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ETHOTOIN

CAS No.86-35-1
Chemical Name:ETHOTOIN
CBNumber:CB0500515
Molecular Formula:C11H12N2O2
Formula Weight:204.23
MOL File:86-35-1.mol

ETHOTOIN Property

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
EWG's Food Scores 1
FDA UNII 46QG38NC4U
ATC code N03AB01
UNSPSC Code 41116107
NACRES NA.24

Safety

Risk Statements :22
HS Code :2933210000
Hazardous Substances Data :86-35-1(Hazardous Substances Data)

NFPA 704:

	0
1		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H302
Precautionary statements P264-P270-P301+P312-P330-P501

ETHOTOIN Chemical Properties,Usage,Production

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Metabolism Ethotoin differs from phenytoin in that one phenyl substituent at position 5 has been replaced by hydrogen, and the N-H at position 3 is replaced by an ethyl group.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.]