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Mibefradil

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Withdrawn antihypertensive drug of the calcium channel blocker class Pharmaceutical compound
Mibefradil
Clinical data
Trade namesPosicor
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa607007
Routes of
administration		By mouth (tablets)
ATC code
Legal status
Legal status
  • Withdrawn from market
Pharmacokinetic data
Bioavailability70%
Protein binding>99%
MetabolismLiver (CYP3A4)
Elimination half-life17–25 hours
Identifiers
IUPAC name
  • (1S,2S)-2-(2-((3-(1H-benzoimidazol-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
FormulaC29H38FN3O3
Molar mass495.639 g·mol
3D model (JSmol)
Melting point128 °C (262 °F) (dihydrochloride salt)
SMILES
  • CC(C)1C2=C(CC1(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
  • Key:HBNPJJILLOYFJU-VMPREFPWSA-N
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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 

References

  1. ^ Bezprozvanny I, Tsien RW (September 1995). "Voltage-dependent blockade of diverse types of voltage-gated Ca2+ channels expressed in Xenopus oocytes by the Ca2+ channel antagonist mibefradil (Ro 40-5967)". Mol. Pharmacol. 48 (3): 540–9. PMID 7565636.
  2. Stolberg, Sheryl Gay (1998-06-09). "Heart Drug Withdrawn as Evidence Shows It Could Be Lethal". The New York Times. Retrieved 2019-01-12.
Ion channel modulators
Calcium
VDCCsTooltip Voltage-dependent calcium channels
Blockers
Activators
Potassium
VGKCsTooltip Voltage-gated potassium channels
Blockers
Activators
IRKsTooltip Inwardly rectifying potassium channel
Blockers
Activators
KCaTooltip Calcium-activated potassium channel
Blockers
Activators
K2PsTooltip Tandem pore domain potassium channel
Blockers
Activators
Sodium
VGSCsTooltip Voltage-gated sodium channels
Blockers
Activators
ENaCTooltip Epithelial sodium channel
Blockers
Activators
ASICsTooltip Acid-sensing ion channel
Blockers
Chloride
CaCCsTooltip Calcium-activated chloride channel
Blockers
Activators
CFTRTooltip Cystic fibrosis transmembrane conductance regulator
Blockers
Activators
Unsorted
Blockers
Others
TRPsTooltip Transient receptor potential channels
LGICsTooltip Ligand gated ion channels
See also: Receptor/signaling modulators • Transient receptor potential channel modulators
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