ETHOTOIN
- CAS NO.:86-35-1
- Empirical Formula: C11H12N2O2
- Molecular Weight: 204.23
- EINECS: 201-665-1
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-10-23 13:36:13
What is ETHOTOIN ?
Absorption
Fairly rapidly absorbed, however, the extent of oral absorption is not known.
Toxicity
Symptoms of overdose include drowsiness, loss of or impaired muscle coordination, nausea, visual disturbance, and, at very high doses, coma.
Originator
Peganone,Abbott,US,1957
The Uses of ETHOTOIN
Ethotoin is a hydantoin based anticonvulsant drug used in the treatment of epilepsy.
The Uses of ETHOTOIN
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.
Background
Ethotoin is a hydantoin derivative and anticonvulsant. Ethotoin exerts an antiepileptic effect without causing general central nervous system depression. The mechanism of action is probably very similar to that of phenytoin. The latter drug appears to stabilize rather than to raise the normal seizure threshold, and to prevent the spread of seizure activity rather than to abolish the primary focus of seizure discharges. Ethotoin is no longer commonly used.
Indications
For the control of tonic-clonic (grand mal) and complex partial (psychomotor) seizures.
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
Pharmacokinetics
Ethotoin is a hydantoin derivative and anticonvulsant. Ethotoin exerts an antiepileptic effect without causing general central nervous system depression. The mechanism of action is probably very similar to that of phenytoin. The latter drug appears to stabilize rather than to raise the normal seizure threshold, and to prevent the spread of seizure activity rather than to abolish the primary focus of seizure discharges.
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
Hepatic. The drug exhibits saturable metabolism with respect to the formation of N-deethyl and p-hydroxyl-ethotoin, the major metabolites.
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.]
Properties of ETHOTOIN
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) |
pka | 8.01±0.70(Predicted) |
form | Solid |
color | White to Off-White |
Safety information for ETHOTOIN
Computed Descriptors for ETHOTOIN
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