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シクロペントラート

Cyclopentolate

HCID 2905
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
512-15-2
標準SMILES
CN(C)CCOC(=O)C(c1ccccc1)C1(O)CCCC1
InChIKey
SKYSRIRYMSLOIN-UHFFFAOYSA-N
分子式
C17H25NO3
平均分子量
291.4 g/mol
単同位体質量
291.18344366

概要

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.

名称と識別子

優先名称
Cyclopentolate
IUPAC
2-(dimethylamino)ethyl 2-(1-hydroxycyclopentyl)-2-phenylacetate
現地名
シクロペントラート
英語名
Cyclopentolate
分子式
C17H25NO3
分子量
291.39

名称と別名

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
名称をさらに表示
サイプレジンシクロペントラートα-(1-ヒドロキシシクロペンチル)ベンゼン酢酸2-(ジメチルアミノ)エチルシクロペントレート2-フェニル-2-(1-ヒドロキシシクロペンタン-1-イル)酢酸2-(ジメチルアミノ)エチル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

物性

構造計算による物性

XLogP
2.7
極性表面積
49.8 Ų
水素結合供与体数
1
水素結合受容体数
4
回転可能結合数
7
重原子数
21
形式電荷
0
複雑度
331

実験および物理化学的性質

DrugsPharmaceuticals
LogP2.4
Solubility1.50e+00 g/L
Human Drugs · 3 件

Breast Feeding; Lactation; Mydriatics; Muscarinic Antagonists; Parasympatholytics

Pharmaceuticals

Diagnostic agents > Ophthalmic medicines

Melting Point · 2 件

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]

物理化学的性質

沸点
409.7 · 409.7±20.0 °C(Predicted)
比重(密度)
1.136 · 1.136±0.06 g/cm3(Predicted)
酸解離定数(Pka)
7.93 · pKa 7.93(H2O ) (Uncertain)

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

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%)

毒性情報

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

安全データ

注意喚起語
警告
危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード H302

化学と産業

薬理情報

ATC Code · 3 件

S01FA04

S - Sensory organs

QS - Sensory organs

Pharmacodynamics · 1 件

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 · 3 件

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

用途と製造

関連反応

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化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

データベース識別子

CAS
512-15-2
PubChem CID
2905
DTXSID
DTXSID3048528
ChEMBL
CHEMBL1201338
ChEBI
CHEBI:4024
UNII
I76F4SHP7J
EC Number
208-136-4
Nikkaji
J264.904G、J264.905E、J6.274J
Uses
Use (kg; approx.) in Germany (2009): >10
Use ClassificationPharmaceuticals

応用分野

使用Cyclopentolate is an effective mydriatic and cycloplegic that begins to act very quickly and has a relatively short duration. It is used also in ophthalmoscopy for causing pre-operational mydriasis.

上流・下流製品情報

上流原料

硝酸マグネシウム·6水和物2-(ジメチルアミノ)-1-クロロエタンフェニル酢酸ナトリウムシクロペンタノン2-ブロモプロパン

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補足説明 · 1 件

定義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.