Propranolol

HCID 4946CAS 13013-17-7

기본 정보

표준 SMILES
CC(C)NCC(O)COc1cccc2ccccc12
InChIKey
AQHHHDLHHXJYJD-UHFFFAOYSA-N
분자식
C16H21NO2
평균 분자량
259.34 g/mol
단동위원소 질량
259.15722891

개요

Propranolol is a propanolamine that is propan-2-ol substituted by a propan-2-ylamino group at position 1 and a naphthalen-1-yloxy group at position 3. It has a role as an anxiolytic drug, a beta-adrenergic antagonist, a vasodilator agent, an antihypertensive agent, a xenobiotic, an anti-arrhythmia drug, an environmental contaminant and a human blood serum metabolite. It is a member of naphthalenes, a secondary amine and a propanolamine. It is functionally related to a 1-naphthol.

이름 및 식별자

우선 이름
Propranolol
IUPAC
1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol
영어명
Propanolol
분자식
C16H21NO2
분자량
259.34

이름 및 동의어

propranolol525-66-6Propanololbeta-PropranololBetalongEuprovasinProprasylytReducorPropanalolAnaprilinepropranololodl-propranolol
이름 더 보기
Avlocardylrac-PropanololAvlocanol208-378-0
Propranololum1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol1-(isopropylamino)-3-(1-naphthyloxy)propan-2-ol9Y8NXQ24VQ1-((1-Methylethyl)amino)-3-(1-naphthalenyloxy)-2-propanol2-Propanol, 1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)-CHEBI:8499DTXSID6023525

데이터베이스 식별자

CAS
13013-17-7、525-66-6
PubChem CID
4946
DTXSID
DTXSID6023525
ChEMBL
CHEMBL27
ChEBI
CHEBI:8499
UNII
9Y8NXQ24VQ
EC Number
208-378-0、235-867-6
Nikkaji
J6.653B

물성

구조 계산 물성

XLogP
3
극성 표면적
41.5 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
3
회전 가능 결합 수
6
무거운 원자 수
19

실험 및 물리화학적 성질

Chemical Classes · 2건

Other Uses -> Pharmaceuticals

Pharmaceutical

Drugs · 3건

Pharmaceuticals -> Antihypertensive drugs

Pharmaceuticals -> Used in Switzerland

Pharmaceuticals

LogP · 2건

3.48

3.09

Solubility0.0617 mg/L at 25 °C
Human Drugs · 5건

Antidepressants -> Beta blockers

Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Adrenergic Beta-Antagonists; Antiarrhythmics

EMA approved medicines: Human medicine

Pharmaceuticals

Antianginal medicines

Melting Point96 °C

물리화학적 성질

녹는점
163 · 163-164 °C
끓는 점
402.6 °C · 402.6°C (rough estimate)
밀도
1.028 · 1.0280 (rough estimate)
굴절률
1.55 · 1.5500 (estimate)
저장 조건
-20 °C · -20°C Freezer, Under inert atmosphere
용해도
DMSO(약간 용해됨), 메탄올(약간 용해됨)

화학적 성질

Colorless crystals.Soluble in water and alcohol; insoluble in benzene and ether.

안전 및 규제

GHS 분류

GHS Classification · 4건

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, 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.

유해성 정보

Regulatory Information · 2건

Status: Active Update: 13-09-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/20584

Propranolol: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 2-Propanol, 1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)-: Human health tier I assessment
Hazards SummaryAllergic contact dermatitis reported in pharmaceutical workers; [Kanerva, p. 1830] See Oxprenolol.
Hazard Classes and CategoriesAcute Tox. 4 (100%)

독성 정보

Hepatotoxicity · 1건

Mild-to-moderate elevations in serum aminotransferase levels occur in less than 2% of patients on propranolol and are usually transient and asymptomatic, resolving even with continuation of therapy. Despite its widespread use, propranolol has not been convincingly linked to instances of clinically apparent liver injury; the few cases reported have generally occurred in patients who were receiving other well known hepatotoxic agents or were associated with elevations in serum enzymes only without jaundice.

Adverse Effects · 2건

Skin Sensitizer - An agent that can induce an allergic reaction in the skin.

Common side effects of using propranolol include bradycardia, gastrointestinal issues, abdominal pain, nausea, erectile dysfunction, and wheezing/bronchospasms. Propranolol use can also cause drowsiness, fatigue, and cold extremities. Some extreme side effects to be aware of include allergic reactions, insulin resistance, and hallucinations. Prescribers need to explain and discuss all of the side effects before giving patients a prescription for propranolol.

Toxicity SummaryIngestion of greater than 1 g of propranolol in 24 hours can potentially be lethal and lead to profound bradycardia, bradyarrhythmia, hypotension, bronchospasm.
Drug Induced Liver Injury · 6건

Benchmark Dataset for the Liver Toxicity Knowledge Base (LTKB)

propranolol

Inderal®

Beta blockers

3

less-DILI-concern drugs

Effects During Pregnancy and Lactation · 2건

◉ Summary of Use during Lactation

◈ What is propranolol?

USGS Health-Based Screening Levels for Evaluating Water-Quality · 3건

Propranolol

Pharmaceutical

Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP

안전 데이터

기존화학 물질
KE-23955

화학 및 산업

약리 정보

ATC Code · 4건

C07AA05

C - Cardiovascular system

QC - Cardiovascular system

C07AA05

Protein BindingApproximately 90% of propranolol is protein bound in plasma. Other studies have reported ranges of 85-96%.
Pharmacodynamics · 1건

Propranolol is a beta-adrenergic receptor antagonist used to treat hypertension. Propranolol has a long duration of action as it is given once or twice daily depending on the indication. When patients abruptly stop taking propranolol, they may experience exacerbations of angina and myocardial infarctions.

Mechanism of Action · 1건

Propranolol is a nonselective β-adrenergic receptor antagonist. Blocking of these receptors leads to vasoconstriction, inhibition of angiogenic factors like vascular endothelial growth factor (VEGF) and basic growth factor of fibroblasts (bFGF), induction of apoptosis of endothelial cells, as well as down regulation of the renin-angiotensin-aldosterone system.

Biological Half-LifeThe elimination half-life of propranolol is approximately 8 hours. The plasma half-life of propranolol is 3 to 6 hours.
Metabolism/Metabolites · 2건

Propranolol undergoes side chain oxidation to α-naphthoxylactic acid, ring oxidation to 4’-hydroxypropranolol, or glucuronidation to propranolol glucuronide. It can also be N-desisopropylated to become N-desisopropyl propranolol. 17% of a dose undergoes glucuronidation and 42% undergoes ring oxidation.

Propranolol has known human metabolites that include (2S,3S,4S,5R)-3,4,5-Trihydroxy-6-[1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-yl]oxyoxane-2-carboxylic acid.

용도 및 제조

Uses · 2건

Used as a beta-blocking agent (antihypertensive drug); [Kanerva, p. 1830]

Use (kg) in Switzerland (2009): >750

Use ClassificationPharmaceuticals

응용 분야

개요Propranolol was responsible for sensitisation of workers in drug synthesis. In one case, epichlorhydrin was used for the production of both propranolol and oxprenolol.

용도Cardiac depressant (anti-arrhythmic); anti-adrenergic (β-receptor).

공급사48 곳

北京华美互利生物化工010-56205725 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
盐城通铭生物科技有限公司15195160625 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
江苏艾康生物医药研发有限公司025-58851090 19370895928 · [email protected]

추가 설명

정의ChEBI: A propanolamine that is propan-2-ol substituted by a propan-2-ylamino group at position 1 and a naphthalen-1-yloxy group at position 3.

관련 반응

17건

연결된 노트

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