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Identification
NameTropicamide
Accession NumberDB00809  (APRD00287)
TypeSmall Molecule
GroupsApproved
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
SynonymLanguageCode
MydriacylNot AvailableNot Available
TropicamidGermanINN
TropicamidaSpanishINN
TropicamideFrenchINN
TropicamidumLatinINN
SaltsNot Available
Brand names
NameCompany
BetterTaiwan Biotech
CamideIbn Sina
CiclomidrinLatinofarma
DilateIncepta
EyetropApex
LoseminOasis
MidaxRompharm
MidricSanbe
Minims TropicamideBausch & Lomb
MydralOcusoft
MydramideFischer
MydriacylAlcon
MydriaticumCiba Vision
MydricolUnimed
Ocu-TropicOcumed
TropicacylAkorn
Brand mixtures
Brand NameIngredients
AugexTropicamide and Phenylephrine
Diophenyl-T SolutionPhenylephrine Hydrochloride + Tropicamide
Drosyn-TTropicamide and Phenylephrine
FotomidTropicamide and Phenylephrine
FotorretinTropicamide and Phenylephrine
MydriasertTropicamide and Phenylephrine
Mydriaticum AgephaTropicamide and Phenylmercuric Nitrate
ParemydTropicamide and Hydroxyamfetamine
Phenyltrope Oph SolnPhenylephrine Hydrochloride + Tropicamide
Categories
CAS number1508-75-4
WeightAverage: 284.3529
Monoisotopic: 284.152477894
Chemical FormulaC17H20N2O2
InChI KeyBGDKAVGWHJFAGW-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
Mass Specshow(8.19 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenylpropylamines
Direct parentPhenylpropylamines
Alternative parentsPyridines and Derivatives; Tertiary Carboxylic Acid Amides; Tertiary Amines; Primary Alcohols; Polyamines; Enolates; Carboxylic Acids
Substituentspyridine; tertiary carboxylic acid amide; carboxamide group; tertiary amine; carboxylic acid derivative; primary alcohol; enolate; carboxylic acid; polyamine; amine; alcohol; organonitrogen compound
Classification descriptionThis compound belongs to the phenylpropylamines. These are compounds containing a phenylpropylamine moiety, which consists of a phenyl group substituted at the third carbon by an propan-1-amine.
Pharmacology
IndicationIndicated 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.
PharmacodynamicsTropicamide 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 actionTropicamide 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein binding45%
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityOverdose can casue dry mouth, blurred vision, photophobia, hallucinations and rapid/irregular pulse.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9943
Blood Brain Barrier + 0.9777
Caco-2 permeable + 0.5986
P-glycoprotein substrate Non-substrate 0.5777
P-glycoprotein inhibitor I Non-inhibitor 0.8947
P-glycoprotein inhibitor II Non-inhibitor 0.9442
Renal organic cation transporter Non-inhibitor 0.6694
CYP450 2C9 substrate Non-substrate 0.7731
CYP450 2D6 substrate Non-substrate 0.7878
CYP450 3A4 substrate Non-substrate 0.7241
CYP450 1A2 substrate Inhibitor 0.9107
CYP450 2C9 substrate Inhibitor 0.895
CYP450 2D6 substrate Non-inhibitor 0.923
CYP450 2C19 substrate Non-inhibitor 0.8184
CYP450 3A4 substrate Inhibitor 0.796
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6008
Ames test Non AMES toxic 0.6905
Carcinogenicity Non-carcinogens 0.7473
Biodegradation Not ready biodegradable 0.8754
Rat acute toxicity 2.4857 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9686
hERG inhibition (predictor II) Non-inhibitor 0.8009
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
FormRouteStrength
LiquidOphthalmic
SolutionOphthalmic
Solution / dropsOphthalmic
Prices
Unit descriptionCostUnit
Tropicamide powder72.83USDg
Mydriacyl 1% Solution 15ml Bottle59.84USDbottle
Tropicamide 0.5% Solution 15ml Bottle17.99USDbottle
Tropicamide 1% Solution 15ml Bottle17.75USDbottle
Mydriacyl 1% Solution 3ml Bottle17.28USDbottle
Tropicamide 1% Solution 3ml Bottle13.99USDbottle
Tropicamide 1% Solution 2ml Bottle7.99USDbottle
Mydriacyl 1% eye drops5.54USDml
Tropicamide 1% eye drops2.52USDml
Paremyd eye drops1.28USDml
Mydriacyl 1 % Solution1.21USDml
Tropicamide 0.5% eye drops1.06USDml
Mydriacyl 0.5 % Solution0.94USDml
Tropicacyl 1% eye drops0.71USDml
Tropicacyl 0.5% eye drops0.67USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point96.5 °CPhysProp
logP1.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.375ALOGPS
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
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00397
PubChem Compound5593
PubChem Substance46505924
ChemSpider5391
Therapeutic Targets DatabaseDAP000345
PharmGKBPA164749389
Drug Product Database2148536
Drugs.comhttp://www.drugs.com/cdi/tropicamide.html
WikipediaTropicamide
ATC CodesS01FA06
AHFS Codes
  • 52:24.00
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(73.1 KB)
Interactions
Drug InteractionsSearched, but no interactions found.
Food InteractionsNot Available

Targets

1. Muscarinic acetylcholine receptor M4

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M4 P08173 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M1 P11229 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M2 P08172 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M3 P20309 Details

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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:12