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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H41ClN4O5
Molecular Weight 537.091
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NARONAPRIDE

SMILES

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=VGDDOIZXGFJDRC-VJTSUQJLSA-N
InChI=1S/C27H41ClN4O5/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)/t22-,24+,25+/m1/s1

HIDE SMILES / InChI

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: cardiovascular safety profile of 5-HT(4) agonists developed for gastrointestinal disorders.
2012 Apr
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 Sat Dec 16 17:13:52 GMT 2023
Edited
by admin
on Sat Dec 16 17:13:52 GMT 2023
Record UNII
058896B00B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NARONAPRIDE
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
ATI-7505
Code English
ATI7505
Code English
NARONAPRIDE [USAN]
Common Name 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
Systematic Name English
1-PIPERIDINEHEXANOIC ACID, 4-((4-AMINO-5-CHLORO-2-METHOXYBENZOYL)AMINO)-3-METHOXY-, 1-AZABICYCLO(2.2.2)OCT-3-YL ESTER, (3S,4R)-
Common Name English
naronapride [INN]
Common Name English
Naronapride [WHO-DD]
Common Name English
Code System Code Type Description
NCI_THESAURUS
C175157
Created by admin on Sat Dec 16 17:13:54 GMT 2023 , Edited by admin on Sat Dec 16 17:13:54 GMT 2023
PRIMARY
ChEMBL
CHEMBL2103858
Created by admin on Sat Dec 16 17:13:54 GMT 2023 , Edited by admin on Sat Dec 16 17:13:54 GMT 2023
PRIMARY
PUBCHEM
11237985
Created by admin on Sat Dec 16 17:13:54 GMT 2023 , Edited by admin on Sat Dec 16 17:13:54 GMT 2023
PRIMARY
DRUG BANK
DB05542
Created by admin on Sat Dec 16 17:13:54 GMT 2023 , Edited by admin on Sat Dec 16 17:13:54 GMT 2023
PRIMARY
CAS
860174-12-5
Created by admin on Sat Dec 16 17:13:54 GMT 2023 , Edited by admin on Sat Dec 16 17:13:54 GMT 2023
PRIMARY
FDA UNII
058896B00B
Created by admin on Sat Dec 16 17:13:54 GMT 2023 , Edited by admin on Sat Dec 16 17:13:54 GMT 2023
PRIMARY
EVMPD
SUB129585
Created by admin on Sat Dec 16 17:13:54 GMT 2023 , Edited by admin on Sat Dec 16 17:13:54 GMT 2023
PRIMARY
INN
9346
Created by admin on Sat Dec 16 17:13:54 GMT 2023 , Edited by admin on Sat Dec 16 17:13:54 GMT 2023
PRIMARY
SMS_ID
100000155491
Created by admin on Sat Dec 16 17:13:54 GMT 2023 , Edited by admin on Sat Dec 16 17:13:54 GMT 2023
PRIMARY
EPA CompTox
DTXSID401006590
Created by admin on Sat Dec 16 17:13:54 GMT 2023 , Edited by admin on Sat Dec 16 17:13:54 GMT 2023
PRIMARY
USAN
WW-117
Created by admin on Sat Dec 16 17:13:54 GMT 2023 , Edited by admin on Sat Dec 16 17:13:54 GMT 2023
PRIMARY
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