 Home > Encyclopedia > Cyclopentolate

Cyclopentolate

Cyclopentolate structure

CAS No:
512-15-2
Formula:
C17H25NO3
Chemical Name:
Cyclopentolate
Synonyms:
Benzeneacetic acid,α-(1-hydroxycyclopentyl)-,2-(dimethylamino)ethyl ester;Cyclopentaneacetic acid,1-hydroxy-α-phenyl-,2-(dimethylamino)ethyl ester;Cyclogyl;β-Dimethylaminoethyl (1-hydroxycyclopentyl)phenylacetate;2-Dimethylaminoethyl 1-hydroxy-α-phenylcyclopentaneacetate;Cyclopentolate;1-Hydroxy-α-phenylcyclopentaneacetic acid,2-(dimethylamino)ethyl ester;Cyclopentylate;DL-Cyclopentolate;Tsiklopentolat;2-(Dimethylamino)ethyl 2-(1-hydroxycyclopentyl)-2-phenylacetate;52715-97-6
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

ChEBI: 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 ydrochloride 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.

Solid

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 mydriatic agent, a parasympatholytic, a muscarinic antagonist and a diagnostic agent. It is a carboxylic ester, a tertiary amino compound and a tertiary alcohol. It derives from a (1-hydroxycyclopentyl)phenylacetic acid and a N,N-dimethylethanolamine.|A parasympatholytic anticholinergic used solely to obtain mydriasis or cycloplegia.

Cyclopentolate Basic Attributes

Molecular Weight：

291.391

Exact Mass：

291.39

EC Number：

208-136-4

DSSTox ID：

DTXSID3048528

ATC Code：

S01FA04|S - Sensory organs

HScode：

2922509090

Characteristics

PSA：

49.8

XLogP3：

2.4

Appearance：

Solid

Density：

1.136g/cm3

Melting Point：

139 °C (hydrochloride salt)

Boiling Point：

409.7ºC at 760mmHg

Flash Point：

201.5ºC

Refractive Index：

1.555

Water Solubility：

1.50e+00 g/L

Toxicity

Toxicity Summary：

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.

Drug Information

Drug 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.

MeSH：

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. (See all compounds classified as Muscarinic Antagonists.)|Agents that inhibit the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the MUSCARINIC ANTAGONISTS. (See all compounds classified as Parasympatholytics.)|Agents that dilate the pupil. They may be either sympathomimetics or parasympatholytics. (See all compounds classified as Mydriatics.)

Absorption：

Absorbed following ophthalmic administration.

Mechanism of Action：

By blocking muscarinic receptors, cyclopentolate produces dilatation of the pupil (mydriasis) and prevents the eye from accommodating for near vision (cycloplegia).

MeSH Entry Terms：

Cyclogyl

Cyclopentolate Use and Manufacturing

Uses

thalidomide derivative for multiple myeloma and myelodysplastic syndromes

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals

Computed Properties

Molecular Weight:291.4
XLogP3:2.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:7
Exact Mass:291.18344366
Monoisotopic Mass:291.18344366
Topological Polar Surface Area:49.8
Heavy Atom Count:21
Complexity:331
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes