 mg/100mL) + Polyethylene glycol 400 (1000 mg/100mL) + Povidone (1000 mg/100mL)Solution / dropsOphthalmicWinCo Foods, LLC2015-01-09Not applicableUS flag
Advanced ReliefTetrahydrozoline hydrochloride (0.5 mg/1mL) + Dextran 70 (1 mg/1mL) + Polyethylene glycol 400 (10 mg/1mL) + Povidone (10 mg/1mL)LiquidOphthalmicKareway Product, Inc.2018-05-30Not applicableUS flag
Advanced reliefTetrahydrozoline hydrochloride (0.5 mg/1mL) + Dextran 70 (1 mg/1mL) + Polyethylene glycol 400 (10 mg/1mL) + Povidone (10 mg/1mL)LiquidOphthalmicSamchundang Pharm. Co., Ltd.2010-08-29Not applicableUS flag
Advanced reliefTetrahydrozoline hydrochloride (0.5 mg/1mL) + Dextran 70 (1 mg/1mL) + Polyethylene glycol 400 (10 mg/1mL) + Povidone (10 mg/1mL)LiquidOphthalmicAmerican Sales Company2011-09-07Not applicableUS flag
Advanced Relief Eye DropsTetrahydrozoline hydrochloride (0.05 %) + Dextran 70 (0.1 %) + Polyethylene glycol 400 (1 %) + Povidone (1 %)SolutionOphthalmicTEVA Canada Limited2010-08-30Not applicableCanada flag
Advanced Relief Eye DropsTetrahydrozoline hydrochloride (0.05 %) + Dextran 70 (0.1 %) + Polyethylene glycol 400 (1 %) + Povidone (1 %)SolutionOphthalmicKc Pharmaceuticals, Inc.Not applicableNot applicableCanada flag
Allergy Eye DropsTetrahydrozoline hydrochloride (0.05 %) + Zinc sulfate (0.25 %)SolutionOphthalmicKc Pharmaceuticals, Inc.Not applicableNot applicableCanada flag
Allergy Eye DropsTetrahydrozoline hydrochloride (0.05 %) + Zinc sulfate (0.25 %)Solution / dropsOphthalmicAlcon, Inc.2005-06-242009-04-24Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
4248 First Aid KitTetrahydrozoline hydrochloride (0.05 g/100mL) + Acetaminophen (325 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Benzethonium chloride (0.2 g/100g) + Benzethonium chloride (0.2 g/100g) + Benzocaine (10 g/100g) + Benzocaine (10 g/100g) + Caffeine (32.4 mg/1) + Calcium carbonate (420 mg/1) + Ethanol (0.5 mL/1mL) + Hydrocortisone acetate (1 g/100g) + Hydrocortisone acetate (1 g/100g) + Isopropyl alcohol (0.7 mL/1mL) + Levomenthol (0.33 g/100g) + Lidocaine hydrochloride (20 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Phenylephrine hydrochloride (5 mg/1) + Polymyxin B sulfate (5000 [iU]/1g) + Salicylamide (152 mg/1) + Water (98.6 mL/100mL)KitOphthalmic; Oral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag

Categories

ATC Codes
S01GA02 — TetryzolineS01GA52 — Tetryzoline, combinationsR01AB03 — TetryzolineR01AA06 — Tetryzoline
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Tetralins
Sub Class
Not Available
Direct Parent
Tetralins
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 / Organic 1,3-dipolar compound / Organic nitrogen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
carboxamidine, imidazolines (CHEBI:28674)

Chemical Identifiers

UNII
S9U025Y077
CAS number
84-22-0
InChI Key
BYJAVTDNIXVSPW-UHFFFAOYSA-N
InChI
InChI=1S/C13H16N2/c1-2-6-11-10(4-1)5-3-7-12(11)13-14-8-9-15-13/h1-2,4,6,12H,3,5,7-9H2,(H,14,15)
IUPAC Name
2-(1,2,3,4-tetrahydronaphthalen-1-yl)-4,5-dihydro-1H-imidazole
SMILES
C1CN=C(N1)C1CCCC2=CC=CC=C12

References

General References
  1. Carr ME, Engebretsen KM, Ho B, Anderson CP: Tetrahydrozoline (Visine(R)) concentrations in serum and urine during therapeutic ocular dosing: a necessary first step in determining an overdose. Clin Toxicol (Phila). 2011 Nov;49(9):810-4. doi: 10.3109/15563650.2011.615064. Epub 2011 Oct 5. [PubMed:21972870]
  2. Spiller H, Griffith J: Prolonged cardiovascular effects after unintentional ingestion of tetrahydrozoline. Clin Toxicol (Phila). 2008 Feb;46(2):171-2. doi: 10.1080/15563650701258070. [PubMed:18259967]
KEGG Drug
D08578
KEGG Compound
C07912
PubChem Compound
5419
PubChem Substance
310264881
ChemSpider
5226
BindingDB
96559
RxNav
37935
ChEBI
28674
ChEMBL
CHEMBL1266
Drugs.com
Drugs.com Drug Page
Wikipedia
Tetrahydrozoline
AHFS Codes
  • 52:32.00 — Vasoconstrictors
FDA label
Download (134 KB)
MSDS
Download (60.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentContact Lens Dry Eye1
3Unknown StatusTreatmentInflammatory Reaction / Pterygium1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
KitOphthalmic; Oral; Respiratory (inhalation); Topical
Solution / dropsOphthalmic
Spray, suspensionNasal0.1 %
Solution / dropsNasal0.1 %
Solution / dropsNasal0.05 %
Solution / dropsOphthalmic0.05 mg/1mL
Solution / dropsTopical0.5 mg/1mL
Solution / dropsOphthalmic1 mg/ml
Solution / dropsOphthalmic.05 %
Solution / dropsOphthalmic0.05 %
SolutionOphthalmic0.5 mg
SuspensionConjunctival; Ophthalmic1 mg
SolutionOphthalmic0.05 g/100mL
Solution / dropsOphthalmic.5 mg/1mL
Solution / dropsOphthalmic0.5 mg/1mL
SolutionOphthalmic
Solution / dropsOphthalmic
LiquidTopical0.5 mg/1mL
Solution / dropsOphthalmic0.5 mg/1mg
Solution / drops; suspension / dropsOphthalmic0.5 mg/ml
Solution / drops; suspension / dropsOphthalmic0.25 mg/0.5ml
SolutionOphthalmic
SolutionOphthalmic; Topical0.5 mg
LiquidOphthalmic0.5 mg/1mL
Suspension / dropsConjunctival0.2 %
Solution / dropsOphthalmic10 ml
LiquidOphthalmic
Solution / dropsOphthalmic0.05 mg/1mg
Solution / dropsOphthalmic0.05 g/100mL
Solution / dropsOphthalmic0.5 mg/10mg
Solution / dropsOphthalmic5 ML
Solution / dropsOphthalmic8 ML
Solution / dropsConjunctival0.3 %
SolutionNasal1 mg/1mL
SolutionNasal0.5 mg/1mL
Solution / dropsNasal100 MG/100ML
Solution / dropsNasal50 MG/100ML
SprayNasal100 MG/100ML
SprayNasal0.1 %
SolutionIntraocular; Ophthalmic0.5 mg
SolutionConjunctival; Ophthalmic11.3962 mg
Solution / dropsOphthalmic0.5 mg/ml
Solution / dropsOphthalmic1 %
LiquidTopical
Solution / drops; suspension / dropsOphthalmic0.423 mg
Solution / drops; suspension / dropsOphthalmic
Solution / drops; suspension / dropsOphthalmic0.211 mg
SolutionConjunctival; Ophthalmic0.5 mg
Solution / dropsOphthalmic150 mg/100ml
Suspension / dropsOphthalmic1 MG/ML
Solution / dropsOphthalmic1.44 g/100ml
Solution / dropsOphthalmic0.1 %
SolutionOphthalmic0.5 mg/1mL
Solution / dropsOphthalmic.05 mg/10mg
SolutionConjunctival; Ophthalmic0.05 mg
LiquidOphthalmic0.05 g/100mL
Solution / dropsOphthalmic15 ml
LiquidOphthalmic
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)256-257Analytical Specifications – TETRAHYDROZOLINE. 2010 National Medical Services, Inc.
Predicted Properties
PropertyValueSource
Water Solubility0.239 mg/mLALOGPS
logP3.11ALOGPS
logP2.24ChemAxon
logS-2.9ALOGPS
pKa (Strongest Basic)10.17ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area24.39 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity61.48 m3·mol-1ChemAxon
Polarizability22.93 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0udi-0390000000-8abf8ed167116d96cf2d

Targets

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. Spiller H, Griffith J: Prolonged cardiovascular effects after unintentional ingestion of tetrahydrozoline. Clin Toxicol (Phila). 2008 Feb;46(2):171-2. doi: 10.1080/15563650701258070. [PubMed:18259967]

Drug created on September 14, 2010 16:21 / Updated on February 24, 2021 19:34