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Details

Stereochemistry RACEMIC
Molecular Formula C17H25NO3
Molecular Weight 291.3859
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYCLOPENTOLATE

SMILES

CN(C)CCOC(=O)C(c1ccccc1)C2(CCCC2)O

InChI

InChIKey=SKYSRIRYMSLOIN-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C17H25NO3
Molecular Weight 291.3859
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/mesh/68003519

Cyclopentolate (cyclopentolate hydrochloride) is a parasympatholytic anticholinergic used solely to obtain mydriasis or cycloplegia. This anticholinergic preparation blocks the responses of the sphincter muscle of the iris and the accommodative muscle of the ciliary body to cholinergic stimulation, producing pupillary dilation (mydriasis) and paralysis of accommodation (cycloplegia). It acts rapidly, but has a shorter duration than atropine. Maximal cycloplegia occurs within 25 to 75 minutes after instillation. Complete recovery of accommodation usually takes 6 to 24 hours. Complete recovery from mydriasis in some individuals may require several days. Heavily pigmented irides may require more doses than lightly pigmented irides.

CNS Activity

Curator's Comment:: This preparation may cause CNS disturbances. This is especially true in younger age groups, but may occur at any age, especially with the stronger cyclopentolate hydrochloride solutions.

Originator

Curator's Comment:: Treves, G.R.; US. Patent 2,554,511; May 29,1951; assigned to Schieffelin & Co.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
10.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
PENTOLAIR

Approved Use

Cyclopentolate Hydrochloride Ophthalmic Solution is used to produce mydriasis and cycloplegia in diagnostic procedures.

Launch Date

7.6757762E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.8 ng/mL
2 drop single, ocular
dose: 2 drop
route of administration: Ocular
experiment type: SINGLE
co-administered:
CYCLOPENTOLATE HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
324 ng × min/mL
2 drop single, ocular
dose: 2 drop
route of administration: Ocular
experiment type: SINGLE
co-administered:
CYCLOPENTOLATE HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
112 min
2 drop single, ocular
dose: 2 drop
route of administration: Ocular
experiment type: SINGLE
co-administered:
CYCLOPENTOLATE HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1 % 1 times / 5 min multiple, topical
Overdose
Dose: 1 %, 1 times / 5 min
Route: topical
Route: multiple
Dose: 1 %, 1 times / 5 min
Sources: Page: e704
unknown, 90 days
n = 1
Health Status: unknown
Condition: mydriasis induction
Age Group: 90 days
Sex: F
Population Size: 1
Sources: Page: e704
Other AEs: Vomiting, Cyanosis...
Other AEs:
Vomiting
Cyanosis
Respiratory distress
Sources: Page: e704
2 % single, topical
Recommended
unknown
Other AEs: Ataxia, Disorder speech...
Other AEs:
Ataxia
Disorder speech
Restlessness
Hallucinations
Hyperactivity
Seizures
Confusion and disorientation
Other specified visual disturbances
Sources:
AEs

AEs

AESignificanceDosePopulation
Cyanosis
1 % 1 times / 5 min multiple, topical
Overdose
Dose: 1 %, 1 times / 5 min
Route: topical
Route: multiple
Dose: 1 %, 1 times / 5 min
Sources: Page: e704
unknown, 90 days
n = 1
Health Status: unknown
Condition: mydriasis induction
Age Group: 90 days
Sex: F
Population Size: 1
Sources: Page: e704
Respiratory distress
1 % 1 times / 5 min multiple, topical
Overdose
Dose: 1 %, 1 times / 5 min
Route: topical
Route: multiple
Dose: 1 %, 1 times / 5 min
Sources: Page: e704
unknown, 90 days
n = 1
Health Status: unknown
Condition: mydriasis induction
Age Group: 90 days
Sex: F
Population Size: 1
Sources: Page: e704
Vomiting
1 % 1 times / 5 min multiple, topical
Overdose
Dose: 1 %, 1 times / 5 min
Route: topical
Route: multiple
Dose: 1 %, 1 times / 5 min
Sources: Page: e704
unknown, 90 days
n = 1
Health Status: unknown
Condition: mydriasis induction
Age Group: 90 days
Sex: F
Population Size: 1
Sources: Page: e704
Ataxia
2 % single, topical
Recommended
unknown
Confusion and disorientation
2 % single, topical
Recommended
unknown
Disorder speech
2 % single, topical
Recommended
unknown
Hallucinations
2 % single, topical
Recommended
unknown
Hyperactivity
2 % single, topical
Recommended
unknown
Other specified visual disturbances
2 % single, topical
Recommended
unknown
Restlessness
2 % single, topical
Recommended
unknown
Seizures
2 % single, topical
Recommended
unknown
PubMed

PubMed

TitleDatePubMed
Evaluation of surgical performance with intracameral mydriatics in phacoemulsification surgery.
2004 Apr
Parameters of drug antagonism: re-examination of two modes of functional competitive drug antagonism on intraocular muscles.
2004 Aug
Indocyanine green angiography in ocular tuberculosis.
2004 Dec
Comparison of 6-month results of implantation of the 1CU accommodative intraocular lens with conventional intraocular lenses.
2004 Feb
Angioedema related to the use of hyaluronidase in cataract surgery.
2004 Jul
Cycloplegic and mydriatic agents for routine ophthalmologic examination: a survey of pediatric ophthalmologists.
2004 Jun
The effect of off-the-visual-axis retinoscopy on objective refractive measurement.
2004 Jun
Comparison of the handheld Retinomax K-Plus2 and on-table autokeratometers in children with and without cycloplegia.
2004 Mar
Grand mal seizure in a child 30 minutes after Cyclogyl (cyclopentolate hydrochloride) and 10% Neo-Synephrine (phenylephrine hydrochloride) eye drops were instilled.
2004 May
Refractive astigmatism and the toricity of ocular components in human infants.
2004 Oct
The effects of cyclopentolate on intraocular pressure and retrobulbar hemodynamics in patients with pseudoexfoliation syndrome and pseudoexfoliation glaucoma.
2004 Sep-Oct
Comparison of tropicamide and cyclopentolate for cycloplegic refractions in myopic adult refractive surgery patients.
2005 Apr
Effect of (+) or (-) camphorsulfonic acid additives to the mobile phase on enantioseparations of some basic drugs on a Chiralcel OD column.
2005 Aug 12
Cholinergic innervation of the mouse isolated vas deferens.
2005 Dec
Quantitative determination of pharmaceuticals using nano-electrospray ionization mass spectrometry after reversed phase mini-solid phase extraction.
2005 Feb 23
Potentially accommodating intraocular lenses--an in vitro and in vivo study using three-dimensional high-frequency ultrasound.
2005 Jan-Feb
Drug-induced intraocular lens movement and near visual acuity after AcrySof intraocular lens implantation.
2005 Jul
Accuracy of a new photo-refractometer in young and adult patients.
2005 Jul
Lack of efficacy of dilated screening for retinoblastoma.
2005 Jul-Aug
Stimulus-driven versus pilocarpine-induced biometric changes in pseudophakic eyes.
2005 Mar
Feasibility of ambulatory overnight oximetry in consecutive patients in a dementia clinic.
2005 Mar
Ultrasound biomicroscopy of the rat eye: effects of cholinergic and anticholinergic agents.
2005 May
Comparison of mydriatic regimens used in screening for retinopathy of prematurity in preterm infants with dark irides.
2005 May-Jun
Axial growth and changes in lenticular and corneal power during emmetropization in infants.
2005 Sep
Macular star associated with Behçet disease.
2006 Apr
Cataract surgery by appointment--a pilot study.
2006 Apr 20
Pseudophakic accommodation and pseudoaccommodation under physiological conditions measured with partial coherence interferometry.
2006 Aug
Changes in astigmatism in children with congenital nystagmus.
2006 Aug
Pseudophakic accommodation with 2 models of foldable intraocular lenses.
2006 Feb
Pharmacological-induced haptic changes and the accommodative performance in patients with the AT-45 accommodative IOL.
2006 Feb
Redilatation with intracameral mydriatics in phacoemulsification surgery.
2006 Feb
Analysis of patients with good uncorrected distance and near vision after monofocal intraocular lens implantation.
2006 Jul
Correctable and non-correctable visual impairment in a population-based sample of 12-year-old Australian children.
2006 Jul
A comparison of autorefraction and subjective refraction with and without cycloplegia in primary school children.
2006 Jul
Factors associated with childhood strabismus: findings from a population-based study.
2006 Jul
Toxic keratolysis from combined use of nonsteroid anti-inflammatory drugs and topical steroids following vitreoretinal surgery.
2006 Jul-Aug
Effects of mydriatics on intraocular pressure and pupil size in the normal feline eye.
2006 Jul-Aug
Accommodative spasm after laser-assisted in situ keratomileusis (LASIK).
2006 Jun
Safety of intracameral mydriasis in phacoemulsification cataract surgery.
2006 Mar
Defining myopia using refractive error and uncorrected logMAR visual acuity >0.3 from 1334 Singapore school children ages 7-9 years.
2006 Mar
Pseudallescheria boydii keratitis.
2006 Mar-Apr
The effect of phenylephrine and cyclopentolate on objective wavefront measurements.
2006 May
A preoperative mixture of anesthetic jelly, dilating drops, antibiotics, and anti-inflammatories for cataract surgery.
2006 May-Jun
[Neurotoxic effects induced by the topical administration of cycloplegics. A case report and review of the literature].
2006 Nov 16-30
[Comparative study of cyclopentolate drops versus spray in cycloplegia in children].
2006 Oct
Cataract surgery management in patients taking tamsulosin staged approach.
2006 Oct
Controls required to assess IOL movement during accommodation.
2006 Oct
Part-time occlusion therapy for anisometropic amblyopia detected in children eight years of age and older.
2006 Sep
Performance of the crystalens.
2006 Sep
Refractive error and patterns of spectacle use in 12-year-old Australian children.
2006 Sep
Patents

Patents

Sample Use Guides

Instill one or two drops of 1% solution in the eye which may be repeated in five to ten minutes if necessary. Complete recovery usually occurs in 24 hours. Complete recovery from mydriasis in some individuals may require several days.
Route of Administration: Other
In Vitro Use Guide
Cultured human corneal epithelial cells showed high-affinity, specific binding to the muscarinic cholinergic antagonist, 3H-quinuclidinyl benzilate (3H-QNB). The binding sites had a dissociation constant of 3.9 nM and a maximal binding capacity of 880 fmol bound/mg protein. Other muscarinic antagonists (cyclopentolate and atropine) effectively competed for binding with 3H-QNB at low concentrations (IC50 = 10 nM).
Substance Class Chemical
Created
by admin
on Sat Jun 26 03:20:29 UTC 2021
Edited
by admin
on Sat Jun 26 03:20:29 UTC 2021
Record UNII
I76F4SHP7J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CYCLOPENTOLATE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
BENZENEACETIC ACID, .ALPHA.-(1-HYDROXYCYCLOPENTYL)-, 2-(DIMETHYLAMINO)ETHYL ESTER
Common Name English
2-(DIMETHYLAMINO)ETHYL (+/-)-1-HYDROXY-.ALPHA.-PHENYLCYCLOPENTANEACETATE
Systematic Name English
CYCLOPENTOLATE [INN]
Common Name English
CYCLOPENTOLATE [WHO-DD]
Common Name English
BELL PENTOLATE
Brand Name English
CYCLOPENTOLATE [MI]
Common Name English
CYCLOPENTOLATE [VANDF]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29704
Created by admin on Sat Jun 26 03:20:29 UTC 2021 , Edited by admin on Sat Jun 26 03:20:29 UTC 2021
WHO-VATC QS01FA04
Created by admin on Sat Jun 26 03:20:29 UTC 2021 , Edited by admin on Sat Jun 26 03:20:29 UTC 2021
WHO-ATC S01BB01
Created by admin on Sat Jun 26 03:20:29 UTC 2021 , Edited by admin on Sat Jun 26 03:20:29 UTC 2021
WHO-ATC S01FA04
Created by admin on Sat Jun 26 03:20:29 UTC 2021 , Edited by admin on Sat Jun 26 03:20:29 UTC 2021
WHO-ATC S01FA54
Created by admin on Sat Jun 26 03:20:29 UTC 2021 , Edited by admin on Sat Jun 26 03:20:29 UTC 2021
NCI_THESAURUS C29706
Created by admin on Sat Jun 26 03:20:29 UTC 2021 , Edited by admin on Sat Jun 26 03:20:29 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL1201338
Created by admin on Sat Jun 26 03:20:29 UTC 2021 , Edited by admin on Sat Jun 26 03:20:29 UTC 2021
PRIMARY
DRUG BANK
DB00979
Created by admin on Sat Jun 26 03:20:29 UTC 2021 , Edited by admin on Sat Jun 26 03:20:29 UTC 2021
PRIMARY
EVMPD
SUB06858MIG
Created by admin on Sat Jun 26 03:20:29 UTC 2021 , Edited by admin on Sat Jun 26 03:20:29 UTC 2021
PRIMARY
ECHA (EC/EINECS)
208-136-4
Created by admin on Sat Jun 26 03:20:29 UTC 2021 , Edited by admin on Sat Jun 26 03:20:29 UTC 2021
PRIMARY
CAS
512-15-2
Created by admin on Sat Jun 26 03:20:29 UTC 2021 , Edited by admin on Sat Jun 26 03:20:29 UTC 2021
PRIMARY
FDA UNII
I76F4SHP7J
Created by admin on Sat Jun 26 03:20:29 UTC 2021 , Edited by admin on Sat Jun 26 03:20:29 UTC 2021
PRIMARY
MESH
D003519
Created by admin on Sat Jun 26 03:20:29 UTC 2021 , Edited by admin on Sat Jun 26 03:20:29 UTC 2021
PRIMARY
NCI_THESAURUS
C61693
Created by admin on Sat Jun 26 03:20:29 UTC 2021 , Edited by admin on Sat Jun 26 03:20:29 UTC 2021
PRIMARY
WIKIPEDIA
Cyclopentolate
Created by admin on Sat Jun 26 03:20:29 UTC 2021 , Edited by admin on Sat Jun 26 03:20:29 UTC 2021
PRIMARY
MERCK INDEX
M4011
Created by admin on Sat Jun 26 03:20:29 UTC 2021 , Edited by admin on Sat Jun 26 03:20:29 UTC 2021
PRIMARY Merck Index
PUBCHEM
2905
Created by admin on Sat Jun 26 03:20:29 UTC 2021 , Edited by admin on Sat Jun 26 03:20:29 UTC 2021
PRIMARY
INN
266
Created by admin on Sat Jun 26 03:20:29 UTC 2021 , Edited by admin on Sat Jun 26 03:20:29 UTC 2021
PRIMARY
LACTMED
Cyclopentolate
Created by admin on Sat Jun 26 03:20:29 UTC 2021 , Edited by admin on Sat Jun 26 03:20:29 UTC 2021
PRIMARY
IUPHAR
7153
Created by admin on Sat Jun 26 03:20:29 UTC 2021 , Edited by admin on Sat Jun 26 03:20:29 UTC 2021
PRIMARY
DRUG CENTRAL
757
Created by admin on Sat Jun 26 03:20:29 UTC 2021 , Edited by admin on Sat Jun 26 03:20:29 UTC 2021
PRIMARY
EPA CompTox
512-15-2
Created by admin on Sat Jun 26 03:20:29 UTC 2021 , Edited by admin on Sat Jun 26 03:20:29 UTC 2021
PRIMARY
RXCUI
3001
Created by admin on Sat Jun 26 03:20:29 UTC 2021 , Edited by admin on Sat Jun 26 03:20:29 UTC 2021
PRIMARY RxNorm
Related Record Type Details
TARGET -> INHIBITOR
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY