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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
(+-)-Cyclopentolate
(±)-cyclopentolate
1-Hydroxy-alpha-phenylcyclopentaneacetic acid 2-(dimethylamino)ethyl ester
2-(dimethylamino)Ethyl 1-hydroxy-alpha-phenylcyclopentaneacetate
2-(dimethylamino)Ethyl 2-(1-hydroxycyclopentyl)-2-phenylacetate
2-Phenyl-2-(1-hydroxycyclopentyl)ethanoic acid beta-(dimethylamino)ethyl ester
alpha-(1-Hydroxycyclopentyl)benzeneacetic acid 2-(dimethylamino)ethyl ester
beta-(dimethylamino)Ethyl (1-hydroxycyclopentyl)phenylacetate
beta-Dimethylaminoethyl (1-hydroxycyclopentyl)phenylacetate
Ciclopentolato
Cyclopentolate
Cyclopentolatum
α-(1-hydroxycyclopentyl)benzeneacetic acid 2-(dimethylamino)ethyl ester
β-dimethylaminoethyl (1-hydroxycyclopentyl)phenylacetate
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cyclogyl Oph Dps 1%drops1 %ophthalmicAlcon Canada Inc1972-12-31Not applicableCanada
Diopentolate 0.5% Solutionsolution.5 %ophthalmicDioptic Pharmaceuticals Inc1994-12-31Not applicableCanada
Diopentolate 1% Solutionsolution1 %ophthalmicDioptic Pharmaceuticals Inc1994-12-31Not applicableCanada
Dom-cyclopentolate HCl Ophtalmic Solution-1%solution1 %ophthalmicDominion Pharmacal1995-12-311996-09-09Canada
Minims Cyclopentolate Hydrochloride 0.5%drops0.5 %ophthalmicValeant Canada Lp Valeant Canada S.E.C.1995-12-31Not applicableCanada
Minims Cyclopentolate Hydrochloride 1%drops1 %ophthalmicValeant Canada Lp Valeant Canada S.E.C.1995-12-31Not applicableCanada
Odan-cyclopentolatesolution1 %ophthalmicOdan Laboratories Ltd1984-12-31Not applicableCanada
Odan-cyclopentolatesolution.5 %ophthalmicOdan Laboratories Ltd1984-12-31Not applicableCanada
Odan-cyclopentolatesolution.5 %ophthalmicOdan Laboratories Ltd1984-12-31Not applicableCanada
PMS-cyclopentolate HCl Oph Solution 1%liquid1 %ophthalmicPharmascience Inc1992-12-31Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ak-pentolatesolution/ drops10 mg/mLophthalmicRebel Distributors Corp.1997-01-13Not applicableUs
Cyclogylsolution/ drops5 mg/mLophthalmicAlcon Laboratories, Inc.1975-10-15Not applicableUs
Cyclogylsolution/ drops20 mg/mLophthalmicAlcon Laboratories, Inc.1975-10-15Not applicableUs
Cyclogylsolution/ drops10 mg/mLophthalmicAlcon Laboratories, Inc.1975-10-15Not applicableUs
Cyclopentolatesolution/ drops5 mg/mLophthalmicAkorn, Inc.2015-12-10Not applicableUs
Cyclopentolate Hydrochloridesolution20 mg/mLophthalmicFalcon Pharmaceuticals, Ltd.2002-08-22Not applicableUs
Cyclopentolate Hydrochloridesolution/ drops10 mg/mLophthalmicAkorn, Inc.1997-01-13Not applicableUs
Cyclopentolate Hydrochloridesolution10 mg/mLophthalmicFalcon Pharmaceuticals, Ltd.2002-08-22Not applicableUs
Cyclopentolate Hydrochloridesolution/ drops20 mg/mLophthalmicAkorn, Inc.1997-01-13Not applicableUs
Cyclopentolate Hydrochloridesolution5 mg/mLophthalmicFalcon Pharmaceuticals, Ltd.2002-08-22Not applicableUs
Cyclopentolate Hydrochloridesolution/ drops10 mg/mLophthalmicPhysicians Total Care, Inc.2013-01-10Not applicableUs
Cyclopentolate Hydrochloridesolution/ drops10 mg/mLophthalmicRebel Distributors Corp1994-04-29Not applicableUs
Cyclopentolate Hydrochloridesolution/ drops10 mg/mLophthalmicBausch & Lomb Incorporated1994-04-29Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
Bell PentolateNot Available
CylateOcusoft
MydrilateIntrapharm
Ocu-PentolateNot Available
PentolairNot Available
Brand mixtures
NameLabellerIngredients
CyclomydrilAlcon Laboratories, Inc.
Salts
Name/CASStructureProperties
Cyclopentolate Hydrochloride
Thumb
  • InChI Key: RHKZVMUBMXGOLL-UHFFFAOYNA-N
  • Monoisotopic Mass: 327.16012141
  • Average Mass: 327.846
DBSALT000476
Categories
UNIII76F4SHP7J
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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetic acid derivatives
Direct ParentPhenylacetic acid derivatives
Alternative Parents
Substituents
  • Phenylacetate
  • Cyclopentanol
  • Tertiary alcohol
  • Cyclic alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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).
Related Articles
AbsorptionAbsorbed following ophthalmic administration.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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
PropertyValueProbability
Human Intestinal Absorption+0.9741
Blood Brain Barrier+0.8234
Caco-2 permeable+0.6395
P-glycoprotein substrateSubstrate0.7831
P-glycoprotein inhibitor INon-inhibitor0.6735
P-glycoprotein inhibitor IINon-inhibitor0.9384
Renal organic cation transporterNon-inhibitor0.5874
CYP450 2C9 substrateNon-substrate0.7938
CYP450 2D6 substrateNon-substrate0.7009
CYP450 3A4 substrateSubstrate0.6036
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9232
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9413
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9518
Ames testNon AMES toxic0.8284
CarcinogenicityNon-carcinogens0.8492
BiodegradationNot ready biodegradable0.931
Rat acute toxicity2.4300 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9335
hERG inhibition (predictor II)Non-inhibitor0.779
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Akorn inc
  • Alcon laboratories inc
  • Alcon universal ltd
  • Sola barnes hind
  • Bausch and lomb pharmaceuticals inc
  • Pharmafair inc
Packagers
Dosage forms
FormRouteStrength
Solution/ dropsophthalmic10 mg/mL
Solution/ dropsophthalmic20 mg/mL
Solution/ dropsophthalmic5 mg/mL
Dropsophthalmic1 %
Solution/ dropsophthalmic
Solutionophthalmic10 mg/mL
Solutionophthalmic20 mg/mL
Solutionophthalmic5 mg/mL
Solutionophthalmic.5 %
Solutionophthalmic1 %
Dropsophthalmic0.5 %
Liquidophthalmic1 %
Prices
Unit descriptionCostUnit
Cyclopentolate HCl 1% Solution 15ml Bottle12.99USD bottle
Cyclogyl 2% eye drops11.76USD ml
Cyclopentolate HCl 1% Solution 2ml Bottle9.99USD bottle
Cyclopentolate 1% eye drops9.35USD ml
Cyclogyl 1% eye drops8.97USD ml
Cylate 1% eye drops5.02USD ml
Cyclogyl 0.5% eye drops3.42USD ml
Cyclogyl 1 % Solution0.91USD ml
Ak-pentolate 1% eye drops0.71USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point134-136Treves, G.R.; US. Patent 2,554,511; May 29,1951; assigned to Schieffelin & Co.
logP2.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.5 mg/mLALOGPS
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 Area49.77 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity82.81 m3·mol-1ChemAxon
Polarizability32.51 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Treves, G.R.; US. Patent 2,554,511; May 29,1951; assigned to Schieffelin & Co.

General References
  1. Link [Link]
External Links
ATC CodesS01FA04S01FA54
AHFS Codes
  • 52:24.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (72.9 KB)
Interactions
Drug Interactions
Drug
AclidiniumAclidinium may increase the anticholinergic activities of Cyclopentolate.
Botulinum Toxin Type ACyclopentolate may increase the anticholinergic activities of Botulinum Toxin Type A.
Botulinum Toxin Type BCyclopentolate may increase the anticholinergic activities of Botulinum Toxin Type B.
Cimetropium BromideCyclopentolate may increase the anticholinergic activities of Cimetropium Bromide.
DronabinolCyclopentolate may increase the tachycardic activities of Dronabinol.
EluxadolineCyclopentolate may increase the activities of Eluxadoline.
Glucagon recombinantThe risk or severity of adverse effects can be increased when Cyclopentolate is combined with Glucagon recombinant.
Ipratropium bromideIpratropium bromide may increase the anticholinergic activities of Cyclopentolate.
ItoprideThe therapeutic efficacy of Itopride can be decreased when used in combination with Cyclopentolate.
MianserinMianserin may increase the anticholinergic activities of Cyclopentolate.
MirabegronThe risk or severity of adverse effects can be increased when Cyclopentolate is combined with Mirabegron.
MorphineThe risk or severity of adverse effects can be increased when Cyclopentolate is combined with Morphine.
Potassium ChlorideCyclopentolate may increase the ulcerogenic activities of Potassium Chloride.
PramlintidePramlintide may increase the anticholinergic activities of Cyclopentolate.
ProcyclidineThe risk or severity of adverse effects can be increased when Procyclidine is combined with Cyclopentolate.
RamosetronCyclopentolate may increase the activities of Ramosetron.
SecretinThe therapeutic efficacy of Secretin can be decreased when used in combination with Cyclopentolate.
SulpirideThe therapeutic efficacy of Sulpiride can be decreased when used in combination with Cyclopentolate.
TacrineThe therapeutic efficacy of Cyclopentolate can be decreased when used in combination with Tacrine.
TiotropiumCyclopentolate may increase the anticholinergic activities of Tiotropium.
TopiramateThe risk or severity of adverse effects can be increased when Cyclopentolate is combined with Topiramate.
TrichlormethiazideThe serum concentration of Trichlormethiazide can be increased when it is combined with Cyclopentolate.
UmeclidiniumUmeclidinium may increase the anticholinergic activities of Cyclopentolate.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
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 action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM1
Uniprot ID:
P11229
Molecular Weight:
51420.375 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 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Identical protein binding
Specific Function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular Weight:
68417.575 Da
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:15121994 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on April 10, 2014 09:51