Milverine (drug)

Last updated
Milverine
Milverine.svg
Clinical data
Other namesFenprin, Fenpyramine, Miospasm
Identifiers
  • N-(3,3-diphenylpropyl)pyridin-4-amine
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
Formula C20H20N2
Molar mass 288.394 g·mol−1
3D model (JSmol)
  • C1=CC=C(C=C1)C(CCNC2=CC=NC=C2)C3=CC=CC=C3
  • 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.svg
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.

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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).