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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

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
Retinoscopy in infants using a near noncycloplegic technique, cycloplegia with tropicamide 1%, and cycloplegia with cyclopentolate 1%.
2001 Apr
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
[Biochemical stress monitoring during cataract surgery; phenylephrine 10% shows no changes in serum-catecholamines in comparison with phenylephrine 5%].
2001 Jul
Efficiency of a video-autorefractometer used as a screening device for amblyogenic factors.
2002 Sep
Prednisolone and flurbiprofen drops to maintain mydriasis during phacoemulsification cataract surgery.
2003 Dec
Intracameral mydriatics in phacoemulsification cataract surgery.
2003 Dec
Acute psychotic reaction caused by topical cyclopentolate use for cycloplegic refraction before refractive surgery: case report and review of the literature.
2003 May
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 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
Comparative study on the safety and efficacy of different cycloplegic agents in children with darkly pigmented irides.
2004 Oct
Drug-induced intraocular lens movement and near visual acuity after AcrySof intraocular lens implantation.
2005 Jul
Macular star associated with Behçet disease.
2006 Apr
Redilatation with intracameral mydriatics in phacoemulsification surgery.
2006 Feb
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 18:34:43 GMT 2025
Edited
by admin
on Mon Mar 31 18:34:43 GMT 2025
Record UNII
I76F4SHP7J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CYCLOPENTOLATE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
BELL PENTOLATE
Preferred 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
CYCLOPENTOLATE [MI]
Common Name English
CYCLOPENTOLATE [VANDF]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29704
Created by admin on Mon Mar 31 18:34:43 GMT 2025 , Edited by admin on Mon Mar 31 18:34:43 GMT 2025
WHO-VATC QS01FA04
Created by admin on Mon Mar 31 18:34:43 GMT 2025 , Edited by admin on Mon Mar 31 18:34:43 GMT 2025
WHO-ATC S01BB01
Created by admin on Mon Mar 31 18:34:43 GMT 2025 , Edited by admin on Mon Mar 31 18:34:43 GMT 2025
WHO-ATC S01FA04
Created by admin on Mon Mar 31 18:34:43 GMT 2025 , Edited by admin on Mon Mar 31 18:34:43 GMT 2025
WHO-ATC S01FA54
Created by admin on Mon Mar 31 18:34:43 GMT 2025 , Edited by admin on Mon Mar 31 18:34:43 GMT 2025
NCI_THESAURUS C29706
Created by admin on Mon Mar 31 18:34:43 GMT 2025 , Edited by admin on Mon Mar 31 18:34:43 GMT 2025
Code System Code Type Description
ChEMBL
CHEMBL1201338
Created by admin on Mon Mar 31 18:34:43 GMT 2025 , Edited by admin on Mon Mar 31 18:34:43 GMT 2025
PRIMARY
DRUG BANK
DB00979
Created by admin on Mon Mar 31 18:34:43 GMT 2025 , Edited by admin on Mon Mar 31 18:34:43 GMT 2025
PRIMARY
EVMPD
SUB06858MIG
Created by admin on Mon Mar 31 18:34:43 GMT 2025 , Edited by admin on Mon Mar 31 18:34:43 GMT 2025
PRIMARY
ECHA (EC/EINECS)
208-136-4
Created by admin on Mon Mar 31 18:34:43 GMT 2025 , Edited by admin on Mon Mar 31 18:34:43 GMT 2025
PRIMARY
CAS
512-15-2
Created by admin on Mon Mar 31 18:34:43 GMT 2025 , Edited by admin on Mon Mar 31 18:34:43 GMT 2025
PRIMARY
FDA UNII
I76F4SHP7J
Created by admin on Mon Mar 31 18:34:43 GMT 2025 , Edited by admin on Mon Mar 31 18:34:43 GMT 2025
PRIMARY
CHEBI
4024
Created by admin on Mon Mar 31 18:34:43 GMT 2025 , Edited by admin on Mon Mar 31 18:34:43 GMT 2025
PRIMARY
MESH
D003519
Created by admin on Mon Mar 31 18:34:43 GMT 2025 , Edited by admin on Mon Mar 31 18:34:43 GMT 2025
PRIMARY
NCI_THESAURUS
C61693
Created by admin on Mon Mar 31 18:34:43 GMT 2025 , Edited by admin on Mon Mar 31 18:34:43 GMT 2025
PRIMARY
WIKIPEDIA
Cyclopentolate
Created by admin on Mon Mar 31 18:34:43 GMT 2025 , Edited by admin on Mon Mar 31 18:34:43 GMT 2025
PRIMARY
MERCK INDEX
m4011
Created by admin on Mon Mar 31 18:34:43 GMT 2025 , Edited by admin on Mon Mar 31 18:34:43 GMT 2025
PRIMARY Merck Index
PUBCHEM
2905
Created by admin on Mon Mar 31 18:34:43 GMT 2025 , Edited by admin on Mon Mar 31 18:34:43 GMT 2025
PRIMARY
INN
266
Created by admin on Mon Mar 31 18:34:43 GMT 2025 , Edited by admin on Mon Mar 31 18:34:43 GMT 2025
PRIMARY
DAILYMED
I76F4SHP7J
Created by admin on Mon Mar 31 18:34:43 GMT 2025 , Edited by admin on Mon Mar 31 18:34:43 GMT 2025
PRIMARY
LACTMED
Cyclopentolate
Created by admin on Mon Mar 31 18:34:43 GMT 2025 , Edited by admin on Mon Mar 31 18:34:43 GMT 2025
PRIMARY
IUPHAR
7153
Created by admin on Mon Mar 31 18:34:43 GMT 2025 , Edited by admin on Mon Mar 31 18:34:43 GMT 2025
PRIMARY
DRUG CENTRAL
757
Created by admin on Mon Mar 31 18:34:43 GMT 2025 , Edited by admin on Mon Mar 31 18:34:43 GMT 2025
PRIMARY
EPA CompTox
DTXSID3048528
Created by admin on Mon Mar 31 18:34:43 GMT 2025 , Edited by admin on Mon Mar 31 18:34:43 GMT 2025
PRIMARY
SMS_ID
100000083774
Created by admin on Mon Mar 31 18:34:43 GMT 2025 , Edited by admin on Mon Mar 31 18:34:43 GMT 2025
PRIMARY
RXCUI
3001
Created by admin on Mon Mar 31 18:34:43 GMT 2025 , Edited by admin on Mon Mar 31 18:34:43 GMT 2025
PRIMARY RxNorm
Related Record Type Details
MUSCARINIC ACETYLCHOLINE RECEPTOR M1
TARGET -> INHIBITOR
Structure of CYCLOPENTOLATE, (S)-
ENANTIOMER -> RACEMATE
Structure of CYCLOPENTOLATE, (R)-
ENANTIOMER -> RACEMATE
Structure of CYCLOPENTOLATE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of CYCLOPENTOLATE
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