DrugBank: Cinitapride (DB08810)

targets (3)

Identification

Name

Cinitapride

Accession Number

DB08810

Type

small molecule

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.

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Not Available

Salts

Not Available

Brand names

Name	Company
Blaston
Cidine
Cinmove
Cintapro
Paxapride
Pemix

Brand mixtures

Not Available

Categories

Antiemetics

CAS number

66564-14-5

Weight

Average: 402.4873
Monoisotopic: 402.226705468

Chemical Formula

C₂₁H₃₀N₄O₄

InChI Key

InChIKey=ZDLBNXXKDMLZMF-UHFFFAOYSA-N

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)

Plain Text

IUPAC Name

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

SMILES

CCOC1=CC(N)=C(C=C1C(=O)NC1CCN(CC2CCC=CC2)CC1)[N+]([O-])=O

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Not Available

Classes

Not Available

Substructures

Not Available

Pharmacology

Indication

For the treatment of gastrointestinal disorders associated with motility disturbances such as gastroesophageal reflux disease, non-ulcer dyspepsia and delayed gastric emptying.

Pharmacodynamics

Not Available

Mechanism of action

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

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.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half life

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

Clearance

Not Available

Toxicity

The symptoms of overdose include drowsiness, confusion and extrapyramidal effects.

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Form	Route	Strength
Tablet	Oral	1mg

Prices

Not Available

Patents

Not Available

Properties

State

solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
water solubility	1.41e-02 g/l	ALOGPS
logP	3.7	ALOGPS
logP	2.79	ChemAxon
logS	-4.5	ALOGPS
pKa (strongest acidic)	13.89	ChemAxon
pKa (strongest basic)	9.74	ChemAxon
physiological charge	1	ChemAxon
hydrogen acceptor count	6	ChemAxon
hydrogen donor count	2	ChemAxon
polar surface area	113.41	ChemAxon
rotatable bond count	7	ChemAxon
refractivity	115.58	ChemAxon
polarizability	44.29	ChemAxon

References

Synthesis Reference

Not Available

General Reference

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

Resource	Link
KEGG Drug	D07700
PharmGKB	PA165958427
Wikipedia	http://en.wikipedia.org/wiki/Cinitapride

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Drug	Interaction
Atropine	Anticholinergic agents like atropine may reduce the action of cinitapride.
Digoxin	Cinitapride can alter the absorption of digoxin as it simulates gastric emptying.
Digoxin Immune Fab	Cinitapride can alter the absorption of digoxin as it simulates gastric emptying.
Methylscopolamine	Anticholinergic agents like methylscopolamine may reduce the action of cinitapride.
Scopolamine	Anticholinergic agents like scopolamine may reduce the action of cinitapride.

Food Interactions

Not Available

Targets
1. 5-hydroxytryptamine 1A receptor Pharmacological action: yes Actions: agonist This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity Organism class: human UniProt ID: P08908 Gene: HTR1A Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report 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, La Casa C, Martin MJ, Motilva V: Effects of cinitapride on gastric ulceration and secretion in rats. Inflamm Res. 1998 Mar;47(3):131-6. Pubmed 2. 5-hydroxytryptamine 2A receptor Pharmacological action: yes Actions: antagonist This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production Organism class: human UniProt ID: P28223 Gene: HTR2A Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report 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, La Casa C, Martin MJ, Motilva V: Effects of cinitapride on gastric ulceration and secretion in rats. Inflamm Res. 1998 Mar;47(3):131-6. Pubmed 3. 5-hydroxytryptamine 4 receptor Pharmacological action: unknown Actions: agonist This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that stimulate adenylate cyclase Organism class: human UniProt ID: Q13639 Gene: HTR4 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report 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, La Casa C, Martin MJ, Motilva V: Effects of cinitapride on gastric ulceration and secretion in rats. Inflamm Res. 1998 Mar;47(3):131-6. Pubmed

Targets

1. 5-hydroxytryptamine 1A receptor

Pharmacological action: yes
Actions: agonist

This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity

Organism class: human
UniProt ID: P08908 Link_out

Gene: HTR1A Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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, La Casa C, Martin MJ, Motilva V: Effects of cinitapride on gastric ulceration and secretion in rats. Inflamm Res. 1998 Mar;47(3):131-6. Pubmed

2. 5-hydroxytryptamine 2A receptor

Pharmacological action: yes
Actions: antagonist

This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production

Organism class: human
UniProt ID: P28223 Link_out

Gene: HTR2A Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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, La Casa C, Martin MJ, Motilva V: Effects of cinitapride on gastric ulceration and secretion in rats. Inflamm Res. 1998 Mar;47(3):131-6. Pubmed

3. 5-hydroxytryptamine 4 receptor

Pharmacological action: unknown
Actions: agonist

Organism class: human
UniProt ID: Q13639 Link_out

Gene: HTR4 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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, La Casa C, Martin MJ, Motilva V: Effects of cinitapride on gastric ulceration and secretion in rats. Inflamm Res. 1998 Mar;47(3):131-6. Pubmed

Comments

Drug created on January 19, 2011 16:47 / Updated on February 08, 2013 16:27