Identification

Name
Tropicamide
Accession Number
DB00809  (APRD00287)
Type
Small Molecule
Groups
Approved, Investigational
Description

One of the muscarinic antagonists with pharmacologic action similar to atropine and used mainly as an ophthalmic parasympatholytic or mydriatic. [PubChem]

Structure
Thumb
Synonyms
  • Tropicamid
  • Tropicamida
  • Tropicamide
  • Tropicamidum
External IDs
Ro 1-7683
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Minims Tropicamide 1%Solution / drops1 %OphthalmicValeant Canada Lp Valeant Canada S.E.C.1995-12-31Not applicableCanada
MydriacylSolution0.5 %OphthalmicNovartis1951-12-31Not applicableCanada
MydriacylSolution1 %OphthalmicNovartis1969-12-31Not applicableCanada
R.O.-tropamideLiquid10 mgOphthalmicRichmond Pharmaceuticals1992-12-311997-08-11Canada
TropicamideSolution1 %OphthalmicEberth Pharmaceuticals Inc1994-12-31Not applicableCanada
TropicamideSolution0.5 %OphthalmicEberth Pharmaceuticals Inc1994-12-31Not applicableCanada
Tropicamide 1% - Liq Oph 10mg/mlLiquid10 mgOphthalmicRivex Ophthalmics Inc.1997-09-152003-07-28Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MydriacylSolution / drops10 mg/1mLOphthalmicAlcon, Inc.1959-04-01Not applicableUs
MydriacylSolution5 mg/1mLOphthalmicALCON LABORATORIES, INC.1959-04-012003-06-30Us
MydriacylSolution / drops10 mg/1mLOphthalmicAlcon, Inc.1959-04-01Not applicableUs
Odan-tropicamideSolution0.5 %OphthalmicOdan Laboratories Ltd1985-12-31Not applicableCanada
Odan-tropicamideSolution1 %OphthalmicOdan Laboratories Ltd1985-12-31Not applicableCanada
PMS-tropicamide Oph Sltn 1%Solution / drops1 %OphthalmicPharmascience Inc1992-12-311996-09-09Canada
TropicamideSolution / drops5 mg/1mLOphthalmicPhysicians Total Care, Inc.2000-09-292005-06-30Us
TropicamideSolution / drops5 mg/1mLOphthalmicAkorn2000-09-29Not applicableUs
TropicamideSolution / drops10 mg/1mLOphthalmicNucare Pharmaceuticals, Inc.1994-07-27Not applicableUs
TropicamideSolution / drops10 mg/1mLOphthalmicSandoz2000-06-13Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Diophenyl-T SolutionTropicamide (0.8 %) + Phenylephrine hydrochloride (5 %)SolutionOphthalmicSandoz Canada Incorporated1994-12-31Not applicableCanada
ParemydTropicamide (2.5 mg/1mL) + Hydroxyamfetamine hydrobromide (10 mg/1mL)SolutionOphthalmicAkorn1992-01-30Not applicableUs
Phenyltrope Oph SolnTropicamide (0.8 %) + Phenylephrine hydrochloride (5.0 %)SolutionOphthalmicSandoz Canada Incorporated1985-12-31Not applicableCanada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Mydriatic-3Tropicamide (10 mg/1mL) + Cyclopentolate Hydrochloride (10 mg/1mL) + Phenylephrine hydrochloride (25 mg/1mL)Solution / dropsOphthalmicImprimis Njof Llc2018-05-01Not applicableUs
Mydriatic-4Tropicamide (10 mg/1mL) + Ketorolac tromethamine (5 mg/1mL) + Phenylephrine hydrochloride (25 mg/1mL) + Proparacaine hydrochloride (5 mg/1mL)Solution / dropsOphthalmicImprimis Njof, Llc2018-05-01Not applicableUs
International/Other Brands
Better (Taiwan Biotech) / Camide (Ibn Sina) / Ciclomidrin (Latinofarma) / Dilate (Incepta) / Eyetrop (Apex) / Losemin (Oasis) / Midax (Rompharm) / Midric (Sanbe) / Minims Tropicamide (Bausch & Lomb) / Mydral (Ocusoft) / Mydramide (Fischer) / Mydriacyl / Mydriaticum (Ciba Vision) / Mydricol (Unimed) / Ocu-Tropic (Ocumed) / Tropicacyl (Akorn)
Categories
UNII
N0A3Z5XTC6
CAS number
1508-75-4
Weight
Average: 284.3529
Monoisotopic: 284.152477894
Chemical Formula
C17H20N2O2
InChI Key
BGDKAVGWHJFAGW-UHFFFAOYSA-N
InChI
InChI=1S/C17H20N2O2/c1-2-19(12-14-8-10-18-11-9-14)17(21)16(13-20)15-6-4-3-5-7-15/h3-11,16,20H,2,12-13H2,1H3
IUPAC Name
N-ethyl-3-hydroxy-2-phenyl-N-(pyridin-4-ylmethyl)propanamide
SMILES
CCN(CC1=CC=NC=C1)C(=O)C(CO)C1=CC=CC=C1

Pharmacology

Indication

Indicated to induce mydriasis (dilation of the pupil) and cycloplegia (paralysis of the ciliary muscle of the eye) in diagnostic procedures, such as measurement of refractive errors and examination of the fundus of the eye.

Pharmacodynamics

Tropicamide belongs to the group of medicines called anti-muscarinics. Tropicamide blocks the receptors in the muscles of the eye (muscarinic receptors). These receptors are involved controlling the pupil size and the shape of the lens. By blocking these receptors, tropicamide produces dilatation of the pupil (mydriasis) and prevents the eye from accommodating for near vision (cycloplegia). Tropicamide is given as eye drops to dilate the pupil and relax the lens so that eye examinations can be carried out thoroughly.

Mechanism of action

Tropicamide binds to and blocks the receptors in the muscles of the eye (muscarinic receptor M4). Tropicamide acts by blocking the responses of the iris sphincter muscle to the iris and ciliary muscles to cholinergic stimulation, producing dilation of the pupil and paralysis of the ciliary muscle.

TargetActionsOrganism
AMuscarinic acetylcholine receptor M4
antagonist
Human
UMuscarinic acetylcholine receptor M1
antagonist
Human
UMuscarinic acetylcholine receptor M2
antagonist
Human
UMuscarinic acetylcholine receptor M3
antagonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding

45%

Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

Overdose can casue dry mouth, blurred vision, photophobia, hallucinations and rapid/irregular pulse.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AclidiniumThe risk or severity of adverse effects can be increased when Tropicamide is combined with Aclidinium.
AgmatineThe risk or severity of adverse effects can be increased when Tropicamide is combined with Agmatine.
AlcuroniumThe risk or severity of adverse effects can be increased when Tropicamide is combined with Alcuronium.
Aluminum sulfateThe therapeutic efficacy of Aluminum sulfate can be decreased when used in combination with Tropicamide.
AmantadineThe risk or severity of adverse effects can be increased when Tropicamide is combined with Amantadine.
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Tropicamide.
AmobarbitalThe risk or severity of adverse effects can be increased when Tropicamide is combined with Amobarbital.
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Tropicamide.
Anisotropine MethylbromideThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Tropicamide.
AprobarbitalThe risk or severity of adverse effects can be increased when Tropicamide is combined with Aprobarbital.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0014947
KEGG Drug
D00397
PubChem Compound
5593
PubChem Substance
46505924
ChemSpider
5391
BindingDB
82371
ChEBI
9757
ChEMBL
CHEMBL1200604
Therapeutic Targets Database
DAP000345
PharmGKB
PA164749389
Drugs.com
Drugs.com Drug Page
Wikipedia
Tropicamide
ATC Codes
S01FA06 — TropicamideS01FA56 — Tropicamide, combinations
AHFS Codes
  • 52:24.00 — Mydriatics
MSDS
Download (73.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedPreventionIntraocular Pressure1
2CompletedTreatmentSialorrhea Secondary to Parkinson's Disease1
3CompletedTreatmentCataracts1
3CompletedTreatmentEye Diseases1
4Active Not RecruitingTreatmentCorneal Transplant / Grafting, Corneal / Keratoplasty, Lamellar / Transplantation, Cornea / Transplantation, Corneal1
4CompletedDiagnosticPreterm, Infant1
4Unknown StatusDiagnosticRefractive Errors1
4Unknown StatusPreventionMyopia1
Not AvailableCompletedNot AvailableFabry's Disease1
Not AvailableCompletedNot AvailableRetinopathy of Prematurity1
Not AvailableCompletedTreatmentCataracts1

Pharmacoeconomics

Manufacturers
  • Alcon laboratories inc
  • Pharmafair inc
  • Akorn inc
  • Alcon universal ltd
  • Bausch and lomb pharmaceuticals inc
  • Miza pharmaceuticals usa inc
  • Watson laboratories inc
Packagers
  • Accutome Inc.
  • Akorn Inc.
  • Alcon Laboratories
  • Bausch & Lomb Inc.
  • Dispensing Solutions
  • Eye Care and Cure Corp.
  • Eye Supply Usa Inc.
  • Falcon Pharmaceuticals Ltd.
  • Medical Ophthalmics
  • Medisca Inc.
  • Physicians Total Care Inc.
  • Wilson Ophthalmic Corp.
Dosage forms
FormRouteStrength
SolutionOphthalmic
SolutionOphthalmic0.5 %
SolutionOphthalmic1 %
SolutionOphthalmic5 mg/1mL
Solution / dropsOphthalmic
Solution / dropsOphthalmic1 %
LiquidOphthalmic10 mg
Solution / dropsOphthalmic10 mg/1mL
Solution / dropsOphthalmic5 mg/1mL
Prices
Unit descriptionCostUnit
Tropicamide powder72.83USD g
Mydriacyl 1% Solution 15ml Bottle59.84USD bottle
Tropicamide 0.5% Solution 15ml Bottle17.99USD bottle
Tropicamide 1% Solution 15ml Bottle17.75USD bottle
Mydriacyl 1% Solution 3ml Bottle17.28USD bottle
Tropicamide 1% Solution 3ml Bottle13.99USD bottle
Tropicamide 1% Solution 2ml Bottle7.99USD bottle
Mydriacyl 1% eye drops5.54USD ml
Tropicamide 1% eye drops2.52USD ml
Paremyd eye drops1.28USD ml
Mydriacyl 1 % Solution1.21USD ml
Tropicamide 0.5% eye drops1.06USD ml
Mydriacyl 0.5 % Solution0.94USD ml
Tropicacyl 1% eye drops0.71USD ml
Tropicacyl 0.5% eye drops0.67USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)96.5 °CPhysProp
logP1.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.375 mg/mLALOGPS
logP1.42ALOGPS
logP1.38ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)15.18ChemAxon
pKa (Strongest Basic)5.02ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area53.43 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity82.53 m3·mol-1ChemAxon
Polarizability29.78 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9943
Blood Brain Barrier+0.9777
Caco-2 permeable+0.5986
P-glycoprotein substrateNon-substrate0.5777
P-glycoprotein inhibitor INon-inhibitor0.8947
P-glycoprotein inhibitor IINon-inhibitor0.9442
Renal organic cation transporterNon-inhibitor0.6694
CYP450 2C9 substrateNon-substrate0.7731
CYP450 2D6 substrateNon-substrate0.7878
CYP450 3A4 substrateNon-substrate0.7241
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorInhibitor0.895
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.8184
CYP450 3A4 inhibitorInhibitor0.796
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6008
Ames testNon AMES toxic0.6905
CarcinogenicityNon-carcinogens0.7473
BiodegradationNot ready biodegradable0.8754
Rat acute toxicity2.4857 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9686
hERG inhibition (predictor II)Non-inhibitor0.8009
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (8.19 KB)
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
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-0290000000-8c6533b9c36099d52c7c
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-1390000000-cf89fdf233a948aed049
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4r-4930000000-ca3db93b017c3a6fb89b

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylacetamides. These are amide derivatives of phenylacetic acids.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylacetamides
Direct Parent
Phenylacetamides
Alternative Parents
Pyridines and derivatives / Tertiary carboxylic acid amides / Heteroaromatic compounds / Azacyclic compounds / Primary alcohols / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Phenylacetamide / Pyridine / Tertiary carboxylic acid amide / Heteroaromatic compound / Carboxamide group / Azacycle / Organoheterocyclic compound / Carboxylic acid derivative / Hydrocarbon derivative / Organic oxygen compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Guanyl-nucleotide exchange factor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM4
Uniprot ID
P08173
Uniprot Name
Muscarinic acetylcholine receptor M4
Molecular Weight
53048.65 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Betz AJ, McLaughlin PJ, Burgos M, Weber SM, Salamone JD: The muscarinic receptor antagonist tropicamide suppresses tremulous jaw movements in a rodent model of parkinsonian tremor: possible role of M4 receptors. Psychopharmacology (Berl). 2007 Oct;194(3):347-59. Epub 2007 Jun 27. [PubMed:17594079]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
Molecular Weight
51420.375 Da
References
  1. Betz AJ, McLaughlin PJ, Burgos M, Weber SM, Salamone JD: The muscarinic receptor antagonist tropicamide suppresses tremulous jaw movements in a rodent model of parkinsonian tremor: possible role of M4 receptors. Psychopharmacology (Berl). 2007 Oct;194(3):347-59. Epub 2007 Jun 27. [PubMed:17594079]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
G-protein coupled acetylcholine receptor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM2
Uniprot ID
P08172
Uniprot Name
Muscarinic acetylcholine receptor M2
Molecular Weight
51714.605 Da
References
  1. Betz AJ, McLaughlin PJ, Burgos M, Weber SM, Salamone JD: The muscarinic receptor antagonist tropicamide suppresses tremulous jaw movements in a rodent model of parkinsonian tremor: possible role of M4 receptors. Psychopharmacology (Berl). 2007 Oct;194(3):347-59. Epub 2007 Jun 27. [PubMed:17594079]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Receptor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM3
Uniprot ID
P20309
Uniprot Name
Muscarinic acetylcholine receptor M3
Molecular Weight
66127.445 Da
References
  1. Betz AJ, McLaughlin PJ, Burgos M, Weber SM, Salamone JD: The muscarinic receptor antagonist tropicamide suppresses tremulous jaw movements in a rodent model of parkinsonian tremor: possible role of M4 receptors. Psychopharmacology (Berl). 2007 Oct;194(3):347-59. Epub 2007 Jun 27. [PubMed:17594079]

Drug created on June 13, 2005 07:24 / Updated on November 16, 2018 08:03