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Details

Stereochemistry RACEMIC
Molecular Formula C17H25NO3.ClH
Molecular Weight 327.846
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYCLOPENTOLATE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=RHKZVMUBMXGOLL-UHFFFAOYSA-N
InChI=1S/C17H25NO3.ClH/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;1H

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 ( + / - )
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

CNS Active
4002
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

Schieffelin
4
Curator's Comment: Treves, G.R.; US. Patent 2,554,511; May 29,1951; assigned to Schieffelin & Co.

Approval Year

1953
193
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
 10.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Approved
8583
PENTOLAIR

Approved Use

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

Launch Date

1994
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.8 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8512760
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8512760
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8512760
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:
https://pubmed.ncbi.nlm.nih.gov/22908101
unknown, 90 days
Health Status: unknown
Age Group: 90 days
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/22908101
Other AEs: Vomiting, Cyanosis...
Other AEs:
Vomiting
Cyanosis
Respiratory distress
Sources:
https://pubmed.ncbi.nlm.nih.gov/22908101
2 % single, topical
Recommended
Dose: 2 %
Route: topical
Route: single
Dose: 2 %
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=ad85b220-6003-4a78-b900-5195ceaf0fd5&type=display
unknown
Health Status: unknown
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=ad85b220-6003-4a78-b900-5195ceaf0fd5&type=display
Other AEs: Ataxia, Disorder speech...
Other AEs:
Ataxia
Disorder speech
Restlessness
Hallucinations
Hyperactivity
Seizures
Confusion and disorientation
Other specified visual disturbances
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=ad85b220-6003-4a78-b900-5195ceaf0fd5&type=display
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:
https://pubmed.ncbi.nlm.nih.gov/22908101
unknown, 90 days
Health Status: unknown
Age Group: 90 days
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/22908101
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:
https://pubmed.ncbi.nlm.nih.gov/22908101
unknown, 90 days
Health Status: unknown
Age Group: 90 days
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/22908101
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:
https://pubmed.ncbi.nlm.nih.gov/22908101
unknown, 90 days
Health Status: unknown
Age Group: 90 days
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/22908101
Ataxia
2 % single, topical
Recommended
Dose: 2 %
Route: topical
Route: single
Dose: 2 %
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=ad85b220-6003-4a78-b900-5195ceaf0fd5&type=display
unknown
Health Status: unknown
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=ad85b220-6003-4a78-b900-5195ceaf0fd5&type=display
Confusion and disorientation
2 % single, topical
Recommended
Dose: 2 %
Route: topical
Route: single
Dose: 2 %
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=ad85b220-6003-4a78-b900-5195ceaf0fd5&type=display
unknown
Health Status: unknown
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=ad85b220-6003-4a78-b900-5195ceaf0fd5&type=display
Disorder speech
2 % single, topical
Recommended
Dose: 2 %
Route: topical
Route: single
Dose: 2 %
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=ad85b220-6003-4a78-b900-5195ceaf0fd5&type=display
unknown
Health Status: unknown
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=ad85b220-6003-4a78-b900-5195ceaf0fd5&type=display
Hallucinations
2 % single, topical
Recommended
Dose: 2 %
Route: topical
Route: single
Dose: 2 %
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=ad85b220-6003-4a78-b900-5195ceaf0fd5&type=display
unknown
Health Status: unknown
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=ad85b220-6003-4a78-b900-5195ceaf0fd5&type=display
Hyperactivity
2 % single, topical
Recommended
Dose: 2 %
Route: topical
Route: single
Dose: 2 %
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=ad85b220-6003-4a78-b900-5195ceaf0fd5&type=display
unknown
Health Status: unknown
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=ad85b220-6003-4a78-b900-5195ceaf0fd5&type=display
Other specified visual disturbances
2 % single, topical
Recommended
Dose: 2 %
Route: topical
Route: single
Dose: 2 %
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=ad85b220-6003-4a78-b900-5195ceaf0fd5&type=display
unknown
Health Status: unknown
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=ad85b220-6003-4a78-b900-5195ceaf0fd5&type=display
Restlessness
2 % single, topical
Recommended
Dose: 2 %
Route: topical
Route: single
Dose: 2 %
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=ad85b220-6003-4a78-b900-5195ceaf0fd5&type=display
unknown
Health Status: unknown
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=ad85b220-6003-4a78-b900-5195ceaf0fd5&type=display
Seizures
2 % single, topical
Recommended
Dose: 2 %
Route: topical
Route: single
Dose: 2 %
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=ad85b220-6003-4a78-b900-5195ceaf0fd5&type=display
unknown
Health Status: unknown
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=ad85b220-6003-4a78-b900-5195ceaf0fd5&type=display
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:4024
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4024
eMolecules
36554207
https://www.emolecules.com/cgi-bin/more?vid=36554207
MolPort
MolPort-005-935-560
https://www.molport.com/shop/molecule-link/MolPort-005-935-560
PubMed

PubMed

TitleDatePubMed
[Neurotoxic effects induced by the topical administration of cycloplegics. A case report and review of the literature].
2006-11-14
[Comparative study of cyclopentolate drops versus spray in cycloplegia in children].
2006-10
Cataract surgery management in patients taking tamsulosin staged approach.
2006-10
Controls required to assess IOL movement during accommodation.
2006-10
Toxic keratolysis from combined use of nonsteroid anti-inflammatory drugs and topical steroids following vitreoretinal surgery.
2006-09-05
Part-time occlusion therapy for anisometropic amblyopia detected in children eight years of age and older.
2006-09
Performance of the crystalens.
2006-09
Refractive error and patterns of spectacle use in 12-year-old Australian children.
2006-09
Pseudophakic accommodation and pseudoaccommodation under physiological conditions measured with partial coherence interferometry.
2006-08
Cataractous changes due to posterior chamber flattening with a posterior chamber phakic intraocular lens secondary to the administration of pilocarpine.
2006-08
Changes in astigmatism in children with congenital nystagmus.
2006-08
Analysis of patients with good uncorrected distance and near vision after monofocal intraocular lens implantation.
2006-07
Correctable and non-correctable visual impairment in a population-based sample of 12-year-old Australian children.
2006-07
A comparison of autorefraction and subjective refraction with and without cycloplegia in primary school children.
2006-07
Factors associated with childhood strabismus: findings from a population-based study.
2006-07
Effects of mydriatics on intraocular pressure and pupil size in the normal feline eye.
2006-06-15
A preoperative mixture of anesthetic jelly, dilating drops, antibiotics, and anti-inflammatories for cataract surgery.
2006-06-06
Accommodative spasm after laser-assisted in situ keratomileusis (LASIK).
2006-06
The effect of phenylephrine and cyclopentolate on objective wavefront measurements.
2006-05
Cataract surgery by appointment--a pilot study.
2006-04-20
Pseudallescheria boydii keratitis.
2006-04-08
Macular star associated with Behçet disease.
2006-04
Safety of intracameral mydriasis in phacoemulsification cataract surgery.
2006-03
Defining myopia using refractive error and uncorrected logMAR visual acuity >0.3 from 1334 Singapore school children ages 7-9 years.
2006-03
Pseudophakic accommodation with 2 models of foldable intraocular lenses.
2006-02
Pharmacological-induced haptic changes and the accommodative performance in patients with the AT-45 accommodative IOL.
2006-02
Redilatation with intracameral mydriatics in phacoemulsification surgery.
2006-02
Higher-order aberrations in children.
2006-01
Optical biometry of the anterior eye segment: interexaminer and intraexaminer reliability of ACMaster.
2005-12
Cholinergic innervation of the mouse isolated vas deferens.
2005-12
Axial growth and changes in lenticular and corneal power during emmetropization in infants.
2005-09
Lack of efficacy of dilated screening for retinoblastoma.
2005-08-27
Effect of (+) or (-) camphorsulfonic acid additives to the mobile phase on enantioseparations of some basic drugs on a Chiralcel OD column.
2005-08-12
Drug-induced intraocular lens movement and near visual acuity after AcrySof intraocular lens implantation.
2005-07
Accuracy of a new photo-refractometer in young and adult patients.
2005-07
Comparison of mydriatic regimens used in screening for retinopathy of prematurity in preterm infants with dark irides.
2005-06-28
Ultrasound biomicroscopy of the rat eye: effects of cholinergic and anticholinergic agents.
2005-05
Comparison of tropicamide and cyclopentolate for cycloplegic refractions in myopic adult refractive surgery patients.
2005-04
Stimulus-driven versus pilocarpine-induced biometric changes in pseudophakic eyes.
2005-03
Feasibility of ambulatory overnight oximetry in consecutive patients in a dementia clinic.
2005-03
Potentially accommodating intraocular lenses--an in vitro and in vivo study using three-dimensional high-frequency ultrasound.
2005-02-24
Quantitative determination of pharmaceuticals using nano-electrospray ionization mass spectrometry after reversed phase mini-solid phase extraction.
2005-02-23
Indocyanine green angiography in ocular tuberculosis.
2004-12
The effects of cyclopentolate on intraocular pressure and retrobulbar hemodynamics in patients with pseudoexfoliation syndrome and pseudoexfoliation glaucoma.
2004-10-28
Refractive astigmatism and the toricity of ocular components in human infants.
2004-10
Comparative study on the safety and efficacy of different cycloplegic agents in children with darkly pigmented irides.
2004-10
Parameters of drug antagonism: re-examination of two modes of functional competitive drug antagonism on intraocular muscles.
2004-08
Angioedema related to the use of hyaluronidase in cataract surgery.
2004-07
Cycloplegic and mydriatic agents for routine ophthalmologic examination: a survey of pediatric ophthalmologists.
2004-06
The effect of off-the-visual-axis retinoscopy on objective refractive measurement.
2004-06
Patents

Patents

US2554511
4

Sample Use Guides

In Vivo Use Guide
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 Mon Mar 31 21:27:41 GMT 2025
Edited
by admin
on Mon Mar 31 21:27:41 GMT 2025
Record UNII
736I6971TE
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CYCLOPENTOLATE HYDROCHLORIDE
EP   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common Name English
CYCLOMYDRIL COMPONENT CYCLOPENTOLATE HYDROCHLORIDE
Preferred Name English
MYDRILATE
Brand Name English
CYCLOGYL
Brand Name English
CYLATE
Brand Name English
CYCLOPENTOLATE HYDROCHLORIDE [VANDF]
Common Name English
CYCLOPENTOLATE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
AK-PENTOLATE
Brand Name English
CYCLOPENTOLATE HCL
Common Name English
CYCLOPENTOLATE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
NSC-756706
Code English
CYCLOPENTOLATE HYDROCHLORIDE [MI]
Common Name English
CYCLOPENTOLATE HYDROCHLORIDE [JAN]
Common Name English
CYCLOPENTOLATE HYDROCHLORIDE [USP-RS]
Common Name English
Cyclopentolate hydrochloride [WHO-DD]
Common Name English
CYCLOPENTOLATE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
CYPLEGIN
Brand Name English
CYCLOPENTOLATE HYDROCHLORIDE [MART.]
Common Name English
PENTOLAIR
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C29706
Created by admin on Mon Mar 31 21:27:41 GMT 2025 , Edited by admin on Mon Mar 31 21:27:41 GMT 2025
NCI_THESAURUS C29704
Created by admin on Mon Mar 31 21:27:41 GMT 2025 , Edited by admin on Mon Mar 31 21:27:41 GMT 2025
Code System Code Type Description
ChEMBL
CHEMBL1201338
Created by admin on Mon Mar 31 21:27:41 GMT 2025 , Edited by admin on Mon Mar 31 21:27:41 GMT 2025
PRIMARY
MERCK INDEX
m4011
Created by admin on Mon Mar 31 21:27:41 GMT 2025 , Edited by admin on Mon Mar 31 21:27:41 GMT 2025
PRIMARY Merck Index
CAS
5870-29-1
Created by admin on Mon Mar 31 21:27:41 GMT 2025 , Edited by admin on Mon Mar 31 21:27:41 GMT 2025
PRIMARY
DAILYMED
736I6971TE
Created by admin on Mon Mar 31 21:27:41 GMT 2025 , Edited by admin on Mon Mar 31 21:27:41 GMT 2025
PRIMARY
DRUG BANK
DBSALT000476
Created by admin on Mon Mar 31 21:27:41 GMT 2025 , Edited by admin on Mon Mar 31 21:27:41 GMT 2025
PRIMARY
NCI_THESAURUS
C28948
Created by admin on Mon Mar 31 21:27:41 GMT 2025 , Edited by admin on Mon Mar 31 21:27:41 GMT 2025
PRIMARY
ECHA (EC/EINECS)
227-521-8
Created by admin on Mon Mar 31 21:27:41 GMT 2025 , Edited by admin on Mon Mar 31 21:27:41 GMT 2025
PRIMARY
CHEBI
4025
Created by admin on Mon Mar 31 21:27:41 GMT 2025 , Edited by admin on Mon Mar 31 21:27:41 GMT 2025
PRIMARY
NSC
756706
Created by admin on Mon Mar 31 21:27:41 GMT 2025 , Edited by admin on Mon Mar 31 21:27:41 GMT 2025
PRIMARY
EVMPD
SUB01529MIG
Created by admin on Mon Mar 31 21:27:41 GMT 2025 , Edited by admin on Mon Mar 31 21:27:41 GMT 2025
PRIMARY
RS_ITEM_NUM
1156000
Created by admin on Mon Mar 31 21:27:41 GMT 2025 , Edited by admin on Mon Mar 31 21:27:41 GMT 2025
PRIMARY
FDA UNII
736I6971TE
Created by admin on Mon Mar 31 21:27:41 GMT 2025 , Edited by admin on Mon Mar 31 21:27:41 GMT 2025
PRIMARY
EPA CompTox
DTXSID9045390
Created by admin on Mon Mar 31 21:27:41 GMT 2025 , Edited by admin on Mon Mar 31 21:27:41 GMT 2025
PRIMARY
PUBCHEM
22162
Created by admin on Mon Mar 31 21:27:41 GMT 2025 , Edited by admin on Mon Mar 31 21:27:41 GMT 2025
PRIMARY
SMS_ID
100000092411
Created by admin on Mon Mar 31 21:27:41 GMT 2025 , Edited by admin on Mon Mar 31 21:27:41 GMT 2025
PRIMARY
RXCUI
106029
Created by admin on Mon Mar 31 21:27:41 GMT 2025 , Edited by admin on Mon Mar 31 21:27:41 GMT 2025
PRIMARY RxNorm
Related Record Type Details
Structure of CYCLOPENTOLATE HYDROCHLORIDE, (+)-
ENANTIOMER -> RACEMATE
Structure of CYCLOPENTOLATE HYDROCHLORIDE, (-)-
ENANTIOMER -> RACEMATE
Structure of CYCLOPENTOLATE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of CYCLOPENTOLATE
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