Mibefradil

Mibefradil

Clinical data
Trade names	Posicor
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a607007
Routes of administration	By mouth (tablets)
ATC code	C08CX01 (WHO)
Legal status
Legal status	Withdrawn from market
Pharmacokinetic data
Bioavailability	70%
Protein binding	>99%
Metabolism	Liver
Elimination half-life	17–25 hours
Identifiers
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
CAS Number	116644-53-2 Y
PubChem CID	60662
IUPHAR/BPS	2522
DrugBank	DB01388 N
ChemSpider	54673 N
UNII	27B90X776A
KEGG	D08217 Y
ChEMBL	CHEMBL45816 N
Chemical and physical data
Formula	C29H38FN3O3
Molar mass	495.63 g/mol
3D model (JSmol)	Interactive image
Melting point	128 °C (262 °F) (dihydrochloride salt)
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
NY (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.

The mechanism of action of mibefradil is characterized by the selective blockade of transient, low-voltage-activated (T-type) calcium channels over long-lasting, high-voltage-activated (L-type) calcium channels, which is probably responsible for many of its unique properties.

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