3-{4-[2-(diethylamino)ethoxy]phenyl}-2-(phenylformamido)-N,N-dipropylpropanamide hydrochloride

• ChemBase ID: 178675
• Molecular Formular: C28H42ClN3O3
• Molecular Mass: 504.10438
• Monoisotopic Mass: 503.2914699
• SMILES: c1c(ccc(c1)CC(C(=O)N(CCC)CCC)NC(=O)c1ccccc1)OCCN(CC)CC.Cl
• Canonical SMILES: CCCN(C(=O)C(NC(=O)c1ccccc1)Cc1ccc(cc1)OCCN(CC)CC)CCC.Cl
• InChI: InChI=1S/C28H41N3O3.ClH/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);1H
• InChIKey: SVCQSEFEZWMYSA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{4-[2-(diethylamino)ethoxy]phenyl}-2-(phenylformamido)-N,N-dipropylpropanamide hydrochloride
• IUPAC Traditional name: tiropramide hydrochloride
• Synonyms: (±)-α-(Benzoylamino)-4-[2-(diethylamino)ethoxy]-N,N-dipropylbenzenepropanamide Hydrochloride; Alfospas; Maiorad; Tiromid; Tiropramide Hydrochloride

Database IDs

• CAS Number: 53567-47-8
• PubChem SID: 164234585
• PubChem CID: 134448

CALCULATED PROPERTIES

• Acid pKa: 15.036327
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.3932353
• LogD (pH = 7.4): 2.8106062
• Log P: 4.7242956
• Molar Refractivity: 139.3709 cm^3
• Polarizability: 53.79513 Å^3
• Polar Surface Area: 61.88 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T446900

Tiropramide is an antispasmodic agent. Studies sugges that Tiropramide has a pure musculotropic smooth muscle relaxant activity. Tiropramide is considered to be useful to inhibit the contractile response of the urinary bladder.

REFERENCES

• Myung, S.-W. et al.: J. Appl. Pharmacol., 8, 262 (2000)
• Kwon, O.-S. et al.: Arzneim.-Forsch., 53, 578 (2000)
• Jhee, O.H. et al.: Clin. Chim. Acta, 366, 179 (2000)
• Takayanagi, I. et al.: Gen, Pharmacol., 20, 335 (2000)