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ChemicalBook >> CAS DataBase List >>(S)-MEPHENYTOIN

(S)-MEPHENYTOIN

(S)-MEPHENYTOIN Structure
(S)-MEPHENYTOIN structure
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
Molecular Weight:
218.25
MDL Number:
MFCD00270025
MOL File:
50-12-4.mol
MSDS File:
SDS
Last updated:2023-06-27 14:18:49
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(S)-MEPHENYTOIN Properties

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)
form solid
pka pKa 8.1 (Uncertain)
color off-white
CAS DataBase Reference 50-12-4(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII R420KW629U
ATC code N03AB04,N03AB54
EPA Substance Registry System Mephenytoin (50-12-4)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P305+P351+P338
Hazard Codes  Xn
Risk Statements  22-36/37/38
Safety Statements  26-36
WGK Germany  2
HS Code  2933210000
Toxicity LD50 i.p. in mice: 300 mg/kg (Dzhagatspanyan)

(S)-MEPHENYTOIN price More Price(8)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Tocris 3276 Mephenytoin ≥98%(HPLC) 50-12-4 10 $282 2021-12-16 Buy
Usbiological 255787 Mephenytoin 50-12-4 10mg $545 2021-12-16 Buy
TRC M224985 rac-Mephenytoin 50-12-4 5mg $90 2021-12-16 Buy
ChemScene CS-4793 Mephenytoin 99.68% 50-12-4 10mg $150 2021-12-16 Buy
ChemScene CS-4793 Mephenytoin 99.68% 50-12-4 50mg $250 2021-12-16 Buy
Product number Packaging Price Buy
3276 10 $282 Buy
255787 10mg $545 Buy
M224985 5mg $90 Buy
CS-4793 10mg $150 Buy
CS-4793 50mg $250 Buy

(S)-MEPHENYTOIN Chemical Properties,Uses,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

rac-Mephenytoin is an anticonvulsant agent.

Uses

Anticonvulsant.

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 synthesis

2216-93-5
74-88-4
50-12-4
Synthesis of (S)-MEPHENYTOIN from 2,4-Imidazolidinedione, 5-ethyl-5-phenyl-, (+-)- and Iodomethane

(S)-MEPHENYTOIN Preparation Products And Raw materials

Raw materials

Cyanide, Quant Test Strips Dilute hydrochloric acid Propiophenone POTASSIUM CYANIDE Ammonium carbonate
Sodium bisulfite Sodium MEPHOBARBITAL 1-(1-cyano-1-phenylpropyl)-3-methylurea 2,4-Imidazolidinedione, 5-ethyl-5-phenyl-, (+-)-
Methylamine Methylurea Iodomethane N,N-Dimethylformamide dimethyl acetal

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Preparation Products

(S)-MEPHENYTOIN Suppliers

Global( 104)Suppliers
Supplier Tel Email Country ProdList Advantage
TargetMol Chemicals Inc. 		+1-781-999-5354 +1-00000000000 marketing@targetmol.com United States 19892 58
Dideu Industries Group Limited 		+86-29-89586680 +86-15129568250 1026@dideu.com China 29220 58
Alfa Chemistry 		+1-5166625404 Info@alfa-chemistry.com United States 21317 58
InvivoChem 		+1-708-310-1919 +1-13798911105 sales@invivochem.cn United States 6393 58
Shaanxi Didu New Materials Co. Ltd 		+86-89586680 +86-13289823923 1026@dideu.com China 9116 58
Nantong HI-FUTURE Biology Co., Ltd. 		+undefined18051384581 sales@chemhifuture.com China 3136 58
Zibo Hangyu Biotechnology Development Co., Ltd 		+86-0533-2185556 +8617865335152 Mandy@hangyubiotech.com China 11013 58
Mainchem Co., Ltd. +86-0592-6210733 sale@mainchem.com China 32360 55
3B Pharmachem (Wuhan) International Co.,Ltd. 821-50328103-801 18930552037 3bsc@sina.com China 15848 69
WUHAN SUN-SHINE BIO-TECHNOLOGY Co., Ltd. 17702719238 17702719238 sales@sun-shinechem.com China 905 64
Supplier Advantage
TargetMol Chemicals Inc. 		58
Dideu Industries Group Limited 		58
Alfa Chemistry 		58
InvivoChem 		58
Shaanxi Didu New Materials Co. Ltd 		58
Nantong HI-FUTURE Biology Co., Ltd. 		58
Zibo Hangyu Biotechnology Development Co., Ltd 		58
Mainchem Co., Ltd. 55
3B Pharmachem (Wuhan) International Co.,Ltd. 69
WUHAN SUN-SHINE BIO-TECHNOLOGY Co., Ltd. 64

View Lastest Price from (S)-MEPHENYTOIN manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
(S)-MEPHENYTOIN pictures 2021-08-12 (S)-MEPHENYTOIN
50-12-4
 US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd
(S)-MEPHENYTOIN USP/EP/BP pictures 2021-07-23 (S)-MEPHENYTOIN USP/EP/BP
50-12-4
 US $1.10 / g 1g 99.9% 100 Tons min Dideu Industries Group Limited
  • (S)-MEPHENYTOIN pictures
  • (S)-MEPHENYTOIN
    50-12-4
  • US $15.00-10.00 / KG
  • 99%+ HPLC
  • Zhuozhou Wenxi import and Export Co., Ltd

50-12-4((S)-MEPHENYTOIN)Related Search:

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(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 (+/-)-MEPHENYTOIN MEPHENYTOIN Epiazin Epilan Fenantoin Gerot-epilan Hydantoin, 5-ethyl-3-methyl-5-phenyl- Insulton mephenetoinum Mephentoin Mesantoin Mesdontoin Mesontoin Methoin Methyl hydantoin Methylphenetoin Metydan NSC-34652 Phenantoin Phenylethylmethylhydantoin Sacerno Sedantional Sedantoin Sedantoinal Triantoin 2,4-Imidazolidinedione, 5-ethyl-3-methyl-5-phenyl- 3-Ethylnirvanol 3-Methyl-5,5-ethylphenylhydantoin 3-Methyl-5,5-phenylethylhydantoin 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 (5R)-5-Ethyl-3-methyl-5-phenyl-2,4-imidazolidinedione (5R)-5-Ethyl-3-methyl-5-phenylhydantoin (5R)-5α-Ethyl-3-methyl-5-phenylhydantoin 5-ethyl-3-methyl-5-phenyl-imidazolidine-2,4-dione 5-Ethyl-3-methyl-5-phenethylhydantoin 5-ethyl-3-methyl-5-phenylimidazolidine-2,4-dione Mephenytoin (250 mg) Mephenytoin-d3 MEPHENYTOIN; METHOIN; MESANTOIN; PHENANTOIN; METHYLPHENETOIN; INSULTON. (S)-MEPHENYTOIN USP/EP/BP Mephenitoin 50-12-4 1950-12-4