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Identification
Name Tropicamide
Accession Number DB00809 (APRD00287)
Type small molecule
Groups approved
Description

One of the muscarinic antagonists with pharmacologic action similar to atropine and used mainly as an ophthalmic parasympatholytic or mydriatic. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
I-Picamide
Minims Tropicamide
Mydriacyl
Mydriafair
Mydriaticum
Ocu-Tropic
Opticyl
Paremyd
Spectro-Cyl
Tropicacyl
Brand mixtures
Brand Name Ingredients
Diophenyl-T Solution Phenylephrine Hydrochloride + Tropicamide
Phenyltrope Oph Soln Phenylephrine Hydrochloride + Tropicamide
Categories
  • Mydriatics
  • Muscarinic Antagonists
  • Diagnostic aid, cycloplegic
  • Diagnostic aid, mydriatic
CAS number 1508-75-4
Weight Average: 284.3529
Monoisotopic: 284.152477894
Chemical Formula C17H20N2O2
InChI Key InChIKey=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
Plain Text
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
Plain Text
Mass Spec show (8.19 KB)
Taxonomy
Kingdom Organic
Classes
  • Phenethylamines
Substructures
  • Hydroxy Compounds
  • Amino Ketones
  • Pyridines and Derivatives
  • Benzene and Derivatives
  • Aliphatic and Aryl Amines
  • Alcohols and Polyols
  • Phenethylamines
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
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.
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
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
Dosage forms
Form Route Strength
Liquid Ophthalmic
Solution Ophthalmic
Solution / drops Ophthalmic
Prices
Unit description Cost Unit
Tropicamide powder 72.83 USD g
Mydriacyl 1% Solution 15ml Bottle 59.84 USD bottle
Tropicamide 0.5% Solution 15ml Bottle 17.99 USD bottle
Tropicamide 1% Solution 15ml Bottle 17.75 USD bottle
Mydriacyl 1% Solution 3ml Bottle 17.28 USD bottle
Tropicamide 1% Solution 3ml Bottle 13.99 USD bottle
Tropicamide 1% Solution 2ml Bottle 7.99 USD bottle
Mydriacyl 1% eye drops 5.54 USD ml
Tropicamide 1% eye drops 2.52 USD ml
Paremyd eye drops 1.28 USD ml
Mydriacyl 1 % Solution 1.21 USD ml
Tropicamide 0.5% eye drops 1.06 USD ml
Mydriacyl 0.5 % Solution 0.94 USD ml
Tropicacyl 1% eye drops 0.71 USD ml
Tropicacyl 0.5% eye drops 0.67 USD ml
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Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 96.5 °C PhysProp
logP 1.3 Not Available
Predicted Properties
Property Value Source
water solubility 3.75e-01 g/l ALOGPS
logP 1.42 ALOGPS
logP 1.38 ChemAxon
logS -2.9 ALOGPS
pKa (strongest acidic) 15.18 ChemAxon
pKa (strongest basic) 5.02 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 3 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 53.43 ChemAxon
rotatable bond count 6 ChemAxon
refractivity 82.53 ChemAxon
polarizability 29.78 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00397 Link_out
PubChem Compound 5593 Link_out
PubChem Substance 46505924 Link_out
ChemSpider 5391 Link_out
Therapeutic Targets Database DAP000345 Link_out
PharmGKB PA164749389 Link_out
Drug Product Database 2148536 Link_out
Drugs.com http://www.drugs.com/cdi/tropicamide.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Tropicamide Link_out
ATC Codes
  • S01FA06
AHFS Codes
  • 52:24.00
PDB Entries Not Available
FDA label Not Available
MSDS show (73.1 KB)
Interactions
Drug Interactions Searched, but no interactions found.
Food Interactions Not Available
Targets

1. Muscarinic acetylcholine receptor M4

Pharmacological action: yes
Actions: antagonist

The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is inhibition of adenylate cyclase

Organism class: human
UniProt ID: P08173 Link_out
Gene: CHRM4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  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
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Muscarinic acetylcholine receptor M1

Pharmacological action: unknown
Actions: antagonist

The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover

Organism class: human
UniProt ID: P11229 Link_out
Gene: CHRM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

3. Muscarinic acetylcholine receptor M2

Pharmacological action: unknown
Actions: antagonist

The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition

Organism class: human
UniProt ID: P08172 Link_out
Gene: CHRM2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

4. Muscarinic acetylcholine receptor M3

Pharmacological action: unknown
Actions: antagonist

The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover

Organism class: human
UniProt ID: P20309 Link_out
Gene: CHRM3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19