INDISETRON

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H23N5O
Molecular Weight	313.3974
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1C[C@@H]2C[C@@H](C[C@H](C1)N2C)NC(=O)C3=NNC4=C3C=CC=C4

InChI

InChIKey=MHNNVDILNTUWNS-UHFFFAOYSA-N

InChI=1S/C17H23N5O/c1-21-9-12-7-11(8-13(10-21)22(12)2)18-17(23)16-14-5-3-4-6-15(14)19-20-16/h3-6,11-13H,7-10H2,1-2H3,(H,18,23)(H,19,20)

HIDE SMILES / InChI

Molecular Formula	C17H23N5O
Molecular Weight	313.3974
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	2 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.pharmacodia.com/yaodu/html/v1/chemicals/e94550c93cd70fe748e6982b3439ad3b.html
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/18633256 http://www.lifescience.co.jp/yk/yk04/nov/ab5.htm

Indisetron dihydrochloride (N-3389) was approved by Pharmaceuticals and Medical Devices Agency of Japan (PMDA) on January 29, 2004. It was co-developed and co-marketed as Sinseron by Kyorin & Yakult Honsha in Japan. Indisetron is a dual serotonin 5-HT3 and 5-HT4 receptor antagonist. It is indicated for the treatment of prophylaxis of chemotherapy-induced nausea and vomiting, it’s administered once daily. Indisetron is metabolized in the liver, and CYP1A1, CYP2C9, CYP2D6, and CYP3A4 are involved in its metabolism. However, indisetron is unlikely to cause drug interactions at clinical doses because the effective plasma concentrations are lower than those necessary for inhibiting the metabolic enzymes. No drug interaction has been reported. Indisetron antagonizes 5-HT4 receptors, as well as 5-HT3 receptors, and this characteristic is expected to contribute to its clinical efficacy.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 3 (5-HT3) receptor 59 Target ID: CHEMBL2111332 Sources: http://www.ncbi.nlm.nih.gov/pubmed/7698198	Antagonist 2849		8.77 null [pKi]
Serotonin 4 (5-HT4) receptor 38 Target ID: CHEMBL1875 Sources: http://www.ncbi.nlm.nih.gov/pubmed/7698198	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Nausea 63 Sources: http://www.pharmacodia.com/yaodu/html/v1/chemicals/e94550c93cd70fe748e6982b3439ad3b.html	Preventing		Approved 8583	Sinseron Approved Use Unknown Launch Date 2004
Vomiting 38 Sources: http://www.pharmacodia.com/yaodu/html/v1/chemicals/e94550c93cd70fe748e6982b3439ad3b.html	Preventing		Approved 8583	Sinseron Approved Use Unknown Launch Date 2004

C_max

Value	Dose	Analyte	Population
34.7 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2004/P200400003/53011600_21600AMZ00038_X100_1.pdf#page=17	4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered:	INDISETRON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
59 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2004/P200400003/53011600_21600AMZ00038_X100_1.pdf#page=17	8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered:	INDISETRON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
164.59 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2004/P200400003/53011600_21600AMZ00038_X100_1.pdf#page=17	16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered:	INDISETRON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
339.1 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2004/P200400003/53011600_21600AMZ00038_X100_1.pdf#page=17	32 mg single, oral dose: 32 mg route of administration: Oral experiment type: SINGLE co-administered:	INDISETRON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
128.5 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2004/P200400003/53011600_21600AMZ00038_X100_1.pdf#page=18	16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered:	INDISETRON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
185.6 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2004/P200400003/53011600_21600AMZ00038_X101_1.pdf#page=2	16 mg 2 times / day multiple, oral dose: 16 mg route of administration: Oral experiment type: MULTIPLE co-administered:	INDISETRON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
200.6 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2004/P200400003/53011600_21600AMZ00038_X101_1.pdf#page=2	16 mg 2 times / day multiple, oral dose: 16 mg route of administration: Oral experiment type: MULTIPLE co-administered:	INDISETRON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
277.3 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2004/P200400003/53011600_21600AMZ00038_X100_1.pdf#page=17	4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered:	INDISETRON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
438.4 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2004/P200400003/53011600_21600AMZ00038_X100_1.pdf#page=17	8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered:	INDISETRON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1208.34 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2004/P200400003/53011600_21600AMZ00038_X100_1.pdf#page=17	16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered:	INDISETRON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2488.7 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2004/P200400003/53011600_21600AMZ00038_X100_1.pdf#page=17	32 mg single, oral dose: 32 mg route of administration: Oral experiment type: SINGLE co-administered:	INDISETRON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1103.6 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2004/P200400003/53011600_21600AMZ00038_X100_1.pdf#page=18	16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered:	INDISETRON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
1229.7 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2004/P200400003/53011600_21600AMZ00038_X101_1.pdf#page=2	16 mg 2 times / day multiple, oral dose: 16 mg route of administration: Oral experiment type: MULTIPLE co-administered:	INDISETRON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1664.3 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2004/P200400003/53011600_21600AMZ00038_X101_1.pdf#page=2	16 mg 2 times / day multiple, oral dose: 16 mg route of administration: Oral experiment type: MULTIPLE co-administered:	INDISETRON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
5.93 h OTHER GOV'T https://www.pmda.go.jp/drugs/2004/P200400003/53011600_21600AMZ00038_X100_1.pdf#page=17	4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered:	INDISETRON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
4.4 h OTHER GOV'T https://www.pmda.go.jp/drugs/2004/P200400003/53011600_21600AMZ00038_X100_1.pdf#page=17	8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered:	INDISETRON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
6.25 h OTHER GOV'T https://www.pmda.go.jp/drugs/2004/P200400003/53011600_21600AMZ00038_X100_1.pdf#page=17	16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered:	INDISETRON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
6.09 h OTHER GOV'T https://www.pmda.go.jp/drugs/2004/P200400003/53011600_21600AMZ00038_X100_1.pdf#page=17	32 mg single, oral dose: 32 mg route of administration: Oral experiment type: SINGLE co-administered:	INDISETRON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
6.04 h OTHER GOV'T https://www.pmda.go.jp/drugs/2004/P200400003/53011600_21600AMZ00038_X100_1.pdf#page=18	16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered:	INDISETRON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
5.1 h OTHER GOV'T https://www.pmda.go.jp/drugs/2004/P200400003/53011600_21600AMZ00038_X101_1.pdf#page=2	16 mg 2 times / day multiple, oral dose: 16 mg route of administration: Oral experiment type: MULTIPLE co-administered:	INDISETRON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
6.71 h OTHER GOV'T https://www.pmda.go.jp/drugs/2004/P200400003/53011600_21600AMZ00038_X101_1.pdf#page=2	16 mg 2 times / day multiple, oral dose: 16 mg route of administration: Oral experiment type: MULTIPLE co-administered:	INDISETRON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
21.5% OTHER GOV'T https://www.pmda.go.jp/drugs/2004/P200400003/53011600_21600AMZ00038_X101_1.pdf#page=3	16 mg 2 times / day multiple, oral dose: 16 mg route of administration: Oral experiment type: MULTIPLE co-administered:		INDISETRON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
23.5% OTHER GOV'T https://www.pmda.go.jp/drugs/2004/P200400003/53011600_21600AMZ00038_X101_1.pdf#page=3	16 mg 2 times / day multiple, oral dose: 16 mg route of administration: Oral experiment type: MULTIPLE co-administered:		INDISETRON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
8 mg 1 times / day multiple, oral Recommended Dose: 8 mg, 1 times / day Route: oral Route: multiple Dose: 8 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/23364217/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/23364217/	Other AEs: Constipation... Other AEs: Constipation (grade 1, 4.8%) Sources: https://pubmed.ncbi.nlm.nih.gov/23364217/
8 mg single, oral Recommended Dose: 8 mg Route: oral Route: single Dose: 8 mg Sources: https://pubmed.ncbi.nlm.nih.gov/23364217/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/23364217/	Other AEs: Headache... Other AEs: Headache (grade 1, 4.8%) Sources: https://pubmed.ncbi.nlm.nih.gov/23364217/

AEs

AE	Significance	Dose	Population
Constipation	grade 1, 4.8%	8 mg 1 times / day multiple, oral Recommended Dose: 8 mg, 1 times / day Route: oral Route: multiple Dose: 8 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/23364217/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/23364217/
Headache	grade 1, 4.8%	8 mg single, oral Recommended Dose: 8 mg Route: oral Route: single Dose: 8 mg Sources: https://pubmed.ncbi.nlm.nih.gov/23364217/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/23364217/

PubMed

Title	Date	PubMed
[The efficacy and safety of indisetron hydrochloride for the management of nausea/vomiting caused by chemotherapy for gynecologic cancer].	2008-07	18633256
Antagonistic activities of N-3389, a newly synthesized diazabicyclo derivative, at 5-HT3 and 5-HT4 receptors.	1994-12-12	7698198

Patents

Sample Use Guides

In Vivo Use Guide

8 mg once a day

Route of Administration: Oral

In Vitro Use Guide

N-3389 (INDISETRON ) (3 x 10(-7)-3 x 10(-6) M) was found to inhibit the increase of electrically stimulated twitch responses induced by 5-HT (10(-8) M) longitudinal muscle myenteric plexus preparation of the guinea-pig ileum

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:20:35 GMT 2025` Edited by `admin` on `Mon Mar 31 18:20:35 GMT 2025`
Record UNII	89RBZ66NVC
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

INDISETRON

Official Name

English

Indisetron [WHO-DD]

Preferred Name

English

indisetron [INN]

Common Name

English

N-(3,9-DIMETHYL-ENDO-3,9-DIAZABICYCLO(3.3.1)NON-7-YL)-1H-INDAZOLE-3-CARBOXAMIDE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C94726