Cinitapride
Basic information
- CAS
66564-14-5- Standard SMILES
CCOc1cc(N)c([N+](=O)[O-])cc1C(=O)NC1CCN(CC2CC=CCC2)CC1- InChIKey
ZDLBNXXKDMLZMF-UHFFFAOYSA-N- Molecular formula
- C21H30N4O4
- Average molar mass
- 402.5 g/mol
- Monoisotopic mass
- 402.22670545
Overview
Cinitapride is an aromatic ether and a C-nitro compound.
Names & identifiers
- Preferred name
- Cinitapride
- IUPAC
- 4-amino-N-[1-(cyclohex-3-en-1-ylmethyl)piperidin-4-yl]-2-ethoxy-5-nitrobenzamide
- English name
- Cinitapride hydrogen tartrate
- Molecular formula
- C21H30N4O4
- Molecular weight
- 402.49
Names & synonyms
Cinitapride66564-14-5PaxaprideCinitapridaCinitapridum4-amino-N-[1-(cyclohex-3-en-1-ylmethyl)piperidin-4-yl]-2-ethoxy-5-nitrobenzamideR8I97I2L24DTXSID608672324-Amino-N-(1-(3-cyclohexen-1-ylmethyl)-4-piperidyl)-2-ethoxy-5-nitrobenzamide4-amino-N-(1-(cyclohex-3-en-1-ylmethyl)piperidin-4-yl)-2-ethoxy-5-nitrobenzamideRefChem:126231A03FA08
Show more names
CidineCinmoveRMA-862CintaproLAS-17177D5-CinitaprideCinitaprideTartrateCinitapride, 10 mM in DMSOCinitaprideTartrate IMurity
DTXCID40815433Benzamide, 4-amino-N-(1-(3-cyclohexen-1-ylmethyl)-4-piperidinyl)-2-ethoxy-5-nitro-Cinitapride [INN]BlastonCinitapride (INN)Cinitapridum [INN-Latin]Cinitaprida [INN-Spanish]cidin
Database identifiers
- CAS
66564-14-5- PubChem CID
- 68867
- DTXSID
DTXSID60867232- ChEMBL
CHEMBL2104523- ChEBI
CHEBI:135642- UNII
- R8I97I2L24
- Nikkaji
- J18.746A
Properties
Computed structural properties
- XLogP
- 3.6
- Topological polar surface area
- 113 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 6
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 586
Experimental & physicochemical properties
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 197 °C · >197°C (dec.)
- Boiling point
- 579.8 · 579.8±50.0 °C(Predicted)
- Density
- 1.24 · 1.24
- storage temp.
- Refrigerator
- solubility
- DMSO (Slightly), Methanol (Slightly), Water (Slightly)
- pka
- 12.62 · 12.62±0.20(Predicted)
- form
- Solid
- color
- Yellow
- FDA UNII
- 8 I97I2L24 · R8I97I2L24
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
CINITAPRIDE
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Chemistry & industry
Pharmacology
ATC Code
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
Mechanism of ActionCinitapride is a substituted benzamide with 5-HT receptor antagonist and agonist activity.
Biological Half-Life3-5 h during the first 8 h and a residual half-life greater than 15 h thereafter.
MeSH Pharmacological Classification
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.
Absorption, Distribution and Excretion
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.
Cellular LocationsMembrane
Applications
DescriptionCinitapride is a substituted benzamide dopamine receptor antagonist effective in the treatment of gastroesophageal reflux and a variety of gastrointestinal motility disorders. It generates strong procholinergic activity in the gastrointestinal tract by elevating the serotonergic transmission in the mysenteric plexus.
UsesA 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 (1,2,3).
Usesserotonin-norepinephrine reuptake inhibitor, antidepressant
Related reactions
0 records
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Compound notes
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