The post TIOTIXENE or THIOTHIXENE Synthesis, SAR, MCQ,Structure,Chemical Properties and Therapeutic Uses appeared first on Gpatindia: Pharmacy Jobs, Admissions, Scholarships, Conference,Grants, Exam Alerts.
]]>(9Z)-N,N-dimethyl-9-[3-(4-methylpiperazin-1-yl)propylidene]-9H-thioxanthene-2-sulfonamide.
Tiotixene is a thioxanthene antipsychotic drug.
S. NO. | PHYSICAL AND CHEMICAL PROPERTIES | |
1 | Molecular weight | 443.6 g/mol |
2 | Physical appearance | White to tan crystalline powder |
3 | Melting point | 114-118°C |
4 | Solubility | Practically insoluble in water |
5 | Octanol/water partition coefficient | 3.78 |
6 | Presence of ring | Piperazine, thioxanthene |
7 | Number of chiral centers | 2 |
Tiotixene hydrochloride acts as antagonist for following postsynaptic receptors:
Structure activity relationship of phenothiazine like compounds can be described as follows:
i. 9H-thioxantene is reacted with chlorosulfonic acid to give 9H-thioxanten-2-sulfonic acid.
ii. On reaction with thionyl chloride and dimethylamine, the product transforms into 2-dimethylaminosulfonyl-9H-thioxantene.
iii. On reaction of the above formed compound with butyllithium and then with methyl acetate gives the product 9-acetyl-2-dimethylaminosulfonyl-9H-thioxantene.
iv. Aminomethylation of the resulting product with dimethylamine and formaldehyde gives 9-(2-dimethylamineopropionyl)-2-dimethylaminosulfonyl-9H-thioxantene.
v. On reaction with 1-N-methylpiperazine lead to the substitution of the dimethylamine group with N-methyliperazine group.
vi. On reduction of the carbonyl group of the product to secondary hydroxyl group using sodium borohydride, followed by dehydration with the help of phosphorus oxychloride produces the desired tiotixene [2]
Tiotixene is used for:
Side Effects
Side effects of Tiotixene are:
Q.1 What can be the correct IUPAC nomenclature of Tiotixene?
a) (9Z)-N,N-dimethyl-9-[3-(4-methylpiperazin-1-yl)propylidene]-9H-thioxanthene-2-sulfonamide.
b) (9Z)-N,N-dimethyl-9-[3-(4-methylpiperazin-1-yl)propylidene]-9H-thioxanthene-2-sulfonic acid
c) 3-(2-chlorophenothiazin-10-yl)-N,N-dimethylpropan-1-amine;hydrochloride
d) N,N-dimethyl-3-phenothiazin-10-ylpropan-1-amine;hydrochloride
Q.2 Which amongst the following statements is/are INCORRECT related to the SAR of tiotixene?
I. A piperazine side chain provides more Van der Waal’s contacts with 2-substituent than the alkylamino side chain. Thus, piperizine phenothiazine are more potent in antischizophrenic effects than alkylamino phenothiazines.
II. Hydroxyethylpiperazine side chain phenothiazines displays more favorable Van der Waal’s interactions with ring A than simple piperazines.
III. In the thioxanthene and xanthenes containing ring systems, the cis forms are more potent neuroleptics than the trans isomers.
IV. Phenothiazine analogues having the presence of exolytic double bond are more potent than the corresponding compounds lacking the exolytic double bonds.
a) I, III, IV
b) I, II
c) III, IV
d) None
Q.3 Number of chiral carbons present in the structure of tiotixene?
a) 0
b) 1
c) 2
d) 3
Q.4 Side effects of drug Tiotixene is/are?
a) Blurred vision
b) Insomnia
c) Muscle spasms
d) All of the above
Q.5 Match the following drugs with their correct melting points:
i. Tiotixene | A. 116oC |
ii. Thiopental | B.190oC |
iii. Favipiravir | C. 159oC |
iv. Secobarbital | D.100oC |
a) i-A, ii-C, iii-B, iv-D
b) i-C, ii-A, iii-D, iv-B
c) i-C, ii-A, iii-B, iv-D
d) i-B, ii-D, iii-A, iv-C
Q.6 An example of drug from class Thioxanthene antipsychotic drug is?
a) Donepezil
b) Promazine
c) Tiotixene
d) Both a) and b)
Q.7 The type of ring system found in Tiotixene?
a) Phenothiazine
b) Piperizine ring
c) Thioxanthene ring
d) Both b) and c)
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1-a
2-d
3-c
4-d
5-a
6-c
7-d
The post TIOTIXENE or THIOTHIXENE 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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