Lacidipine

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Lacidipine
Lacidipine structure.svg
Systematic (IUPAC) name
Diethyl 4-{o-[(E)-2-tert-butoxycarbonylethenyl]phenyl}-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
Clinical data
Trade names Lacipil, Motens
AHFS/Drugs.com International Drug Names
Routes of
administration
Oral
Legal status
Legal status
  • ℞ (Prescription only)
Pharmacokinetic data
Bioavailability ~10%
Protein binding >95%
Metabolism Hepatic
Onset of action 30–50 min
Biological half-life 13–19 hours
Excretion Feces (~70%)
Identifiers
CAS Number 103890-78-4
ATC code C08CA09 (WHO)
PubChem CID 5311217
ChemSpider 4470736
UNII 260080034N YesY
KEGG D04657 YesY
Chemical data
Formula C26H33NO6
Molar mass 455.543 g/mol
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Lacidipine (tradenames Lacipil (GSK) or Motens (Boehringer Ingelheim)) is a calcium channel blocker. It is available as tablets containing 2 or 4 mg.

Synthesis[edit]

Lacidipine synthesis: C. Semeraro et al., DE 3529997 ; eidem, U.S. Patent 4,801,599 (1986, 1989 both to Glaxo).

The synthesis starts with the Wittig reaction of phthalaldehyde (1) with the ylide from triphenylphosphonium salt (2). The trans stereochemistry of the product (3) follows from the fact that the rxn is not carried out under salt-free conditions; selectivity for monoalkylation is probably due to steric hindrance from the newly introduced adjacent side chain to the adjacent formyl group. reaction of tat intermediate with ethyl acetoacetate and ammonia gives the dihydropyridine lacidipine (5).

Notes[edit]

Teludipine synthesis: Claudio Semeraro, et al. U.S. Patent 5,162,345 (1992 to Glaxo).

Further modification of this compound depends on the allylic nature of the ring methyl groups. Thus reaction of 5 with pyridinium perbromide leads to the bromination of one groups and the formation of 6. The displacement of halogen by dimethylamine leads to the tertiary amine teludipine (7).

External links[edit]