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Also known as: 66564-14-5, Paxapride, Cidine, Cinitapride [inn], Cinitapride hydrogen tartrate, 4-amino-n-[1-(cyclohex-3-en-1-ylmethyl)piperidin-4-yl]-2-ethoxy-5-nitrobenzamide
Molecular Formula
C21H30N4O4
Molecular Weight
402.5  g/mol
InChI Key
ZDLBNXXKDMLZMF-UHFFFAOYSA-N
FDA UNII
R8I97I2L24

CAS 66564-14-5
Cinitapride is a gastroprokinetic agent and antiulcer benzamide with agonist activity at 5-HT1 and 5-HT4 receptors and antagonist activity at 5-HT2 receptors. It is marketed in Spain and Mexico.
1 2D Structure

CAS 66564-14-5

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-amino-N-[1-(cyclohex-3-en-1-ylmethyl)piperidin-4-yl]-2-ethoxy-5-nitrobenzamide
2.1.2 InChI
InChI=1S/C21H30N4O4/c1-2-29-20-13-18(22)19(25(27)28)12-17(20)21(26)23-16-8-10-24(11-9-16)14-15-6-4-3-5-7-15/h3-4,12-13,15-16H,2,5-11,14,22H2,1H3,(H,23,26)
2.1.3 InChI Key
ZDLBNXXKDMLZMF-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCOC1=CC(=C(C=C1C(=O)NC2CCN(CC2)CC3CCC=CC3)[N+](=O)[O-])N
2.2 Other Identifiers
2.2.1 UNII
R8I97I2L24
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 4-amino-n-(1-(3-cyclohexen-1-ylmethyl)-4-piperidyl)-2-ethoxy-5-nitrobenzamide

2. Blaston

3. Cidine

4. Cinitapride Tartrate

2.3.2 Depositor-Supplied Synonyms

1. 66564-14-5

2. Paxapride

3. Cidine

4. Cinitapride [inn]

5. Cinitapride Hydrogen Tartrate

6. 4-amino-n-[1-(cyclohex-3-en-1-ylmethyl)piperidin-4-yl]-2-ethoxy-5-nitrobenzamide

7. R8i97i2l24

8. 66564-14-5 (free Base)

9. Cinitapride (inn)

10. 4-amino-n-(1-(3-cyclohexen-1-ylmethyl)-4-piperidyl)-2-ethoxy-5-nitrobenzamide

11. Cinitaprida

12. Cinitapridum

13. Cinitapridum [inn-latin]

14. Cinitaprida [inn-spanish]

15. Cidin

16. Unii-r8i97i2l24

17. Paxapride (tn)

18. Cinitapride [mi]

19. 96623-56-2

20. Cinitapride [mart.]

21. (non-labelled)cinitapride-d5

22. Cinitapride [who-dd]

23. Schembl476454

24. Chembl2104523

25. Schembl19235643

26. Dtxsid60867232

27. Chebi:135642

28. Bcp04096

29. Hy-b2089

30. Akos015909742

31. Bcp9000531

32. Db08810

33. Bcp0726000107

34. Cs-0017505

35. Ft-0665049

36. D07700

37. Q5121012

2.3.3 Other Synonyms

1. Cas 66564-14-5

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 402.5 g/mol
Molecular Formula C21H30N4O4
XLogP33.6
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count6
Exact Mass g/mol
Monoisotopic Mass g/mol
Topological Polar Surface Area113
Heavy Atom Count29
Formal Charge0
Complexity586
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

It is indicated to treat gastrointestinal disorders associated with motility disturbances like gastroesophageal reflux disease (GERD), non-ulcer dyspepsia and delayed gastric emptying.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anti-Ulcer Agents

Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief. (See all compounds classified as Anti-Ulcer Agents.)


5.2 ATC Code

A - Alimentary tract and metabolism

A03 - Drugs for functional gastrointestinal disorders

A03F - Propulsives

A03FA - Propulsives

A03FA08 - Cinitapride


5.3 Absorption, Distribution and Excretion

Absorption

The absorption of cinitapride (12mg) following oral administration was rapid, with peak levels being achieved 2 h after dosing; absorption following intramuscular administration (4mg) was even more rapid, with peak levels (50% more that oral levels) being achieved 1 h after dosing.


5.4 Biological Half-Life

3-5 h during the first 8 h and a residual half-life greater than 15 h thereafter.


5.5 Mechanism of Action

Cinitapride is a substituted benzamide with 5-HT receptor antagonist and agonist activity.


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