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
Structure for Cyclopentolate (DB00979)
- 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.
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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).
Target Actions Organism AMuscarinic acetylcholine receptor M1 antagonistHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAclidinium The risk or severity of adverse effects can be increased when Cyclopentolate is combined with Aclidinium. Alloin The therapeutic efficacy of Alloin can be decreased when used in combination with Cyclopentolate. Amantadine The risk or severity of adverse effects can be increased when Amantadine is combined with Cyclopentolate. Amitriptyline The risk or severity of adverse effects can be increased when Amitriptyline is combined with Cyclopentolate. Amobarbital The risk or severity of adverse effects can be increased when Cyclopentolate is combined with Amobarbital. Amoxapine The risk or severity of adverse effects can be increased when Amoxapine is combined with Cyclopentolate. Anisotropine methylbromide The risk or severity of adverse effects can be increased when Anisotropine methylbromide is combined with Cyclopentolate. Aripiprazole The risk or severity of adverse effects can be increased when Cyclopentolate is combined with Aripiprazole. Atracurium The risk or severity of adverse effects can be increased when Cyclopentolate is combined with Atracurium. Atracurium besylate The risk or severity of adverse effects can be increased when Atracurium besylate is combined with Cyclopentolate. 
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- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Cyclopentolate hydrochloride 736I6971TE 5870-29-1 RHKZVMUBMXGOLL-UHFFFAOYSA-N - International/Other Brands
- Bell Pentolate / Cylate (Ocusoft) / Mydrilate (Intrapharm) / Ocu-Pentolate / Pentolair
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cyclogyl Solution / drops 1 % w/v Ophthalmic Alcon, Inc. 1972-12-31 Not applicable Canada 
Cyclopentolate Solution 0.5 % Ophthalmic Pharma Stulln Inc. 1994-12-31 2020-01-15 Canada Cyclopentolate Solution 1 % Ophthalmic Pharma Stulln Inc. 1994-12-31 2020-01-15 Canada Minims Cyclopentolate Hydrochloride Solution 1 % w/v Ophthalmic Bausch & Lomb Inc 1995-12-31 Not applicable Canada Minims Cyclopentolate Hydrochloride Solution 0.5 % w/v Ophthalmic Bausch & Lomb Inc 1995-12-31 Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ak-pentolate Solution / drops 10 mg/1mL Ophthalmic Rebel Distributors 1997-01-13 Not applicable US 
Cyclogyl Solution / drops 20 mg/1mL Ophthalmic ALCON LABORATORIES, INC. 1975-10-15 Not applicable US Cyclogyl Solution 20 mg/1mL Ophthalmic Physicians Total Care, Inc. 2002-11-01 2012-06-30 US Cyclogyl Solution / drops 10 mg/1mL Ophthalmic ALCON LABORATORIES, INC. 1975-10-15 Not applicable US Cyclogyl Solution 10 mg/1mL Ophthalmic Physicians Total Care, Inc. 1996-08-30 2012-06-30 US Cyclogyl Solution / drops 5 mg/1mL Ophthalmic ALCON LABORATORIES, INC. 1975-10-15 Not applicable US Cyclopentolate Solution / drops 5 mg/1mL Ophthalmic Akorn 2015-12-10 Not applicable US Cyclopentolate Hydrochloride Solution / drops 10 mg/1mL Ophthalmic Bausch & Lomb Incorporated 1994-04-29 Not applicable US Cyclopentolate Hydrochloride Solution 10 mg/1mL Ophthalmic Sandoz Inc. 2002-08-22 Not applicable US Cyclopentolate Hydrochloride Solution / drops 20 mg/1mL Ophthalmic Akorn 1997-01-13 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Cyclomydril Cyclopentolate hydrochloride (2 mg/1mL) + Phenylephrine hydrochloride (10 mg/1mL) Solution / drops Ophthalmic ALCON LABORATORIES, INC. 1958-06-30 Not applicable US CYCLOMYDRIL STERILE OPHTHALMIC SOLUTION Cyclopentolate hydrochloride (0.2 %) + Phenylephrine hydrochloride (1 %) Solution Ophthalmic ALCON PTE LTD 1991-12-09 Not applicable Singapore 
- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Mydriatic-3 Cyclopentolate hydrochloride (10 mg/1mL) + Phenylephrine hydrochloride (25 mg/1mL) + Tropicamide (10 mg/1mL) Solution / drops Ophthalmic Imprimis Njof Llc 2018-05-01 2019-07-01 US
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
- Link [Link]
- External Links
- Human Metabolome Database
- HMDB0015114
- KEGG Compound
- C06932
- PubChem Compound
- 2905
- PubChem Substance
- 46504517
- ChemSpider
- 2802
- BindingDB
- 82375
- 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
Phase Status Purpose Conditions Count 4 Completed Diagnostic Retinopathy of Prematurity (ROP) 1 4 Completed Treatment Cycloplegia 1 4 Unknown Status Diagnostic Refractive Errors 1 4 Unknown Status Other Adverse Drug Reaction (ADR) / Cataracts / Dilatation of the pupil 1 3 Completed Treatment Keratitis; Infectious Disease (Manifestation) 1 2 Unknown Status Prevention Cataracts / Miosis 1 1 Withdrawn Not Available Refractive Error - Myopia 1 Not Available Completed Diagnostic Amblyopia / Anisometropia / Strabismus 1 Not Available Completed Prevention Posterior Synechiae of Iris 1 Not Available Completed Screening Retinopathy of Prematurity (ROP) 1
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
Form Route Strength Solution Conjunctival; Ophthalmic 10 mg Solution Ophthalmic 10 mg/1mL Solution Ophthalmic 20 mg/1mL Solution / drops Ophthalmic 1 % w/v Solution Ophthalmic 1 % Solution / drops Ophthalmic Solution Ophthalmic 0.2 % Solution / drops Ophthalmic Solution / drops Ophthalmic 5 mg/1mL Solution Ophthalmic 5 mg/1mL Solution / drops Ophthalmic 10 mg/1mL Solution / drops Ophthalmic 20 mg/1mL Solution Ophthalmic 0.5 % w/v Solution Ophthalmic 1 % w/v Solution Ophthalmic 0.5 % Liquid Ophthalmic 1 % Solution Ophthalmic 10.000 mg Solution / drops Ophthalmic 1 % - Prices
Unit description Cost Unit Cyclopentolate HCl 1% Solution 15ml Bottle 12.99USD bottle Cyclogyl 2% eye drops 11.76USD ml Cyclopentolate HCl 1% Solution 2ml Bottle 9.99USD bottle Cyclopentolate 1% eye drops 9.35USD ml Cyclogyl 1% eye drops 8.97USD ml Cylate 1% eye drops 5.02USD ml Cyclogyl 0.5% eye drops 3.42USD ml Cyclogyl 1 % Solution 0.91USD ml Ak-pentolate 1% eye drops 0.71USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 134-136 Treves, G.R.; US. Patent 2,554,511; May 29,1951; assigned to Schieffelin & Co. logP 2.4 Not Available - Predicted Properties
Property Value Source Water Solubility 1.5 mg/mL ALOGPS logP 2.09 ALOGPS logP 2.32 Chemaxon logS -2.3 ALOGPS pKa (Strongest Acidic) 14.19 Chemaxon pKa (Strongest Basic) 8.42 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 49.77 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 82.81 m3·mol-1 Chemaxon Polarizability 32.51 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - 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 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9232 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available GC-MS Spectrum - EI-B GC-MS splash10-0a4i-9000000000-0f0d4362f3985858a9e0 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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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
- 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]
- 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]
- Tokoro T: [Developmental mechanism of low myopia and therapeutic possibilities. A review]. Nippon Ganka Gakkai Zasshi. 1998 Dec;102(12):796-812. [Article]
- 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]
- 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
- 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 at June 13, 2005 13:24 / Updated at September 25, 2023 04:25