SOLIFENACIN 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 Drug Inspector Exam Model Questions of Med Chem, GPAT Asked question, New Question Bank Medicinal Chemistry, NIPER Model Question from Chemistry, Pharmacist Exam Guess Questions for chemistry, SOLIFENACIN, Solifenacin Blurred vision, SOLIFENACIN chemical properties, Solifenacin Constipation, Solifenacin Dry eyes, Solifenacin Dry mouth, SOLIFENACIN gpat questions, SOLIFENACIN gpatindia, Solifenacin Headache, SOLIFENACIN mechanism of action, SOLIFENACIN MELTING POINT, SOLIFENACIN MOLECULAR WEIGHT, SOLIFENACIN NUMBER OF CHIRAL CARBONS, SOLIFENACIN OCTANOL WATER COEFFICIENT, SOLIFENACIN physical properties, SOLIFENACIN Reducing the frequent trips to bathroom, SOLIFENACIN Reducing the leakage of urine, SOLIFENACIN Reducing the urge for frequent voids, SOLIFENACIN RING STRUCTURE, SOLIFENACIN SAR, SOLIFENACIN side effects, SOLIFENACIN SOLUBILITY, SOLIFENACIN structure, SOLIFENACIN synthesis, SOLIFENACIN therapeutic uses, Solifenacin Tiredness, SOLIFENACIN Treatment of overactive bladder, Solifenacin Weakness Solifenacin IUPAC nomenclature (3R)-1-Azabicyclo[2 2 2]oct-3-yl (1S)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate Classification Solifenacin is an acetylcholine antagonist. It is a muscarinic antagonist. Physiochemical Properties S. NO. PHYSICAL AND CHEMICAL PROPERTIES 1 Molecular weight 362.5 g/mol 2 Physical appearance Solid 3 Melting point 134-136°C 4 Solubility Soluble in organic solvents 5 Presence of ring Quiniclidine, quinoline, benzene 6 Number of chiral centers 2 Mechanism of Action Solifenacin functions as antagonist for muscarinic receptors M3, M1 and M2 receptors. Antagonism of M3 receptors prevents the contraction of the detrusor muscles and antagonism of the M2 receptors prevents the contraction of smooth muscle in 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 i. 1,2,3,4-tetrahydro-1-phenylisoquinoline reacts with ethyl chloroformate to give ethyl 3,4-dihydro-1-phenylisoquinoline-2(1H)-carboxylate. ii. The latter compound on reacting with quiniclidin-3-ol, in presence of sodium hydride produces Solifenacin.  Therapeutic Uses Solifenacin 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 Solifenacin are: Constipation Headache Dry mouth Blurred vision Dry eyes Tiredness Weakness MCQ Q.1 Subtypes of Muscarinic receptors antagonize by soilifenacin are? a) M1, M2, M3 b) M2, M4, M5 c) M1, M2 d) M4, M5 Q.2 Therapeutic use of drug Solifenacin is/are? a) Treatment of Alzheimer’s disease b) Treatment of overactive bladder c) Treatment of cancer d) All of the above Q.3 Which amongst the following are the correct statements with respect to the SAR of drug Solifenacin? I. Either R1 or R2 must be heterocyclic or carbocyclic. II. The R3 group can be hydrogen, hydroxyl, hydroxymethyl or amide. III. Most potent derivatives has X as an ester. IV. ‘X’ can also be either oxygen or absent completely. a) I, IV b) I, II, IV c) I, II, III, IV d) II, III, IV Q.4 Type of ring structures present in the structure of solifenacin? a) Quiniclidine b) Quinoline c) Benzene d) All of the above Q.5 Correct sequence for the True/False for the physiochemical properties of the drug solifenacin? I. Molecular weight is 363.5 gm/mol II. Present in solid form III. Melting point is between 134-136°C IV. Soluble in organic solvents a) TFTF b) TTTT c) FFFF d)FFFT Q.6 Correct statements for the IUPAC nomenclatures of the are? I. Solifenacin: (3R)-1-Azabicyclo[2 2 2]oct-3-yl (1S)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate II. Zaleplon: N-(3-(3-cyanopyrazolo[1,5-a] pyrimidin-7-yl)phenyl)-N-ethylacetamide III. Alprazolam: 7-Chloro-1,3-dihydro-1-methyl-5-phenyl-3H-1,4-benzodiazepin-2-one IV. Diazepam: 8-Chloro-1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a] [1,4]benzodiazepine a) II, IV b) I, II c) I, III, IV d) I, II, III, IV Q.7 Match the following drugs with their correct classifications- i. Solifenacin A. Barbiturate sedative-hypnotic ii. Thiobarbital B. Benzodiazepine sedative-hypnotic iii. Diazepam C. Acetylcholine antagonist iv. Zaleplon D. Nonbenzodiazepine sedative-hypnotic a) i-C, ii-A, iii-B, iv-D b) i-A, ii-B, iii-C, iv-D c) i-D, ii-B, iii-A, iv-C d) i-D, ii-B, iii-C, iv-A 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-c 4-d 5-b 6-b 7-a REFERENCES  Morales-Olivas FJ, Estañ L. Solifenacin pharmacology. Arch Esp Urol. 2010;63(1):43-52.  Serrano JP, Camps P, inventors; Medichem SA, assignee. Process for the synthesis of solifenacin. United States patent US 7,741,489. 2010 Jun 22.