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Itopride

HCID 3792
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
122898-67-3
Standard SMILES
COc1ccc(C(=O)NCc2ccc(OCCN(C)C)cc2)cc1OC
InChIKey
QQQIECGTIMUVDS-UHFFFAOYSA-N
Molecular formula
C20H26N2O4
Average molar mass
358.4 g/mol
Monoisotopic mass
358.18925731

Overview

N-[[4-[2-(dimethylamino)ethoxy]phenyl]methyl]-3,4-dimethoxybenzamide is a member of benzamides.

Names & identifiers

Preferred name
Itopride
IUPAC
N-[[4-[2-(dimethylamino)ethoxy]phenyl]methyl]-3,4-dimethoxybenzamide
English name
Itopride
Molecular formula
C20H26N2O4
Molecular weight
358.43

Names & synonyms

Itopride122898-67-3ItaxitopridaN-({4-[2-(dimethylamino)ethoxy]phenyl}methyl)-3,4-dimethoxybenzamide81BMQ80QRLN-[[4-[2-(dimethylamino)ethoxy]phenyl]methyl]-3,4-dimethoxybenzamideNSC-759643DTXSID7048320N-(p-(2-(Dimethylamino)ethoxy)benzyl)veratramideN-(p-(2-(dimethylamino)ethoxy)benzyl)veratramide hydrochlorideitopridum
Show more names
EtoprideItopride BaseItopride USP/EP/BPN-(4-(2-(Dimethylamino)Itopride Powder USP StandardITOPRIDE HYDROCHLORIDE 98-102%N-[[4-(2-dimethylaminoethoxy)phenyl]methyl]-33,4-Dimethoxy-N-[4-[2-(dimethylamino)ethoxy]benzyl]benzamide
N-((4-(2-(dimethylamino)ethoxy)phenyl)methyl)-3,4-dimethoxybenzamideRefChem:150204DTXCID5028295N-(4-(2-(Dimethylamino)ethoxy)benzyl)-3,4-dimethoxybenzamideItopride [INN]Itopride (INN)n-{4-[2-(dimethylamino)ethoxy]benzyl}-3,4-dimethoxybenzamideItopride free base

Database identifiers

Properties

Computed structural properties

XLogP
2.3
Topological polar surface area
60 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
5
Rotatable bonds
9
Heavy atoms
26
Formal charge
0
Complexity
411

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
Endocrine DisruptorsPotential endocrine disrupting compound

Physicochemical properties

Melting point
111 · 111-112°
Boiling point
510.1 · 510.1±50.0 °C(Predicted)
Density
1.122 · 1.122±0.06 g/cm3(Predicted)
storage temp.
2 · 2-8°C
pka
13.98 · 13.98±0.46(Predicted)
CAS DataBase Reference
122898 · 122898-67-3(CAS DataBase Reference)
FDA UNII
81 BMQ80QRL · 81BMQ80QRL
ATC code
3 FA07 · A03FA07
Symbol(GHS)
9 · GHS09
Signal word
Warning
Hazard statements
400 · H400

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

P273, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAquatic Acute 1 (100%)

Toxicology

Drug Induced Liver Injury · 4 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Itopride

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

Safety data

Signal word
Warning
Symbol(GHS)
GHS09
Hazard statements
H400
Precautionary statements
P273-P391-P501

Chemistry & industry

Pharmacology

ATC Code · 2 items

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

Mechanism of Action · 1 item

Itopride has anticholinesterase (AchE) activity as well as dopamine D2 receptor antagonistic activity. It is well established that M3 receptors exist on the smooth muscle layer throughout the gut and acetylcholine (ACh) released from enteric nerve endings stimulates the contraction of smooth muscle through M3 receptors. The enzyme AChE hydrolyses the released ACh, inactivates it and thus inhibits the gastric motility leading to various digestive disorders. Besides ACh, dopamine is present in significant amounts in the gastrointestinal tract and has several inhibitory effects on gastrointestinal motility, including reduction of lower esophageal sphincter and intragastric pressure. These effects appear to result from suppression of ACh release from the myenteric motor neurons and are mediated by the D2 subtype of dopamine receptors. Itopride, by virtue of its dopamine D2 receptor antagonism, removes the inhibitory effects on Ach release. It also inhibits the enzyme AchE which prevents the degradation of ACh. The net effect is an increase in ACh concentration, which in turn, promotes gastric motility, increases the lower esophageal sphincter pressure, accelerates gastric emptying and improves gastro-duodenal coordination. This dual mode of action of Itopride is unique and different from the actions of other prokinetic agents available in the market.

Metabolism/MetabolitesFlavin-containing monooxygenase (FMO) is involved in N-oxygenation, the major metabolic pathway of itopride (PMID: 10997945).

Applications

Usesdyspepsia therapy

Upstream & downstream products

Upstream raw materials

4-[2-(DIMETHYLAMINO)ETHOXY]BENZYLAMINE3,4-DIMETHOXYBENZOYL CHLORIDE

Related reactions

2 records
New reaction record
HRID 703528 reaction equation
HRID 703528As productuspto-grants-1991_01
HRID 1231930 reaction equation
HRID 1231930As productTraining data from https://doi.org/10.1039/C8SC04228D (5/10)

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
CAS
122898-67-3
PubChem CID
3792
DTXSID
DTXSID7048320
ChEMBL
CHEMBL2107457
ChEBI
CHEBI:94809
UNII
81BMQ80QRL
EC Number
694-655-5
Nikkaji
J354.055C
Precautionary statements
273 · P273-P391-P501
Diisopropyl ether
Sodium hydroxide

Suppliers70 total

武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
合肥曼奇诺生物医药技术有限公司19719236623 · [email protected]
HubeiwidelychemicaltechnologyCo.,Ltd18627774460 · [email protected]
普善实业(陕西)有限公司029-81310890 18165209495 · [email protected]
Sinoway Industrial co., ltd.+86-0592-5800732 +86-13806035118 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
欧利希(湖北)医药科技有限公司17316404525 17316404525 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海沛灵生物科技有限公司13127581762 13127581762 · [email protected]
上海瀚香生物科技有限公司177-54423994 17754423994 · [email protected]
NANJING YINGWEN BIOTECHNOLOGY CO LTD+8613382787392 · [email protected]
河北茹麒科技有限公司176-03256889 17603256889 · [email protected]
BOC Sciences1-631-485-4226; 16314854226 · [email protected]
玺标(上海)科技有限公司18512111473 18512111473 · [email protected]
上海乔木化学科技有限公司021-60451683 15021268886 · [email protected]
上海遐瑞医药科技有限公司+86 21 61551611
苏州亚科科技股份有限公司0512-87182055 13451648594 · [email protected]
上海陶素生化科技有限公司021-33632979 · [email protected]
PT CHEM GROUP LIMITED+86-85511178; +86-85511178 · [email protected]
上海御略医药科技有限公司021-60345187 13671753212 · [email protected]
上海孚一生物科技有限公司+86 (21) 61124340
Xiamen Eagle Chemical Limited Corporation+86-18900207489 · [email protected]
LUYUNJIA CHEMISTRY XIAMEN LIMITED+86-592-5360779 +86-13055435203
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
西安美川生物科技有限公司029-89275612 +8618991951683 · [email protected]
湖北魏氏化学试剂股份有限公司13125137732 18686406941 · [email protected]
武汉多普乐生物医药有限公司+86-02787215551 19945035818 · [email protected]
陕西缔都医药化工有限公司+86-29-81139210 +86-17392587031 · [email protected]
上海炎泽化工有限公司15345144255 19901447308 · [email protected]
深圳市森迪生物科技有限公司18126413629 0755-23311925 2355327053 · [email protected]
湖北威德利化学科技有限公司027-83991130 18627774460 · [email protected]
深圳市森迪生物科技有限公司18124570582 TEL:0755-23574479 2355327139 · [email protected]
武汉曙欧科技有限公司17792809151;18872220797 · [email protected]
威尔曼医药集团有限公司15807197853 18971451745 · [email protected]
airuikechemical co., ltd.+86-18353166132 · [email protected]
杭州洁汉化工有限公司+86-571-86217390; +8618058761490 · [email protected]
Capot Chemical Co.,Ltd.+86-(0)57185586718 +86-13336195806 · [email protected]
深圳市森迪生物科技有限公司0755-23311925 18102838259 · [email protected]
江苏艾康生物医药研发有限公司025-58859352 15955137747 · [email protected]
佛山道麒生物科技有限公司18062666947 · [email protected]
厦门盈融达化工有限公司+86-0592-6210733 · [email protected]
career henan chemical co+86-0371-86658258 · [email protected]
湖北康鑫源顺医药化工有限公司027-51831887 15337167856 · [email protected]
南京克罗托鲁宁医药科技有限公司13382066392
郑州艾克姆化工有限公司0371-63315541 13323832564 · [email protected]
陕西缔都医药化工有限公司029-88380327 17691182729 · [email protected]
台州市创源工业技术有限公司0576-85289468; 13757609826 · [email protected]
浙江泽天精细化工有限公司0571-87682782 18957127338 · [email protected]
海蔚化学86-21-51086038 · [email protected]
湖北摩科化学有限公司18627753421; 18627756402 · [email protected]

Additional notes

DefinitionChEBI: N-[[4-[2-(dimethylamino)ethoxy]phenyl]methyl]-3,4-dimethoxybenzamide is a member of benzamides.