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 ;
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 (INN) is an antispasmodic.^[1]

Synthesis

Thieme ChemDrug Synthesis:^[2] Patent:^[3]

The acylation of DL-Tyrosine [556-03-6] (1) with benzoyl chloride gives N,O-dibenzoyl-Tyrosine [14325-35-0] (2). Esterification with n-dipropylamine [142-84-7] (3) via the mixed anhydride method gave N,O-Dibenzoyl-DL-tyrosyl-N',N'-dipropylamide [57227-08-4] (4). Saponification of the ester in base gave N-Benzoyl-DL-tyrosyl-N',N'-dipropylamide [57227-09-5] (5). Ether formation with 2-Chlorotriethylamine [100-35-6] (6) completed the synthesis of Tiropramide (7).

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.
^ Serradell, MN; de Angelis, L.; Blancafort, P.; Castaer, J.; Tiropramide. Drugs Fut 1982, 7, 6, 413.
^ DE2503992 idem Francesco Makovec, Luigi Rovati, Paolo Senin, U.S. patent 4,004,008 (1977 to Rotta Research Laboratorium S.P.A.).

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[1] 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.

[2] Serradell, MN; de Angelis, L.; Blancafort, P.; Castaer, J.; Tiropramide. Drugs Fut 1982, 7, 6, 413.

[3] DE2503992 idem Francesco Makovec, Luigi Rovati, Paolo Senin, U.S. patent 4,004,008 (1977 to Rotta Research Laboratorium S.P.A.).

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