ChemicalBook > CAS DataBase List > (S)-MEPHENYTOIN

(S)-MEPHENYTOIN

Product Name
(S)-MEPHENYTOIN
CAS No.
50-12-4
Chemical Name
(S)-MEPHENYTOIN
Synonyms
Epilan;Epiazin;Methoin;Metydan;Sacerno;Insulton;Fenantoin;Mesantoin;Mesontoin;NSC-34652
CBNumber
CB0225135
Molecular Formula
C12H14N2O2
Formula Weight
218.25
MOL File
50-12-4.mol
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(S)-MEPHENYTOIN Property

Melting point:
135-138 °C
Boiling point:
358.94°C (rough estimate)
Density 
1.154±0.06 g/cm3 (20 ºC 760 Torr)
refractive index 
1.6660 (estimate)
storage temp. 
2-8°C
solubility 
DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
pka
pKa 8.1 (Uncertain)
form 
solid
color 
off-white
CAS DataBase Reference
50-12-4(CAS DataBase Reference)
EPA Substance Registry System
Mephenytoin (50-12-4)
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Safety

Hazard Codes 
Xn
Risk Statements 
22-36/37/38
Safety Statements 
26-36
WGK Germany 
2
HS Code 
2933210000
Hazardous Substances Data
50-12-4(Hazardous Substances Data)
Toxicity
LD50 i.p. in mice: 300 mg/kg (Dzhagatspanyan)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Tocris
Product number
3276
Product name
Mephenytoin
Purity
≥98%(HPLC)
Packaging
10
Price
$282
Updated
2021/12/16
Usbiological
Product number
255787
Product name
Mephenytoin
Packaging
10mg
Price
$545
Updated
2021/12/16
TRC
Product number
M224985
Product name
rac-Mephenytoin
Packaging
5mg
Price
$90
Updated
2021/12/16
ChemScene
Product number
CS-4793
Product name
Mephenytoin
Purity
99.68%
Packaging
10mg
Price
$150
Updated
2021/12/16
ChemScene
Product number
CS-4793
Product name
Mephenytoin
Purity
99.68%
Packaging
50mg
Price
$250
Updated
2021/12/16
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(S)-MEPHENYTOIN Chemical Properties,Usage,Production

Description

Mephenytoin is N-methylated at position 3 with an ethyl group replacing one of the phenyl substituents at position 5. It is indicated for focal and jacksonian seizures in patients refractory to less toxic AEDs. Mephenytoin produces more sedation than phenytoin and should be used only when safer drugs have failed, because it is associated with an increased incidence of serious toxicities, such as severe rash, agranulocytosis, and hepatitis. Its N-desmethyl metabolite, 5-phenyl- 5-ethylhydantoin, contributes to both efficacy and toxicity for mephenytoin. The drug is no longer commercially available inside but is still available outside the United States.

Originator

Mesantoin,Sandoz

Uses

Anticonvulsant.

Uses

rac-Mephenytoin is an anticonvulsant agent.

Definition

ChEBI: Mephenytoin is an imidazolidine-2,4-dione (hydantoin) in which the imidazolidine nucleus carries a methyl group at N-3 and has ethyl and phenyl substituents at C-5. An anticonvulsant, it is no longer available in the USA or the UK but is still studied largely because of its interesting hydroxylation polymorphism. It has a role as an anticonvulsant.

Manufacturing Process

23 parts sodium was dissolved in 300 parts of ethanol and added to 160 parts of 5-phenylcyanacetamide in 750 parts of ethanol. A mixture was cooled straight away and a sodium salt of amide precipitated as a white powder. 200 parts of ethyl iodide was added to this mixture and heated for 1.5 hours. The ethanol was distilled off, water was added to the residue and rapidly hardened oil precipitated. After recrystallization from ethanol, 5-ethyl-5- phenylacetamide afforded; MP: 116°C.
100 parts of sodium hydroxide was solved in 500 parts of water and added to 83 parts of bromine by cooling. 5-Ethyl-5-phenylacetamide was added to above prepared mixture. It dissolved quickly, whereupon all mass was heated some time, cooled and stood at room temperature some hours. Then a solution of sodium bisulfite was added before the formed precipitate dissolved. The reaction mixture was filtered, the filtrate was acidified to give rapidly hardened oil. After recrystallization from ethanol 5-ethyl-3-methyl-5-phenylhydantoin was yielded as the bright needles; MP: 201°-202°C.

brand name

Mesantoin (Novartis).

Therapeutic Function

Anticonvulsant, Antiepileptic

Biological Activity

CYP2C19 substrate. Anticonvulsant.

Biochem/physiol Actions

CYP2B6 and CYP2C19 substrate; anticonvulsive, antiepileptic.

Side effects

Side effects, including rash, fever, and fatal blood dyscrasia, prevent the use as an anticonvulsant drug of first choice.

Safety Profile

Poison by ingestion and intraperitoneal routes. Human systemic effects by ingestion: somnolence, hemorrhage, changes in teeth and supporting structures. Human mutation data reported. An experimental teratogen. An FDA proprietary drug used as an anticonvulsant. When heated to decomposition it emits toxic fumes of NOx.

(S)-MEPHENYTOIN Preparation Products And Raw materials

Raw materials

Preparation Products

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(S)-MEPHENYTOIN Suppliers

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View Lastest Price from (S)-MEPHENYTOIN manufacturers

Zhuozhou Wenxi import and Export Co., Ltd
Product
(S)-MEPHENYTOIN 50-12-4
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-08-11

50-12-4, (S)-MEPHENYTOINRelated Search:


  • (S)-(+)-5-ETHYL-3-METHYL-5-PHENYL-2,4-IMIDAZOLIDINEDIONE
  • (S)-(+)-5-ETHYL-3-METHYL-5-PHENYLHYDANTOIN
  • (S)-5-ETHYL-3-METHYL-5-PHENYLHYDANTOIN
  • (S)-(+)-MEPHENYTOIN
  • (+/-)-5-ETHYL-3-METHYL-5-PHENYL-2,4-IMIDAZOLIDINEDIONE
  • (+/-)-5-ETHYL-3-METHYL-5-PHENYLHYDANTOIN
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  • 3-Methyl-5-ethyl-5-phenylhydantoin
  • 5-Ethyl-3-methyl-5-phenyl-2,4(3H,5H)-imidazoledione
  • 5-ethyl-3-methyl-5-phenyl-4-imidazolidinedione
  • 5-ethyl-3-methyl-5-phenyl-hydantoi
  • 5-Ethyl-3-methyl-5-phenylimidazolidin-2,4-dione
  • 5-Ethyl-5-fenyl-3-methylhydantoin
  • (±)-5-Ethyl-3-methyl-5-phenyl-2,4-imidazolidinedione, (±)-5-Ethyl-3-methyl-5-phenylhydantoin
  • DL-Mephenytoin
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  • (5R)-5α-Ethyl-3-methyl-5-phenylhydantoin
  • 5-ethyl-3-methyl-5-phenyl-imidazolidine-2,4-dione
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  • MEPHENYTOIN; METHOIN; MESANTOIN; PHENANTOIN; METHYLPHENETOIN; INSULTON.
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  • 50-12-4
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