CHEBI:4024 - cyclopentolate

ChEBI IDCHEBI:4024
ChEBI Namecyclopentolate
Stars
DefinitionA carboxylic ester resulting from the formal condensation of (1-hydroxycyclopentyl)(phenyl)acetic acid with N,N-dimethylethanolamine. A tertiary amine antimuscarinic with actions similar to atropine, it is used as its hydrochloride salt to produce mydriasis (excessive dilation of the pupil) and cycloplegia (paralysis of the ciliary muscle of the eye) for opthalmic diagnostic procedures. It acts more quickly than atropine and has a shorter duration of action.
Last Modified22 February 2017
DownloadsMolfile
FormulaC17H25NO3
Net Charge0
Average Mass291.391
Monoisotopic Mass291.18344
SMILESCN(C)CCOC(=O)C(c1ccccc1)C1(O)CCCC1
InChIInChI=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
InChIKeySKYSRIRYMSLOIN-UHFFFAOYSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
muscarinic antagonist  A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
parasympatholytic  Any cholinergic antagonist that inhibits the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the muscarinic antagonists.
Applications:
diagnostic agent  A substance administered to aid diagnosis of a disease.
mydriatic agent  Agent that dilates the pupil. Used in eye diseases and to facilitate eye examination. It may be either a sympathomimetic or parasympatholytic. The latter cause cycloplegia or paralysis of accommodation at high doses and may precipitate glaucoma.
muscarinic antagonist  A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
parasympatholytic  Any cholinergic antagonist that inhibits the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the muscarinic antagonists.
ChEBI Ontology
Outgoing Relation(s)
cyclopentolate (CHEBI:4024) has functional parent (1-hydroxycyclopentyl)phenylacetic acid (CHEBI:59684)
cyclopentolate (CHEBI:4024) has functional parent N,N-dimethylethanolamine (CHEBI:271436)
cyclopentolate (CHEBI:4024) has role diagnostic agent (CHEBI:33295)
cyclopentolate (CHEBI:4024) has role muscarinic antagonist (CHEBI:48876)
cyclopentolate (CHEBI:4024) has role mydriatic agent (CHEBI:50513)
cyclopentolate (CHEBI:4024) has role parasympatholytic (CHEBI:50370)
cyclopentolate (CHEBI:4024) is a carboxylic ester (CHEBI:33308)
cyclopentolate (CHEBI:4024) is a tertiary alcohol (CHEBI:26878)
cyclopentolate (CHEBI:4024) is a tertiary amino compound (CHEBI:50996)
Incoming Relation(s)
cyclopentolate hydrochloride (CHEBI:4025) has part cyclopentolate (CHEBI:4024)
(R)-cyclopentolate (CHEBI:59688) is a cyclopentolate (CHEBI:4024)
(S)-cyclopentolate (CHEBI:59689) is a cyclopentolate (CHEBI:4024)
IUPAC Name 
2-(dimethylamino)ethyl (1-hydroxycyclopentyl)(phenyl)acetate
INNs  Source
cyclopentolateChemIDplus
ciclopentolatoChemIDplus
cyclopentolatumChemIDplus
cyclopentolateWHO MedNet
Synonyms  Source
CyclopentolateKEGG COMPOUND
2-(dimethylamino)ethyl 1-hydroxy-α-phenylcyclopentaneacetateChemIDplus
β-dimethylaminoethyl (1-hydroxycyclopentyl)phenylacetateChEBI
2-phenyl-2-(1-hydroxycyclopentyl)ethanoic acid β-(dimethylamino)ethyl esterChEBI
1-hydroxy-α-phenylcyclopentaneacetic acid 2-(dimethylamino)ethyl esterChEBI
α-(1-hydroxycyclopentyl)benzeneacetic acid 2-(dimethylamino)ethyl esterChEBI
Manual XrefsDatabases
C06932KEGG COMPOUND
D07759KEGG DRUG
DB00979DrugBank
US2554511Patent
CyclopentolateWikipedia
HMDB0015114HMDB
LSM-1800LINCS
757DrugCentral
Registry NumbersSources
Reaxys:2147087Reaxys
CAS:512-15-2KEGG COMPOUND
CAS:512-15-2ChemIDplus
CAS:512-15-2NIST Chemistry WebBook