Tenitramine

IUPAC nomenclature

2-[2-[bis(2-nitrooxyethyl)amino]ethyl-(2-nitrooxyethyl)amino]ethyl nitrate.

Classification

• Organic nitrate antianginal drug

Physiochemical Properties

Mechanism of Action

i. Like other organic nitrate, Tenitramine releases NO.

ii. Activation of enzyme gunanylate cyclase

iii. Increase in concentration of cGMP within vascular smooth muscles

iv. Vasodilation occurs due to cGMP-dependent protein kinase.

Structure Activity Relationship

General structure activity of organic nitrate antianginal drugs can be summarized as:

• The number of nitrate groups determines the potency of organic nitrate for guanylate cyclase activation.
• Increase in nitric group increases the potency.
• Increase in lipophillicity doesn’t have major effect over activation of drug.

Method of synthesis

Nitration of (I) produces tenitramine.

Medicinal Uses

Tenitramine is a vasodilator

Side Effects

Side effects of Tenitramine are:

• Dizziness
• Headache
• Flushing
• Nausea
• Vomiting
• Weakness
• Restlessness
• Allergic reactions

MCQs

Q.1 Match the following with correct SAR of Organic nitrate antianginal drugs-

a) i-A, ii-C

b) i-A, ii-D

c) i-B, ii-C

d) i-B, ii-D

Q.2 Correct sequence for the True/False for correct IUPAC names of the drug can be?

• Tenitramine: 2-[2-[bis(2-nitrooxyethyl)amino]ethyl-(2-nitrooxyethyl)amino]ethyl nitrate
• Chlorothiazide: 6-chloro-1,1-dioxo-2H-1,2,4-benzothiadiazine-7-sulfonamide.
• Amlodipine: 3-O-ethyl 5-O-methyl 2-(2-aminoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate
• Azatadine: 11-(1-Methylpiperidin-4-ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine

a) FFTF

b) FFFF

c) TFFT

d) TTTT

Q.3 Molecular weight of drug Tenitramine is?

a) 416.3 gm/mol

b) 452.3 gm/mol

c) 248.5 gm/mol

d) 978.1 gm/mol

Q.4 Mechanism of action of Tenitramine includes?

a) Inhibition of sodium-potassium-chloride cotransportors

b) Release of NO

c) Inhibition of hydrogen-potassium pump

d) All of the above

Q.5 Which amongst the following is a therapeutic use of drug Tenitramine?

a) As an anticonvulsant

b) As a vasodilator

c) As an antipsychotic

d) As an anesthetic

Q.6 Which of the following drug and their classification are correct?

I. Tenitramine: Antianginal drug

II. Furosemide: Diuretics

III. Disopyramide: Anti-arrhythmic drug

IV. Verapamil: Calcium channel blocker

a) I ,II, IV

b) II, IV

c) I, II, III, IV

d) I, III 

Q.7 Type of ring present in the structure of Tenitramine?

a) No ring present

b) Pyridine

c) Pyrimidine

d) Pyridine

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ANSWERS

1-a

2-d

3-a

4-b

5-b

6-c

7-a