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Tiropramide

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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

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The acylationofracemic 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.^[2]^[3]

[edit]

^ 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.