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  1. World Encyclopedia
  2. Phenacemide - Wikipedia
Phenacemide - Wikipedia
From Wikipedia, the free encyclopedia
Anticonvulsant

Pharmaceutical compound
Phenacemide
Clinical data
Trade namesPhenurone
AHFS/Drugs.comMicromedex Detailed Consumer Information
ATC code
  • N03AX07 (WHO)
Pharmacokinetic data
Elimination half-life22–25 hours
Identifiers
IUPAC name
  • N-Carbamoyl-2-phenyl-acetamide
CAS Number
  • 63-98-9 checkY
PubChem CID
  • 4753
IUPHAR/BPS
  • 7265
DrugBank
  • DB01121 checkY
ChemSpider
  • 4589 checkY
UNII
  • PAI7J52V09
KEGG
  • D00504 checkY
ChEMBL
  • ChEMBL918 checkY
CompTox Dashboard (EPA)
  • DTXSID6023442 Edit this at Wikidata
ECHA InfoCard100.000.519 Edit this at Wikidata
Chemical and physical data
FormulaC9H10N2O2
Molar mass178.191 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • O=C(NC(=O)N)Cc1ccccc1
InChI
  • InChI=1S/C9H10N2O2/c10-9(13)11-8(12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H3,10,11,12,13) checkY
  • Key:XPFRXWCVYUEORT-UHFFFAOYSA-N checkY
  (verify)

Phenacemide (INN, BAN) (brand name Phenurone), also known as phenylacetylurea, is an anticonvulsant of the ureide (acetylurea) class.[1] It is a congener and ring-opened analogue of phenytoin (a hydantoin),[2][3] and is structurally related to the barbiturates and to other hydantoins.[4] Phenacemide was introduced in 1949 for the treatment of epilepsy, but was eventually withdrawn due to toxicity.[2][3]

See also

[edit]
  • Pheneturide

References

[edit]
  1. ^ Ganellin CR, Triggle DJ (21 November 1996). Dictionary of Pharmacological Agents. CRC Press. pp. 1578–. ISBN 978-0-412-46630-4.
  2. ^ a b Prasad JP (2010). "Central Nervous System". Conceptual Pharmacology. Universities Press. pp. 236–. ISBN 978-81-7371-679-9.
  3. ^ a b Saxena AK, Saxena M (1995). "Developments in anticonvulsants". In deStevens G, Zingel V, Leschke C, Hoeprich P, Schultz R, Mehrotra P, et al. (eds.). Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des recherches pharmaceutiques. Vol. 44. Basel: Birkhäuser. pp. 185–291. doi:10.1007/978-3-0348-7161-7_6. ISBN 978-3-0348-7161-7. PMID 7644666. {{cite book}}: |journal= ignored (help)
  4. ^ Kadam SS, Mahadik KR, Bothara KG (1 July 2007). "Central Nervous System Depresants". Principles of Medicinal Chemistry. Vol. II. Pragati Books Pvt. Ltd. pp. 147–. ISBN 978-81-85790-03-9.

Further reading

[edit]
  • Coker SB (1986). "The use of phenacemide for intractable partial complex epilepsy in children". Pediatric Neurology. 2 (4): 230–232. doi:10.1016/0887-8994(86)90053-6. PMID 3508693.
  • Coker SB, Holmes EW, Egel RT (December 1987). "Phenacemide therapy of complex partial epilepsy in children: determination of plasma drug concentrations". Neurology. 37 (12): 1861–1866. doi:10.1212/wnl.37.12.1861. PMID 3683877. S2CID 219205208.

External links

[edit]
  • Diseases Database (DDB): 34078
  • MedlinePlus DrugInfo uspdi-202454
  • v
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Anticonvulsants (N03)
GABAergics
GABAAR 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
  • v
  • t
  • e
Ion channel modulators
Calcium
VDCCsTooltip Voltage-dependent calcium channels
Blockers
  • L-type-selective: Dihydropyridines: Amlodipine (+telmisartan and indapamide)
  • Aranidipine
  • Azelnidipine
  • Barnidipine
  • Clevidipine
  • Cronidipine
  • Darodipine
  • Dexniguldipine
  • Elgodipine
  • Elnadipine
  • Felodipine
  • Flordipine
  • Furnidipine
  • Iganidipine
  • Isradipine
  • Lacidipine
  • Lemildipine
  • Lercanidipine
  • Levamlodipine
  • Levniguldipine
  • Manidipine
  • Mepirodipine
  • Mesudipine
  • Nicardipine
  • Nifedipine
  • Niguldipine
  • Niludipine
  • Nilvadipine
  • Nimodipine
  • Nisoldipine
  • Nitrendipine
  • Olradipine
  • Oxodipine
  • Palonidipine
  • Pranidipine
  • Ryodipine (riodipine)
  • Sagandipine
  • Sornidipine
  • Teludipine
  • Tiamdipine
  • Trombodipine
  • Vatanidipine; Diltiazem derivatives: Clentiazem
  • Diltiazem
  • Iprotiazem
  • Nictiazem
  • Siratiazem; Phenylalkylamines: Anipamil
  • Dagapamil
  • Devapamil
  • Dexverapamil
  • Emopamil
  • Etripamil
  • Falipamil
  • Gallopamil
  • Levemopamil
  • Nexopamil
  • Norverapamil
  • Ronipamil
  • Tiapamil
  • Verapamil; Others: AH-1058
  • Brinazarone
  • Budiodarone
  • Celivarone
  • Cyproheptadine
  • Dronedarone
  • Fantofarone
  • SR-33805
  • Tetrahydropalmatine
  • N-type-selective: ω-Conotoxins
  • ω-Conotoxin GVIA
  • Caroverine
  • Huwentoxin XVI
  • Leconotide (ω-conotoxin CVID)
  • PD-173212
  • Ralfinamide
  • Safinamide
  • Z160
  • Ziconotide (ω-conotoxin MVIIA)
  • P-type-selective: ω-Agatoxin IVA
  • ω-Agatoxin IVB
  • R-type-selective: SNX-482
  • T-type-selective: ABT-639
  • ML-218
  • Niflumic acid
  • NNC 55-0396
  • ProTx I
  • Z944
  • Zonisamide
  • Non-selective: ω-Agatoxin TK
  • ω-Conotoxin MVIIC
  • Benidipine
  • Bepridil
  • Cilnidipine
  • Cinnarizine
  • Dotarizine
  • Efonidipine
  • Flunarizine
  • Lamotrigine
  • Levetiracetam
  • Lomerizine
  • Loperamide
  • Mibefradil
  • NP078585
  • Ruthenium red
  • TROX-1
  • α2δ subunit-selective (gabapentinoids): 4-Methylpregabalin
  • Arbaclofen
  • Arbaclofen placarbil
  • Atagabalin
  • Baclofen
  • Gabapentin
  • Gabapentin enacarbil
  • Imagabalin
  • Mirogabalin
  • PD-200,347
  • PD-217,014
  • PD-299,685
  • Phenibut
  • Pregabalin
  • Others/unsorted: Bencyclane
  • Berbamine
  • Bevantolol
  • Canadine
  • Carboxyamidotriazole
  • Cycleanine
  • Dauricine
  • Dimeditiapramine
  • Diproteverine
  • Enpiperate
  • Eperisone
  • Elpetrigine
  • Ethadione
  • Ethanol (alcohol)
  • Ethosuximide
  • Fasudil
  • Fendiline
  • Fostedil
  • Imepitoin
  • JTV-519
  • Lidoflazine
  • Magnesium
  • Manoalide
  • Mesuximide
  • Monatepil
  • Naftopidil
  • Ochratoxin A
  • Osthol
  • Otilonium bromide
  • Paramethadione
  • Phensuximide
  • Pinaverium bromide
  • Prenylamine
  • Rhynchophylline
  • Sesamodil
  • Silperisone
  • Sipatrigine
  • Terodiline
  • Tetrandrine
  • Tolperisone
  • Trimethadione
  • Valperinol
Activators
  • L-type-selective: Bay K8644
Potassium
VGKCsTooltip Voltage-gated potassium channels
Blockers
  • 3,4-Diaminopyridine (amifampridine)
  • 4-Aminopyridine (fampridine/dalfampridine)
  • Adekalant
  • Almokalant
  • Amiodarone
  • Azimilide
  • Bretylium
  • Bunaftine
  • Charybdotoxin
  • Clamikalant
  • Conotoxins
  • Dalazatide
  • Dendrotoxin
  • Dofetilide
  • Dronedarone
  • E-4031
  • Hanatoxin
  • HgeTx1
  • HsTx1
  • Ibutilide
  • Inakalant
  • Kaliotoxin
  • Linopirdine
  • Lolitrem B
  • Maurotoxin
  • Nifekalant
  • Notoxin
  • Paxilline
  • Pinokalant
  • Quinidine
  • ShK-186
  • Sotalol
  • Tedisamil
  • Terikalant
  • Tetraethylammonium
  • Vernakalant
  • hERG (KCNH2, Kv11.1)-specific: Ajmaline
  • Amiodarone
  • AmmTX3
  • Astemizole
  • Azaspiracid
  • AZD1305
  • Azimilide
  • Bedaquiline
  • BeKm-1
  • BmTx3
  • BRL-32872
  • Chlorpromazine
  • Cisapride
  • Clarithromycin
  • Darifenacin
  • Dextropropoxyphene
  • Diallyl trisulfide
  • Domperidone
  • E-4031
  • Ergtoxins
  • Erythromycin
  • Gigactonine
  • Haloperidol
  • Ketoconazole
  • Norpropoxyphene
  • Orphenadrine
  • Pimozide
  • PNU-282,987
  • Promethazine
  • Quinidine
  • Ranolazine
  • Roxithromycin
  • Sertindole
  • Solifenacin
  • Tamulotoxin
  • Terodiline
  • Terfenadine
  • Thioridazine
  • Tolterodine
  • Vanoxerine
  • Vernakalant
  • KCNQ (Kv7)-specific: Linopirdine
  • XE-991
  • Spooky toxin (SsTx)
Activators
  • KCNQ (Kv7)-specific: Flupirtine
  • Retigabine
IRKsTooltip Inwardly rectifying potassium channel
Blockers
  • KATPTooltip 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
  • KATPTooltip 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)
KCaTooltip Calcium-activated potassium channel
Blockers
  • BKCa-specific: Ethanol (alcohol)
  • GAL-021
Activators
  • BKCa-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
  • Antiarrhythmics (class I): Ajmaline
  • Aprindine
  • Disopyramide
  • Dronedarone
  • Encainide
  • Flecainide
  • Lidocaine
  • Lorajmine
  • Lorcainide
  • Mexiletine
  • Moricizine
  • Pilsicainide
  • Prajmaline
  • Procainamide
  • Propafenone
  • Quinidine
  • Sparteine
  • Tocainide
  • Anticonvulsants: Acetylpheneturide
  • Carbamazepine
  • Cenobamate
  • Chlorphenacemide
  • Elpetrigine
  • Eslicarbazepine acetate
  • Ethotoin
  • Fosphenytoin
  • Lamotrigine
  • Lacosamide
  • Licarbazepine
  • Mephenytoin
  • Oxcarbazepine
  • Oxitriptyline
  • Phenacemide
  • Pheneturide
  • Phenytoin
  • Rufinamide
  • Sipatrigine
  • Topiramate
  • Sodium valproate
  • Valnoctamide
  • Valproate pivoxil
  • Valproate semisodium
  • Valproic acid
  • Valpromide
  • Zonisamide
  • Local anesthetics: pFBT
  • Amylocaine
  • Articaine
  • Benzocaine
  • Bupivacaine (Levobupivacaine, Ropivacaine)
  • Butacaine
  • Butamben
  • Chloroprocaine
  • Cinchocaine
  • Cocaine
  • Cyclomethycaine
  • Dimethocaine
  • Diphenhydramine
  • Etidocaine
  • Hexylcaine
  • Iontocaine
  • Lidocaine
  • Mepivacaine
  • Meprylcaine
  • Metabutoxycaine
  • Orthocaine
  • Piperocaine
  • Prilocaine
  • Procaine
  • Propoxycaine
  • Proxymetacaine
  • Risocaine
  • Tetracaine
  • Trimecaine
  • Analgesics: AZD-3161
  • DSP-2230
  • Funapide
  • GDC-0276
  • NKTR-171
  • PF-04531083
  • PF-05089771
  • Ralfinamide
  • Raxatrigine
  • RG7893 (GDC-0287)
  • Suzetrigine
  • Toxins: Conotoxins
  • Neosaxitoxin
  • Saxitoxin
  • Tetrodotoxin
  • Zetekitoxin AB
  • Others: Buprenorphine
  • Evenamide
  • Menthol (mint)
  • Safinamide
  • Tricyclic antidepressants
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
  • See here instead.
LGICsTooltip Ligand gated ion channels
  • See here instead.
See also: Receptor/signaling modulators • Transient receptor potential channel modulators
Stub icon

This anticonvulsant-related article is a stub. You can help Wikipedia by adding missing information.

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