2-(dimethylamino)ethyl 2-(1-hydroxycyclopentyl)-2-phenylacetate

• ChemBase ID: 854
• Molecular Formular: C17H25NO3
• Molecular Mass: 291.3853
• Monoisotopic Mass: 291.18344367
• SMILES: OC1(CCCC1)C(c1ccccc1)C(=O)OCCN(C)C
• Canonical SMILES: CN(CCOC(=O)C(C1(O)CCCC1)c1ccccc1)C
• InChI: 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
• InChIKey: SKYSRIRYMSLOIN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(dimethylamino)ethyl 2-(1-hydroxycyclopentyl)-2-phenylacetate
• IUPAC Traditional name: cyclopentolate
• Brand Name: AK-Pentolate; Akpentolate; Cyclogyl; Cylate; Minims Cyclopentolate; Mydrilate; Ocu-Pentolate; Pentolair
• Synonyms: Ciclopentolato [INN-Spanish]; Cyclopentolate HCL; Cyclopentolatum [INN-Latin]; Cyclopentylate; Cyclopentoiate; Diopentolate; Cyclopentolate

Database IDs

• CAS Number: 512-15-2
• PubChem SID: 46504517; 160964317
• PubChem CID: 2905
• CHEBI ID: 4024
• ATC CODE: S01FA04
• CHEMBL: 1200473
• Chemspider ID: 2802
• DrugBank ID: DB00979
• KEGG ID: D07759
• Unique Ingredient Identifier: I76F4SHP7J
• Wikipedia Title: Cyclopentolate

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.18693
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.501637
• LogD (pH = 7.4): 1.259811
• Log P: 2.3162184
• Molar Refractivity: 82.8058 cm^3
• Polarizability: 32.763153 Å^3
• Polar Surface Area: 49.77 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.09
• LOG S: -2.29
• Solubility (Water): 1.50e+00 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 2.4

Pharmacology Properties

• Admin Routes: Topic
• Pregnancy Category: C

DETAILS

DrugBank - DB00979

• Drug Groups: approved
• Description: A parasympatholytic anticholinergic used solely to obtain mydriasis or cycloplegia. [PubChem]
• Indication: Used mainly to produce mydriasis and cycloplegia for diagnostic purposes.
• Pharmacology: 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.
• Toxicity: Oral LD₅₀ in the rat is 4000 mg/kg and 960 mg/kg in the mouse. Symptoms of overdose include tachycardia, dizziness, dry mouth, behavioral disturbances, uncoordination and drowsiness.
• Affected Organisms: Humans and other mammals
• Absorption: Absorbed following ophthalmic administration.
• References: [Link]
• External Links: Wikipedia; Drugs.com

REFERENCES

• Link