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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H41ClN4O5.2ClH
Molecular Weight 610.013
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NARONAPRIDE DIHYDROCHLORIDE

SMILES

Cl.Cl.CO[C@H]1CN(CCCCCC(=O)O[C@H]2CN3CCC2CC3)CC[C@H]1NC(=O)C4=C(OC)C=C(N)C(Cl)=C4

InChI

InChIKey=ZKVOMYDQQYOJKE-HTKGJVFSSA-N
InChI=1S/C27H41ClN4O5.2ClH/c1-35-23-15-21(29)20(28)14-19(23)27(34)30-22-9-13-31(17-25(22)36-2)10-5-3-4-6-26(33)37-24-16-32-11-7-18(24)8-12-32;;/h14-15,18,22,24-25H,3-13,16-17,29H2,1-2H3,(H,30,34);2*1H/t22-,24+,25+;;/m1../s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C27H41ClN4O5
Molecular Weight 537.091
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Naronapride (ATI-7505), an orally administered, cisapride analogue and serotonin4 (5HT4) receptor agonist, is being developed by Renexxion for the treatment of multiple gastrointestinal disorders. Sinovant is initially developing naronapride for the treatment of irritable bowel syndrome – constipation (IBS-C), a disease that affects millions of Chinese patients and for which few effective treatment options are available. Naronapride has been evaluated in over 900 subjects in multiple randomized controlled clinical studies and has demonstrated promising results in patients with gastroesophageal reflux disease (GERD), erosive esophagitis (EE), and chronic idiopathic constipation (CIC). Naronapride’s low systemic absorption and high specificity for 5HT4 and D2 receptors is thought to improve its safety and tolerability profile relative to other members of the class.

Approval Year

PubMed

PubMed

TitleDatePubMed
Metabolism and pharmacokinetics of naronapride (ATI-7505), a serotonin 5-HT(4) receptor agonist for gastrointestinal motility disorders.
2011 Jul
Systematic review with meta-analysis: highly selective 5-HT4 agonists (prucalopride, velusetrag or naronapride) in chronic constipation.
2014 Feb
Patents

Sample Use Guides

A randomized, parallel-group, double-blind, placebo-controlled study evaluated effects of 9-day treatment with Naronapride (3, 10 or 20 mg t.i.d.) on scintigraphic GI and colonic transit in healthy volunteers.
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Thu Jul 06 00:39:37 UTC 2023
Edited
by admin
on Thu Jul 06 00:39:37 UTC 2023
Record UNII
898PE2W8US
Record Status Validated (UNII)
Record Version
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Name Type Language
NARONAPRIDE DIHYDROCHLORIDE
USAN   WHO-DD  
USAN  
Official Name English
ATI-7505 DIHYDROCHLORIDE
Code English
ATI-7505 2HCL
Code English
(3R)-1-AZABICYCLO(2.2.2)OCT-3-YL 6-((3S,4R)-4-((4-AMINO-5-CHLORO-2- METHOXYBENZOYL)AMINO)-3-METHOXYPIPERIDIN-1-YL)HEXANOATE DIHYDROCHLORIDE
Systematic Name English
ATI-7505 BIS HCL
Code English
NARONAPRIDE DIHYDROCHLORIDE [USAN]
Common Name English
1-PIPERIDINEHEXANOIC ACID, 4-((4-AMINO-5-CHLORO-2-METHOXYBENZOYL)AMINO)-3-METHOXY-, (3R)-1-AZABICYCLO(2.2.2)OCT-3-YL ESTER, HYDROCHLORIDE (1:2), (3S,4R)-
Systematic Name English
Naronapride dihydrochloride [WHO-DD]
Common Name English
Code System Code Type Description
PUBCHEM
49843901
Created by admin on Thu Jul 06 00:39:37 UTC 2023 , Edited by admin on Thu Jul 06 00:39:37 UTC 2023
PRIMARY
FDA UNII
898PE2W8US
Created by admin on Thu Jul 06 00:39:37 UTC 2023 , Edited by admin on Thu Jul 06 00:39:37 UTC 2023
PRIMARY
USAN
WW-118
Created by admin on Thu Jul 06 00:39:37 UTC 2023 , Edited by admin on Thu Jul 06 00:39:37 UTC 2023
PRIMARY
ChEMBL
CHEMBL2103858
Created by admin on Thu Jul 06 00:39:37 UTC 2023 , Edited by admin on Thu Jul 06 00:39:37 UTC 2023
PRIMARY
SMS_ID
300000044482
Created by admin on Thu Jul 06 00:39:37 UTC 2023 , Edited by admin on Thu Jul 06 00:39:37 UTC 2023
PRIMARY
NCI_THESAURUS
C175158
Created by admin on Thu Jul 06 00:39:37 UTC 2023 , Edited by admin on Thu Jul 06 00:39:37 UTC 2023
PRIMARY
CAS
860169-57-9
Created by admin on Thu Jul 06 00:39:37 UTC 2023 , Edited by admin on Thu Jul 06 00:39:37 UTC 2023
PRIMARY
EPA CompTox
DTXSID60235356
Created by admin on Thu Jul 06 00:39:37 UTC 2023 , Edited by admin on Thu Jul 06 00:39:37 UTC 2023
PRIMARY
DRUG BANK
DBSALT002600
Created by admin on Thu Jul 06 00:39:37 UTC 2023 , Edited by admin on Thu Jul 06 00:39:37 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
PARENT -> SALT/SOLVATE
SOLVATE->ANHYDROUS
Related Record Type Details
ACTIVE MOIETY