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Tiropramide

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
Tiropramide
Clinical data
Other namesN-[3-[4-(2-Diethylaminoethoxy)phenyl]-1-(dipropylamino)-1-oxopropan-2-yl]benzamide
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • Nα-benzoyl-O-[2-(diethylamino)ethyl]-N,N-dipropyltyrosinamide
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC28H41N3O3
Molar mass467.654 g·mol−1
3D model (JSmol)
  • CCCN(CCC)C(=O)C(Cc1ccc(cc1)OCCN(CC)CC)NC(=O)c2ccccc2
  • 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 theInternational nonproprietary name of anantispasmodic drug.[1]

Synthesis

[edit]

Theacylation ofracemictyrosine (1) withbenzoyl chloride gives N,O-dibenzoyl-tyrosine (2).Amide formation withdipropylamine (3) using themixed anhydride method gives the intermediate (4).Hydrolysis of thephenolic ester withsodium hydroxide forms (5), which isalkylated withClCH2CH2N(CH2CH3)2 to produce theether tiropramide.[2][3]

References

[edit]
  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. ^Francesco Makovec, Luigi Rovati, Paolo Senin,U.S. patent 4,004,008 (1977 to Rotta Research Laboratorium S.P.A.)
  3. ^"Tiropramide". Thieme. Retrieved2024-07-01.
Drugs for
functional
bowel
disorders
Antimuscarinics
Tertiary
amino group
Quaternary
ammonium

compounds
Phosphodiesterase
inhibitors
Acting on
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Belladonna
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