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

• ChemBase ID: 6410
• Molecular Formular: C21H30N4O4
• Molecular Mass: 402.4873
• Monoisotopic Mass: 402.22670546
• SMILES: O=C(NC1CCN(CC2CCC=CC2)CC1)c1c(OCC)cc(N)c([N+](=O)[O-])c1
• Canonical SMILES: CCOc1cc(N)c(cc1C(=O)NC1CCN(CC1)CC1CCC=CC1)[N+](=O)[O-]
• 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)
• InChIKey: ZDLBNXXKDMLZMF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-N-[1-(cyclohex-3-en-1-ylmethyl)piperidin-4-yl]-2-ethoxy-5-nitrobenzamide
• IUPAC Traditional name: cinitapride; 4-amino-N-[1-(cyclohex-3-en-1-ylmethyl)piperidin-4-yl]-2-ethoxy-5-nitrobenzamide
• Brand Name: Cintapro; Cidine; Blaston; Pemix; Paxapride; Cinmove
• Synonyms: Cinitapride; 4-Amino-N-[1-(3-cyclohexen-1-ylmethyl)-4-piperidinyl]-2-ethoxy-5-nitrobenzamide

Database IDs

• CAS Number: 66564-14-5
• PubChem SID: 160969717
• PubChem CID: 68867
• Chemspider ID: 62099
• DrugBank ID: DB08810
• KEGG ID: D07700
• Unique Ingredient Identifier: R8I97I2L24
• Wikipedia Title: Cinitapride

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.891745
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.64240825
• LogD (pH = 7.4): 0.46945193
• Log P: 2.7869248
• Molar Refractivity: 115.5827 cm^3
• Polarizability: 42.47106 Å^3
• Polar Surface Area: 113.41 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.7
• LOG S: -4.45
• Solubility (Water): 1.41e-02 g/l

PROPERTIES

Pharmacology Properties

• Admin Routes: Oral
• Legal Status: Rx-only

DETAILS

DrugBank - DB08810

• Drug Groups: approved
• Description: Cinitapride is a gastroprokinetic agent and antiulcer agent of the benzamide class which is marketed in Spain and Mexico. It acts as an agonist of the 5-HT1 and 5-HT4 receptors and as an antagonist of the 5-HT2 receptors.
• Indication: For the treatment of gastrointestinal disorders associated with motility disturbances such as gastroesophageal reflux disease, non-ulcer dyspepsia and delayed gastric emptying.
• Toxicity: The symptoms of overdose include drowsiness, confusion and extrapyramidal effects.
• Affected Organisms: Humans and other mammals
• 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.
• Half Life: 3-5 h during the first 8 h and a residual half-life greater than 15 h thereafter.
• References: Alarcon-de-la-Lastra Romero C, Lopez A, Martin MJ, la Casa C, Motilva V: Cinitapride protects against ethanol-induced gastric mucosal injury in rats: role of 5-hydroxytryptamine, prostaglandins and sulfhydryl compounds. Pharmacology. 1997 Apr;54(4):193-202. [Pubmed]
• External Links: Wikipedia

Toronto Research Chemicals - C441990

A novel prokinetic benzamide-stimulating gastrointestinal motility agent and antiucer agent. It acts as an agonist of the 5-HT1 and 5-HT4 receptors and as an antagonist of the 5-HT2 receptors.

REFERENCES

• Alarcon-de-la-Lastra Romero C, Lopez A, Martin MJ, la Casa C, Motilva V: Cinitapride protects against ethanol-induced gastric mucosal injury in rats: role of 5-hydroxytryptamine, prostaglandins and sulfhydryl compounds. Pharmacology. 1997 Apr;54(4):193-202. Pubmed
• Alarcon de la Lastra, C. et al.: Pharmacol, 54, 193 (1997)
• Robert, M. et al.: Drug Metab. Disp., 35, 1149 (1997)
• Alarcon de la Lastra, C. et al.: Inflam. Res., 47, 131 (1997)