ETHOTOIN Chemical Properties

Melting point:

94°C

Boiling point:

342.72°C (rough estimate)

Density 

1.1754 (rough estimate)

refractive index 

1.5200 (estimate)

storage temp. 

Refrigerator

solubility 

Dichloromethane (Slightly), DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

8.01±0.70(Predicted)

color 

White to Off-White

Safety Information

Risk Statements 

22

HS Code 

2933210000

Hazardous Substances Data

86-35-1(Hazardous Substances Data)

ETHOTOIN Usage And Synthesis

Originator

Peganone,Abbott,US,1957

Uses

Ethotoin is less active and less toxic than phenytoin. It is used for the same indications as is phenytoin, i.e. for control of major and complex epileptic attacks.

Uses

Ethotoin is a hydantoin based anticonvulsant drug used in the treatment of epilepsy.

Definition

ChEBI: An imidazolidine-2,4-dione that is hydantoin substituted by ethyl and phenyl at positions 3 and 5, respectively. An antiepileptic, it is less toxic than phenytoin but also less effective.

Manufacturing Process

Benzaldehyde cyanohydrin is reacted with urea to displace the hydroxyl group of the cyanohydrin. That intermediate is treated with HCl to convert the urea nitrogen to a nitrile. The resultant imine is hydrolyzed to the phenylhydantoin. Alkylation with ethyl iodide gives ethotoin, as described by A. Pinner in Chem. Ber. 21, 2325 (1888).

brand name

Peganone (Ovation.

Therapeutic Function

Anticonvulsant

Synthesis

Ethotoin, 3-ethyl-5-phenylimidazolidine-2,4-dione (9.1.5), is synthesized in basically the same manner as described above, which in this case involves the reaction of benzaldehyde oxynitrile (9.1.2), with urea or ammonium hydrocarbonate, which forms the intermediate urea derivative (9.1.3) which on acidic conditions (9.1.3) cyclizes to 5-phenylhydantoin (9.1.4). Alkylation of this product using ethyliodide leads to the formation of ethotoin (9.1.5) [3,4].

Metabolism

Ethotoin differs from phenytoin in that one phenyl substituent at position 5 has been replaced by hydrogen, and the N-H at position 3 is replaced by an ethyl group. It may be indicated for treatment of tonic-clonic and complex partial (psychomotor) seizures. Because it is considered to be less toxic but also less effective and more sedating than phenytoin, ethotoin usually is reserved for use as an add-on drug. Ethotoin does not share phenytoin's profile of antiarrhythmic action. The metabolism of ethotoin, like phenytoin, is saturable and nonlinear. Its administration is contraindicated in patients with hepatic abnormalities and hematologic disorders.

Purification Methods

It is an anticonvulsant and is used in epilepsy. [Dudley et al. J Heterocycl Chem 10 173 1973, Pinner Chem Ber 21 2320 1888, Beilstein 25 III/IV 963, 27 II 860.]

ETHOTOIN (86-35-1)Related Product Information

• ETHOTOIN
• 5-Phenylhydantoin
• Hydantoin
• Ropitoin
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• [4-(4-METHOXY-PHENYL)-4-METHYL-2,5-DIOXO-IMIDAZOLIDIN-1-YL]-ACETIC ACID
• 5,5-DIPHENYLHYDANTOIN-3-BUTYRIC ACID
• (2,5-DIOXO-3',4'-DIHYDRO-1H,2'H-SPIRO[IMIDAZOLIDINE-4,1'-NAPHTHALEN]-1-YL)ACETIC ACID
• 1-(4-(2-Hydroxyethyl)-1-piperazine-2-propanolo)-3-ethyl-5,5-diphenylhy dantoin 2HCl hydrate
• [4-(4-FLUOROPHENYL)-4-METHYL-2,5-DIOXOIMIDAZOLIDIN-1-YL]ACETIC ACID
• (4-[4-(2-AMINO-2-OXOETHOXY)PHENYL]-4-METHYL-2,5-DIOXOIMIDAZOLIDIN-1-YL)ACETIC ACID
• 2,4-Imidazolidinedione, 5,5-diphenyl-3-ethyl-1-(2-hydroxy-3-(1-piperid inyl)propyl)-, monohydrochloride
• [4-METHYL-4-(2-NAPHTHYL)-2,5-DIOXOIMIDAZOLIDIN-1-YL]ACETIC ACID
• [4-METHYL-4-(4-METHYLPHENYL)-2,5-DIOXOIMIDAZOLIDIN-1-YL]ACETIC ACID
• (4-ETHYL-2,5-DIOXO-4-PHENYLIMIDAZOLIDIN-1-YL)ACETIC ACID
• (4-METHYL-2,5-DIOXO-4-PHENYL-IMIDAZOLIDIN-1-YL)-ACETIC ACID
• (2',5'-DIOXO-2,3-DIHYDRO-1'H-SPIRO[CHROMENE-4,4'-IMIDAZOLIDIN]-1'-YL)ACETIC ACID
• (2,5-DIOXO-2',3'-DIHYDRO-1H-SPIRO[IMIDAZOLIDINE-4,1'-INDEN]-1-YL)ACETIC ACID