Synthesis of atenolol imprinted polymer using bulk and precipitation polymerization the purpose of the synthesis by two methods is to see the effectiveness of each polymer produced. Lipasecatalyzed green synthesis of enantiopure atenolol. Apr 20, 2015 synthesis reaction summary 3chloroaniline is reacted with chlorosulfonic acid to yield 4amino6chlorobenzene1,3disulfonyldichlordie molecule which on subsequent amination yields 4amino6chlorobenzene1,3disulfonamide, upon further treatment with formic acid it yields chlorothiazide. C for 72 hours, then cooled to room temperature, filtered and washed with dmf, ethanol and thf, so the residue were dried in an oven for overnight and the solid modified mwcnt with atenolol was ready for more evaluations. The molecular and structural formula is as shown figure 1. Atenolol, however, appears not to improve mortality in those with high blood pressure. Synthesis and characterization of sustained release atenolol. Reaction summary starting reaction occurs inbetween hydrazine hydrate and ammonium thiocyanate that produces 1, 2bis thiocarbamoyl hydrazine which on. Synthesis atenolol impurity c 242rsoxrain2ylmethoxyphenylacetamide 2. It can also be used with other blood pressure medications. Synthesis of atenololimprinted polymers with methyl. A phase transfer catalytic process for the preparation of epoxide and halohydrin intermediates, which can be subsequently and directly reacted with isopropylamine to produce betaadrenergic antagonists such as atenolol, propanolol and their derivatives. Synthesis and modification of carboxylated multi wall nanotubes with atenolol.
Atenolol is in a group of drugs called betablockers. Preparation and characterization of atenolol laden. Pai and swapnali suhas patil department of chemistry, d. Design, synthesis, and in vitro kinetics study of atenolol prodrugs for the use in aqueous formulations rafikkaraman, 1,2 alaaqtait, 1 khulodkhayyatdajani, 3 andsalehabulafi 1 faculty of pharmacy, alquds university, p. Synthesis of the atenolol prod 1 was accomplished using kirbys procedure 38 figure 1. Dec 25, 2015 reaction summary starting reaction occurs inbetween hydrazine hydrate and ammonium thiocyanate that produces 1, 2bis thiocarbamoyl hydrazine which on further treatment with phosgene undergoes rearrangements, particularly molecular rearrangementthrough loss of ammonia to form 5amino2mercapto1, 3, 4thiadiazole. Atenolol is a beta blocker medication primarily used to treat high blood pressure and heartassociated chest pain. Tenormin is contraindicated in those patients with a history of hypersensitivity to the atenolol or any of the drug. Pdf synthesis of atenololimprinted polymers with methyl.
It is a relatively polar hydrophilic compound with water solubility. Impurity impurity are chemical substances inside a confined amount of liquid, gas, or solid, which differ from the chemical composition of the material or compound. Synthesis and spectroscopic studies ofatenolol derivatives. In vitro kinetic study of atenolol prodrug prod 1 demonstrated that the was largely. Pdf design, synthesis, and in vitro kinetics study of atenolol. In molecularimprinting processes, the selection of the functional monomer is an important factor that affects the binding affinity and specificity of the imprinted. Atenolol may also be used to treat irregular heartbeat, heart failure, alcohol withdrawal symptoms, and to prevent migraine headaches. Cheminform is a weekly abstracting service, delivering concise information at a glance that was extracted from about 100 leading journals. The aim of this research was to synthesis impurities of atenolol viz.
The structure of the nitrile intermediate, 14cyanomethylphenoxy2hydroxy3isopropylaminopropane, has been. Atn selective sites were synthesized by using suspension polymerization in silicon oil. A new green route is proposed for the synthesis of enantiopure atenolol a. Discovery and development of betablockers wikipedia. Gas chromatography with headspace is widely used for the. Pdf based on dft, mp2, and the density functional from truhlar group hybrid gga. Scheme for the synthesis of atenolol showing usage of methanol. Kinetic resolution of r,satenolol with the use of lipases in various organic solvents volume. Atenolol is a betaadrenaceptor antagonist commonly known as beta blocker. The enzymatic method are used for the direct resolution of racemic atenolol. Journal of chemical and pharmaceutical research, 2012, 41.
Atn, methacrylic acid, and ethylene glycol dimethacrylate were used as enantiomerically pure template, functional monomer, and cross. Box, jerusalem, palestine department of sciences, university of basilicata, via dell ateneo lucano, potenza, italy. Chemoenzymatic synthesis of r and s atenolol and propranolol employing lipase catalyzed enantioselective esterification and hydrolysis. Several methods have been reported on the synthesis of spropranolol and satenolol including the use of. Atenolol possesses numerous mechanisms that may contribute to its efficacy in preventing migraine headaches. Design, synthesis, and in vitro kinetics study of atenolol prodrugs. The novel prodrug design approach that was utilized for the synthesis and.
Research article design, synthesis, and in vitro kinetics study of atenolol prodrugs for the use in aqueous formulations rafikkaraman, 1,2 alaaqtait, 1 khulodkhayyatdajani, 3 andsalehabulafi 1 faculty of pharmacy, alquds university, p. A synthesis of atenolol using a nitrile hydration catalyst american. Enzymatic kinetic resolution approach was used to synthesize the enantiopure intermediates r and s2. Synthesis and modification of carboxylated multi wall. Tenormin atenolol dose, indications, adverse effects. Lowering high blood pressure helps prevent strokes, heart attacks, and kidney problems. Betablockade can prevent arterial dilation, inhibit renin secretion, and block catecholamineinduced lipolysis. The reaction mechanism to form sustained release atenolol microspheres were determined by optical microscopic method and evaluated by using ftir spectroscopy.
This can be done following two paths which both involve alkylation of an appropriate phenoxide with epichlorohydrin ech. Porkar yazdi department of chemistry, sistan and baluchestan university, zahedan 985674, islamic. In the process disclosed in the present invention, quaternary ammonium salts of high alkyl groups or tertiary ammonium salts of lower alkyl. It works by blocking the action of certain natural. Synthetic approaches towards the synthesis of beta. Other uses include the prevention of migraines and treatment of certain irregular heart beats. Methanol is used during synthesis of atenolol and therefore present as organic impurity in bulk drug. The invention provides a method for preparing i s iatenolol.
Kinetic resolution of r,satenolol with the use of lipases. Blocking lipolysis, decreases arachidonic acid synthesis and. In this work, nanosized chiral imprinted polymers containing s. Atenolol is an ethanolamine compound having a 4carbamoylmethylphenoxymethyl group at the 1position and an nisopropyl. Learn about its side effects, dosage, uses, and more.
Tenormin is contraindicated in those patients with a history of hypersensitivity to the atenolol or any of the drug products components. Atenolol has been linked to rare cases of drug induced liver injury, some of which have been fatal. It describes atenolols synthesis, its physical properties, the method of analysis, and drug metabolism. Synthesis of 4 hydroxyl phenyl acetic acid to 4 hydroxyl phenyl acid methyl ester. Pdf lipase catalyzed green synthesis of enantiopure atenolol. Synthesis and comparative skin permeability of atenolol and propranolol esters b. Green synthesis of magnetic fe3o4sio2hap nanocomposite. Methods to quantify enantiomers in environmental matrices are scarce.
This chapter describes the analytical profile of atenolol. The prepared chiral imprinted polymers were used as the carrier. Atenolol is one of the beta1 blocker drugs that is misused by athletes to increase their performance during competition. Enantioselective hplc analysis and biodegradation of atenolol. C for 72 hours, then cooled to room temperature, filtered and washed with dmf, ethanol and thf, so the residue were dried in an.
Atenolol is a cardioselective betablocker that is widely used in the treatment of hypertension and angina pectoris. The catalytic activities of nine commercially available lipases were firstly compared, then all enzymes were tested for the kinetic resolution of r,s atenolol by enantioselective acetylation in different reaction mediums. Inhibition of prostaglandin synthesis by indomethacin. This medication is also used to treat chest pain and to improve survival after a heart attack atenolol belongs to a class of drugs known as betablockers. Sep 21, 2012 the accurate quantification of enantiomers is crucial for assessing the biodegradation of chiral pharmaceuticals in the environment. An enzymatic kinetic resolution approach was used to synthesize the enantiopure intermediates r and s243chloro2hydroxypropoxyphenylacetamide from the corresponding racemic alcohol. It is known that optically pure atenolol can be obtained by asymmetric synthesis. After oral administration atenolol is incompletely absorbed from the intestine, so about 50 % of the beta blocker are finally biovailable. Atenolol tenormin is used to treat high blood pressure and angina, and to reduce heart attack risk. Possessing the ability to reduce the hearts need for oxygen. Atenolol is used with or without other medications to treat high blood pressure hypertension.
Atenolol is a hydrophilic betareceptor blocking drug, which is predominantly eliminated via the kidneys, only about 5% of the atenolol is metabolised by the liver. Synthesis of atenololimprinted polymers with methyl methacrylate as functional monomer in propanol using bulk and precipitation polymerization method article pdf available may 2019. Synthesis of atenololimprinted polymer using bulk and precipitation polymerization the purpose of the synthesis by two methods is to see the effectiveness of each polymer produced. Synthesis and reactivity in inorganic, metalorganic, and nanometal chemistry.
Synthesis of chlorothiazide medicinalchemistrynotes. Of the commercially available lipases screened, candida antarctica lipasea clea showed maximum. Atenolol may be chemically described as a benzene acetamide, 421 hydroxy 31 1 methyl ethyl amino propoxy. The particle size of atenolol ranged from 80 to 186 m. Mpw1k calculations for an acidcatalyzed hydrolysis of nine kirbys. The catalytic reaction may be employed as the final step in the synthesis or in the preparation of the intermediate 4hydroxyphenylacetamide.
The accurate quantification of enantiomers is crucial for assessing the biodegradation of chiral pharmaceuticals in the environment. Atenolol was synthesized from 4hydroxy phenylacetamide via the twostep chemical reactions, condensation and amination, after the method of condensation was improved, the mp of condensate increased from 167. The preparation method that can be used in separating atenolol in sample is molecular imprinting solidphase extraction mispe because it has good selectivity and sensitivity. Synthesis of the atenolol prod 1 was accomplished using kirbys procedure figure 1. Therefore, it is important to analyze atenolol levels in blood selectively. Enantioselective hplc analysis and biodegradation of. Here, we used an enantioselective method, highperformance liquid chromatography with fluorescence detection hplcfd, to analyze two betablockers, metoprolol and atenolol, and the. The interaction of inhibition of prostaglandin pg synthesis by indomethacin 75 mgday with the antihypertensive effect of atenolol 50 mg b. Department of medicinal chemistry, collegium medicum in bydgoszcz, faculty of pharmacy, nicolaus copernicus university in toru, dr. The synthesis of atenolol is described using a platinum contain ing homogeneous catalyst for the conversion of a nitrile to an amide.
Atenolol is available under the following different brand names. Kazuhiro kitaori a practical synthesis of optically active atenolol from chiral epichlorohydrin. Blocking lipolysis, decreases arachidonic acid synthesis and subsequent prostaglandin production. Synthetic scheme for the preparation of atenolol prod 1 from its parent drug. Design, synthesis, and in vitro kinetics study of atenolol. The synthesis of atenolol is described using a platinum containing homogeneous catalyst for the conversion of a nitrile to an amide. Green synthesis of magnetic fe 3 o 4 sio 2 hap nanocomposite for atenolol. Synthetic approaches towards the synthesis of betablockers. Research article design, synthesis, and in vitro kinetics. Green synthesis of magnetic fe3o4sio2hap nanocomposite for.112 1403 168 1220 147 112 1259 7 11 1319 988 157 1140 1482 96 861 102 789 470 1176 1283 171 235 725 913 443 743 140 1154 267 1438 455 748 1218