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Details

Stereochemistry RACEMIC
Molecular Formula C17H26NO3.Cl
Molecular Weight 327.8468
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYCLOPENTOLATE HYDROCHLORIDE

SMILES

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

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 C17H26NO3
Molecular Weight 292.3939
Charge 1
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula Cl
Molecular Weight 35.4529
Charge -1
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

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
Systemic toxicity of topical and periocular corticosteroid therapy in an 11-year-old male with posterior uveitis.
2000 Aug
Systemic toxicity with cyclopentolate eye drops.
2000 Mar
Haploinsufficient Bmp4 ocular phenotypes include anterior segment dysgenesis with elevated intraocular pressure.
2001
Herpes simplex virus bullous keratitis misdiagnosed as a case of pseudophakic bullous keratopathy with secondary glaucoma: an unusual presentation.
2001
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
Acute gastric dilatation complicating the use of mydriatics in a preterm newborn.
2001 Aug
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
[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
Repeat cycloplegic examinations at the Naval Operational Medicine Institute.
2001 Sep
Pupil location under mesopic, photopic, and pharmacologically dilated conditions.
2002 Jul
Steroid responsive cutaneous Rosai-Dorfman disease associated with uveitis and hypothyroidism.
2002 Jun
[Variability in the effects of topical cycloplegics].
2002 Jun
[Full optical correction after cycloplegia in headache].
2002 Mar
[Cycloplegic effectiveness of cyclopentolate and tropicamide preparations compared with atropinization].
2002 Nov-Dec
[Aberrometry due dilated pupils--Which mydriatic should be used?].
2002 Sep
Efficiency of a video-autorefractometer used as a screening device for amblyogenic factors.
2002 Sep
Changes in intraocular pressure following diagnostic mydriasis with cyclopentolate 1%.
2002 Sep
Intraocular lens movement caused by ciliary muscle contraction.
2003 Apr
Prednisolone and flurbiprofen drops to maintain mydriasis during phacoemulsification cataract surgery.
2003 Dec
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
Neonatal hyphema in precipitous delivery with dinoprostone.
2003 Jun
Surgically induced miosis during phacoemulsification in patients with diabetes mellitus.
2003 Mar
Herpes zoster virus sclerokeratitis and anterior uveitis in a child following varicella vaccination.
2003 Mar
Use of a wick to deliver preoperative mydriatics for cataract surgery.
2003 Nov
Posthypnotic suggestion and the modulation of Stroop interference under cycloplegia.
2003 Sep
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
Pupil dilation and wavefront aberration.
2004 Jan-Feb
The effect of off-the-visual-axis retinoscopy on objective refractive measurement.
2004 Jun
Effect of (+) or (-) camphorsulfonic acid additives to the mobile phase on enantioseparations of some basic drugs on a Chiralcel OD column.
2005 Aug 12
Lack of efficacy of dilated screening for retinoblastoma.
2005 Jul-Aug
Feasibility of ambulatory overnight oximetry in consecutive patients in a dementia clinic.
2005 Mar
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
Changes in astigmatism in children with congenital nystagmus.
2006 Aug
Higher-order aberrations in children.
2006 Jan
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
Pseudallescheria boydii keratitis.
2006 Mar-Apr
[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
Performance of the crystalens.
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 Fri Jun 25 21:04:08 UTC 2021
Edited
by admin
on Fri Jun 25 21:04:08 UTC 2021
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 HYDROCHLORIDE [WHO-DD]
Common 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 [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 Fri Jun 25 21:04:08 UTC 2021 , Edited by admin on Fri Jun 25 21:04:08 UTC 2021
NCI_THESAURUS C29704
Created by admin on Fri Jun 25 21:04:08 UTC 2021 , Edited by admin on Fri Jun 25 21:04:08 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL1201338
Created by admin on Fri Jun 25 21:04:08 UTC 2021 , Edited by admin on Fri Jun 25 21:04:08 UTC 2021
PRIMARY
MERCK INDEX
M4011
Created by admin on Fri Jun 25 21:04:08 UTC 2021 , Edited by admin on Fri Jun 25 21:04:08 UTC 2021
PRIMARY Merck Index
CAS
5870-29-1
Created by admin on Fri Jun 25 21:04:08 UTC 2021 , Edited by admin on Fri Jun 25 21:04:08 UTC 2021
PRIMARY
USP_CATALOG
1156000
Created by admin on Fri Jun 25 21:04:08 UTC 2021 , Edited by admin on Fri Jun 25 21:04:08 UTC 2021
PRIMARY USP-RS
DRUG BANK
DBSALT000476
Created by admin on Fri Jun 25 21:04:08 UTC 2021 , Edited by admin on Fri Jun 25 21:04:08 UTC 2021
PRIMARY
NCI_THESAURUS
C28948
Created by admin on Fri Jun 25 21:04:08 UTC 2021 , Edited by admin on Fri Jun 25 21:04:08 UTC 2021
PRIMARY
ECHA (EC/EINECS)
227-521-8
Created by admin on Fri Jun 25 21:04:08 UTC 2021 , Edited by admin on Fri Jun 25 21:04:08 UTC 2021
PRIMARY
EVMPD
SUB01529MIG
Created by admin on Fri Jun 25 21:04:08 UTC 2021 , Edited by admin on Fri Jun 25 21:04:08 UTC 2021
PRIMARY
FDA UNII
736I6971TE
Created by admin on Fri Jun 25 21:04:08 UTC 2021 , Edited by admin on Fri Jun 25 21:04:08 UTC 2021
PRIMARY
EPA CompTox
5870-29-1
Created by admin on Fri Jun 25 21:04:08 UTC 2021 , Edited by admin on Fri Jun 25 21:04:08 UTC 2021
PRIMARY
PUBCHEM
22162
Created by admin on Fri Jun 25 21:04:08 UTC 2021 , Edited by admin on Fri Jun 25 21:04:08 UTC 2021
PRIMARY
RXCUI
106029
Created by admin on Fri Jun 25 21:04:08 UTC 2021 , Edited by admin on Fri Jun 25 21:04:08 UTC 2021
PRIMARY RxNorm
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY