tiropramide

{{Short description|Chemical compound}}

{{cs1 config|name-list-style=vanc}}

{{Drugbox

| verifiedrevid = 437195625

| IUPAC_name = Nα-benzoyl-O-[2-(diethylamino)ethyl]-N,N-dipropyltyrosinamide

| image = Tiropramide.svg

| tradename =

| Drugs.com = {{drugs.com|international|tiropramide}}

| pregnancy_AU =

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| routes_of_administration =

| bioavailability =

| protein_bound =

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| CAS_number = 55837-29-1

| ATC_prefix = A03

| ATC_suffix = AC05

| ATC_supplemental =

| PubChem = 42262

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = R7S0904CN2

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D07087

| ChemSpiderID = 38541

| ChEMBL = 2104688

| chemical_formula =

| C=28 | H=41 | N=3 | O=3

| synonyms = N-[3-[4-(2-Diethylaminoethoxy)phenyl]-1-(dipropylamino)-1-oxopropan-2-yl]benzamide

| StdInChI = 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)

| StdInChIKey = FDBWMYOFXWMGEY-UHFFFAOYSA-N

| smiles = CCCN(CCC)C(=O)C(Cc1ccc(cc1)OCCN(CC)CC)NC(=O)c2ccccc2

}}

Tiropramide is the International nonproprietary name of an antispasmodic drug.{{cite journal | vauthors = Vidal y Plana RR, Cifarelli A, Setnikar I | title = Mechanism of smooth muscle relaxation by tiropramide | journal = The Journal of Pharmacy and Pharmacology | volume = 33 | issue = 1 | pages = 19–24 | date = January 1981 | pmid = 6114146 | doi = 10.1111/j.2042-7158.1981.tb13694.x | s2cid = 22487894 }}

Synthesis

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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 {{chem2|ClCH2CH2N(CH2CH3)2}} to produce the ether tiropramide.Francesco Makovec, Luigi Rovati, Paolo Senin, {{US patent|4004008}} (1977 to Rotta Research Laboratorium S.P.A.){{cite web |url=https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-20-0113 |title=Tiropramide |publisher=Thieme |access-date=2024-07-01 }}

References