Milverine (drug)

Milverine
Clinical data
Other names	Fenprin, Fenpyramine, Miospasm
Identifiers
	IUPAC name N-(3,3-diphenylpropyl)pyridin-4-amine;
CAS Number	75437-14-8;
PubChem CID	71139;
ChemSpider	64284;
UNII	83B517YUVM;
ChEBI	CHEBI:135196;
ChEMBL	ChEMBL2105255;
CompTox Dashboard (EPA)	DTXSID50868359 ;
Chemical and physical data
Formula	C20H20N2
Molar mass	288.394 g·mol−1
3D model (JSmol)	Interactive image;
	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]

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

↑ Carpenedo F, Santi-Soncin E (May 1970). "[Spasmolytic activity of a new diphenylpropylaminic derivative, N-(4'-pyridyl)-3,3-diphenyl 1-aminopropane]". Minerva Medica (in Italian). 61 (43): 2417–24. PMID 5425728.
↑ Baldi F, Ferrarini F, Balestra R, Borioni D, Longanesi A, Miglioli M (1984). "Effect of oral fenpyramine on meal-stimulated human sigmoid motility". Current Therapeutic Research. 36 (2): 267–272.
↑ Fossati A, Sosio A, Pellegrini R, Frigo GM, D'Angelo L, Lecchini S, Marcoli M, Caravaggi M, Crema A (September 1986). "Milverine: in vitro and in vivo activity on the animal and human colon". Il Farmaco; Edizione Pratica. 41 (9): 279–89. PMID 3770157.
↑ EP 0143082, Pellegrini R, Clavenna G, Bellani P, "Use of fenpyramin as platelet-antiaggregating, vasodilating, antithrombotic and antianginous medicine", assigned to Rbs Pharma (Roger Bellon Schoum) SpA
↑ DE 3002909, Masi P, Monopoli A, Saravalle AC, Zio C, "Method for Producing N- (4'-Pyridyl)-3,3-diphenyl-propylamine", published 31 July 1980, assigned to Italiana Schoum Sp

[pmid5425728-1] Carpenedo F, Santi-Soncin E (May 1970). "[Spasmolytic activity of a new diphenylpropylaminic derivative, N-(4'-pyridyl)-3,3-diphenyl 1-aminopropane]". Minerva Medica (in Italian). 61 (43): 2417–24. PMID 5425728.

[2] Baldi F, Ferrarini F, Balestra R, Borioni D, Longanesi A, Miglioli M (1984). "Effect of oral fenpyramine on meal-stimulated human sigmoid motility". Current Therapeutic Research. 36 (2): 267–272.

[pmid3770157-3] Fossati A, Sosio A, Pellegrini R, Frigo GM, D'Angelo L, Lecchini S, Marcoli M, Caravaggi M, Crema A (September 1986). "Milverine: in vitro and in vivo activity on the animal and human colon". Il Farmaco; Edizione Pratica. 41 (9): 279–89. PMID 3770157.

[4] EP 0143082, Pellegrini R, Clavenna G, Bellani P, "Use of fenpyramin as platelet-antiaggregating, vasodilating, antithrombotic and antianginous medicine", assigned to Rbs Pharma (Roger Bellon Schoum) SpA

[5] DE 3002909, Masi P, Monopoli A, Saravalle AC, Zio C, "Method for Producing N- (4'-Pyridyl)-3,3-diphenyl-propylamine", published 31 July 1980, assigned to Italiana Schoum Sp

[1]

[2]

[3]

[4]

[5]

v t e Urologicals, including antispasmodics (G04B)
Acidifiers	Ammonium chloride Calcium chloride
Urinary antispasmodics (primarily antimuscarinics)	Darifenacin Desfesoterodine Emepronium Fesoterodine Flavoxate Imidafenacin Meladrazine Mirabegron Oxybutynin Propiverine Solifenacin Terodiline Tolterodine Trospium chloride Vibegron
Other urologicals	Urea analogues: Acetohydroxamic acid Salicylhydroxamic acid Other: Collagen Dapoxetine Dimethyl sulfoxide Magnesium hydroxide Pentosan polysulfate Phenazopyridine Phenyl salicylate Succinimide Tiopronin

v t e Irritable bowel syndrome (IBS)
Management	Low-FODMAP diet Gluten-free diet Soluble fiber Laxatives Antispasmodics Psychotherapy Tricyclic antidepressants SSRIs Probiotics Eluxadoline
Related topics	Gut–brain axis Hypothalamic–pituitary–adrenal axis Sympathetic nervous system

This page was redesigned at the edge.

Synthesis

References