The post GABAPENTIN Synthesis, SAR, MCQ, Structure, Chemical Properties and Therapeutic Uses appeared first on Gpatindia: Pharmacy Jobs, Admissions, Scholarships, Conference,Grants, Exam Alerts.
]]>1-(Aminomethyl)cyclohexaneacetic acid
Gabapentin is an anticonvulsant drug.
S. NO. | PHYSICAL AND CHEMICAL PROPERTIES | |
1 | Molecular weight | 171.24g/mol |
2 | Physical appearance | White to off-white crystalline solid |
3 | Melting point | 162-166°C |
4 | Solubility | Freely soluble in water, alkaline and acidic solutions. |
5 | Octanol/water partition coefficient | 1.25 |
6 | Presence of ring | Cyclohexyl ring |
7 | Number of chiral centers | Not present |
Gabapentin inhibits the action of α2δ-1 subunits. Due to this, there is decrease in density of pre-synaptic voltage-gated calcium channels and subsequent release of excitory neurotransmitters. This inhibition is also responsible for the anti-epileptic action of the drug.
Method of synthesis
i. 1,1-cyclohexane diacetic acid anhydride is converted to 1,1-cyclohexane diacetic acid monoamide by reacting the former with a composition that produces free ammonia in solution
ii. 1,1-cyclohexane diacetic acid monoamide undergoes Hoffmann reaction to produce gabapentin. [2]
Therapeutic Uses
Gabapentin is used for:
Side Effects
Side effects of Gabapentin are:
MCQs
Q.1 Choose the correct statements related with the physicochemical properties of drug Gabapentin.
I. Molecular weight = 278.19 gm/mol
II. It is white to off-white crystalline solid
III. Melting point is 215oC
IV. It is freely soluble in water
a) I, III, IV
b) II, IV
c) I, IV
d) I, II, IV
Q.2 Match the following of the drugs with their correct IUPAC names.
i. Gabapentin | A. 8-chloro-6-(4-methylpiperazin-1-yl)benzo[b][1,4]benzoxazepine |
ii. Loxapine | B. 5H-dibenzo[b,f]azepine-5-carboxamide |
iii. Carbamazepine | C. 1-(Aminomethyl)cyclohexaneacetic acid |
iv. Thiopental | D. 5-ethyl-5-pentan-2-yl-2-sulfanylidene-1,3-diazinane-4,6-dione |
a) i-C, ii-A, iii-B, iv-D
b) i-D, ii-A, iii-C, iv-B
c) i-D, ii-A, iii-B, iv-C
d) i-A, ii-C, iii-B, iv-D
Q.3 Correct steps for the mechanism of action of the drug Gabapentin are?
I. Inhibition of the action of α2δ-1 subunits
II. Stimulation of the action of α2δ-1 subunits
III. Increase in density of pre-synaptic voltage-gated calcium channels
IV. Decrease in density of pre-synaptic voltage –gated calcium channels
a) I – IV
b)II – III
c) III – I
d) IV- II
Q.4 Correct sequence for True/false for the classification of the drug can be?
a) TFFT
b) TTTT
c) TFFT
d) FFTF
Q.5 Original isobutyl side chain of the gabapentin is?
a) Optimal at C-2 position
b) Optimal at C-3 position
c) Produces optimal activity at C-5 position
d) Produces optimal activity at C-4 position
Q.6 Correct steps for the synthesis of gabapentin from 1,1-cyclohexane diacetic acid anhydride are?
I. Reduction
II. Hoffman reaction
III. Reaction with free ammonia
IV. Treatment with Baeyer’s reagent
a) II, IV
b) II, IV
c) I, III
d) III, II
Q.7 Side effect of drug Gabapentin include?
a) Hyperactivity
b) Shallow breathing
c) Increase in blood counts
d) Tremors
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ANSWERS
1-b
2-a
3-a
4-a
5-b
6-d
7-d
REFERENCES
[1] ] Belliotti TR, Capiris T, Ekhato IV, Kinsora JJ, Field MJ, Heffner TG, Meltzer LT, Schwarz JB, Taylor CP, Thorpe AJ, Vartanian MG. Structure− activity relationships of Pregabalin and analogues that target the α2-δ protein. Journal of medicinal chemistry. 2005 Apr 7;48(7):2294-307. [2] Kumar A, Soudagar SR, Nijasure AM, Panda NB, Gautam P, Thakur GR, inventors; Ipca Laboratories, assignee. Process For Synthesis Of Gabapentin. United States patent application US 11/923,352. 2008 May 1.The post GABAPENTIN Synthesis, SAR, MCQ, Structure, Chemical Properties and Therapeutic Uses appeared first on Gpatindia: Pharmacy Jobs, Admissions, Scholarships, Conference,Grants, Exam Alerts.
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