Bay K8644

Bay K8644^[1]
Names


IUPAC name Methyl 2,6-dimethyl-5-nitro-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3-carboxylate
Identifiers
CAS Number	71145-03-4^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:34555^N
ChEMBL	ChEMBL513599^N
ChemSpider	2213^N
ECHA InfoCard	100.163.930
IUPHAR/BPS	2511
PubChem	2303
InChI InChI=1S/C16H15F3N2O4/c1-8-12(15(22)25-3)13(14(21(23)24)9(2)20-8)10-6-4-5-7-11(10)16(17,18)19/h4-7,13,20H,1-3H3^N Key: ZFLWDHHVRRZMEI-UHFFFAOYSA-N^N InChI=1/C16H15F3N2O4/c1-8-12(15(22)25-3)13(14(21(23)24)9(2)20-8)10-6-4-5-7-11(10)16(17,18)19/h4-7,13,20H,1-3H3 Key: ZFLWDHHVRRZMEI-UHFFFAOYAV
SMILES CC1=C(C(C(=C(N1)C)[N+](=O)[O-])C2=CC=CC=C2C(F)(F)F)C(=O)OC
Properties
Chemical formula	C₁₆H₁₅F₃N₂O₄
Molar mass	356.30 g·mol⁻¹
Solubility in water	Insoluble
Solubility in other solvents	DMSO: 184 mg/mL; methanol and ethanol: 63 mg/mL
Hazards
EU classification (DSD)	Xi
R-phrases	R36/38
S-phrases	S26 S36
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

Bay K8644 is a chemical compound that functions as a calcium channel agonist. Bay K8644 is used primarily as a biochemical research tool for this effect.^[2] It is a structural analog of nifedipine with positive inotropic activity, and as an aromatic it is highly lipid soluble.

Mechanism of Action

Bay K8644 targets Voltage-sensitive dihydropyridine (DHP) Calcium Channels (L-Type). It is the first positive inotropic agent shown to act specifically and directly on calcium channels.^[3]

References

↑ (±)-Bay K8644 at Sigma-Aldrich
↑ Bay K8644 at PubChem
↑ Thomas, G; Chung, M; Cohen, CJ (January 1985). "A dihydropyridine (Bay k 8644) that enhances calcium currents in guinea pig and calf myocardial cells. A new type of positive inotropic agent.". Circ Res. PMID 2578336.

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

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