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Bethanechol

HCID 2370
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
674-38-4
표준 SMILES
CC(C[N+](C)(C)C)OC(N)=O
InChIKey
NZUPCNDJBJXXRF-UHFFFAOYSA-O
분자식
C7H17N2O2+
평균 분자량
161.22 g/mol
단동위원소 질량
161.12900279

개요

Bethanechol is the carbamic acid ester of 2-methylcholine. A slowly hydrolysed muscarinic agonist with no nicotinic effects, it is used as its chloride salt to increase smooth muscle tone, as in the gastrointestinal tract following abdominal surgery, treatment of gastro-oesophageal reflux disease, and as an alternative to catheterisation in the treatment of non-obstructive urinary retention. It has a role as a muscarinic agonist. It is a carbamate ester and a quaternary ammonium ion.

이름 및 식별자

우선 이름
Bethanechol
IUPAC
2-carbamoyloxypropyl(trimethyl)azanium
영어명
Bethanechol
분자식
C7H17N2O2
분자량
161.22

이름 및 동의어

bethanechol674-38-4AmidopropyldimethylbetaineCarbamyl-beta-methylcholineCarbamoyl-beta-methylcholine(2-Hydroxypropyl)trimethylammonium carbamateBesacholine2-carbamoyloxypropyl-trimethylazaniumbeta-Methyl carbachol chlorideBethaine choline chloride2-(carbamoyloxy)-N,N,N-trimethylpropan-1-aminiumUro-Carb
이름 더 보기
Carbamyl-β-methylcholineCarbamoyl-β-methylcholine1-Propanaminium, 2-[(aminocarbonyl)oxy]-N,N,N-trimethyl-Ammonium, (2-hydroxypropyl)trimethyl-, carbamate (ester) (8CI)
004F72P8F4CHEBI:3084DTXSID50483981-Propanaminium, 2-((aminocarbonyl)oxy)-N,N,N-trimethyl-BethanecolHermes, MyoRefChem:54534PMS Bethanechol Chloride

데이터베이스 식별자

CAS
674-38-4
PubChem CID
2370
DTXSID
DTXSID5048398
ChEMBL
CHEMBL1482
ChEBI
CHEBI:3084
UNII
004F72P8F4
Nikkaji
J7.089K

물성

구조 계산 물성

XLogP
0
극성 표면적
52.3 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
2
회전 가능 결합 수
4
무거운 원자 수
11
형식 전하
1
복잡도
140

실험 및 물리화학적 성질

DrugsPharmaceuticals
Solubility3.11e-01 g/L
Human DrugsBreast Feeding; Lactation; Muscarinic Agonists; Parasympathomimetics
Animal DrugsPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Melting Point217 - 221 °C (chloride salt)
Physical DescriptionSolid
Collision Cross Section131.37 Ų [M]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

안전 및 규제

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

독성 정보

Treatment · 1건

Atropine Sulfate is a specific antidote. The recommended dose for adults is 0.6 mg. Repeat doses can be given every two hours, according to clinical response. The recommended dosage in infants and children up to 12 years of age is 0.01 mg/kg (to a maximum single dose of 0.4 mg) repeated every two hours as needed until the desired effect is obtained or adverse effects of atropine preclude further usage. Subcutaneous injection of atropine is preferred except in emergencies when the intravenous route may be employed. (L1712)

Adverse EffectsThe adverse drug reactions of bethanechol are described below.
Exposure RoutesOral
Toxicity Summary · 2건

Atropine sulfate competes with bethanechol at the muscarinic receptor junction, competitively blocking its binding at the postganglionic arch receptors and preventing parasympathetic cholinergic activation. A 0.6 mg dosage of atropine is recommended for adults and is repeatable every 2 hours as needed, depending on therapeutic responses. Dosages that range from 0.01 to 0.4 mg/kg can be administered in the pediatric population (infant/children) and should be repeated every 2 hours as needed, depending on therapeutic responses. The subcutaneous route via injection is also an option. An emergency indicates the use of the intravenous administration route.

Bethanechol directly stimulates cholinergic receptors in the parasympathetic nervous system while stimulating the ganglia to a lesser extent. Its effects are predominantly muscarinic, inducing little effect on nicotinic receptors and negligible effects on the cardiovascular system.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 6건

Benchmark Dataset for the Liver Toxicity Knowledge Base (LTKB)

bethanechol

Urecholine®

Cholinergics

Not Applicable

no-DILI-concern

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

화학 및 산업

약리 정보

ATC Code · 3건

N07AB02

N - Nervous system

QN - Nervous system

Pharmacodynamics · 1건

Bethanechol is selective for muscarinic receptors and has little to no impact on nicotinic receptors. The charged quaternary amine in the structure of bethanechol prevents it from crossing the blood-brain barrier which minimizes central nervous system related adverse effects.

Mechanism of Action · 1건

Bethanechol is a direct muscarinic agonist and stimulates the parasympathetic nervous system by binding to postganglionic muscarinic receptors. Though there are 5 types of muscarinic receptors (M1, M2, M3, M4, M5), binding of bethanechol to M3 is most clinically significant since M3 receptors are present in intestinal smooth muscle and the bladder. The cholinergic effects of bethanechol lead to increased detrusor muscle tone to promote bladder emptying and increased smooth muscle tone which restores gastrointestinal peristalsis and motility. As a result of selectivity for muscarinic receptors, bethanechol produces minimal to no nicotinic effects.

FDA Pharmacological Classification · 5건

004F72P8F4

BETHANECHOL

Established Pharmacologic Class [EPC] - Cholinergic Muscarinic Agonist

Mechanisms of Action [MoA] - Cholinergic Muscarinic Agonists

Bethanechol is a Cholinergic Muscarinic Agonist. The mechanism of action of bethanechol is as a Cholinergic Muscarinic Agonist.

MeSH Pharmacological Classification · 2건

Drugs that mimic the effects of parasympathetic nervous system activity. Included here are drugs that directly stimulate muscarinic receptors and drugs that potentiate cholinergic activity, usually by slowing the breakdown of acetylcholine (CHOLINESTERASE INHIBITORS). Drugs that stimulate both sympathetic and parasympathetic postganglionic neurons (GANGLIONIC STIMULANTS) are not included here.

Drugs that bind to and activate muscarinic cholinergic receptors (RECEPTORS, MUSCARINIC). Muscarinic agonists are most commonly used when it is desirable to increase smooth muscle tone, especially in the GI tract, urinary bladder and the eye. They may also be used to reduce heart rate.

Absorption, Distribution and Excretion · 1건

After oral administration of bethanechol, maximum effectiveness of the drug on the bladder and GI tract typically occur after 60-90 minutes; however, effects may present as early as 30 minutes after administration. The duration of action of a typical oral dose of bethanechol is around 1 hour while higher doses (300-400 mg) may be effective for up to 6 hours. Subcutaneously administered bethanechol produces effects more rapidly after 5-15 minutes with maximum effectiveness achieved after 15-30 minutes. The effects of subcutaneous bethanechol subside within 2 hours of administration.

Cellular LocationsMembrane

용도 및 제조

Uses · 2건

Use (kg; approx.) in Germany (2009): >100

For the treatment of acute postoperative and postpartum nonobstructive (functional) urinary retention and for neurogenic atony of the urinary bladder with retention.

Use ClassificationPharmaceuticals -> Animal Drugs -> Approved in Taiwan

응용 분야

용도Cholinergic.

공급사11 곳

北京华美互利生物化工010-56205725 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
河北贞佳新材料有限公司0319-5925599 13315915972 · [email protected]
杭州洁汉化工有限公司+86-571-86217390; +8618058761490 · [email protected]
Musechem+1-800-259-7612 · [email protected]
深圳聚合生化科技有限公司+86-400-002-6226 13028896684 · [email protected]
范德(北京)生物科技有限责任公司15911056312 · [email protected]
InvivoChem+1-708-310-1919 +1-13798911105 · [email protected]
추가 설명 · 1건

정의ChEBI: The carbamic acid ester of 2-methylcholine. A slowly hydrolysed muscarinic agonist with no nicotinic effects, it is used as its chloride salt to increase smooth muscle tone, as in the gastrointestinal tract following abdominal surgery, treatment of gastro- esophageal reflux disease, and as an alternative to catheterisation in the treatment of non-obstructive urinary retention.

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