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트로피카마이드

Tropicamide

HCID 5593
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
1508-75-4
표준 SMILES
CCN(Cc1ccncc1)C(=O)C(CO)c1ccccc1
InChIKey
BGDKAVGWHJFAGW-UHFFFAOYSA-N
분자식
C17H20N2O2
평균 분자량
284.35 g/mol
단동위원소 질량
284.15247789

개요

Tropicamide is a member of acetamides.

이름 및 식별자

우선 이름
Tropicamide
IUPAC
N-ethyl-3-hydroxy-2-phenyl-N-(pyridin-4-ylmethyl)propanamide
현지명
트로피카마이드
영어명
Tropicamide
분자식
C17H20N2O2
분자량
284.35

이름 및 동의어

tropicamide1508-75-4MydriacylBistropamideTropicacylN-ethyl-3-hydroxy-2-phenyl-N-(pyridin-4-ylmethyl)propanamideMydriafairVisumidriaticTropicamidumTropicamidaTropimilRo 1-7683
이름 더 보기
N-에틸-N-(4-피리딜메틸)트로파미드트로피카마이드Tropicamidropicamidemydrinmydrummydriatro1-7683Mydrapid
N-Ethyl-2-phenyl-N-(4-pyridylmethyl)hydracrylamideDTXSID8045220N-Ethyl-N-(4-pyridylmethyl)tropamideN-Ethyl-alpha-(hydroxymethyl)-N-(4-pyridinylmethyl)benzeneacetamideN0A3Z5XTC6NSC-757372Benzeneacetamide, N-ethyl-alpha-(hydroxymethyl)-N-(4-pyridinylmethyl)-RO-1-7683

데이터베이스 식별자

CAS
1508-75-4
PubChem CID
5593
DTXSID
DTXSID8045220
ChEMBL
CHEMBL1200604
ChEBI
CHEBI:9757
UNII
N0A3Z5XTC6
EC Number
216-140-2
Nikkaji

물성

구조 계산 물성

XLogP
1.5
극성 표면적
53.4 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
3
회전 가능 결합 수
6
무거운 원자 수
21
형식 전하
0
복잡도
310

실험 및 물리화학적 성질

LogP1.3
Solubility · 2건

3.75e-01 g/L

>42.7 [ug/mL] (The mean of the results at pH 7.4)

Human Drugs · 5건

Breast Feeding; Lactation; Mydriatics; Muscarinic Antagonists; Parasympatholytics

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Pharmaceuticals

Diagnostic agents > Ophthalmic medicines

Melting Point96.5 °C
Physical DescriptionSolid
Collision Cross Section · 2건

170.4 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

169.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

물리화학적 성질

녹는점
98 °C · 98 °C
끓는 점
492.8 · 492.8±45.0 °C(Predicted)
밀도
1.161 · 1.161±0.06 g/cm3(Predicted)
저장 조건
2 · 2-8°C
용해도
45 % · 45%(w/v) 수성 2-히드록시프로필-β-시클로덱스트린: 4.3mg/mL

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

Danger

H302 (98.4%): Harmful if swallowed [Warning Acute toxicity, oral]

P233, P260, P261, P264, P264+P265, P270, P271, P272, P280, P284, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 62 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Hazard Classes and CategoriesAcute Tox. 4 (98.4%)

독성 정보

Adverse EffectsOcular adverse events include transient stinging, photophobia, superficial punctate keratitis, blurred vision, and a rise in intraocular pressure.
Toxicity Summary · 1건

Although tropicamide is a short-acting drug, and the frequency of associated adverse events is rare, there are certain instances when reversal of mydriasis is necessary, including decreasing the risk of angle-closure glaucoma, improving blurry vision, and decreasing recovery time for patient comfort. Presumably, a cholinergic agent like pilocarpine should be able to undo the effects of an anticholinergic drug. However, several studies have reported conflicting pupillary responses. At times, only a partial reversal was observed.

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

안전 데이터

wgk
3
rtecs

화학 및 산업

약리 정보

ATC Code · 4건

S01FA06

S - Sensory organs

QS - Sensory organs

S01FA06

Protein BindingThe extent of protein binding has not been established. Tropicamide binds to albumin.
Pharmacodynamics · 1건

Tropicamide is an anticholinergic drug and that works by non‐selectively blocking muscarinic receptors to cause mydriasis and cycloplegia. It relaxes the pupillary sphincter to dilate the pupil. The onset of tropicamide‐induced mydriasis is about 10 to 15 minutes, with optimal effect occurring 25 to 30 minutes post-administration. Mydriasis caused by tropicamide wears off within four to eight hours, but it was seen up to 24 hours in some individuals. Tropicamide hinders accommodation by causing the contraction of the ciliary muscle. The cycloplegic effect occurs within 20 to minutes following administration, with a duration of action of four to 10 hours. Tropicamide can elevate intraocular pressure. The ophthalmic use of tropicamide is not typically associated with serious systemic adverse events. One randomized pilot study showed that oral tropicamide alleviated perceived symptoms of sialorrhea in patients with Parkinson's Disease: anticholinergics are believed to restore the dopaminergic to cholinergic activity imbalance in neurodegenerative diseases. Similarly in one case report, tropicamide administered via ophthalmic solution relieved clozapine-induced sialorrhea. Interestingly, in rodent models, tropicamide suppressed drug-induced tremulous jaw movements which are often used as a model of parkinsonian tremor: the significance of this finding requires further investigations.

Mechanism of Action · 1건

Muscarinic acetylcholine receptors are involved in numerous ocular functions. The M<sub>3</sub> subtype is predominantly expressed by smooth muscle cells of the sphincter pupillae, which is a circular muscle of the iris, and ciliary muscles. In response to light or binding of acetylcholine, M<sub>3</sub> receptor signalling leads to contraction of the sphincter pupillae and pupil constriction. Contraction of the ciliary muscle via M<sub>3</sub> receptor signalling also leads to accommodation, adjusting the lens for near vision. The eye is also innervated by parasympathetic nerves: ciliary ganglion neurons project to the ciliary body and the sphincter pupillae muscle of the iris to control ocular accommodation and pupil constriction. Tropicamide is a non-selective muscarinic antagonist that binds to all subtypes of muscarinic receptors. By binding to muscarinic receptors, tropicamide relaxes the pupillary sphincter muscle and causes pupil dilation. By blocking the muscarinic receptors of the ciliary body, tropicamide also prevents accommodation. Like other muscarinic antagonists, tropicamide inhibits the parasympathetic drive, allowing the sympathetic nervous system responses to dominate. Tropicamide is thought to ameliorate sialorrhea by blocking M<sub>4</sub> receptors expressed on salivary glands and reducing hypersalivation.

관련 반응

0건
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화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
J3.670F
물리적 상태
고체
산도 계수 (pKa)
5.3 · pKa 5.3 (Uncertain)
색상
하얀색
수용성
0.2 g/L · 0.2g/L(25℃)
Merck
14 · 14,9780
주요 응용
의약품(소분자)
InChI
InChI=1S/C17H20N2O2/c1-2-19(12-14-8-10-18-11-9-14)17(21)16(13-20)15-6-4-3-5-7-15/h3-11,16,20H,2,12-13H2,1H3
InChIKey
BGDKAVGWHJFAGW-UHFFFAOYSA-N
SMILES
C(CO)(C(=O)N(CC)CC1=CC=NC=C1)C1C=CC=CC=1
NIST
Tropicamide(1508-75-4)

화학적 성질

Crystalline Solid

CY1487860
HS 번호
29333990
risk_code
20/21/22-36/37/38-42/43-41-37/38-22
hazard_code
Xn,Xi
safety_code
22-26-36-36/37/39
Hazard Classifications
Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Skin Irrit. 2Skin Sens. 1STOT SE 3
스토리지 클래스
11 - Combustible Solids
Biological Half-LifeTropicamide has a plasma half-life of 30 minutes.
Metabolism/MetabolitesNo information can be found.
FDA Pharmacological Classification · 6건

N0A3Z5XTC6

TROPICAMIDE

Established Pharmacologic Class [EPC] - Anticholinergic

Mechanisms of Action [MoA] - Cholinergic Antagonists

Tropicamide is an Anticholinergic. The mechanism of action of tropicamide is as a Cholinergic Antagonist.

TROPICAMIDE

MeSH Pharmacological Classification · 2건

Agents that dilate the pupil. They may be either sympathomimetics or parasympatholytics.

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 Excretion · 4건

Following ocular administration of 40 μL drops of 0.5% tropicamide in female subjects, tropicamide reached its mean peak concentration in plasma of 2.8 ± 1.7 ng/mL (mean ± SD) at five minutes.

No information can be found.

No information can be found.

No information can be found.

Cellular LocationsMembrane

용도 및 제조

UsesUse (kg; approx.) in Germany (2009): >10
Use ClassificationPharmaceuticals
응용 분야 · 2건

용도Tropicamide, like cyclopentolate, is used in ophthalmoscopy for reaching pre-operational mydraises and for testing narrow-angle glaucoma.

일반 설명Tropicamide, N-ethyl-2-phenyl-N-(4-pyridylmethyl)hydracrylamide (Mydriacyl), is aneffective anticholinergic for ophthalmic use when mydriasisis produced by relaxation of the sphincter muscle ofthe iris, allowing adrenergic innervation of the radial muscleto dilate the pupil. Its maximum effect is achieved inabout 20 to 25 minutes and lasts for about 20 minutes,with complete recovery in about 6 hours. Its action ismore rapid in onset and wears off more rapidly thanthat of most other mydriatics. To achieve mydriasis, either0.5% or 1.0% concentration may be used, althoughcycloplegia is achieved only with the stronger solution.Its uses are much the same as those described above formydriatics in general, but opinions differ on whether thedrug is as effective as homatropine, for example, inachieving cycloplegia. For mydriatic use, however, in examinationof the fundus and treatment of acute iritis,iridocyclitis, and keratitis, it is quite adequate; and becauseof its shorter duration of action, it is less prone toinitiate a rise in intraocular pressure than the more potent,longer-lasting drugs. As with other mydriatics, however,pupil dilation can lead to increased intraocular pressure.In common with other mydriatics, it is contraindicated inpatients with glaucoma, either known or suspected, andshould not be used in the presence of a shallow anteriorchamber. Thus far, no allergic reactions or ocular damagehas been observed with this drug. The ability to clone thevarious muscarinic receptor subtypes has allowed the observationthat tropicamide has modest selectivity for theM4 receptor.

상·하류 제품 정보

상류 원료

에틸아민염산Ethanamine, N-(4-pyridinylmethylene)-Acetyltropylic chloride2-페닐-말론산모노에틸에스테르메틸-4-피리딘메틸아민4'-히드록시-2,4-디메톡시벤조페논Diethyl phenylmalonate이소니코틴알데하이드

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