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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H41ClN4O5.2ClH.3H2O
Molecular Weight 664.059
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Naronapride dihydrochloride trihydrate

SMILES

O.O.O.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=BLYKZEFLIVFJIG-HYDSBGGBSA-N
InChI=1S/C27H41ClN4O5.2ClH.3H2O/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;3*1H2/t22-,24+,25+;;;;;/m1...../s1

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 Fri Jul 07 00:39:46 UTC 2023
Edited
by admin
on Fri Jul 07 00:39:46 UTC 2023
Record UNII
N69ZMW833X
Record Status Validated (UNII)
Record Version
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Name Type Language
Naronapride dihydrochloride trihydrate
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, hydrate (1:2:3), (3S,4R)-
Systematic Name English
(3S,4R)-6-[4-(4-Amino-5-chloro-2-methoxybenzoylamino)-3-methoxypiperidin-1-yl]hexanoic acid (3R)-1-azabicyclo[2.2.2]oct-3-yl ester dihydrochloride trihydrate
Systematic Name English
ATI-7505 dihydrochloride, trihydrate
Common Name English
Code System Code Type Description
PUBCHEM
166451425
Created by admin on Fri Jul 07 00:39:46 UTC 2023 , Edited by admin on Fri Jul 07 00:39:46 UTC 2023
PRIMARY
CAS
2411560-43-3
Created by admin on Fri Jul 07 00:39:46 UTC 2023 , Edited by admin on Fri Jul 07 00:39:46 UTC 2023
PRIMARY
FDA UNII
N69ZMW833X
Created by admin on Fri Jul 07 00:39:46 UTC 2023 , Edited by admin on Fri Jul 07 00:39:46 UTC 2023
PRIMARY
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PARENT -> SALT/SOLVATE
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY