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  2. /화합물

아트로핀

Npc209773

HCID 174174
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
16175-85-2
표준 SMILES
CN1[C@@H]2CC[C@H]1CC(OC(=O)C(CO)c1ccccc1)C2
InChIKey
RKUNBYITZUJHSG-SPUOUPEWSA-N
분자식
C17H23NO3
평균 분자량
289.4 g/mol
단동위원소 질량
289.1677936

개요

Atropine is a racemate composed of equimolar concentrations of (S)- and (R)-atropine. It is obtained from deadly nightshade (Atropa belladonna) and other plants of the family Solanaceae. It has a role as an antidote to sarin poisoning, a oneirogen, a bronchodilator agent, an anti-arrhythmia drug, a muscarinic antagonist, a parasympatholytic, a mydriatic agent, an anaesthesia adjuvant and a plant metabolite. It contains a (S)-atropine and a (R)-atropine.

이름 및 식별자

우선 이름
Npc209773
IUPAC
[(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate
현지명
아트로핀
영어명
Atropine
분자식
C17H23NO3
분자량
289.37

이름 및 동의어

RefChem:1092872Npc209773ATROPINE51-55-8dl-HyoscyamineAtropenAtropinTropine tropatedl-TropyltropateAtropinolEyesulesIsopto-atropine
이름 더 보기
아트로핀아트로핀,그염류및유도체d-hyoscyamineHSDB2199Atropisol
Troyl tropateAtropinaAtropin-flexiolen(+,-)-Tropyl tropateAtropin [German]Atropina [Italian]hyoscyamine(+/-)-Atropine

데이터베이스 식별자

CAS
16175-85-2、51-55-8
PubChem CID
174174
DTXSID
DTXSID4020113
ChEMBL
CHEMBL254656、CHEMBL475124
ChEBI
CHEBI:16684
UNII
7C0697DR9I、HA7DL7YA9K
Nikkaji
J1.385.555B、J1.566.306E

물성

구조 계산 물성

XLogP
1.8
극성 표면적
49.8 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
4
회전 가능 결합 수
5
무거운 원자 수
21
형식 전하
0
복잡도
353

실험 및 물리화학적 성질

Solubility>43.4 [ug/mL] (The mean of the results at pH 7.4)
Animal DrugsPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Dissociation Constants · 3건

9.84

9.84

9.43

Collision Cross Section171.5 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]

물리화학적 성질

녹는점
115 · 115-118 °C
끓는 점
431.53 °C · 431.53°C (rough estimate)
밀도
1.047 · 1.0470 (rough estimate)
굴절률
1.52 · 1.5200 (estimate)
인화점
2 ℃ · 2℃
저장 조건
-20 °C · -20°C
용해도
2 O: · H2O: 2 mg/mL
물리적 상태
가루
산도 계수 (pKa)
9.7 · 9.7(at 21℃)
색상
하얀색
수용성
1.6 g/L · 1.6g/L(18℃)

안전 및 규제

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

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
CK0700000
ridadr
1544
독성
LD50 orally in rats: 750 mg/kg (Cahen, Tvede)
HS 번호
29399900
risk_code
26/28-36/37/38-20/21/22-36-11
hazard_code
T+,Xn,F
safety_code
25-45-36-26-36/37-16
포장분류
III
위험 등급
6.1
F 고인화성물질
8-10-23
Hazard Classifications
Acute Tox. 2 InhalationAcute Tox. 2 Oral
스토리지 클래스
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
유해 물질 데이터
51-55-8(Hazardous Substances Data)

화학 및 산업

약리 정보

ATC CodeA03BA01
Protein BindingThe protein binding of atropine ranges from 14% to 44%, and is saturable between 2 and 20 μg/mL.
Pharmacodynamics · 1건

Atropine is an antimuscarinic agent that antagonizes the effects of acetylcholine. In small doses, atropine slows heart rate, and tachycardia develops due to paralysis of vagal control. Compared to [scopolamine], atropine has a more potent and prolonged effect on the heart, intestine and bronchial muscle, but a weaker effect on the iris, ciliary body and certain secretory glands. Atropine leads to increased respiratory rate and depth of respiration, possibly due to the drug-induced bronchiolar dilatation rather than its mild effect on vagal excitation. At an adequate dose, atropine abolishes different types of reflex vagal cardiac slowing or asystole. Atropine can be used to prevent or abolish bradycardia or asystole induced by the injection of choline esters, anticholinesterase agents or other parasympathomimetic drugs, and cardiac arrest produced by stimulation of the vagus. When vagal activity is an etiologic factor, atropine may also lessen the degree of partial heart block. In clinical doses, atropine counteracts the peripheral dilatation and abrupt decrease in blood pressure produced by choline esters. However, when given by itself, atropine does not exert a striking or uniform effect on blood vessels or blood pressure. The use of topical atropine in the eye induces mydriasis by inhibiting the contraction of the circular pupillary sphincter muscle normally stimulated by acetylcholine. This results in the contraction of the countering radial pupillary dilator muscle and pupil dilation. The use of atropine may precipitate acute glaucoma and convert partial organic pyloric stenosis into complete obstruction. Atropine may also lead to complete urinary retention in patients with prostatic hypertrophy and cause the thickening of bronchial secretions and formation of viscid plugs in patients with chronic lung disease.

Mechanism of Action · 1건

Atropine binds to and inhibits muscarinic acetylcholine receptors, competitively blocking the effects of acetylcholine and other choline esters. It acts as a reversible non-specific antagonist of muscarinic receptors, showing affinity for the M1, M2, M3, M4 and M5 receptor subtypes. Atropine antagonizes the effects of acetylcholine on tissues innervated by postganglionic cholinergic nerves, such as smooth muscle, cardiac tissue, exocrine glands and the central nervous system. Also, it acts in less innervated smooth muscle that responds to endogenous acetylcholine. The actions of atropine can be overcome by increasing the concentration of acetylcholine at receptor sites (for instance, the use of anticholinesterase agents that inhibit the hydrolysis of acetylcholine).

관련 반응

0건
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화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
Merck
14 · 14,875
BRN
91260 · 91260
주요 응용
제약
InChI
1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15+,16
InChIKey
RKUNBYITZUJHSG-SPUOUPEWSA-N
SMILES
CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)C(CO)c3ccccc3
NIST
Atropine(51-55-8)
EPA
Atropine (51-55-8)

화학적 성질

Atropine, also known as daturine, C17H23NO3, white, crystalline substance, optically inactive, but usually contains levorotatory hyoscyamine. Compound is soluble in alcohol, ether, chloroform, and glycerol; slightly soluble in water.

Biological Half-Life · 1건

Following intravenous and intramuscular doses of atropine, half-life values range from approximately 2 to 4 hours. In geriatric patients (65-75 years old), intravenous atropine has a longer half-life (10 hours). Also, the half-life of atropine is slightly shorter (approximately 20 minutes) in females than in males. In healthy volunteers given 30 µL of atropine sulfate by topical ocular administration, the half-life of atropine was approximately 2.5 hours.

Metabolism/Metabolites · 1건

Atropine is mainly metabolized by enzymatic hydrolysis in the liver. The major metabolites of atropine are noratropine, atropin-n-oxide, tropine, and tropic acid. The metabolism of atropine is inhibited by organophosphate pesticides.[L42815,​​L42835]

Absorption, Distribution and Excretion · 4건

Intravenous atropine follows a non-linear pharmacokinetic model at doses between 0.5 and 4 mg. After intramuscular administration, atropine is rapidly absorbed. In adults given 1.67 mg of atropine intramuscularly, the Cmax was 9.6 ng/mL and the Tmax went from 3 to 60 minutes. In healthy subjects given 30 µL of atropine ophthalmic solution, the Cmax and Tmax were 288 pg/mL and 28 minutes, respectively. Atropine is well absorbed in the gastrointestinal tract and rapidly delivered to systemic circulation. When administered intramuscularly, atropine has a bioavailability of 50%. The AUC0-INF and Cmax of atropine are higher in females than males (15%).

Approximately 13 to 50% of atropine is excreted unchanged in the urine. In healthy volunteers given intravenous atropine, 29% of tropine was excreted in urine, along with 15% of an unidentified metabolite.

Atropine is distributed throughout the body. Following intravenous administration, the total apparent volume of distribution of atropine ranged between 1.0 and 1.7 L/kg.

Following intravenous administration, the total clearance of atropine ranged between 5.9 and 6.8 mL/min/kg. Exercise, before and after intramuscular administration, decreases the clearance of atropine.

용도 및 제조

Use ClassificationPharmaceuticals -> Animal Drugs -> Approved in Taiwan
응용 분야 · 3건

개요Atropine is considered to be the most effective antidote for both OP and CB intoxication. By effectively competing with acetylcholine for the same cellular receptors, it prevents overstimulation of the autonomous parasympathetic system. Most importantly, it helps prevent asphixia, the main cause of death. In human subjects, it is customary to constantly infuse atropine in order to maintain optimal concentration throughout recovery from the “cholinergic crisis.” In wildlife rehabilitation, this is impractical and subjects need to be repeatedly injected with atropine.

용도Atropine is used in medicine and is an antidote for cholinesteraseinhibiting compounds, such as organophosphorus insecticides and certain nerve gases. Atropine is commonly offered as the sulfate. Atropine is used in connection with the treatment of disturbances of cardiac rhythm and conductance, notably in the therapy of sinus bradycardia and sick sinus syndrome. Atropine is also used in some cases of heart block. In particularly high doses, atropine may induce ventricular tachycardia in an ischemic myocardium. Atropine is frequently one of several components in brand name prescription drugs.

일반 설명Atropine is the tropine ester of racemictropic acid and is optically inactive. It possibly occurs naturallyin various Solanaceae, although some claim, with justification,that whatever atropine is isolated from naturalsources results from racemization of (-)-hyoscyamine duringthe isolation process. Conventional methods of alkaloidisolation are used to obtain a crude mixture of atropine andhyoscyamine from the plant material. This crude mixture isracemized to atropine by refluxing in chloroform or by treatmentwith cold dilute alkali. Because the racemizationprocess makes atropine, an official limit is set on thehyoscyamine content by restricting atropine to a maximumlevorotation under specified conditions.Atropine occurs in the form of optically inactive, white,odorless crystals possessing a bitter taste. It is not very solublein water (1:460, 1:90 at 80°C) but is more soluble inalcohol (1:2, 1:1.2 at 60°C). It is soluble in glycerin (1:27),in chloroform (1:1), and in ether (1:25). Saturated aqueoussolutions are alkaline in reaction (pH 9.5). The free baseis useful when nonaqueous solutions are to be made, such asin oily vehicles and ointment bases. Atropine has a plasmahalf-life of about 2 to 3 hours. It is metabolized in the liverto several products, including tropic acid and tropine.

제조 방법

생산 방법Atropine is prepared by extraction from Datura stramonium, or synthesized. The compound is toxic and allergenic.

상·하류 제품 정보

상류 원료

클로로포름

하류 제품

Atropine sulfate monohydrate엔도-(±)-8-아자-8-이소프로필비시클로[3.2.1]옥트-3-일(히드록시메틸)페닐아세테이트ATROPINE METHYL NITRATE

공급사100 곳

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추가 설명

정의An alkaloid that is the 3(s)-endo isomer of atropine.