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Identification
NameCyclopentolate
Accession NumberDB00979  (APRD00893)
Typesmall molecule
Groupsapproved
Description

A parasympatholytic anticholinergic used solely to obtain mydriasis or cycloplegia. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
(±)-cyclopentolateNot AvailableNot Available
CiclopentolatoSpanishINN
CyclopentolatumLatinINN
α-(1-hydroxycyclopentyl)benzeneacetic acid 2-(dimethylamino)ethyl esterNot AvailableNot Available
β-dimethylaminoethyl (1-hydroxycyclopentyl)phenylacetateNot AvailableNot Available
Salts
Name/CAS Structure Properties
Cyclopentolate Hydrochloride
Thumb
  • InChI Key: RHKZVMUBMXGOLL-UHFFFAOYNA-N
  • Monoisotopic Mass: 327.16012141
  • Average Mass: 327.846
DBSALT000476
Brand names
NameCompany
Bell PentolateNot Available
CyclogylNot Available
CylateNot Available
MydrilateNot Available
Ocu-PentolateNot Available
PentolairNot Available
Brand mixturesNot Available
Categories
CAS number512-15-2
WeightAverage: 291.3853
Monoisotopic: 291.183443671
Chemical FormulaC17H25NO3
InChI KeyInChIKey=SKYSRIRYMSLOIN-UHFFFAOYSA-N
InChI
InChI=1S/C17H25NO3/c1-18(2)12-13-21-16(19)15(14-8-4-3-5-9-14)17(20)10-6-7-11-17/h3-5,8-9,15,20H,6-7,10-13H2,1-2H3
IUPAC Name
2-(dimethylamino)ethyl 2-(1-hydroxycyclopentyl)-2-phenylacetate
SMILES
CN(C)CCOC(=O)C(C1=CC=CC=C1)C1(O)CCCC1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenylacetic Acid Derivatives
Direct parentPhenylacetic Acid Derivatives
Alternative parentsTertiary Alcohols; Tertiary Amines; Cyclic Alcohols and Derivatives; Carboxylic Acid Esters; Enolates; Polyamines; Ethers
Substituentstertiary alcohol; cyclic alcohol; carboxylic acid ester; tertiary amine; carboxylic acid derivative; ether; polyamine; enolate; amine; alcohol; organonitrogen compound
Classification descriptionThis compound belongs to the phenylacetic acid derivatives. These are compounds containing a phenylacetic acid moiety, which consists of a phenyl group substituted at the second position by an acetic acid.
Pharmacology
IndicationUsed mainly to produce mydriasis and cycloplegia for diagnostic purposes.
PharmacodynamicsCyclopentolate is an anti-muscarinic in the same class as atropine and scopolamine. Cyclopentolate 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. Cyclopentolate thus induces relaxation of the sphincter of the iris and the ciliary muscles. When applied topically to the eyes, it causes a rapid, intense cycloplegic and mydriatic effect that is maximal in 15 to 60 minutes; recovery usually occurs within 24 hours. The cycloplegic and mydriatic effects are slower in onset and longer in duration in patients who have dark pigmented irises.
Mechanism of actionBy blocking muscarinic receptors, cyclopentolate produces dilatation of the pupil (mydriasis) and prevents the eye from accommodating for near vision (cycloplegia).
AbsorptionAbsorbed following ophthalmic administration.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityOral LD50 in the rat is 4000 mg/kg and 960 mg/kg in the mouse. Symptoms of overdose include tachycardia, dizziness, dry mouth, behavioral disturbances, uncoordination and drowsiness.
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 + 0.9741
Blood Brain Barrier + 0.8234
Caco-2 permeable + 0.6395
P-glycoprotein substrate Substrate 0.7831
P-glycoprotein inhibitor I Non-inhibitor 0.6735
P-glycoprotein inhibitor II Non-inhibitor 0.9384
Renal organic cation transporter Non-inhibitor 0.5874
CYP450 2C9 substrate Non-substrate 0.7938
CYP450 2D6 substrate Non-substrate 0.7009
CYP450 3A4 substrate Substrate 0.6036
CYP450 1A2 substrate Non-inhibitor 0.9046
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Non-inhibitor 0.9232
CYP450 2C19 substrate Non-inhibitor 0.9025
CYP450 3A4 substrate Non-inhibitor 0.9413
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9518
Ames test Non AMES toxic 0.8284
Carcinogenicity Non-carcinogens 0.8492
Biodegradation Not ready biodegradable 0.931
Rat acute toxicity 2.4300 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9335
hERG inhibition (predictor II) Non-inhibitor 0.779
Pharmacoeconomics
Manufacturers
  • Akorn inc
  • Alcon laboratories inc
  • Alcon universal ltd
  • Sola barnes hind
  • Bausch and lomb pharmaceuticals inc
  • Pharmafair inc
Packagers
Dosage forms
FormRouteStrength
LiquidOphthalmic
SolutionOphthalmic
Solution / dropsOphthalmic
Prices
Unit descriptionCostUnit
Cyclopentolate HCl 1% Solution 15ml Bottle12.99USDbottle
Cyclogyl 2% eye drops11.76USDml
Cyclopentolate HCl 1% Solution 2ml Bottle9.99USDbottle
Cyclopentolate 1% eye drops9.35USDml
Cyclogyl 1% eye drops8.97USDml
Cylate 1% eye drops5.02USDml
Cyclogyl 0.5% eye drops3.42USDml
Cyclogyl 1 % Solution0.91USDml
Ak-pentolate 1% eye drops0.71USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point139 °C (hydrochloride salt)Not Available
logP2.4Not Available
Predicted Properties
PropertyValueSource
water solubility1.50e+00 g/lALOGPS
logP2.09ALOGPS
logP2.32ChemAxon
logS-2.3ALOGPS
pKa (strongest acidic)14.19ChemAxon
pKa (strongest basic)8.42ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count1ChemAxon
polar surface area49.77ChemAxon
rotatable bond count7ChemAxon
refractivity82.81ChemAxon
polarizability32.51ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. Link
External Links
ResourceLink
KEGG CompoundC06932
PubChem Compound2905
PubChem Substance46504517
ChemSpider2802
ChEBI4024
ChEMBLCHEMBL1201338
Therapeutic Targets DatabaseDAP001111
PharmGKBPA164743019
Drug Product Database2148382
Drugs.comhttp://www.drugs.com/cdi/cyclopentolate.html
WikipediaCyclopentolate
ATC CodesS01FA04
AHFS Codes
  • 52:24.00
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(72.9 KB)
Interactions
Drug Interactions
Drug
TacrineThe therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Cyclopentolate, may be reduced due to antagonism. The interaction may be beneficial when the anticholinergic action is a side effect. Monitor for decreased efficacy of both agents.
TriprolidineTriprolidine and Cyclopentolate, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
TrospiumTrospium and Cyclopentolate, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Food InteractionsNot Available

1. Muscarinic acetylcholine receptor M1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M1 P11229 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

1. Cholinesterase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cholinesterase P06276 Details

References:

  1. Demayo AP, Reidenberg MM: Grand mal seizure in a child 30 minutes after Cyclogyl (cyclopentolate hydrochloride) and 10% Neo-Synephrine (phenylephrine hydrochloride) eye drops were instilled. Pediatrics. 2004 May;113(5):e499-500. Pubmed

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