318-98-9 Usage
Description
Propranolol hydrochloride is a non-selective β-adrenergic receptor blocker, which is an off-white to light-yellow crystalline solid. It is easily soluble in ethanol and water. Propranolol hydrochloride is commonly known by the brand names Inderal (Wyeth) and Innopran (Reliant).
Uses
Used in Cardiovascular Applications:
Propranolol hydrochloride is used as an antihypertensive agent for the treatment of high blood pressure. It functions as an antianginal medication to decrease the number of angina attacks, which are caused by an inadequate oxygen supply to the heart. Additionally, it serves as an antiarrhythmic (class II) to prevent and manage heart-rhythm problems.
Used in Endocrine Applications:
Propranolol hydrochloride is utilized as a treatment for overactive thyroid conditions, helping to regulate thyroid hormone levels and alleviate symptoms.
Used in Neurological Applications:
The drug is employed for the prophylaxis of migraine headaches, reducing the frequency and severity of these episodes.
Used in Post-Heart Attack Recovery:
Propranolol hydrochloride is used after a heart attack to prevent further damage to the heart and support the recovery process.
Used in Research and Development:
(±)-Propranolol hydrochloride has been used in various research applications, such as determining the role of the autonomic nervous system in skin microcirculation in rats, reducing arrhythmogenic events, and studying its effects on oxygen-induced retinopathy in mice.
Biochem/physiol Actions
Propranolol hydrochloride is a β-adrenoceptor antagonist. Its action at β2 receptor results in bronchoconstriction. Due to its lipophilic nature, propranolol can penetrate to the central nervous system and has a negative effect. It serves as a 5-HT1/5-HT2 serotonin receptor antagonist. Propranolol hydrochloride is useful as an antihypertensive drug, cardiac depressant and also in the treatment of angina pectoris. It decreases the effect of stress and exercise on heart by reducing the rate of contraction and conduction of impulse. It is known to competitively block the action of catecholamines.
Clinical Use
Beta-adrenoceptor blocker:
Hypertension
Phaeochromocytoma
Angina
Arrhythmias
Anxiety
Migraine prophylaxis
Veterinary Drugs and Treatments
While propranolol is used for hypertension, migraine headache prophylaxis,
and angina in human patients, it is used primarily in veterinary
medicine for its antiarrhythmic effects. Dysrhythmias treated
with propranolol include: atrial premature complexes, ventricular
premature complexes, supraventricular premature complexes and
tachyarrhythmias, ventricular or atrial tachyarrhythmias secondary
to digitalis, atrial tachycardia secondary to Wolff-Parkinson-White (WPW) with normal QRS complexes, and atrial fibrillation (generally
in combination with digoxin). Propranolol reportedly improves
cardiac performance in animals with hypertrophic cardiomyopathy.
It has been used to treat systemic hypertension and clinical signs associated
with thyrotoxicosis and pheochromocytoma.
Drug interactions
Potentially hazardous interactions with other drugs
Anaesthetics: enhanced hypotensive effect; risk of
bupivacaine toxicity increased.
Analgesics: NSAIDs antagonise hypotensive effect.
Anti-arrhythmics: increased risk of myocardial
depression and bradycardia; increased risk of
bradycardia, myocardial depression and AV block
with amiodarone; concentration increased by
propafenone and possibly dronedarone; increased
risk of myocardial depression and bradycardia with
flecainide; increased risk of lidocaine toxicity.
Antibacterials: metabolism increased by rifampicin.
Antidepressants: enhanced hypotensive effect with
MAOIs; concentration increased by fluvoxamine;
concentration of imipramine increased.
Antihypertensives; enhanced hypotensive effect;
increased risk of withdrawal hypertension with
clonidine; increased risk of first dose hypotensive
effect with post-synaptic alpha-blockers such as
prazosin.
Antimalarials: increased risk of bradycardia with
mefloquine.
Antipsychotics enhanced hypotensive effect with
phenothiazines; concentration of both drugs
increased with chlorpromazine.
Calcium-channel blockers: increased risk of
bradycardia and AV block with diltiazem;
hypotension and heart failure possible with
nifedipine and nisoldipine; asystole, severe
hypotension and heart failure with verapamil.
Cytotoxics: possible increased risk of bradycardia
with crizotinib.
Diuretics: enhanced hypotensive effect.
Fingolimod: possibly increased risk of bradycardia.
Moxisylyte: possible severe postural hypotension.
Sympathomimetics: severe hypertension with
adrenaline and noradrenaline and possibly with
dobutamine.
Metabolism
Propranolol is subject to considerable hepatic-tissue
binding and first-pass metabolism. It is metabolised in the
liver to an active metabolite (4-hydroxypropranolol) and
several inactive ones.
The metabolites and small amounts of unchanged drug
are excreted in the urine.
Check Digit Verification of cas no
The CAS Registry Mumber 318-98-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,1 and 8 respectively; the second part has 2 digits, 9 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 318-98:
(5*3)+(4*1)+(3*8)+(2*9)+(1*8)=69
69 % 10 = 9
So 318-98-9 is a valid CAS Registry Number.
InChI:InChI=1/C16H21NO2.ClH/c1-12(2)17-10-14(18)11-19-16-9-5-7-13-6-3-4-8-15(13)16;/h3-9,12,14,17-18H,10-11H2,1-2H3;1H
318-98-9Relevant articles and documents
Synthetic method of propranolol hydrochloride
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Paragraph 0015; 0019; 0022-0023; 0026-0033; 0037-0038; 0042, (2021/09/04)
The invention belongs to the field of medicines, and particularly relates to a synthetic method of propranolol hydrochloride. The preparation method comprises the following steps: by taking epoxy chloropropane and methyl naphthol as raw materials and acetonitrile as a solvent, firstly reacting in tetramethylammonium hydroxide to obtain an intermediate product, then reacting the intermediate product with isopropylamine in the presence of a metal salt Ni/alpha-Al2O3 catalyst to obtain propranolol, and finally salinizing to obtain the propranolol hydrochloride. The method can significantly improve the yield and purity of the propranolol hydrochloride.
Preparation method of propranolole hydrochloride
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Paragraph 0067; 0068; 0069, (2018/10/11)
The invention belongs to the field of medical chemistry, and especially relates to a preparation method of propranolole hydrochloride. The preparation method comprises following steps: 1, 1-naphthol is reacted with 1,3-dibromo(iodo)propanone in a sodium hydroxide solution so as to obtain 1-bromo(iodo)-3-(1-naphthyloxy)-2-propanone; 2, 1-bromo(iodo)-3-(1-naphthyloxy)-2-propanone is subjected to reduction with sodium borohydride in an organic solvent so as to obtain 1-bromo(iodo)-3-(1-naphthyloxy)-2-propanol; 3, 1-bromo(iodo)-3-(1-naphthyloxy)-2-propanol is reacted with isopropylamine in an organic solvent so as to obtain 1-isopropylamino-3-(1-naphthyloxy)-2-propanol; and 4, 1-isopropylamino-3-(1-naphthyloxy)-2-propanol is reacted with hydrochloric acid so as to obtain 1-(isopropylamino)-3-(1-naphthyloxy)-2-propanol hydrochloride (propranolole hydrochloride). The preparation method is capable of avoiding using of chloropropylene oxide, is more safe and friendly to the environment, no intermediate containing ethylene oxide structure is adopted in reaction process, so that the drug safety is higher.
Covalent Organic Frameworks with Chirality Enriched by Biomolecules for Efficient Chiral Separation
Zhang, Sainan,Zheng, Yunlong,An, Hongde,Aguila, Briana,Yang, Cheng-Xiong,Dong, Yueyue,Xie, Wei,Cheng, Peng,Zhang, Zhenjie,Chen, Yao,Ma, Shengqian
supporting information, p. 16754 - 16759 (2018/11/27)
The separation of racemic compounds is important in many fields, such as pharmacology and biology. Taking advantage of the intrinsically strong chiral environment and specific interactions featured by biomolecules, here we contribute a general strategy is developed to enrich chirality into covalent organic frameworks (COFs) by covalently immobilizing a series of biomolecules (amino acids, peptides, enzymes) into achiral COFs. Inheriting the strong chirality and specific interactions from the immobilized biomolecules, the afforded biomolecules?COFs serve as versatile and highly efficient chiral stationary phases towards various racemates in both normal and reverse phase of high-performance liquid chromatography (HPLC). The different interactions between enzyme secondary structure and racemates were revealed by surface-enhanced Raman scattering studies, accounting for the observed chiral separation capacity of enzymes?COFs.