Mephenytoin: Difference between revisions

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			{{short description\|Chemical compound}}
	{{Drugbox		{{Drugbox
			\| Watchedfields = changed
	\| verifiedrevid = ~~408590253~~		\| verifiedrevid = 459493896
	\| IUPAC_name = ''5-~~ethyl~~-3-methyl-5-phenyl-imidazolidine-2,4-dione''		\| IUPAC_name = 5-Ethyl-3-methyl-5-phenyl-imidazolidine-2,4-dione
	\| image = Mephenytoin.svg		\| image = Mephenytoin.svg
			\| alt = Structural formula of mephenytoin
	\| width = ~~120~~		\| width = 135
			\| image2 = Mephenytoin 3D spacefill.png
			\| alt2 = Space-filling model of the mephenytoin molecule
			\| width2 = 160

	<!--Clinical data-->		<!--Clinical data-->
	\| tradename =		\| tradename =
	\| Drugs.com = {{drugs.com\|CONS\|mephenytoin}}		\| Drugs.com = {{drugs.com\|CONS\|mephenytoin}}
	\| MedlinePlus = a611020		\| MedlinePlus = a611020
	\| pregnancy_US = C		\| pregnancy_US = C
		⚫	\| legal_status =
	\| routes_of_administration = Oral		\| routes_of_administration = Oral

	<!--Pharmacokinetic data-->		<!--Pharmacokinetic data-->
		⚫	\| bioavailability =
		⚫	\| metabolism = ]
	\| elimination_half-life = 7 hours		\| elimination_half-life = 7 hours
		⚫	\| excretion =

	<!--Identifiers-->		<!--Identifiers-->
			\| IUPHAR_ligand = 7223
	\| ~~CASNo_Ref~~ = {{cascite\|correct\|~~CAS~~}}		\| CAS_number_Ref = {{cascite\|correct\|??}}
	\| CAS_number = 50-12-4		\| CAS_number = 50-12-4
	\| ATC_prefix = N03		\| ATC_prefix = N03
	\| ATC_suffix = AB04		\| ATC_suffix = AB04
		⚫	\| ATC_supplemental=
	\| PubChem = 4060		\| PubChem = 4060
	\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}		\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
	\| DrugBank = ~~APRD00512~~		\| DrugBank = DB00532
	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}		\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 3920		\| ChemSpiderID = 3920
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	<!--Chemical data-->		<!--Chemical data-->
	\| C=12 \| H=14 \| N=2 \| O=2		\| C=12 \| H=14 \| N=2 \| O=2
	\| molecular_weight = 218.252
	\| smiles = O=C2N(C(=O)NC2(c1ccccc1)CC)C		\| smiles = O=C2N(C(=O)NC2(c1ccccc1)CC)C
	\| InChI = 1/C12H14N2O2/c1-3-12(9-7-5-4-6-8-9)10(15)14(2)11(16)13-12/h4-8H,3H2,1-2H3,(H,13,16)
	\| InChIKey = GMHKMTDVRCWUDX-UHFFFAOYAK
	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChI = 1S/C12H14N2O2/c1-3-12(9-7-5-4-6-8-9)10(15)14(2)11(16)13-12/h4-8H,3H2,1-2H3,(H,13,16)		\| StdInChI = 1S/C12H14N2O2/c1-3-12(9-7-5-4-6-8-9)10(15)14(2)11(16)13-12/h4-8H,3H2,1-2H3,(H,13,16)
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	\| StdInChIKey = GMHKMTDVRCWUDX-UHFFFAOYSA-N		\| StdInChIKey = GMHKMTDVRCWUDX-UHFFFAOYSA-N
	}}		}}

	<!--
⚫	\| ATC_supplemental=
⚫	\| bioavailability=
⚫	\| metabolism = ~~Cyp 2C19~~
⚫	\| excretion =
⚫	\| legal_status =
	-->
	'''Mephenytoin''' (marketed as '''Mesantoin''' by Novartis) is a ], used as an ]. It was introduced approximately 10 years after ], in the late 1940s. The significant ] of mephenytoin is ] (5-ethyl-5-phenylhydantoin), which was the first hydantoin (briefly used as a ]). However, nirvanol is quite toxic and mephenytoin was only considered after other less toxic anticonvulsants had failed. It can cause potentially fatal blood ] in 1% of patients.		'''Mephenytoin''' (marketed as '''Mesantoin''' by Novartis) is a ], used as an ]. It was introduced approximately 10 years after ], in the late 1940s. The significant ] of mephenytoin is ] (5-ethyl-5-phenylhydantoin), which was the first hydantoin (briefly used as a ]). However, nirvanol is quite toxic and mephenytoin was only considered after other less toxic anticonvulsants had failed. It can cause potentially fatal blood ] in 1% of patients.

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	==References==		==References==
			{{refbegin}}
	* ''The Treatment of Epilepsy'' edited by S. D. Shorvon, David R. Fish, Emilio Perucca, W. Edwin Dodson. Blackwell Publishing. 2004. ISBN 0-632-06046-8
	* ~~''The~~ ~~Medical~~ Treatment of Epilepsy'' by ~~Stanley~~ R ~~Resor.~~ ~~Published~~ by ~~Marcel~~ ~~Dekker~~ ~~(1991).~~ ~~ISBN~~ 0-~~8247~~-~~8549~~-5.		* {{cite book \| title = The Treatment of Epilepsy \| veditors = Shorvon SD, Fish DR, Perucca E, Dodson WE \| publisher = Blackwell Publishing \| date = 2004 \| isbn = 0-632-06046-8 }}
			* {{cite book \| title = The Medical Treatment of Epilepsy \| vauthors = Resor SR \| publisher = Marcel Dekker \| date = 1991 \| isbn = 0-8247-8549-5 }}
	*		* {{cite web \| url = http://ctdbase.org/detail.go?type=chem&acc=D008617 \| work = The Comparative Toxicogenomics Database \| title = Mephenytoin }}
			{{refend}}

	{{Anticonvulsants}}		{{Anticonvulsants}}

Latest revision as of 13:06, 13 January 2023

Chemical compound Pharmaceutical compound

Mephenytoin
Clinical data


AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a611020
Routes of administration	Oral
ATC code	N03AB04 (WHO)
Pharmacokinetic data
Metabolism	CYP2C19
Elimination half-life	7 hours
Identifiers
IUPAC name 5-Ethyl-3-methyl-5-phenyl-imidazolidine-2,4-dione
CAS Number	50-12-4
PubChem CID	4060
IUPHAR/BPS	7223
DrugBank	DB00532
ChemSpider	3920
UNII	R420KW629U
KEGG	D00375
ChEMBL	ChEMBL861
CompTox Dashboard (EPA)	DTXSID9023257
ECHA InfoCard	100.000.012
Chemical and physical data
Formula	C₁₂H₁₄N₂O₂
Molar mass	218.256 g·mol
3D model (JSmol)	Interactive image
SMILES O=C2N(C(=O)NC2(c1ccccc1)CC)C
InChI InChI=1S/C12H14N2O2/c1-3-12(9-7-5-4-6-8-9)10(15)14(2)11(16)13-12/h4-8H,3H2,1-2H3,(H,13,16) Key:GMHKMTDVRCWUDX-UHFFFAOYSA-N
(verify)

Mephenytoin (marketed as Mesantoin by Novartis) is a hydantoin, used as an anticonvulsant. It was introduced approximately 10 years after phenytoin, in the late 1940s. The significant metabolite of mephenytoin is nirvanol (5-ethyl-5-phenylhydantoin), which was the first hydantoin (briefly used as a hypnotic). However, nirvanol is quite toxic and mephenytoin was only considered after other less toxic anticonvulsants had failed. It can cause potentially fatal blood dyscrasia in 1% of patients.

Mephenytoin is no longer available in the US or the UK. It is still studied largely because of its interesting hydroxylation polymorphism.

References

Shorvon SD, Fish DR, Perucca E, Dodson WE, eds. (2004). The Treatment of Epilepsy. Blackwell Publishing. ISBN 0-632-06046-8.
Resor SR (1991). The Medical Treatment of Epilepsy. Marcel Dekker. ISBN 0-8247-8549-5.
"Mephenytoin". The Comparative Toxicogenomics Database.

Anticonvulsants (N03)

GABAergics

GABA_AR PAMs	Barbiturates: Barbexaclone Metharbital Methylphenobarbital Pentobarbital Phenobarbital Primidone; Carbamates: Cenobamate Felbamate; Benzodiazepines: Clobazam Clonazepam Clorazepate Diazepam Lorazepam Midazolam Nimetazepam Nitrazepam Temazepam; Others: Bromide (potassium bromide, sodium bromide) Imepitoin Paraldehyde Stiripentol
GABA-T inhibitors	Fatty acids (and related): Valproate Valpromide Valproate pivoxil Vigabatrin
Others	GABAR agonists: Progabide; GAT-1 inhibitors: Tiagabine

Channel
modulators

Sodium blockers	Hydantoins: Ethotoin Fosphenytoin Mephenytoin Phenytoin; Ureides: Acetylpheneturide Chlorphenacemide Phenacemide Pheneturide; Fatty acids: Valproate Valpromide Valproate pivoxil; Carboxamides: Carbamazepine Eslicarbazepine acetate Oxcarbazepine; Others: Lacosamide Lamotrigine Rufinamide Topiramate Zonisamide
Calcium blockers	Oxazolidinediones: Ethadione Paramethadione Trimethadione; Succinimides: Ethosuximide Mesuximide Phensuximide; Gabapentinoids: Gabapentin Pregabalin; Others: Imepitoin Lamotrigine Topiramate Zonisamide
Potassium openers	Retigabine

Others

CA inhibitors	Sulfonamides: Acetazolamide Ethoxzolamide Sultiame Topiramate Zonisamide
Others	Albutoin Beclamide Brivaracetam Cannabidiol Carisbamate Etiracetam Fenfluramine Ganaxolone Levetiracetam Perampanel

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

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