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Pheneturide

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From Wikipedia, the free encyclopedia

Chemical compound

Pharmaceutical compound

Pheneturide
Clinical data

AHFS/Drugs.com	International Drug Names
ATC code	N03AX13 (WHO)
Identifiers
IUPAC name (RS)-N-Carbamoyl-2-phenyl-butanamide
CAS Number	90-49-3^N
PubChemCID	72060
ChemSpider	65046^Y
UNII	878CEJ4HGX
KEGG	D01190^Y
CompTox Dashboard(EPA)	DTXSID4020612
ECHA InfoCard	100.001.817
Chemical and physical data
Formula	C₁₁H₁₄N₂O₂
Molar mass	206.245 g·mol⁻¹
3D model (JSmol)	Interactive image
Chirality	Racemic mixture
SMILES O=C(N)NC(=O)C(c1ccccc1)CC
InChI InChI=1S/C11H14N2O2/c1-2-9(10(14)13-11(12)15)8-6-4-3-5-7-8/h3-7,9H,2H2,1H3,(H3,12,13,14,15)^Y Key:AJOQSQHYDOFIOX-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

Pheneturide (INN,BAN) (brand namesBenuride,Deturid,Pheneturid,Septotence,Trinuride),^[1] also known asphenylethylacetylurea (orethylphenacemide), is ananticonvulsant of theureide class.^[2]^[3] Conceptually, it can be formed in the body as a metabolic degradation product fromphenobarbital. It is considered to be obsolete^[4] and is now seldom used.^[5] It is marketed inEurope, including inPoland,Spain and theUnited Kingdom.^[6] Pheneturide has a similar profile of anticonvulsant activity and toxicity relative tophenacemide.^[7]^[8] As such, it is only used in cases of severe epilepsy when other, less-toxic drugs have failed.^[8] Pheneturide inhibits the metabolism and thus increases the levels of other anticonvulsants, such asphenytoin.^[5]^[6]

References

[edit]

^Muller (19 June 1998).European Drug Index: European Drug Registrations, Fourth Edition. CRC Press. pp. 998–.ISBN 978-3-7692-2114-5.
^Elks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 959–.ISBN 978-1-4757-2085-3.
^Byrne B, Rothchild R (1999). "1H NMR studies of drugs with achiral and chiral lanthanide shift reagents: applications to the anticonvulsant pheneturide".Chirality.11 (7):529–35.doi:10.1002/(SICI)1520-636X(1999)11:7<529::AID-CHIR3>3.0.CO;2-K.PMID 10423278.
^Levy RH (2002).Antiepileptic Drugs. Lippincott Williams & Wilkins. pp. 210–.ISBN 978-0-7817-2321-3.
^^a ^bDenham MJ (6 December 2012).The Treatment of Medical Problems in the Elderly. Springer Science & Business Media. pp. 335–.ISBN 978-94-011-6223-4.
^^a ^bVida J (19 July 2013).Anticonvulsants. Elsevier. pp. 4, 42.ISBN 978-0-323-14395-0.
^deStevens G, Zingel V, Leschke C, Hoeprich PD, Schultz RM, Mehrotra PK, Batra S, Bhaduri AP, Saxena AK, Saxena M, eds. (11 November 2013).Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des Recherches Pharmaceutiques. Basel: Birkhäuser. pp. 217–.ISBN 978-3-0348-7161-7. Retrieved3 September 2016.
^^a ^bLancaster R (22 October 2013).Pharmacology in Clinical Practice. Elsevier. pp. 222–.ISBN 978-1-4831-9294-9.

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 Magnesium sulfate^#

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Ion channel modulators

Calcium

VDCCsTooltip Voltage-dependent calcium channels

Blockers

R-type-selective:SNX-482

Activators

L-type-selective:Bay K8644

Potassium

VGKCsTooltip Voltage-gated potassium channels

Blockers

Activators

KCNQ (K_v7)-specific:Flupirtine
Retigabine

IRKsTooltip Inwardly rectifying potassium channel

Blockers

K_ATPTooltip ATP-sensitive potassium channel-specific:Acetohexamide
Carbutamide
Chlorpropamide
Glibenclamide (glyburide)
Glibornuride
Glicaramide
Gliclazide
Glimepiride
Glipizide
Gliquidone
Glisoxepide
Glyclopyramide
Glycyclamide
Metahexamide
Mitiglinide
Nateglinide
Repaglinide
Tolazamide
Tolbutamide

GIRKTooltip G protein-coupled inwardly rectifying potassium channel-specific:Barium
Caramiphen
Cloperastine
Clozapine
Dextromethorphan
Ethosuximide
Ifenprodil
Tertiapin
Tipepidine

Activators

K_ATPTooltip ATP-sensitive potassium channel-specific:Aprikalim
Bimakalim
Cromakalim
Diazoxide
Emakalim
Levcromakalim
Mazokalim
Minoxidil
Minoxidil sulfate
Naminidil
Nicorandil
Pinacidil
Rilmakalim
Sarakalim

GIRKTooltip G protein-coupled inwardly rectifying potassium channel-specific:ML-297 (VU0456810)

K_CaTooltip Calcium-activated potassium channel

Blockers	BK_Ca-specific:Ethanol (alcohol) GAL-021
Activators	BK_Ca-specific:Flufenamic acid Meclofenamic acid Niflumic acid Nimesulide Rottlerin (mallotoxin) Tolfenamic acid

K2PsTooltip Tandem pore domain potassium channel

Blockers	12-O-Tetradecanoylphorbol-13-acetate Arachidonic acid Fluoxetine Norfluoxetine
Activators	Riluzole

Sodium

VGSCsTooltip Voltage-gated sodium channels

Blockers

Antianginals:Ranolazine

Activators

Aconitine
Atracotoxins (ω-Atracotoxin,Robustoxin,Versutoxin)
Batrachotoxin
Ciguatoxins
Grayanotoxins
Poneratoxin

ENaCTooltip Epithelial sodium channel

Blockers	Amiloride Benzamil Triamterene
Activators	Solnatide

ASICsTooltip Acid-sensing ion channel

Blockers	A-317567 Amiloride Aspirin Ibuprofen PcTX1

Chloride

CaCCsTooltip Calcium-activated chloride channel

Blockers	Crofelemer DIDS Ethacrynic acid Flufenamic acid Fluoxetine Furosemide Glibenclamide Mefloquine Mibefradil Niflumic acid
Activators	Carbachol

CFTRTooltip Cystic fibrosis transmembrane conductance regulator

Blockers	Glibenclamide Lonidamine Piretanide
Activators	1,7-Phenanthroline 1,10-Phenanthroline 4,7-Phenanthroline 7,8-Benzoquinoline Ivacaftor Phenanthridine

Unsorted

Blockers	Bumetanide Flufenamic acid Meclofenamic acid Mefenamic acid Mepacrine Niflumic acid Talniflumate Tolfenamic acid Trifluoperazine

Others

TRPsTooltip Transient receptor potential channels	Seehere instead.
LGICsTooltip Ligand gated ion channels	Seehere instead.

See also:Receptor/signaling modulators •Transient receptor potential channel modulators

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