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Ethotoin

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Ethotoin
Skeletal formula of ethotoin
Clinical data
AHFS/Drugs.comConsumer Drug Information
MedlinePlusa682022
Pregnancy
category
  • C
Routes of
administration
By mouth (tablets)
ATC code
Pharmacokinetic data
Eliminationhalf-life3–9 hours
Identifiers
  • 3-Ethyl-5-phenyl-imidazolidine-2,4-dione
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.001.514Edit this at Wikidata
Chemical and physical data
FormulaC11H12N2O2
Molar mass204.229 g·mol−1
3D model (JSmol)
  • O=C2NC(c1ccccc1)C(=O)N2CC
  • InChI=1S/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) checkY
  • Key:SZQIFWWUIBRPBZ-UHFFFAOYSA-N checkY
  (verify)

Ethotoin (previously marketed asPeganone) is ananticonvulsant drug used in the treatment ofepilepsy.[1] It is ahydantoin, similar tophenytoin. It is not available in the United States.

Mechanism of action

[edit]

Themechanism of action of ethotoin is similar to that of phenytoin.[citation needed]

Approval history

[edit]
  • 1957 Peganone was grantedFood and Drug Administration (FDA) approval toAbbott Laboratories for treatment of grand mal (tonic clonic) and partial complex (psychomotor) seizures.
  • 2003 Peganone was acquired from Abbott Laboratories by Ovation Pharmaceuticals (specialty pharmaceutical company who acquire underpromoted branded pharmaceutical products).
  • 2018 It was announced by Recordati Rare Diseases Inc. that due to a combination of low product demand and complex manufacturing difficulties, product manufacturing, distribution and sale was being discontinued.

Indications and usage

[edit]

Ethotoin is indicated for tonic-clonic and partial complex seizures.[2]

Dosing

[edit]

Ethotoin is available in 250 mg tablets.[3][4] It is taken orally in 4 to 6 divided doses per day, preferably after food.

Side effects

[edit]

Side effects includeataxia, visual disturbances, rash, andgastrointestinal problems.[citation needed]

Chemistry

[edit]

Ethotoin is synthesized by the reaction of benzaldehyde oxynitrile (2) withurea orammonium bicarbonate, which forms an intermediate urea derivative (3) which on acidic conditions cyclizes to 5-phenylhydantoin (4).[5] Alkylation of this product usingethyl iodide leads to the formationof ethotoin (5).

Synthesis of ethotoin

References

[edit]
  1. ^Schwade ED, Richards RK, Everett GM (May 1956). "Peganone, a new antiepileptic drug".Dis Nerv Syst.17 (5):155–8.PMID 13317788.
  2. ^Shorvon, S.D.; Fish, David R.; Perucca, Emilio; Dodson, W. Edwin, eds. (2004).The Treatment of Epilepsy. Blackwell Publishing.ISBN 0-632-06046-8.
  3. ^"Ethotoin".drugs.com.
  4. ^"PEGANONE 250 mg Ethotoin Tablets, USP"(PDF).
  5. ^A. Pinner, Chem. Ber., 21, 2324 (1888); W.J. Close,U.S. patent 2,793,157 (1946)
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