This is PDF form for basic knowledge of Pharmaceutical chemistry

1. TOPIC: ANTICONVULSANT
MAHATMA GANDHI INSTITUE OF PHARMACY,
LUCKNOW
Presented by:-
MOHHAMAD AFAQUE
Assistant Professor
Department Of Pharmaceutical Chemistry
(M. Pharm)

2. ➢Anticonvulsant also known as antiepileptic drugs or anti-seizure drugs.
➢They are used for managing and controlling CNS disorder manifested by
recurrent of disturbed brain function and produce convulsion, sensory and
psychic.
➢ The term epilepsy, based on the Greek word epilambian (meaning to seize),
has been first mentioned by Hippocrates.

3. Classification of Anticonvulsant:-
Based on chemical structure:-
1. Hydantoin:- e.g. 1. Phenytoin , 2. Methoin, 3. Mephenytoin
2. Barbiturates:- e.g. Phenobarbitone, 2. Mephobarbital
3. Succinimides:- e.g. 1. Ethosuximide, 2. Phensuximide
4. Oxazolidine :- e.g. 1. Troxidone, 2. Trimethadione
5. Dibenzapines:- e.g. 1. Carbamazepine

4. 1. Phenytoins:-
➢ Phenytoin is the hydantoin derivative.
➢ Phenytoin is an anticonvulsant drugs.
➢ It is used in several types of seizures.
Structure:-
5,5-Diphenylhydantoin
N
H
NH
O
O
C6H5
C6H5
1
4
3
5
2
NH
N
H
Imiazolidine
NH
N
H O
O
Imidazolidine-2,4-dione
or
Hydantoin
1
2
3
4
5

5. Chemistry:-
➢ Phenytoin is the 2,4-diketo derivative of imidazolidine, Which is the
completely saturatyed form of imidazole.
➢ Phenytoin is 5,5-diphenylhydantoin, in which two phenyl group attached at 5th
position.
➢ IUPAC Name:- 5,5-diphenyl-imidazolidine-2,4-dione

6. Physical properties:-
➢ Phenytoin is a white, crystalline powder.
➢It has no odour.
➢It melts at temperature 295-298℃.
➢It is very slightly soluble in water, soluble in ethanol and less soluble in ether
and chloroform.
Chemical properties:-
➢ When phenytoin sodium is dissolved in water and acidified with dilute HCl, it
is decomposed and phenytoin give white precipitate.

7. ➢If phenytoin sodium is dissolved in a 10% solution of pyridine, cupric
sulphate with pyridine solution is added and it is allowed to stand for 10 mint,
a blue precipitate is obtained.
Stability and storage:-
➢ It is slightly hygroscopic, so it can store in tightly-closed containers.
Official:-
1. Phenytoin, B.P, 2. Phenytoin sodium, I.P, B.P, 3. Phenytoin capsules,
B.P
2. Brand Name:- Epsolin, Eptoin, Dilantin, Solantoin.

8. Uses:-
1. It is one of the most popular drugs for epilepsy.
2. It is used in the treatment of grand mal.
3. It is also used in the treatment of cardiac arrhythmias.

9. Methoin (Mephenytoin):-
➢ Methoin is also hydantoin derivative.
Structure:-
IUPAC Name:- 5-ethyl-3-methyl-5-phenyl imidazolidine 2,4-dione.
or
5-ethyl-3-methyl-5-phenyl hydantoin
Physical Properties:-
➢ It is a colourless, crystalline powder.
N
H
N
O
O
H3CH2C
C6H5
CH3
1
2
3
4
5

10. ➢ It has melting point at 136-137℃.
➢ It is insoluble in water and soluble in organic solvent.
Stability and storage:-
➢ It should be store in well closed container.
Brand Name:-
1. Methoin, 2. Phenatoin, 3. Nesantoin.
Uses:-
1. It is in the treatment of epilepsy.
2. It is also used as a sedative properties.

11. Ethosuximide:-
➢ These are obtained from succinic acid which is having a dicarboxylic acid.
Structure of succinic acid:-
Structure of Succinimide:-
2HC
CH2
COOH
COOH
Succinic acid
N
H
O O
Pyrrolidine-2,5-dione
N
H
Pyrrolidine
N
H
Pyrrole

12. Structure of Ethosuximide:-
IUPAC Name:- 3-ethyl-3-methyl-pyrrolidine-2,4-dione
Chemistry:-
➢ Succinimide is the 2,4- diketo derivative of pyrrolidine, which is the
completely saturated form of pyrrolidine.
➢ Ethosuximide is 3-ethyl-3-methyl-pyrrolidine-2,4-dione, that is two alkyl
group is atteched at 3-position.
N
H
O
O
C2H5
H3C

13. Physical Properties:-
➢ It is a white powder or waxy solid.
➢ It melts at 45-50℃.
➢ It is freely soluble in water and very soluble in ethanol and ether.
Chemical Properties:-
➢ When ethosuximide is dissolved in methanol and cobalt chloride, calcium and
sodium hydroxide solutions are added, to produced purple colour.
➢ But it is not produced precipitate.
Storage and stability:- 1. It should be stored in well closed container and protect
from light.

14. Official:-
1. Ethosuximide, I.P, B.P
2. Ethosuximide capsules, I.P, B.P
3. Ethosuximide syrup, B.P
Brand Name:-
1. Zarontin
2. Mesentol
3. Ethynal
Uses:-
1. It is used as anti-convulsant for the treatment of petit mal.

15. Carbamazepine:-
Structure:-
Carbamazepine
Chemistry:-
➢These are the derivatives of dibenzazepine in which two benzene rings are
fused with the azepine moiety at the positions 2,3 and 6, 7.
➢ In carbamazepine the amide (CONH2) group is attached at one position to
nitrogen atom.
N
CONH2
1
2
3
4
5
6
7

16. Physical Properties:-
➢ It is a white or yellowish-white, crystalline powder.
➢ It has no ordour.
➢ It has melts at 189-193℃.
➢ It is practically insoluble in water as well as ether and soluble in ethanol and
acetone.
Stability and storage:-
➢ It is stable in air.
➢ It should be store in well close containers.
Official:- 1. Carbamazepine, I.P, B.P, 2. Carbamazepine tablets, I.P, B.P.
Brand Name:- 1. Tegretol, 2. Carbatol, 3. Mazetol.

17. Uses:-
➢ Carbamazepine is anticonvulsant drugs which is used in the treatment of
epilepsy.
➢ It is highly useful in the treatment of psychomotor epilepsy, grand mal and
cortical focal epilepsy.
Oxazolidinediones:-
Structure of Oxazolidinedione:-
O
N
Oxazole
O
NH
Oxazolidine
O
NH
O
O
Oxazolidine-2,4-dione
1
2
3
4
5

18. Chemistry of Oxazolidine2,4-dione:-
➢ This a compound of oxazolidine which is the saturated form of oxazole.
➢ Two keto group attached at 2 and 4 position of oxazolidine moiety.
➢ IUPAC Name Oxazolidine2,4-dione.
Troxidone (Trimethadione):-
Structure of trimethadione:-
O
N
O O
CH3
CH3
CH3
3,5,5-Trimethyl-oxazolidine-2,4-dione
1
2
3
4
5

19. Chemistry of trimethadione:-
➢ Trimethadione is a compound of oxazolidine which is the saturated of oxazole.
➢ It contains two keto group present at 2 and 4 positions.
➢ it also contains three methyl group at position three one methyl group and two
methyl group at position at 5th position.
➢ IUPAC Name:- 3,5,5-trimethyl-oxazolidine-2,4-dione.
Physical Properties:-
➢ It consists of almost colourless crystals powder.
➢It has melting point 45-47℃.
➢ It is soluble in water and very soluble in chloroform, ethanol and ether.

20. Chemical Properties:-
➢ If troxidone is dissolved in carbon dioxide-free water and barium hydroxide
solution is added, a white precipitate is formed.
Stability and storage:-
➢ It is affected by light, so store in well-closed containers protected from light.
Official:-
1. Troxidone, I.P, B.P.
2. Troxidone capsules, I.P.

21. Brand Name:-
1. Tridione, Absentol, Petidone etc.
Uses:-
1. It is use as a anticonvulsant in the treatment of petit ma.