Grundinformationen
- CAS
512-15-2- Standard-SMILES
CN(C)CCOC(=O)C(c1ccccc1)C1(O)CCCC1- InChIKey
SKYSRIRYMSLOIN-UHFFFAOYSA-N- Summenformel
- C17H25NO3
- Durchschnittliche Molmasse
- 291,4 g/mol
- Monoisotopische Masse
- 291,18344366
Überblick
Cyclopentolate is a 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. It has a role as a diagnostic agent, a muscarinic antagonist, a parasympatholytic and a mydriatic agent. It is a tertiary alcohol, a carboxylic ester and a tertiary amino compound. It is functionally related to a N,N-dimethylethanolamine and a (1-hydroxycyclopentyl)phenylacetic acid.
Namen und Bezeichner
- Bevorzugter Name
- Cyclopentolate
- IUPAC
- 2-(dimethylamino)ethyl 2-(1-hydroxycyclopentyl)-2-phenylacetate
- Lokaler Name
- Cyclopentolat
- Englischer Name
- Cyclopentolate
- Summenformel
- C17H25NO3
- Molmasse
- 291.39
Namen und Synonyme
cyclopentolate512-15-2Ciclopentolato2-(dimethylamino)ethyl 2-(1-hydroxycyclopentyl)-2-phenylacetateCyclopentolatumBell Pentolate(+-)-cyclopentolateI76F4SHP7J2-(Dimethylamino)ethyl 1-hydroxy-alpha-phenylcyclopentaneacetate1-hydroxy-alpha-phenylcyclopentaneacetic acid 2-(dimethylamino)ethyl esteralpha-(1-hydroxycyclopentyl)benzeneacetic acid 2-(dimethylamino)ethyl esterbeta-dimethylaminoethyl (1-hydroxycyclopentyl)phenylacetate
Weitere Namen anzeigen
CypleginMydrilateyclopentolateCyclopentylateCyclopentoiateDL-Cyclopentolateβ-Dimethylaminoethyl (1-hydroxycyclopentyl)phenylacetate2-(Dimethylamino)ethyl (1-hydroxycyclopentyl)(phenyl)acetate
CHEBI:4024beta-(Dimethylamino)ethyl (1-hydroxycyclopentyl)phenylacetateDTXSID30485282-phenyl-2-(1-hydroxycyclopentyl)ethanoic acid beta-(dimethylamino)ethyl esterBenzeneacetic acid, alpha-(1-hydroxycyclopentyl)-, 2-(dimethylamino)ethyl esterRefChem:56554DTXCID4027995S01FA04
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,7
- Polarare Oberfläche (TPSA)
- 49,8 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 7
- Schwere Atome
- 21
- Formalladung
- 0
- Komplexität
- 331
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals
LogP2.4
Solubility1.50e+00 g/L
Human Drugs
Breast Feeding; Lactation; Mydriatics; Muscarinic Antagonists; Parasympatholytics
Pharmaceuticals
Diagnostic agents > Ophthalmic medicines
Melting Point
134-136
139 °C (hydrochloride salt)
Physical DescriptionSolid
Collision Cross Section166.35 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physikochemische Eigenschaften
- Siedepunkt
- 409.7 · 409.7±20.0 °C(Predicted)
- Dichte
- 1.136 · 1.136±0.06 g/cm3(Predicted)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory InformationREACH registered substance: Cyclopentolate (EC: 208-136-4)
Other Safety InformationIMAP assessments - Benzeneacetic acid, .alpha.-(1-hydroxycyclopentyl)-, 2-(dimethylamino)ethyl ester: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxikologische Informationen
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Sicherheitsdaten
- Alarmwort
- Warnung
- Gefahrenhinweise
- Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H302
Chemie und Industrie
Pharmakologische Informationen
ATC Code
S01FA04
S - Sensory organs
QS - Sensory organs
Pharmacodynamics
Cyclopentolate is an anti-muscarinic in the same class as atropine and scopolamine. Cyclopentolate blocks the receptors in the muscles of the eye (muscarinic receptors). These receptors are involved controlling the pupil size and the shape of the lens. Cyclopentolate thus induces relaxation of the sphincter of the iris and the ciliary muscles. When applied topically to the eyes, it causes a rapid, intense cycloplegic and mydriatic effect that is maximal in 15 to 60 minutes; recovery usually occurs within 24 hours. The cycloplegic and mydriatic effects are slower in onset and longer in duration in patients who have dark pigmented irises.
Mechanism of ActionBy blocking muscarinic receptors, cyclopentolate produces dilatation of the pupil (mydriasis) and prevents the eye from accommodating for near vision (cycloplegia).
MeSH Pharmacological Classification
Agents that dilate the pupil. They may be either sympathomimetics or parasympatholytics.
Agents that inhibit the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the MUSCARINIC ANTAGONISTS.
Drugs that bind to but do not activate MUSCARINIC RECEPTORS, thereby blocking the actions of endogenous ACETYLCHOLINE or exogenous agonists. Muscarinic antagonists have widespread effects including actions on the iris and ciliary muscle of the eye, the heart and blood vessels, secretions of the respiratory tract, GI system, and salivary glands, GI motility, urinary bladder tone, and the central nervous system.
Absorption, Distribution and ExcretionAbsorbed following ophthalmic administration.
Cellular LocationsCytoplasm
Verwendung und Herstellung
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