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Tiropramide

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Chemical compound

Pharmaceutical compound
Tiropramide
Clinical data
Other namesN--1-(dipropylamino)-1-oxopropan-2-yl]benzamide
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
IUPAC name
  • Nα-benzoyl-O--N,N-dipropyltyrosinamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC28H41N3O3
Molar mass467.654 g·mol
3D model (JSmol)
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.

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.

References

  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. Retrieved 2024-07-01.
Drugs for functional gastrointestinal disorders (A03)
Drugs for
functional
bowel
disorders
Antimuscarinics
Tertiary
amino group
Quaternary
ammonium
compounds
Phosphodiesterase
inhibitors
Acting on
serotonin receptors
Other
Belladonna
and derivatives
(antimuscarinics)
Propulsives


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