Identification

Name
Cyclopentolate
Accession Number
DB00979  (APRD00893)
Type
Small Molecule
Groups
Approved
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
Product Ingredients
IngredientUNIICASInChI Key
Cyclopentolate Hydrochloride736I6971TE5870-29-1RHKZVMUBMXGOLL-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CyclogylSolution / drops1 %OphthalmicNovartis1972-12-31Not applicableCanada
CyclopentolateSolution0.5 %OphthalmicEberth Pharmaceuticals Inc1994-12-31Not applicableCanada
CyclopentolateSolution1 %OphthalmicEberth Pharmaceuticals Inc1994-12-31Not applicableCanada
Minims Cyclopentolate Hydrochloride 0.5%Solution / drops0.5 %OphthalmicValeant Canada Lp Valeant Canada S.E.C.1995-12-31Not applicableCanada
Minims Cyclopentolate Hydrochloride 1%Solution / drops1 %OphthalmicValeant Canada Lp Valeant Canada S.E.C.1995-12-31Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ak-pentolateSolution / drops10 mg/1mLOphthalmicRebel Distributors1997-01-13Not applicableUs
CyclogylSolution / drops20 mg/1mLOphthalmicAlcon, Inc.1975-10-15Not applicableUs
CyclogylSolution / drops10 mg/1mLOphthalmicAlcon, Inc.1975-10-15Not applicableUs
CyclogylSolution20 mg/1mLOphthalmicPhysicians Total Care, Inc.2002-11-012012-06-30Us
CyclogylSolution / drops5 mg/1mLOphthalmicAlcon, Inc.1975-10-15Not applicableUs
CyclogylSolution10 mg/1mLOphthalmicPhysicians Total Care, Inc.1996-08-302012-06-30Us
CyclopentolateSolution / drops5 mg/1mLOphthalmicAkorn2015-12-10Not applicableUs
Cyclopentolate HydrochlorideSolution / drops20 mg/1mLOphthalmicAkorn1997-01-13Not applicableUs
Cyclopentolate HydrochlorideSolution / drops10 mg/1mLOphthalmicBauch & Lomb Incorporated1994-04-29Not applicableUs
Cyclopentolate HydrochlorideSolution / drops10 mg/1mLOphthalmicPhysicians Total Care, Inc.2013-01-10Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
CyclomydrilCyclopentolate Hydrochloride (2 mg/1mL) + Phenylephrine hydrochloride (10 mg/1mL)Solution / dropsOphthalmicAlcon, Inc.1958-06-30Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Mydriatic-3Cyclopentolate Hydrochloride (10 mg/1mL) + Phenylephrine hydrochloride (25 mg/1mL) + Tropicamide (10 mg/1mL)Solution / dropsOphthalmicImprimis Njof Llc2018-05-01Not applicableUs
International/Other Brands
Bell Pentolate / Cylate (Ocusoft) / Mydrilate (Intrapharm) / Ocu-Pentolate / Pentolair
Categories
UNII
I76F4SHP7J
CAS number
512-15-2
Weight
Average: 291.3853
Monoisotopic: 291.183443671
Chemical Formula
C17H25NO3
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

Pharmacology

Indication

Used mainly to produce mydriasis and cycloplegia for diagnostic purposes.

Associated Conditions
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
Human
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
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.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
1,10-PhenanthrolineThe therapeutic efficacy of Cyclopentolate can be decreased when used in combination with 1,10-Phenanthroline.
AclidiniumCyclopentolate may increase the anticholinergic activities of Aclidinium.
AgmatineThe risk or severity of adverse effects can be increased when Cyclopentolate is combined with Agmatine.
AlcuroniumThe risk or severity of adverse effects can be increased when Cyclopentolate is combined with Alcuronium.
AlfentanilThe risk or severity of adverse effects can be increased when Cyclopentolate is combined with Alfentanil.
AlphacetylmethadolThe risk or severity of adverse effects can be increased when Cyclopentolate is combined with Alphacetylmethadol.
AlphaprodineThe risk or severity of adverse effects can be increased when Cyclopentolate is combined with Alphaprodine.
AmbenoniumThe therapeutic efficacy of Cyclopentolate can be decreased when used in combination with Ambenonium.
AmikacinThe therapeutic efficacy of Cyclopentolate can be decreased when used in combination with Amikacin.
AmitriptylineThe risk or severity of adverse effects can be increased when Cyclopentolate is combined with Amitriptyline.
Food Interactions
Not 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
Human Metabolome Database
HMDB0015114
KEGG Compound
C06932
PubChem Compound
2905
PubChem Substance
46504517
ChemSpider
2802
BindingDB
82375
ChEBI
4024
ChEMBL
CHEMBL1201338
Therapeutic Targets Database
DAP001111
PharmGKB
PA164743019
Drugs.com
Drugs.com Drug Page
Wikipedia
Cyclopentolate
ATC Codes
S01FA54 — Cyclopentolate, combinationsS01FA04 — Cyclopentolate
AHFS Codes
  • 52:24.00 — Mydriatics
MSDS
Download (72.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1WithdrawnNot AvailableRefractive Error - Myopia1
4Not Yet RecruitingOtherAdverse Drug Events / Cataracts / Mydriasis1
4Unknown StatusDiagnosticRefractive Errors1
Not AvailableCompletedScreeningRetinopathy of Prematurity (ROP)1
Not AvailableRecruitingOtherCataracts1

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
SolutionOphthalmic10 mg/1mL
SolutionOphthalmic20 mg/1mL
Solution / dropsOphthalmic5 mg/1mL
SolutionOphthalmic5 mg/1mL
Solution / dropsOphthalmic10 mg/1mL
Solution / dropsOphthalmic20 mg/1mL
Solution / dropsOphthalmic0.5 %
Solution / dropsOphthalmic1 %
Solution / dropsOphthalmic
SolutionOphthalmic0.5 %
SolutionOphthalmic1 %
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

Taxonomy

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
Monocyclic benzene moiety / Cyclopentanol / Cyclic alcohol / Tertiary alcohol / Amino acid or derivatives / Carboxylic acid ester / Tertiary aliphatic amine / Tertiary amine / Carboxylic acid derivative / Monocarboxylic acid or derivatives
show 11 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
tertiary alcohol, tertiary amino compound, carboxylic ester (CHEBI:4024)

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...
Gene Name
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
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
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. [PubMed:15121994]

Drug created on June 13, 2005 07:24 / Updated on September 22, 2018 22:28