DARIFENACIN Synthesis, SAR, MCQ,Structure,Chemical Properties and Therapeutic Uses April 14, 2020 huzefakifayet GPAT Preparation, How to prepare for gpat, MCQ, NIPER JEE Examination (Masters/Ph.D. Admission), Pharmacy Exam Questions, Quiz, Study Material DARIFENACIN, Darifenacin Blurred vision, DARIFENACIN chemical properties, Darifenacin Constipation, Darifenacin Dry eyes, Darifenacin Dry mouth, DARIFENACIN gpat questions, DARIFENACIN gpatindia, Darifenacin Headache, DARIFENACIN mechanism of action, DARIFENACIN MELTING POINT, DARIFENACIN MOLECULAR WEIGHT, DARIFENACIN NUMBER OF CHIRAL CARBONS, DARIFENACIN OCTANOL WATER COEFFICIENT, DARIFENACIN physical properties, Darifenacin Reducing the frequent trips to bathroom, Darifenacin Reducing the leakage of urine, Darifenacin Reducing the urge for frequent voids, DARIFENACIN RING STRUCTURE, DARIFENACIN SAR, DARIFENACIN side effects, DARIFENACIN SOLUBILITY, Darifenacin Stomach pain, Darifenacin Stomach upset, DARIFENACIN structure, DARIFENACIN synthesis, DARIFENACIN therapeutic uses, Darifenacin Tiredness Darifenacin Weakness, Darifenacin Treatment of overactive bladder, Demo Question for GPAT, Demo Question for Pharmacist Exam, Demo Questions for NIPER JEE, Exam Trial For GPAT, gpatindia, Model MCQ of Medicinal Chemistry, Model Question for GPAT exam Medicinal Chemistry, Model Questions from Anticholinergics Darifenacin IUPAC nomenclature (S)-2-[1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl] pyrrolidin-3-yl] -2,2-diphenyl-acetamide Classification Darifenacin is an acetylcholine antagonist. It is a muscarinic antagonist. Physiochemical Properties S. NO. PHYSICAL AND CHEMICAL PROPERTIES 1 Molecular weight 426.5 g/mol 2 Physical appearance White crystalline powder 3 Melting point More than 230°C 4 Solubility Slightly soluble in water 5 Octanol/water partition coefficient 4.5 5 Presence of ring Dihydrobenzofuran, cyclopentyle, phenyl 6 Number of chiral centers 2 Mechanism of Action Darifenacin acts as selective antagonist for the muscarinic receptors (M3). M3 receptors are involved in contraction of bladder, and hence, the drug helps in relaxing bladder.  Structure Activity Relationship Either R1 or R2 must be heterocyclic or carbocyclic. The R3 group can be hydrogen, hydroxyl, hydroxymethyl or amide. Most potent derivatives has X as an ester. X can also be either oxygen or absent completely. The N substituent can be quaternary ammonium salt or tertiary amine or both with different alkyl groups. Maximum potency obtained when the distance between the ring substituted carbons is 2 carbon units. Method of synthesis Reaction of 3-(S)-(-)-(1-carbamoyl-1,1-diphenylmethyl)- pyrrolidine with 5-(2-bromoethyl)benzo[2,3-b]furan in presence of anhydrous K2CO3 in acetonitrile to get darifenacin.  Therapeutic Uses Darifenacin is used for: Treatment of overactive bladder Reducing the frequent trips to bathroom Reducing the urge for frequent voids Reducing the leakage of urine Side Effects Side effects of Darifenacin are: Constipation Headache Dry mouth Blurred vision Dry eyes Tiredness Weakness Stomach upset Stomach pain MCQ Q.1 What can be the correct IUPAC nomenclature of Darifenacin? a) (S)-2-[1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl] pyrrolidin-3-yl] -2,2-diphenyl-acetamide b) (S)-2-[3-(Diisopropylamino)-1-phenylpropyl]-4-methylphenol. c) 7-Chloro-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepine-3-carboxylic acid d) N,N-Dimethyl-2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetamide hemitartrate Q.2 Which amongst the following statements is/are incorrect related to the SAR of Darifenacin? I. Either R1 or R2 must be heterocyclic or carbocyclic. II. The R3 group can be hydrogen, hydroxyl, hydroxymethyl or amide. III. Poorest derivatives has X as an ester. IV. ‘X’ can also be either oxygen or absent completely. a) I, II b) III c) III, IV d) II Q.3 Darifenacin can be obtained by reaction of 3-(S)-(-)-(1-carbamoyl-1,1-diphenylmethyl)- pyrrolidine with? a) 5-(2-bromoethyl)benzo[2,3-b]furan b) 1-phenylpropyl-4-methylphenol c) 1,4-benzodiazepine-3-carboxylic acid d) None of the above Q.4 Side effects of drug darifenacin is/are? a) Constipation b) Headache c) Dry mouth d) All of the above Q.5 Match the following drugs with their correct molecular weights- i. Darifenacin A.426.5 gm/mol ii. Tolterodine B.307.4gm/mol iii. Chlorazepate C. 325.5 gm/mol iv. Zolpidem D. 314.72 gm/mol a) i-C, ii-B, iii-A, iv-D b) i-C, ii-B, iii-D, iv-A c) i-A, ii-C, iii-D, iv-B d) i-B, ii-A, iii-D, iv-C Q.6 An example of drug from class Acetylcholine antagonist? a) Zolpidem b) Chlorazepate c) Amphetamine d) Darifenacin Q.7 The type of ring system found in the structure of darifenacin? a) Dihydrobenzofurane b) Pyrrolopyrimidine c) Naphthalene d) Pyrrolopyrrole ring For More Standard and Quality Question Bank you can Join Our Test Series Programme for GPAT, NIPER JEE, Pharmacist Recruitment Exam, Drug Inspector Recruitment Exams, PhD Entrance Exam for Pharmacy Participate in Free Online Test for GPAT, Pharmacist,Drug Inspector ANSWERS 1-a 2-b 3-a 4-d 5-c 6-d 7-a REFERENCES  Steers WD. Darifenacin: pharmacology and clinical usage. Urologic Clinics. 2006 Nov 1;33(4):475-82.  Vasantha M, Lakshmanarao V, Rao SY, Devi SA, Suryanarayana VM. Synthesis/Isolation of darifenacin hydrobromide by-products.