Encainide

Encainide
Clinical data

Trade names	Enkaid
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a605040
ATC code	C01BC08 (WHO)
Legal status
Legal status	Withdrawn
Identifiers
IUPAC name 4-methoxy-N-[2-(1-methyl-2-piperidin-1-ylethyl)phenyl]benzamide
CAS Number	66778-36-7^Y
PubChem (CID)	48041
DrugBank	DB01228^Y
ChemSpider	43697^Y
UNII	SY3J0147NB^Y
KEGG	D07894^Y
ChEBI	CHEBI:4788^Y
ChEMBL	CHEMBL315838^N
Chemical and physical data
Formula	C₂₂H₂₈N₂O₂
Molar mass	352.47 g/mol
3D model (Jmol)	Interactive image
SMILES CN1CCCCC1CCC2=CC=CC=C2NC(=O)C3=CC=C(C=C3)OC
InChI InChI=1S/C22H28N2O2/c1-24-16-6-5-8-19(24)13-10-17-7-3-4-9-21(17)23-22(25)18-11-14-20(26-2)15-12-18/h3-4,7,9,11-12,14-15,19H,5-6,8,10,13,16H2,1-2H3,(H,23,25)^Y Key:PJWPNDMDCLXCOM-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

Encainide (trade name Enkaid) is a class Ic antiarrhythmic agent. It is no longer used because of its frequent proarrhythmic side effects.^[1]

Synthesis

Encainide synthesis:^[2]^[3]^[4]

References

↑ Echt, D. S.; Liebson, P. R.; Mitchell, L. B.; Peters, R. W.; Obias-Manno, D.; Barker, A. H.; Arensberg, D.; Baker, A.; Friedman, L.; Greene, H. L.; Huther, M. L.; Richardson, D. W. (1991). "Mortality and Morbidity in Patients Receiving Encainide, Flecainide, or Placebo". New England Journal of Medicine. 324 (12): 781–788. doi:10.1056/NEJM199103213241201. PMID 1900101.
↑ S.J. Dykstra, J.L. Minelli, DE 2210154 (1972).
↑ S.J. Dykstra, J.L. Minelli, U.S. Patent 3,931,195 (1976).
↑ Dykstra, Stanley J. (1973). "Lysergic acid and quinidine analogs. 2-(o-Acylaminophenethyl)piperidines". Journal of Medicinal Chemistry. 16 (9): 1015–1020. doi:10.1021/jm00267a012. PMID 4745503.

Ion channel modulators

Calcium (Ca²⁺)

Blockers	L-type-selective: Dihydropyridines: Amlodipine 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 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 Ethosuximide Fasudil Fendiline Fostedil JTV-519 Lidoflazine Magnesium Manoalide Mesuximide Monatepil Naftopidil Ochratoxin A Osthol Otilonium bromide Paramethadione Phensuximide Pinaverium Prenylamine Rhynchophylline Sesamodil Silperisone Sipatrigine Terodiline Tetrahydropalmatine Tetrandrine Tolperisone Trimethadione Valperinol

Openers	L-type-selective: Bay K8644

Potassium (K⁺)

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 ShK-186 Sotalol Tedisamil Terikalant Tetraethylammonium Vernakalant GIRK blockers: Barium Caramiphen Cloperastine Clozapine Dextromethorphan Ethosuximide Ifenprodil Tertiapin Tipepidine hERG blockers: 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 Ranolazine Roxithromycin Sertindole Solifenacin Tamulotoxin Terodiline Terfenadine Thioridazine Tolterodine Vanoxerine Vernakalant K_ATP blockers: Acetohexamide Carbutamide Chlorpropamide Glibenclamide (glyburide) Glibornuride Glicaramide Gliclazide Glimepiride Glipizide Gliquidone Glisoxepide Glyclopyramide Glycyclamide Metahexamide Mitiglinide Nateglinide Repaglinide Tolazamide Tolbutamide

Openers	K_ATP openers: Aprikalim Bimakalim Cromakalim Emakalim Levcromakalim Mazokalim Rilmakalim Sarakalim Others: Diazoxide Flupirtine Minoxidil ML-297 Naminidil Nicorandil Pinacidil Retigabine Rottlerin

Sodium (Na⁺)

Blockers	VGSC 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 Lacosamide Licarbazepine Mephenytoin Oxcarbazepine Oxitriptyline Phenacemide Pheneturide Phenytoin Rufinamide Sipatrigine Topiramate Sodium valproate Valnoctamide Valproate pivoxil Valproate semisodium Valproic acid Valpromide Zonisamide; Diuretics: Amiloride Benzamil Triamterene; 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); Toxins: Conotoxins Neosaxitoxin Saxitoxin Tetrodotoxin; Others: Buprenorphine Evenamide Menthol Safinamide Tricyclic antidepressants

Openers	VGSC openers: Atracotoxins (Robustoxin, Versutoxin) Ciguatoxins ENaC openers: Solnatide

Chloride (Cl⁻)

Blockers	Bumetanide DIDS Flufenamic acid Furosemide Glibenclamide Lonidamine Meclofenamic acid Mefenamic acid Mepacrine Niflumic acid Piretanide Talniflumate Tolfenamic acid Trifluoperazine

Openers	CFTR openers: 1,7-Phenanthroline 1,10-Phenanthroline 4,7-Phenanthroline 7,8-Benzoquinoline Phenanthridine

Antiarrhythmic agents (C01B)

Channel blockers

class I
(Na⁺ channel blockers)

class Ia (Phase 0→ and Phase 3→)	Ajmaline Disopyramide Lorajmine Prajmaline Procainamide^# Quinidine^# Sparteine

class Ib (Phase 3←)	IV (Lidocaine^#) enteral (Aprindine Mexiletine Tocainide)

class Ic (Phase 0→)	Encainide^‡ Ethacizine Flecainide Indecainide^‡ Lorcainide Moracizine^‡ Propafenone

class III
(Phase 3→, K⁺ channel blockers)

class IV
(Phase 4→, Ca²⁺ channel blockers)

Diltiazem
Verapamil^#

Receptor agonists
and antagonists

class II (Phase 4→, β blockers)	Nadolol Pindolol Propranolol cardioselective (Acebutolol Atenolol Esmolol Metoprolol)

A₁ agonist	Adenosine Benzodiazepines Barbiturates

M₂	muscarinic antagonist: Atropine Disopyramide Quinidine muscarinic agonist: Digoxin

α receptors	Amiodarone Bretylium Quinidine Verapamil

Ion transporters

Na⁺/ K⁺-ATPase	Digoxin

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

This article is issued from Wikipedia - version of the 4/2/2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.

Encainide

Synthesis

See also

References