86-35-1 Usage
Originator
Peganone,Abbott,US,1957
Uses
Different sources of media describe the Uses of 86-35-1 differently. You can refer to the following data:
1. 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.
2. 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Ethotoin differs from phenytoin in that one phenyl substituent at position 5 has been replaced by hydrogen, and the N-H at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.]
Check Digit Verification of cas no
The CAS Registry Mumber 86-35-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 6 respectively; the second part has 2 digits, 3 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 86-35:
(4*8)+(3*6)+(2*3)+(1*5)=61
61 % 10 = 1
So 86-35-1 is a valid CAS Registry Number.
InChI:InChI=1/C11H12N2O2/c1-2-13-10(14)9(12-11(13)15)8-6-4-3-5-7-8/h3-7,9H,2H2,1H3,(H,12,15)
86-35-1Relevant articles and documents
Facile One-Pot Synthesis of Substituted Hydantoins from Carbamates
Tanwar, Dinesh Kumar,Ratan, Anjali,Gill, Manjinder Singh
supporting information, p. 2285 - 2290 (2017/10/06)
A novel and simple approach for the preparation of 3-substituted, 5-substituted, or 3,5-disubstituted hydantoins is reported. It involves the reaction of α-amino methyl ester hydrochlorides with carbamates to yield the corresponding ureido derivatives, which subsequently cyclize under basic conditions to produce substituted hydantoins in good yields. By applying this method, the bioactive anticonvulsant drug ethotoin was synthesized in good yield. The process avoids conventional multistep protocols and does not use the hazardous, irritant, toxic, or moisture-sensitive reagents, such as isocyanates or chloroformates, that are commonly used for the synthesis of these important compounds.
Phenceptin: A biomimetic model of the phenytoin receptor
Wolfe,Bowers,Shin,Sohn,Weaver,Yang
, p. 2751 - 2762 (2007/10/02)
-
