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Details

Stereochemistry RACEMIC
Molecular Formula C17H25NO3
Molecular Weight 291.3853
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYCLOPENTOLATE

SMILES

CN(C)CCOC(=O)C(C1=CC=CC=C1)C2(O)CCCC2

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 291.3853
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
Randomised controlled trial of ketorolac in the management of corneal abrasions.
2001 Apr
Does instilling proxymetacaine before cyclopentolate significantly reduce stinging? The implications of paediatric cycloplegia.
2001 Feb
[Experiences with cycloplegic drops in German-speaking centers of pediatric ophthalmology and stabology--results of a 1999 survey].
2001 Jan
Ocular injury from the venom of the Southern walkingstick.
2001 Jan
[Biochemical stress monitoring during cataract surgery; phenylephrine 10% shows no changes in serum-catecholamines in comparison with phenylephrine 5%].
2001 Jul
Valsalva retinopathy-like hemorrhage associated with combined trabeculotomy-trabeculectomy in a patient with developmental glaucoma.
2001 Jul-Aug
[Full optical correction after cycloplegia in headache].
2002 Mar
[Cycloplegic effectiveness of cyclopentolate and tropicamide preparations compared with atropinization].
2002 Nov-Dec
[F99, a mental disorder not otherwise specified].
2003
Intracameral mydriatics in phacoemulsification cataract surgery.
2003 Dec
Wavefront analysis in eyes with accommodative spasm.
2003 Dec
Comparison of measurements of refractive errors between the hand-held Retinomax and on-table autorefractors in cyclopleged and noncyclopleged children.
2003 Dec
The Tehran Eye Study: research design and eye examination protocol.
2003 Jul 15
Neonatal hyphema in precipitous delivery with dinoprostone.
2003 Jun
Herpes zoster virus sclerokeratitis and anterior uveitis in a child following varicella vaccination.
2003 Mar
Relationship between cycloplegic and wavefront-derived refraction.
2003 Nov-Dec
Evaluation of surgical performance with intracameral mydriatics in phacoemulsification surgery.
2004 Apr
Comparison of 6-month results of implantation of the 1CU accommodative intraocular lens with conventional intraocular lenses.
2004 Feb
Accuracy of noncycloplegic autorefraction in school-age children in China.
2004 Jan
Pupil dilation and wavefront aberration.
2004 Jan-Feb
Cycloplegic and mydriatic agents for routine ophthalmologic examination: a survey of pediatric ophthalmologists.
2004 Jun
Grand mal seizure in a child 30 minutes after Cyclogyl (cyclopentolate hydrochloride) and 10% Neo-Synephrine (phenylephrine hydrochloride) eye drops were instilled.
2004 May
Optical biometry of the anterior eye segment: interexaminer and intraexaminer reliability of ACMaster.
2005 Dec
Cholinergic innervation of the mouse isolated vas deferens.
2005 Dec
Potentially accommodating intraocular lenses--an in vitro and in vivo study using three-dimensional high-frequency ultrasound.
2005 Jan-Feb
Lack of efficacy of dilated screening for retinoblastoma.
2005 Jul-Aug
Axial growth and changes in lenticular and corneal power during emmetropization in infants.
2005 Sep
Pseudophakic accommodation and pseudoaccommodation under physiological conditions measured with partial coherence interferometry.
2006 Aug
Cataractous changes due to posterior chamber flattening with a posterior chamber phakic intraocular lens secondary to the administration of pilocarpine.
2006 Aug
Changes in astigmatism in children with congenital nystagmus.
2006 Aug
Pseudophakic accommodation with 2 models of foldable intraocular lenses.
2006 Feb
A comparison of autorefraction and subjective refraction with and without cycloplegia in primary school children.
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
Pseudallescheria boydii keratitis.
2006 Mar-Apr
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 Thu Jul 06 00:06:43 UTC 2023
Edited
by admin
on Thu Jul 06 00:06:43 UTC 2023
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
Cyclopentolate [WHO-DD]
Common Name English
2-(DIMETHYLAMINO)ETHYL (±)-1-HYDROXY-.ALPHA.-PHENYLCYCLOPENTANEACETATE
Systematic Name English
cyclopentolate [INN]
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 Thu Jul 06 00:06:43 UTC 2023 , Edited by admin on Thu Jul 06 00:06:43 UTC 2023
WHO-VATC QS01FA04
Created by admin on Thu Jul 06 00:06:43 UTC 2023 , Edited by admin on Thu Jul 06 00:06:43 UTC 2023
WHO-ATC S01BB01
Created by admin on Thu Jul 06 00:06:43 UTC 2023 , Edited by admin on Thu Jul 06 00:06:43 UTC 2023
WHO-ATC S01FA04
Created by admin on Thu Jul 06 00:06:43 UTC 2023 , Edited by admin on Thu Jul 06 00:06:43 UTC 2023
WHO-ATC S01FA54
Created by admin on Thu Jul 06 00:06:43 UTC 2023 , Edited by admin on Thu Jul 06 00:06:43 UTC 2023
NCI_THESAURUS C29706
Created by admin on Thu Jul 06 00:06:43 UTC 2023 , Edited by admin on Thu Jul 06 00:06:43 UTC 2023
Code System Code Type Description
ChEMBL
CHEMBL1201338
Created by admin on Thu Jul 06 00:06:43 UTC 2023 , Edited by admin on Thu Jul 06 00:06:43 UTC 2023
PRIMARY
DRUG BANK
DB00979
Created by admin on Thu Jul 06 00:06:43 UTC 2023 , Edited by admin on Thu Jul 06 00:06:43 UTC 2023
PRIMARY
EVMPD
SUB06858MIG
Created by admin on Thu Jul 06 00:06:43 UTC 2023 , Edited by admin on Thu Jul 06 00:06:43 UTC 2023
PRIMARY
ECHA (EC/EINECS)
208-136-4
Created by admin on Thu Jul 06 00:06:43 UTC 2023 , Edited by admin on Thu Jul 06 00:06:43 UTC 2023
PRIMARY
CAS
512-15-2
Created by admin on Thu Jul 06 00:06:43 UTC 2023 , Edited by admin on Thu Jul 06 00:06:43 UTC 2023
PRIMARY
FDA UNII
I76F4SHP7J
Created by admin on Thu Jul 06 00:06:43 UTC 2023 , Edited by admin on Thu Jul 06 00:06:43 UTC 2023
PRIMARY
CHEBI
4024
Created by admin on Thu Jul 06 00:06:43 UTC 2023 , Edited by admin on Thu Jul 06 00:06:43 UTC 2023
PRIMARY
MESH
D003519
Created by admin on Thu Jul 06 00:06:43 UTC 2023 , Edited by admin on Thu Jul 06 00:06:43 UTC 2023
PRIMARY
NCI_THESAURUS
C61693
Created by admin on Thu Jul 06 00:06:43 UTC 2023 , Edited by admin on Thu Jul 06 00:06:43 UTC 2023
PRIMARY
WIKIPEDIA
Cyclopentolate
Created by admin on Thu Jul 06 00:06:43 UTC 2023 , Edited by admin on Thu Jul 06 00:06:43 UTC 2023
PRIMARY
MERCK INDEX
M4011
Created by admin on Thu Jul 06 00:06:43 UTC 2023 , Edited by admin on Thu Jul 06 00:06:43 UTC 2023
PRIMARY Merck Index
PUBCHEM
2905
Created by admin on Thu Jul 06 00:06:43 UTC 2023 , Edited by admin on Thu Jul 06 00:06:43 UTC 2023
PRIMARY
INN
266
Created by admin on Thu Jul 06 00:06:43 UTC 2023 , Edited by admin on Thu Jul 06 00:06:43 UTC 2023
PRIMARY
DAILYMED
I76F4SHP7J
Created by admin on Thu Jul 06 00:06:43 UTC 2023 , Edited by admin on Thu Jul 06 00:06:43 UTC 2023
PRIMARY
LACTMED
Cyclopentolate
Created by admin on Thu Jul 06 00:06:43 UTC 2023 , Edited by admin on Thu Jul 06 00:06:43 UTC 2023
PRIMARY
IUPHAR
7153
Created by admin on Thu Jul 06 00:06:43 UTC 2023 , Edited by admin on Thu Jul 06 00:06:43 UTC 2023
PRIMARY
DRUG CENTRAL
757
Created by admin on Thu Jul 06 00:06:43 UTC 2023 , Edited by admin on Thu Jul 06 00:06:43 UTC 2023
PRIMARY
EPA CompTox
DTXSID3048528
Created by admin on Thu Jul 06 00:06:43 UTC 2023 , Edited by admin on Thu Jul 06 00:06:43 UTC 2023
PRIMARY
SMS_ID
100000083774
Created by admin on Thu Jul 06 00:06:43 UTC 2023 , Edited by admin on Thu Jul 06 00:06:43 UTC 2023
PRIMARY
RXCUI
3001
Created by admin on Thu Jul 06 00:06:43 UTC 2023 , Edited by admin on Thu Jul 06 00:06:43 UTC 2023
PRIMARY RxNorm
Related Record Type Details
TARGET -> INHIBITOR
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY