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Tiropramide

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Also known as: 55837-29-1, Tiropramide [inn], Cr-605, R7s0904cn2, Tiropramide (inn), Benzenepropanamide, alpha-(benzoylamino)-4-(2-(diethylamino)ethoxy)-n,n-dipropyl-, (+-)-

Molecular Formula

C₂₈H₄₁N₃O₃

Molecular Weight

467.6 g/mol

InChI Key

FDBWMYOFXWMGEY-UHFFFAOYSA-N

FDA UNII

R7S0904CN2

Tiropramide is under investigation in clinical trial NCT01629212 (Comparison of the Efficacy and Safety of Tiropramide and Octylonium in the Treatment of Irritable Bowel Syndrome).

1 2D Structure

Tiropramide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-[3-[4-[2-(diethylamino)ethoxy]phenyl]-1-(dipropylamino)-1-oxopropan-2-yl]benzamide

2.1.2 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)

2.1.3 InChI Key

FDBWMYOFXWMGEY-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCCN(CCC)C(=O)C(CC1=CC=C(C=C1)OCCN(CC)CC)NC(=O)C2=CC=CC=C2

2.2 Other Identifiers

2.2.1 UNII

R7S0904CN2

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cr 605

2.3.2 Depositor-Supplied Synonyms

1. 55837-29-1

2. Tiropramide [inn]

3. Cr-605

4. R7s0904cn2

5. Tiropramide (inn)

6. Benzenepropanamide, Alpha-(benzoylamino)-4-(2-(diethylamino)ethoxy)-n,n-dipropyl-, (+-)-

7. Tiropramida [spanish]

8. Tiropramida

9. Tiropramidum

10. Tiropramidum [inn-latin]

11. Tiropramida [inn-spanish]

12. N-(3-(4-(2-(diethylamino)ethoxy)phenyl)-1-(dipropylamino)-1-oxopropan-2-yl)benzamide

13. N-[3-[4-[2-(diethylamino)ethoxy]phenyl]-1-(dipropylamino)-1-oxopropan-2-yl]benzamide

14. (+/-)-tiropramide

15. Brn 4162600

16. Maioral

17. Tirospan

18. Unii-r7s0904cn2

19. O-(diethylaminoethyl)-n-benzoyl-dl-tyrosyl-di-n-propylamide

20. Tiropramide [mi]

21. Dl-alpha-benzamido-para-(2-(diethylamino)ethoxy)-n,n-dipropylhydrocinnamamide

22. (+-)-alpha-(benzoylamino)-4-(2-(diethylamino)ethoxy)-n,n-dipropylbenzenepropanamide

23. Schembl25693

24. Tiropramide [who-dd]

25. Chembl2104688

26. Dtxsid70866514

27. Chebi:135758

28. Akos015909639

29. Dl-alpha-benzamido-p-(2-(diethylamino)ethoxy)-n,n-dipropylhydrocinnamamide

30. Db13091

31. D07087

32. Q7809264

33. (+/-)-.alpha.-benzamido-p-(2-(diethylamino)ethoxy)-n,n-dipropylhydrocinnamamide

34. Dl-.alpha.-benzamido-p-(2-(diethylamino)ethoxy)-n,n-dipropylhydrocinnamamide

35. N-(2-{4-[2-(diethylamino)ethoxy]phenyl}-1-(dipropylcarbamoyl)ethyl)benzenecarboximidic Acid

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₂₈H₄₁N₃O₃
Molecular Weight	467.6 g/mol
XLogP3	5.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	15
Exact Mass	467.31479218 g/mol
Monoisotopic Mass	467.31479218 g/mol
Topological Polar Surface Area	61.9 Å²
Heavy Atom Count	34
Formal Charge	0
Complexity	561
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Parasympatholytics

Agents that inhibit the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the MUSCARINIC ANTAGONISTS. (See all compounds classified as Parasympatholytics.)

4.2 ATC Code

A - Alimentary tract and metabolism

A03 - Drugs for functional gastrointestinal disorders

A03A - Drugs for functional gastrointestinal disorders

A03AC - Synthetic antispasmodics, amides with tertiary amines

A03AC05 - Tiropramide