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Mibefradil

Mibefradil

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Mibefradil
Mibefradil.svg
Clinical data
Trade names Posicor
AHFS/Drugs.com Micromedex Detailed Consumer Information
MedlinePlus a607007
Routes of
administration
By mouth (tablets)
ATC code
Legal status
Legal status
  • Withdrawn from market
Pharmacokinetic data
Bioavailability 70%
Protein binding >99%
Metabolism Liver (CYP3A4)
Elimination half-life 17–25 hours
Identifiers
  • (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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
Chemical and physical data
Formula C29H38FN3O3
Molar mass 495.639 g·mol−1
3D model (JSmol)
Melting point 128 °C (262 °F) (dihydrochloride salt)
  • 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=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
 ☒NcheckY (what is this?)  (verify)

Mibefradil (trade name Posicor) was a pharmaceutical drug used for the treatment of hypertension and chronic angina pectoris. It is a nonselective calcium channel blocker. It was voluntary pulled from the market ten months after FDA approval, citing potential serious health hazards shown in post release studies.

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.

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.

Synthesis

Mibefradil synthesis: YU 22988  ZW 20087 

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