Cyclopentolate

Identification

Summary

Cyclopentolate is an anticholinergic used to cause mydriasis and cycloplegia for diagnostic testing.

Brand Names
Ak-pentolate, Cyclogyl, Cyclomydril, Minims Cyclopentolate Hydrochloride
Generic Name
Cyclopentolate
DrugBank Accession Number
DB00979
Background

A parasympatholytic anticholinergic used solely to obtain mydriasis or cycloplegia.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 291.3853
Monoisotopic: 291.183443671
Chemical Formula
C17H25NO3
Synonyms
  • (±)-cyclopentolate
  • 1-hydroxy-α-phenylcyclopentaneacetic acid 2-(dimethylamino)ethyl ester
  • 2-(dimethylamino)ethyl 1-hydroxy-α-phenylcyclopentaneacetate
  • 2-(dimethylamino)ethyl 2-(1-hydroxycyclopentyl)-2-phenylacetate
  • 2-phenyl-2-(1-hydroxycyclopentyl)ethanoic acid β-(dimethylamino)ethyl ester
  • Ciclopentolato
  • Cyclopentolate
  • Cyclopentolatum
  • α-(1-hydroxycyclopentyl)benzeneacetic acid 2-(dimethylamino)ethyl ester
  • β-(dimethylamino)ethyl (1-hydroxycyclopentyl)phenylacetate
  • β-dimethylaminoethyl (1-hydroxycyclopentyl)phenylacetate

Pharmacology

Indication

Used mainly to produce mydriasis and cycloplegia for diagnostic purposes.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Cyclopentolate 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 action

By blocking muscarinic receptors, cyclopentolate produces dilatation of the pupil (mydriasis) and prevents the eye from accommodating for near vision (cycloplegia).

TargetActionsOrganism
AMuscarinic acetylcholine receptor M1
antagonist
Humans
Absorption

Absorbed following ophthalmic administration.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Oral 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.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AclidiniumThe risk or severity of adverse effects can be increased when Cyclopentolate is combined with Aclidinium.
AlloinThe therapeutic efficacy of Alloin can be decreased when used in combination with Cyclopentolate.
AmantadineThe risk or severity of adverse effects can be increased when Amantadine is combined with Cyclopentolate.
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Cyclopentolate.
AmobarbitalThe risk or severity of adverse effects can be increased when Cyclopentolate is combined with Amobarbital.
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Cyclopentolate.
Anisotropine methylbromideThe risk or severity of adverse effects can be increased when Anisotropine methylbromide is combined with Cyclopentolate.
AripiprazoleThe risk or severity of adverse effects can be increased when Cyclopentolate is combined with Aripiprazole.
AtracuriumThe risk or severity of adverse effects can be increased when Cyclopentolate is combined with Atracurium.
Atracurium besylateThe risk or severity of adverse effects can be increased when Atracurium besylate is combined with Cyclopentolate.
Interactions
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Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Cyclopentolate hydrochloride6D6X07D6BN5870-29-1RHKZVMUBMXGOLL-UHFFFAOYSA-N
International/Other Brands
Bell Pentolate / Cylate (Ocusoft) / Mydrilate (Intrapharm) / Ocu-Pentolate / Pentolair
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CyclogylSolution / drops1 % w/vOphthalmicAlcon, Inc.1972-12-31Not applicableCanada flag
CyclopentolateSolution0.5 %OphthalmicPharma Stulln Inc.1994-12-312020-01-15Canada flag
CyclopentolateSolution1 %OphthalmicPharma Stulln Inc.1994-12-312020-01-15Canada flag
Minims Cyclopentolate HydrochlorideSolution / drops1 % w/vOphthalmicBausch Health, Canada Inc.1995-12-31Not applicableCanada flag
Minims Cyclopentolate HydrochlorideSolution / drops0.5 % w/vOphthalmicBausch Health, Canada Inc.1995-12-31Not applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ak-pentolateSolution / drops10 mg/1mLOphthalmicRebel Distributors1997-01-13Not applicableUS flag
CyclogylSolution / drops10 mg/1mLOphthalmicALCON LABORATORIES, INC.1975-10-15Not applicableUS flag
CyclogylSolution20 mg/1mLOphthalmicPhysicians Total Care, Inc.2002-11-012012-06-30US flag
CyclogylSolution / drops5 mg/1mLOphthalmicALCON LABORATORIES, INC.1975-10-15Not applicableUS flag
CyclogylSolution10 mg/1mLOphthalmicPhysicians Total Care, Inc.1996-08-302012-06-30US flag
CyclogylSolution / drops20 mg/1mLOphthalmicALCON LABORATORIES, INC.1975-10-15Not applicableUS flag
CyclopentolateSolution / drops5 mg/1mLOphthalmicAkorn, Inc.2015-12-10Not applicableUS flag
Cyclopentolate HydrochlorideSolution10 mg/1mLOphthalmicA-S Medication Solutions2002-08-22Not applicableUS flag
Cyclopentolate HydrochlorideSolution / drops20 mg/1mLOphthalmicAkorn, Inc.1997-01-13Not applicableUS flag
Cyclopentolate HydrochlorideSolution20 mg/1mLOphthalmicFALCON Pharmaceuticals, Ltd.2002-08-222011-08-05US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
CyclomydrilCyclopentolate hydrochloride (2 mg/1mL) + Phenylephrine hydrochloride (10 mg/1mL)Solution / dropsOphthalmicALCON LABORATORIES, INC.1958-06-30Not applicableUS flag
CYCLOMYDRIL STERILE OPHTHALMIC SOLUTIONCyclopentolate hydrochloride (0.2 %) + Phenylephrine hydrochloride (1 %)SolutionOphthalmicALCON PTE LTD1991-12-09Not applicable
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Mydriatic-3Cyclopentolate hydrochloride (10 mg/1mL) + Phenylephrine hydrochloride (25 mg/1mL) + Tropicamide (10 mg/1mL)Solution / dropsOphthalmicImprimis Njof Llc2018-05-012019-07-01US flag

Categories

ATC Codes
S01FA54 — Cyclopentolate, combinationsS01FA04 — Cyclopentolate
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Not Available
Direct Parent
Benzene and substituted derivatives
Alternative Parents
Cyclopentanols / Tertiary alcohols / Trialkylamines / Cyclic alcohols and derivatives / Carboxylic acid esters / Amino acids and derivatives / Monocarboxylic acids and derivatives / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Alcohol / Amine / Amino acid or derivatives / Aromatic homomonocyclic compound / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cyclic alcohol / Cyclopentanol / Hydrocarbon derivative
show 11 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
tertiary alcohol, tertiary amino compound, carboxylic ester (CHEBI:4024)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
I76F4SHP7J
CAS number
512-15-2
InChI Key
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

References

Synthesis Reference

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

General References
  1. Link [Link]
Human Metabolome Database
HMDB0015114
KEGG Compound
C06932
PubChem Compound
2905
PubChem Substance
46504517
ChemSpider
2802
BindingDB
82375
RxNav
3001
ChEBI
4024
ChEMBL
CHEMBL1201338
Therapeutic Targets Database
DAP001111
PharmGKB
PA164743019
Drugs.com
Drugs.com Drug Page
Wikipedia
Cyclopentolate
MSDS
Download (72.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedDiagnosticRetinopathy of Prematurity (ROP)1
4RecruitingOtherAdverse Drug Events (ADEs) / Cataracts / Dilatation of the pupil1
4Unknown StatusDiagnosticRefractive Errors1
3CompletedTreatmentKeratitis; Infectious Disease (Manifestation)1
2Not Yet RecruitingPreventionCataracts / Miosis1
1WithdrawnNot AvailableRefractive Error - Myopia1
Not AvailableCompletedScreeningRetinopathy of Prematurity (ROP)1
Not AvailableRecruitingNot AvailableCataract Surgery1
Not AvailableTerminatedOtherCataracts1

Pharmacoeconomics

Manufacturers
  • Akorn inc
  • Alcon laboratories inc
  • Alcon universal ltd
  • Sola barnes hind
  • Bausch and lomb pharmaceuticals inc
  • Pharmafair inc
Packagers
  • Akorn Inc.
  • Alcon Laboratories
  • A-S Medication Solutions LLC
  • Bausch & Lomb Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Eye Care and Cure Corp.
  • Eye Supply Usa Inc.
  • Falcon Pharmaceuticals Ltd.
  • Ocusoft
  • Palmetto Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Rebel Distributors Corp.
Dosage Forms
FormRouteStrength
SolutionConjunctival; Ophthalmic10 mg
SolutionOphthalmic10 mg/1mL
SolutionOphthalmic20 mg/1mL
SolutionOphthalmic1 %
Solution / dropsOphthalmic
SolutionOphthalmic0.2 %
Solution / dropsOphthalmic
Solution / dropsOphthalmic5 mg/1mL
SolutionOphthalmic5 mg/1mL
Solution / dropsOphthalmic10 mg/1mL
Solution / dropsOphthalmic20 mg/1mL
Solution / dropsOphthalmic0.5 % w/v
Solution / dropsOphthalmic1 % w/v
SolutionOphthalmic0.5 % w/v
SolutionOphthalmic1 % w/v
SolutionOphthalmic0.5 %
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)134-136Treves, 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0a4i-9000000000-0f0d4362f3985858a9e0
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

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
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...
Gene Name
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
Molecular Weight
51420.375 Da
References
  1. Walkenbach RJ, Ye GS: Muscarinic cholinoceptor regulation of cyclic guanosine monophosphate in human corneal epithelium. Invest Ophthalmol Vis Sci. 1991 Mar;32(3):610-5. [Article]
  2. Solanki P, Cuprian-Beltechi AM, Cunnane TC: Cholinergic innervation of the guinea-pig isolated vas deferens. Naunyn Schmiedebergs Arch Pharmacol. 2007 Dec;376(4):265-74. doi: 10.1007/s00210-007-0198-y. Epub 2007 Nov 9. [Article]
  3. Tokoro T: [Developmental mechanism of low myopia and therapeutic possibilities. A review]. Nippon Ganka Gakkai Zasshi. 1998 Dec;102(12):796-812. [Article]
  4. Cuprian-Beltechi AM, Solanki P, Teramoto N, Cunnane TC: High spatial resolution studies of muscarinic neuroeffector junctions in mouse isolated vas deferens. Neuroscience. 2009 Sep 15;162(4):1366-76. doi: 10.1016/j.neuroscience.2009.05.064. Epub 2009 May 29. [Article]
  5. Kyei S, Nketsiah AA, Asiedu K, Awuah A, Owusu-Ansah A: Onset and duration of cycloplegic action of 1% cyclopentolate - 1% tropicamide combination. Afr Health Sci. 2017 Sep;17(3):923-932. doi: 10.4314/ahs.v17i3.36. [Article]

Enzymes

Kind
Protein
Organism
Humans
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
Uniprot Name
Cholinesterase
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. [Article]

Drug created on June 13, 2005 13:24 / Updated on October 19, 2021 07:39