Milverine (drug)

Milverine
Clinical data
Other namesFenprin, Fenpyramine, Miospasm
Identifiers
IUPAC name
  • N-(3,3-diphenylpropyl)pyridin-4-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H20N2
Molar mass288.394 g·mol−1
3D model (JSmol)
SMILES
  • C1=CC=C(C=C1)C(CCNC2=CC=NC=C2)C3=CC=CC=C3
InChI
  • InChI=1S/C20H20N2/c1-3-7-17(8-4-1)20(18-9-5-2-6-10-18)13-16-22-19-11-14-21-15-12-19/h1-12,14-15,20H,13,16H2,(H,21,22)
  • Key:KMZHYAUKFHLFNY-UHFFFAOYSA-N

Milverine (Fenprin, Fenpyramine, Miospasm) is a spasmolytic (antispasmodic) agent that was developed in the latter half of the 20th century.[1][2][3]

The therapeutic use of fenpyramin as a platelet-antiaggregating and antithrombotic as well as vasodilating and antianginous medicine was also identified.[4]

Milverine is a bifunctional molecule; one half of the molecule contains 3,3-Diphenylpropylamine and the other half of the molecule contains fampridine.

Synthesis

The chemical synthesis of milverine was identified.[5]

Milverine synthesis
Milverine synthesis

Conjugate soft addition of benzene to cinnamic acid [140-10-3] (1) gives 3,3-diphenylpropionic acid [606-83-7] (2). Halogenation with thionyl chloride gives 3,3-diphenylpropionyl chloride [37089-77-3] (3). Schotten-Baumann reaction with 4-aminopyridine (Fampridine) [504-24-5] (4) gives 3,3-diphenyl-N-(4-pyridyl)propionamide [75437-13-7] (5). The last step involves reduction of the amide bond giving milverine (6), respectively.

References

  1. ↑ Carpenedo F, Santi-soncin E. [Spasmolytic activity of a new diphenylpropylaminic derivative, N-(4'-pyridyl)-3,3-diphenyl 1-aminopropane]. Minerva Med. 1970;61(43):2417-24. PMID 5425728.
  2. ↑ Baldi, F. et al, Curr. Ther. Res., 1984,36, 267 (pharmacol)
  3. ↑ Fossati A, Sosio A, Pellegrini R, Frigo GM, D'Angelo L, Lecchini S, Marcoli M, Caravaggi M, Crema A. Milverine: in vitro and in vivo activity on the animal and human colon. Farmaco Prat. 1986 Sep;41(9):279-89. PMID 3770157.
  4. ↑ Rinaldo Pellegrini, Gaetano Clavenna, Piero Bellani, EP0143082 (1985 to RBS PHARMA (ROGER BELLON SCHOUM) S.p.A.).
  5. ↑ Paolo Masi, Angela Monopoli, Adone Carlo Saravalle, Cesare Zio, DE3002909 (1980 to Italiana Schoum Spa).
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