Tiropramide

Tiropramide
Clinical data
Other names	N-[3-[4-(2-Diethylaminoethoxy)phenyl]-1-(dipropylamino)-1-oxopropan-2-yl]benzamide
AHFS/Drugs.com	International Drug Names
ATC code	A03AC05 (WHO) ;
Identifiers
	IUPAC name Nα-benzoyl-O-[2-(diethylamino)ethyl]-N,N-dipropyltyrosinamide;
CAS Number	55837-29-1;
PubChem CID	42262;
ChemSpider	38541;
UNII	R7S0904CN2;
KEGG	D07087 Y;
ChEMBL	ChEMBL2104688;
CompTox Dashboard (EPA)	DTXSID70866514 ;
Chemical and physical data
Formula	C28H41N3O3
Molar mass	467.654 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCN(CCC)C(=O)C(Cc1ccc(cc1)OCCN(CC)CC)NC(=O)c2ccccc2;
	InChI InChI=1S/C28H41N3O3/c1-5-18-31(19-6-2)28(33)26(29-27(32)24-12-10-9-11-13-24)22-23-14-16-25(17-15-23)34-21-20-30(7-3)8-4/h9-17,26H,5-8,18-22H2,1-4H3,(H,29,32); Key:FDBWMYOFXWMGEY-UHFFFAOYSA-N;
	(verify)

Tiropramide is the International nonproprietary name of an antispasmodic drug.¹

Synthesis

The acylation of racemic tyrosine (1) with benzoyl chloride gives N,O-dibenzoyl-tyrosine (2). Amide formation with dipropylamine (3) using the mixed anhydride method gives the intermediate (4). Hydrolysis of the phenolic ester with sodium hydroxide forms (5), which is alkylated with ClCH₂CH₂N(CH₂CH₃)₂ to produce the ether tiropramide.²³

References

Vidal y Plana RR, Cifarelli A, Setnikar I (January 1981). "Mechanism of smooth muscle relaxation by tiropramide". The Journal of Pharmacy and Pharmacology. 33 (1): 19–24. doi:10.1111/j.2042-7158.1981.tb13694.x. PMID 6114146. S2CID 22487894.
Francesco Makovec, Luigi Rovati, Paolo Senin, U.S. patent 4,004,008 (1977 to Rotta Research Laboratorium S.P.A.)
"Tiropramide". Thieme. Retrieved 2024-07-01.