BEP

1-ISOBUTOXY-2-PYRROLIDINO-3[N-BENZYLANILINO] PROPANE

Created:	2000-01-24
Last modified:	2020-06-05

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3 entries where BEP is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	61
Chiral Atom Count	1
Bond Count	63
Aromatic Bond Count	12

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Chemical Component Summary
Name	1-ISOBUTOXY-2-PYRROLIDINO-3[N-BENZYLANILINO] PROPANE
Synonyms	BEPRIDIL
Systematic Name (OpenEye OEToolkits)	N-[(2S)-3-(2-methylpropoxy)-2-pyrrolidin-1-yl-propyl]-N-(phenylmethyl)aniline
Formula	C₂₄ H₃₄ N₂ O
Molecular Weight	366.54
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O(CC(C)C)CC(N1CCCC1)CN(c2ccccc2)Cc3ccccc3
SMILES	CACTVS	3.341	CC(C)COC[CH](CN(Cc1ccccc1)c2ccccc2)N3CCCC3
SMILES	OpenEye OEToolkits	1.5.0	CC(C)COCC(CN(Cc1ccccc1)c2ccccc2)N3CCCC3
Canonical SMILES	CACTVS	3.341	CC(C)COC[C@H](CN(Cc1ccccc1)c2ccccc2)N3CCCC3
Canonical SMILES	OpenEye OEToolkits	1.5.0	CC(C)COC[C@H](C[N@@](Cc1ccccc1)c2ccccc2)N3CCCC3
InChI	InChI	1.03	InChI=1S/C24H34N2O/c1-21(2)19-27-20-24(25-15-9-10-16-25)18-26(23-13-7-4-8-14-23)17-22-11-5-3-6-12-22/h3-8,11-14,21,24H,9-10,15-20H2,1-2H3/t24-/m0/s1
InChIKey	InChI	1.03	UIEATEWHFDRYRU-DEOSSOPVSA-N

Drug Info: DrugBank

DrugBank ID	DB01244
Name	Bepridil
Groups	approved withdrawn
Description	A long-acting, non selective, calcium channel blocker with significant anti-anginal activity. The drug produces significant coronary vasodilation and modest peripheral effects. It has antihypertensive and selective anti-arrhythmia activities and acts as a calmodulin antagonist. It is no longer marketed in the United States, as it has been implicated in causing ventricular arrhythmias (ie. Torsade de pointes).
Synonyms	Bepridil Bepadin Bepridil hydrochloride
Indication	For the treatment of hypertension, and chronic stable angina (classic effort-associated angina).
Categories	Agents causing hyperkalemia Antiarrhythmic agents Antihypertensive Agents Bradycardia-Causing Agents Calcium Channel Blockers Calcium-Regulating Hormones and Agents Cardiovascular Agents Cytochrome P-450 CYP2D6 Inhibitors Cytochrome P-450 CYP2D6 Inhibitors (strength unknown) Cytochrome P-450 CYP2D6 Substrates Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Highest Risk QTc-Prolonging Agents Hypotensive Agents Membrane Transport Modulators Non-Selective Calcium Channel Blockers P-glycoprotein inhibitors Phenylalkylamine Derivatives Pyrrolidines QTc Prolonging Agents Vasodilating Agents
ATC-Code	C08EA02
CAS number	64706-54-3

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Voltage-dependent P/Q-type calcium channel subunit alpha-1A	MARFGDEMPARYGGGGSGAAAGVVVGSGGGRGAGGSRQGGQPGAQRMYKQ...	unknown	inhibitor
Voltage-dependent T-type calcium channel subunit alpha-1H	MTEGARAADEVRVPLGAPPPGPAALVGASPESPGAPGREAERGSELGVSP...	unknown	inhibitor
Voltage-dependent calcium channel subunit alpha-2/delta-2	MAVPARTCGASRPGPARTARPWPGCGPHPGPGTRRPTSGPPRPLWLLLPL...	unknown	inhibitor
Sodium/potassium-transporting ATPase subunit alpha-1	MGKGVGRDKYEPAAVSEQGDKKGKKGKKDRDMDELKKEVSMDDHKLSLDE...	unknown	inhibitor
Potassium voltage-gated channel subfamily KQT member 1	MAAASSPPRAERKRWGWGRLPGARRGSAGLAKKCPFSLELAEGGPAGGAL...	unknown	inhibitor
Troponin C, slow skeletal and cardiac muscles	MDDIYKAAVEQLTEEQKNEFKAAFDIFVLGAEDGCISTKELGKVMRMLGQ...	unknown	other
Calmodulin	MADQLTEEQIAEFKEAFSLFDKDGDGTITTKELGTVMRSLGQNPTEAELQ...	unknown	binder
Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1B	MELSPRSPPEMLEESDCPSPLELKSAPSKKMWIKLRSLLRYMVKQLENGE...	unknown	inhibitor
Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1A	MGSSATEIEELENTTFKYLTGEQTEKMWQRLKGILRCLVKQLERGDVNVV...	unknown	inhibitor
Potassium voltage-gated channel subfamily H member 2	MPVRRGHVAPQNTFLDTIIRKFEGQSRKFIIANARVENCAVIYCNDGFCE...	unknown	inhibitor
Cytochrome P450 2D6	MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...	unknown	substrate,inhibitor
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	inhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682