NARONAPRIDE

U.S. Department of Health & Human Services Divider Arrow

National Institutes of Health Divider Arrow

NCATS

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

Structure Search

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

Description
Sources: https://adisinsight.springer.com/drugs/800019926 | https://roivant.com/

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.

Originator

Approval Year

PubMed

PubMed

Title	Date	PubMed

Patents

Patents

Sample Use Guides

In Vivo Use Guide

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

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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					N69ZMW833X

Naronapride dihydrochloride trihydrate

SALT/SOLVATE -> PARENT

Amount:

058896B00B

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Interaction Type:

MAJOR

Qualification:

FECAL

Amount:


					898PE2W8US

NARONAPRIDE DIHYDROCHLORIDE

SALT/SOLVATE -> PARENT

Amount:


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Interaction Type:

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Amount:


					7H1P16DG5J

5-HYDROXYTRYPTAMINE RECEPTOR 4

TARGET -> AGONIST

Amount:


					19GBD6T9L7

D(2) DOPAMINE RECEPTOR

TARGET -> INHIBITOR

Amount:

058896B00B

EXCRETED UNCHANGED

Interaction Type:

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Qualification:

URINE

Amount:

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					PCZ4T836HV

ATI-7400

METABOLITE -> PARENT

Qualification:

URINE

Amount:


					YW3X9WSN6K

1-PIPERIDINEACETIC ACID, 4-((4-AMINO-5-CHLORO-2-METHOXYBENZOYL)AMINO)-3-METHOXY-, (3S,4R)-

METABOLITE -> PARENT

Qualification:

URINE

Amount:


					4NFH4K764S

(3S,4R)-4-((4-AMINO-5-CHLORO-2-METHOXYBENZOYL)AMINO)-3-METHOXY-1-PIPERIDINEHEXANOIC ACID

METABOLITE -> PARENT

Interaction Type:

MINOR

Qualification:

URINE

Amount:


					YW3X9WSN6K

1-PIPERIDINEACETIC ACID, 4-((4-AMINO-5-CHLORO-2-METHOXYBENZOYL)AMINO)-3-METHOXY-, (3S,4R)-

METABOLITE -> PARENT

Qualification:

PLASMA

Amount:


					4NFH4K764S

(3S,4R)-4-((4-AMINO-5-CHLORO-2-METHOXYBENZOYL)AMINO)-3-METHOXY-1-PIPERIDINEHEXANOIC ACID

METABOLITE -> PARENT

Qualification:

PLASMA

Amount:


					PCZ4T836HV

ATI-7400

METABOLITE -> PARENT

Qualification:

PLASMA

Amount:


					OP5227X5ZU

(2S,3S,4S,5R,6R)-6-(2-CHLORO-4-(((3S,4R)-1-(6-HYDROXY-6-OXO-HEXYL)-3-METHOXY-4-PIPERIDYL)CARBAMOYL)-5-METHOXY-ANILINO)-3,4,5-TRIHYDROXY-TETRAHYDROPYRAN-2-CARBOXYLIC ACID

METABOLITE -> PARENT

Qualification:

FECAL; PLASMA; URINE

Amount:


					LEU25W9UQP

(2S,3S,4S,5R,6R)-6-(2-CHLORO-5-METHOXY-4-(((3S,4R)-3-METHOXY-1-(6-OXO-6-((3R)-QUINUCLIDIN-3-YL)OXY-HEXYL)-4-PIPERIDYL)CARBAMOYL)ANILINO)-3,4,5-TRIHYDROXY-TETRAHYDROPYRAN-2-CARBOXYLIC ACID

METABOLITE -> PARENT

Amount:


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ATI-7400

METABOLITE -> PARENT

Qualification:

FECAL

Amount:


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NORCISAPRIDE, (+)-

METABOLITE -> PARENT

Qualification:

FECAL; PLASMA; URINE

Amount:


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(3S,4R)-4-((4-AMINO-5-CHLORO-2-METHOXYBENZOYL)AMINO)-3-METHOXY-1-PIPERIDINEHEXANOIC ACID

METABOLITE -> PARENT

Interaction Type:

MAJOR

Qualification:

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Amount:


					N8KGY3AU55

6-OXO-6-((3R)-QUINUCLIDIN-3-YL)OXY-HEXANOIC ACID

METABOLITE -> PARENT

Amount:


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3-QUINUCLIDINOL, (-)-

METABOLITE -> PARENT

Qualification:

FECAL; PLASMA; URINE

Amount:


					YW3X9WSN6K

1-PIPERIDINEACETIC ACID, 4-((4-AMINO-5-CHLORO-2-METHOXYBENZOYL)AMINO)-3-METHOXY-, (3S,4R)-

METABOLITE -> PARENT

Qualification:

FECAL

Amount:

Related Record Type Details

058896B00B

ACTIVE MOIETY

Amount:

Name	Property Type	Amount	Referenced Substance	Defining	Parameters	References
Biological Half-life	PHARMACOKINETIC

Tmax	PHARMACOKINETIC