U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
3913
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
2778
 10.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Approved
8429
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
Page: e704
unknown, 90 days
n = 1
Health Status: unknown
Condition: mydriasis induction
Age Group: 90 days
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/22908101
Page: e704
Other AEs: Vomiting, Cyanosis...
Other AEs:
Vomiting
Cyanosis
Respiratory distress
Sources:
https://pubmed.ncbi.nlm.nih.gov/22908101
Page: e704
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
Condition: mydriasis induction
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
Page: e704
unknown, 90 days
n = 1
Health Status: unknown
Condition: mydriasis induction
Age Group: 90 days
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/22908101
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:
https://pubmed.ncbi.nlm.nih.gov/22908101
Page: e704
unknown, 90 days
n = 1
Health Status: unknown
Condition: mydriasis induction
Age Group: 90 days
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/22908101
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:
https://pubmed.ncbi.nlm.nih.gov/22908101
Page: e704
unknown, 90 days
n = 1
Health Status: unknown
Condition: mydriasis induction
Age Group: 90 days
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/22908101
Page: e704
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
Condition: mydriasis induction
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
Condition: mydriasis induction
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
Condition: mydriasis induction
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
Condition: mydriasis induction
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
Condition: mydriasis induction
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
Condition: mydriasis induction
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
Condition: mydriasis induction
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
Condition: mydriasis induction
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
MolPort
MolPort-005-935-560
https://www.molport.com/shop/molecule-link/MolPort-005-935-560
eMolecules
36554207
https://www.emolecules.com/cgi-bin/more?vid=36554207
PubMed

PubMed

TitleDatePubMed
[Cycloplegic effectiveness of cyclopentolate and tropicamide preparations compared with atropinization].
2002 Nov-Dec
Prednisolone and flurbiprofen drops to maintain mydriasis during phacoemulsification cataract surgery.
2003 Dec
Intracameral mydriatics in phacoemulsification cataract surgery.
2003 Dec
Clinical evaluation of an eccentric infrared photorefractor: the PowerRefractor.
2003 Dec
Surgically induced miosis during phacoemulsification in patients with diabetes mellitus.
2003 Mar
Higher order ocular aberrations after cycloplegic and non-cycloplegic pupil dilation.
2003 May-Jun
Wave-front analysis as screening technique for amblyogenic ametropia with and without cycloplegia.
2003 Sep
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
[Phacoemulsification without mydriasis before surgery: benefits to the patient].
2004 Feb
Accuracy of noncycloplegic autorefraction in school-age children in China.
2004 Jan
[Syndrome of confusion as side-effect of cycloplegic collyrium].
2004 Jan
Pupil dilation and wavefront aberration.
2004 Jan-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
Comparative study on the safety and efficacy of different cycloplegic agents in children with darkly pigmented irides.
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
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
Correctable and non-correctable visual impairment in a population-based sample of 12-year-old Australian 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
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
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
Part-time occlusion therapy for anisometropic amblyopia detected in children eight years of age and older.
2006 Sep
Performance of the crystalens.
2006 Sep
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 Sat Dec 16 05:13:23 GMT 2023
Edited
by admin
on Sat Dec 16 05:13:23 GMT 2023
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
MYDRILATE
Brand Name English
CYCLOGYL
Brand Name English
CYLATE
Brand Name English
CYCLOPENTOLATE HYDROCHLORIDE COMPONENT OF CYCLOMYDRIL
Common 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
CYCLOMYDRIL COMPONENT CYCLOPENTOLATE HYDROCHLORIDE
Common Name 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 Sat Dec 16 05:13:23 GMT 2023 , Edited by admin on Sat Dec 16 05:13:23 GMT 2023
NCI_THESAURUS C29704
Created by admin on Sat Dec 16 05:13:23 GMT 2023 , Edited by admin on Sat Dec 16 05:13:23 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL1201338
Created by admin on Sat Dec 16 05:13:23 GMT 2023 , Edited by admin on Sat Dec 16 05:13:23 GMT 2023
PRIMARY
MERCK INDEX
m4011
Created by admin on Sat Dec 16 05:13:23 GMT 2023 , Edited by admin on Sat Dec 16 05:13:23 GMT 2023
PRIMARY Merck Index
CAS
5870-29-1
Created by admin on Sat Dec 16 05:13:23 GMT 2023 , Edited by admin on Sat Dec 16 05:13:23 GMT 2023
PRIMARY
DAILYMED
736I6971TE
Created by admin on Sat Dec 16 05:13:23 GMT 2023 , Edited by admin on Sat Dec 16 05:13:23 GMT 2023
PRIMARY
DRUG BANK
DBSALT000476
Created by admin on Sat Dec 16 05:13:23 GMT 2023 , Edited by admin on Sat Dec 16 05:13:23 GMT 2023
PRIMARY
NCI_THESAURUS
C28948
Created by admin on Sat Dec 16 05:13:23 GMT 2023 , Edited by admin on Sat Dec 16 05:13:23 GMT 2023
PRIMARY
ECHA (EC/EINECS)
227-521-8
Created by admin on Sat Dec 16 05:13:23 GMT 2023 , Edited by admin on Sat Dec 16 05:13:23 GMT 2023
PRIMARY
CHEBI
4025
Created by admin on Sat Dec 16 05:13:23 GMT 2023 , Edited by admin on Sat Dec 16 05:13:23 GMT 2023
PRIMARY
NSC
756706
Created by admin on Sat Dec 16 05:13:23 GMT 2023 , Edited by admin on Sat Dec 16 05:13:23 GMT 2023
PRIMARY
EVMPD
SUB01529MIG
Created by admin on Sat Dec 16 05:13:23 GMT 2023 , Edited by admin on Sat Dec 16 05:13:23 GMT 2023
PRIMARY
RS_ITEM_NUM
1156000
Created by admin on Sat Dec 16 05:13:23 GMT 2023 , Edited by admin on Sat Dec 16 05:13:23 GMT 2023
PRIMARY
FDA UNII
736I6971TE
Created by admin on Sat Dec 16 05:13:23 GMT 2023 , Edited by admin on Sat Dec 16 05:13:23 GMT 2023
PRIMARY
EPA CompTox
DTXSID9045390
Created by admin on Sat Dec 16 05:13:23 GMT 2023 , Edited by admin on Sat Dec 16 05:13:23 GMT 2023
PRIMARY
PUBCHEM
22162
Created by admin on Sat Dec 16 05:13:23 GMT 2023 , Edited by admin on Sat Dec 16 05:13:23 GMT 2023
PRIMARY
SMS_ID
100000092411
Created by admin on Sat Dec 16 05:13:23 GMT 2023 , Edited by admin on Sat Dec 16 05:13:23 GMT 2023
PRIMARY
RXCUI
106029
Created by admin on Sat Dec 16 05:13:23 GMT 2023 , Edited by admin on Sat Dec 16 05:13:23 GMT 2023
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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