Mibefradil

Mibefradil

Systematic (IUPAC) name
(1S,2S)-2-(2-((3-(1H-benzo[d]imidazol-2-yl)propyl) (methyl)amino)ethyl)-6-fluoro-1-isopropyl- 1,2,3,4-tetrahydronaphthalen-2-yl 2-methoxyacetate
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a607007
Legal status	Withdrawn from market
Routes of administration	Oral
Pharmacokinetic data
Bioavailability	70 %
Protein binding	> 99 %
Metabolism	Hepatic
Half-life	17-25 h
Identifiers
CAS Registry Number	116644-53-2 Y
ATC code	C08CX01
PubChem	CID 60662
DrugBank	DB01388 N
ChemSpider	54673 N
UNII	27B90X776A N
KEGG	D08217 Y
ChEMBL	CHEMBL45816 N
Chemical data
Formula	C29H38FN3O3
Molecular mass	495.63 g/mol
SMILES CC(C)[C@H]1C2=C(CC[C@@]1(CCN(C)CCCC3=NC4=CC=CC=C4N3)OC(=O)COC)C=C(C=C2)F
InChI InChI=1S/C29H38FN3O3/c1-20(2)28-23-12-11-22(30)18-21(23)13-14-29(28,36-27(34)19-35-4)15-17-33(3)16-7-10-26-31-24-8-5-6-9-25(24)32-26/h5-6,8-9,11-12,18,20,28H,7,10,13-17,19H2,1-4H3,(H,31,32)/t28-,29-/m0/s1  N Key:HBNPJJILLOYFJU-VMPREFPWSA-N  N
Physical data
Melting point	128 °C (262 °F) (dihydrochloride salt)
N (what is this?)  (verify)

Mibefradil (Posicor) is a drug for the treatment of hypertension and chronic angina pectoris. It belongs to a group known as calcium channel blockers.

It is nonselective.^[1]

On June 8, 1998, Roche announced the voluntary withdrawal of the drug from the market, one year after approval by the FDA, due to the potential for drug interactions, some of them deadly, which may occur when it is taken together with some other medications. ^[2]

Synthesis

Mibefradil synthesis: YU 22988  ZW 20087 

References