Identification

Name
Tetryzoline
Accession Number
DB06764
Type
Small Molecule
Groups
Approved
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 ®.

Structure
Thumb
Synonyms
  • (RS)-2-(1,2,3,4-tetrahydronaphthalen-1-yl)-4,5-dihydro-1H-imidazole
  • Tetrahydrozoline
  • Tetrizolina
  • Tetryzolin
  • Tétryzoline
  • Tetryzolinum
Product Ingredients
IngredientUNIICASInChI Key
Tetrahydrozoline hydrochloride0YZT43HS7D522-48-5BJORNXNYWNIWEY-UHFFFAOYSA-N
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
TyzineSolution1 mg/1mLNasalFougera Pharmaceuticals Inc.1979-11-302013-12-31Us
TyzineSolution1 mg/1mLNasalPharma Derm, A Division Of Fougera Pharmaceuticals Inc.1979-11-302017-01-31Us
Tyzine PediatricSolution0.5 mg/1mLNasalPharma Derm, A Division Of Fougera Pharmaceuticals Inc.1979-11-302017-01-31Us
Tyzine PediatricSolution0.5 mg/1mLNasalFougera Pharmaceuticals Inc.1979-11-302014-12-31Us
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Assured Original Relief EyeSolution0.5 mg/1mLOphthalmicGreenbrier International, Inc.2013-02-28Not applicableUs
CAREALL Eyedrops OriginalSolution / drops.05 mg/1mLOphthalmicNew World Imports2014-06-01Not applicableUs
Circle K Eye Drops Redness RelieverSolution / drops0.5 mg/1mLTopicalLil' Drug Store Products, Inc.2016-05-04Not applicableUs
CVS Redness Relief OriginalSolution / drops0.5 mg/1mLOphthalmicCVS Health2014-03-06Not applicableUs
Dg Health OriginalSolution0.5 mg/1mLOphthalmicHANLIM PHARM. CO., LTD.2010-08-12Not applicableUs
DG Health Sterile Redness ReliefSolution0.5 mg/1mLOphthalmicDolgencorp2014-11-25Not applicableUs
Equate Eye DropsLiquid0.5 mg/1mLOphthalmicPrestige Brands Holdings, Inc.2013-02-11Not applicableUs
Equate Eye DropsLiquid0.5 mg/1mLOphthalmicPrestige Brands Holdings, Inc.2013-02-11Not applicableUs
Eye DropsSolution / drops.05 %OphthalmicRivex Ophthalmics Inc.1997-08-112000-08-03Canada
Eye DropsSolution / drops0.5 mg/1mLOphthalmicRugby2011-10-07Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
8-symptom ReliefTetrahydrozoline hydrochloride (0.05 %) + Zinc sulfate (0.25 %)SolutionOphthalmicTeva2016-07-22Not applicableCanada
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
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.2011-08-11Not applicableUs
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
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
Advanced Relief Eye DropsTetrahydrozoline hydrochloride (0.05 %) + Dextran 70 (0.1 %) + Polyethylene glycol 400 (1 %) + Povidone (1 %)SolutionOphthalmicTeva2010-08-30Not applicableCanada
Advanced Relief Eye DropsTetrahydrozoline hydrochloride (0.05 %) + Dextran 70 (0.1 %) + Polyethylene glycol 400 (1 %) + Povidone (1 %)SolutionOphthalmicKc Pharmaceuticals, Inc.Not applicableNot applicableCanada
Allergy Eye DropsTetrahydrozoline hydrochloride (0.05 %) + Zinc sulfate (0.25 %)Solution / dropsOphthalmicAlcon, Inc.2005-06-242009-04-24Canada
Allergy Eye DropsTetrahydrozoline hydrochloride (0.05 %) + Zinc sulfate (0.25 %)SolutionOphthalmicTeva2007-05-23Not applicableCanada
Allergy Eye DropsTetrahydrozoline hydrochloride (0.05 %) + Zinc sulfate (0.25 %)SolutionOphthalmicKc Pharmaceuticals, Inc.Not applicableNot applicableCanada
Categories
UNII
S9U025Y077
CAS number
84-22-0
Weight
Average: 200.285
Monoisotopic: 200.131348523
Chemical Formula
C13H16N2
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

Pharmacology

Indication

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

Associated Conditions
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
Human
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
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
DrugInteraction
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypertensive activities of Tetryzoline.
AcebutololThe therapeutic efficacy of Tetryzoline can be decreased when used in combination with Acebutolol.
AcepromazineAcepromazine may decrease the vasoconstricting activities of Tetryzoline.
AlfuzosinThe therapeutic efficacy of Tetryzoline can be decreased when used in combination with Alfuzosin.
AmineptineAmineptine may increase the vasopressor activities of Tetryzoline.
AmitriptylineAmitriptyline may increase the vasopressor activities of Tetryzoline.
AmitriptylinoxideAmitriptylinoxide may increase the vasopressor activities of Tetryzoline.
AmoxapineAmoxapine may increase the vasopressor activities of Tetryzoline.
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Tetryzoline.
AripiprazoleAripiprazole may decrease the vasoconstricting activities of Tetryzoline.
Food Interactions
Not Available

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]
External Links
KEGG Drug
D08578
KEGG Compound
C07912
PubChem Compound
5419
PubChem Substance
310264881
ChemSpider
5226
BindingDB
96559
ChEBI
28674
ChEMBL
CHEMBL1266
Drugs.com
Drugs.com Drug Page
Wikipedia
Tetrahydrozoline
ATC Codes
S01GA52 — Tetryzoline, combinationsS01GA02 — TetryzolineR01AA06 — TetryzolineR01AB03 — Tetryzoline
AHFS Codes
  • 52:32.00 — Vasoconstrictors
FDA label
Download (134 KB)
MSDS
Download (60.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2, 3TerminatedPreventionPenetrating Keratoplasty1
Not AvailableRecruitingTreatmentAtropine Allergy / Myopia, Progressive1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Solution / dropsOphthalmic.05 mg/1mL
Solution / dropsTopical0.5 mg/1mL
SolutionOphthalmic
Solution / dropsOphthalmic0.05 g/100mL
Solution / dropsOphthalmic.5 mg
Solution / dropsIntraocular.05 g/100mL
Solution / dropsIntraocular
Solution / dropsOphthalmic0.5 mg/1mL
LiquidTopical0.5 mg/1mL
Solution / dropsOphthalmic0.5 mg/1mg
SolutionOphthalmic0.05 %
SolutionOphthalmic0.5 mg
Solution / dropsOphthalmic.05 %
LiquidOphthalmic0.5 mg/1mL
Solution / dropsOphthalmic.5 mg/1mL
Solution / dropsOphthalmic0.05 mg/1mg
Solution / dropsOphthalmic0.5 mg/10mg
LiquidOphthalmic0.05 g/100mL
SolutionNasal1 mg/1mL
SolutionNasal0.5 mg/1mL
LiquidOphthalmic
Kit
Solution / dropsOphthalmic
Solution / dropsOphthalmic0.05 %
SolutionOphthalmic0.5 mg/1mL
Solution / dropsOphthalmic.05 mg/10mg
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

Taxonomy

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
Tetralin / Imidolactam / 2-imidazoline / Azacycle / Organoheterocyclic compound / Organic 1,3-dipolar compound / Propargyl-type 1,3-dipolar organic compound / Carboximidamide / Carboxylic acid amidine / Amidine
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
carboxamidine, imidazolines (CHEBI:28674)

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) 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 10:21 / Updated on October 16, 2018 08:39