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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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Ciclopentolato [INN-Spanish]
Cyclopentoiate
Cyclopentolate HCL
Cyclopentolatum [INN-Latin]
Cyclopentylate
Diopentolate
Salts Not Available
Brand names
Name Company
AK-Pentolate
Akpentolate
Cyclogyl
Cylate
Minims Cyclopentolate
Mydrilate
Ocu-Pentolate
Pentolair
Brand mixtures Not Available
Categories
  • Mydriatics
  • Muscarinic Antagonists
  • Parasympatholytics
  • Antimuscarinic eye preparations
CAS number 512-15-2
Weight Average: 291.3853
Monoisotopic: 291.183443671
Chemical Formula C17H25NO3
InChI Key InChIKey=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
Plain Text
IUPAC Name
2-(dimethylamino)ethyl 2-(1-hydroxycyclopentyl)-2-phenylacetate
SMILES
CN(C)CCOC(=O)C(C1=CC=CC=C1)C1(O)CCCC1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenylacetates
Substructures
  • Carboxylic Acids and Derivatives
  • Hydroxy Compounds
  • Acetates
  • Phenylacetates
  • Ethers
  • Benzene and Derivatives
  • Aliphatic and Aryl Amines
  • Alcohols and Polyols
  • Aromatic compounds
Pharmacology
Indication Used mainly to produce mydriasis and cycloplegia for diagnostic purposes.
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).
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
Pharmacoeconomics
Manufacturers
  • Akorn inc
  • Alcon laboratories inc
  • Alcon universal ltd
  • Sola barnes hind
  • Bausch and lomb pharmaceuticals inc
  • Pharmafair inc
Packagers
Dosage forms
Form Route Strength
Liquid Ophthalmic
Solution Ophthalmic
Solution / drops Ophthalmic
Prices
Unit description Cost Unit
Cyclopentolate HCl 1% Solution 15ml Bottle 12.99 USD bottle
Cyclogyl 2% eye drops 11.76 USD ml
Cyclopentolate HCl 1% Solution 2ml Bottle 9.99 USD bottle
Cyclopentolate 1% eye drops 9.35 USD ml
Cyclogyl 1% eye drops 8.97 USD ml
Cylate 1% eye drops 5.02 USD ml
Cyclogyl 0.5% eye drops 3.42 USD ml
Cyclogyl 1 % Solution 0.91 USD ml
Ak-pentolate 1% eye drops 0.71 USD 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 139 °C (hydrochloride salt) Not Available
logP 2.4 Not Available
Predicted Properties
Property Value Source
water solubility 1.50e+00 g/l 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 ChemAxon
rotatable bond count 7 ChemAxon
refractivity 82.81 ChemAxon
polarizability 32.51 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. Link
External Links
Resource Link
KEGG Compound C06932 Link_out
PubChem Compound 2905 Link_out
PubChem Substance 46504517 Link_out
ChemSpider 2802 Link_out
ChEBI 4024 Link_out
ChEMBL 4024 Link_out
Therapeutic Targets Database DAP001111 Link_out
PharmGKB PA164743019 Link_out
Drug Product Database 2148382 Link_out
Drugs.com http://www.drugs.com/cdi/cyclopentolate.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Cyclopentolate Link_out
ATC Codes
  • S01FA04
AHFS Codes
  • 52:24.00
PDB Entries Not Available
FDA label Not Available
MSDS show (72.9 KB)
Interactions
Drug Interactions
Drug Interaction
Tacrine The 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.
Triprolidine Triprolidine and Cyclopentolate, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Trospium Trospium and Cyclopentolate, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Food Interactions Not Available
Targets

1. Muscarinic acetylcholine receptor M1

Pharmacological action: yes
Actions: antagonist

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

Organism class: human
UniProt ID: P11229 Link_out
Gene: CHRM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Enzymes

1. Cholinesterase

Actions: substrate

An acylcholine + H(2)O = choline + a carboxylate

UniProt ID: P06276 Link_out
Gene: BCHE Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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 February 08, 2013 16:19