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Details

Stereochemistry ACHIRAL
Molecular Formula C16H20N4O2
Molecular Weight 300.3556
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ITASETRON

SMILES

CN1[C@H]2CC[C@@H]1C[C@@H](C2)NC(=O)N3C(=O)NC4=C3C=CC=C4

InChI

InChIKey=RWXRJSRJIITQAK-ZSBIGDGJSA-N
InChI=1S/C16H20N4O2/c1-19-11-6-7-12(19)9-10(8-11)17-15(21)20-14-5-3-2-4-13(14)18-16(20)22/h2-5,10-12H,6-9H2,1H3,(H,17,21)(H,18,22)/t10-,11+,12-

HIDE SMILES / InChI
Molecular Formula C16H20N4O2
Molecular Weight 300.3556
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 2 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/8891590

DAU 6215 (Itasetron) is a selective 5-hydroxytryptamine3 (5-HT3) antagonist, which was developed by Boehringer Ingelheim. And was investigated for treatment the nausea and vomiting induced by chemotherapy, it was confirmed that this drug possessed antiemetic properties. Also was discovered, that chronic treatment with itasetron significantly improved retention abilities of the aged rats in this memory test. However, development of itasetron was terminated.

CNS Activity

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
 3.8 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Phase III
665
Unknown

Approved Use

Unknown
Secondary
Phase III
665
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
11.4 h
REVIEW
https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1527-3458.1996.tb00297.x
5 mg unknown, oral
dose: 5 mg
route of administration: Oral
experiment type: UNKNOWN
co-administered:
ITASETRON plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
8 mg 2 times / day multiple, oral
Highest studied dose
Dose: 8 mg, 2 times / day
Route: oral
Route: multiple
Dose: 8 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9215605/
https://link.springer.com/article/10.2165/00126839-199902040-00003
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/9215605/
https://link.springer.com/article/10.2165/00126839-199902040-00003
Other AEs: Headache, Constipation...
Other AEs:
Headache
Constipation
Fatigue
Anorexia
bdominal pain
Sources:
https://pubmed.ncbi.nlm.nih.gov/9215605/
https://link.springer.com/article/10.2165/00126839-199902040-00003
280 ug/kg single, intravenous
Highest studied dose
Dose: 280 ug/kg
Route: intravenous
Route: single
Dose: 280 ug/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/10378635/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/10378635/
Other AEs: Nausea, Dehydration...
Other AEs:
Nausea (grade 3, 14.3%)
Dehydration (grade 3, 14.3%)
Dry mouth (grade 1, 14.3%)
Creatinine increased (grade 1-2)
Sources:
https://pubmed.ncbi.nlm.nih.gov/10378635/
AEs

AEs

AESignificanceDosePopulation
Anorexia
8 mg 2 times / day multiple, oral
Highest studied dose
Dose: 8 mg, 2 times / day
Route: oral
Route: multiple
Dose: 8 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9215605/
https://link.springer.com/article/10.2165/00126839-199902040-00003
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/9215605/
https://link.springer.com/article/10.2165/00126839-199902040-00003
Constipation
8 mg 2 times / day multiple, oral
Highest studied dose
Dose: 8 mg, 2 times / day
Route: oral
Route: multiple
Dose: 8 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9215605/
https://link.springer.com/article/10.2165/00126839-199902040-00003
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/9215605/
https://link.springer.com/article/10.2165/00126839-199902040-00003
Fatigue
8 mg 2 times / day multiple, oral
Highest studied dose
Dose: 8 mg, 2 times / day
Route: oral
Route: multiple
Dose: 8 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9215605/
https://link.springer.com/article/10.2165/00126839-199902040-00003
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/9215605/
https://link.springer.com/article/10.2165/00126839-199902040-00003
Headache
8 mg 2 times / day multiple, oral
Highest studied dose
Dose: 8 mg, 2 times / day
Route: oral
Route: multiple
Dose: 8 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9215605/
https://link.springer.com/article/10.2165/00126839-199902040-00003
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/9215605/
https://link.springer.com/article/10.2165/00126839-199902040-00003
bdominal pain
8 mg 2 times / day multiple, oral
Highest studied dose
Dose: 8 mg, 2 times / day
Route: oral
Route: multiple
Dose: 8 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9215605/
https://link.springer.com/article/10.2165/00126839-199902040-00003
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/9215605/
https://link.springer.com/article/10.2165/00126839-199902040-00003
Dry mouth grade 1, 14.3%
280 ug/kg single, intravenous
Highest studied dose
Dose: 280 ug/kg
Route: intravenous
Route: single
Dose: 280 ug/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/10378635/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/10378635/
Creatinine increased grade 1-2
280 ug/kg single, intravenous
Highest studied dose
Dose: 280 ug/kg
Route: intravenous
Route: single
Dose: 280 ug/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/10378635/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/10378635/
Dehydration grade 3, 14.3%
280 ug/kg single, intravenous
Highest studied dose
Dose: 280 ug/kg
Route: intravenous
Route: single
Dose: 280 ug/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/10378635/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/10378635/
Nausea grade 3, 14.3%
280 ug/kg single, intravenous
Highest studied dose
Dose: 280 ug/kg
Route: intravenous
Route: single
Dose: 280 ug/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/10378635/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/10378635/
PubMed

PubMed

TitleDatePubMed
Effect of DAU 6215, a novel 5-HT3 receptor antagonist, on scopolamine-induced amnesia in the rat in a spatial learning task.
1994-01
DAU 6215, a novel 5-HT3-receptor antagonist, selectively antagonizes scopolamine-induced deficit in a passive-avoidance task, but not scopolamine-induced hypermotility in rats.
1993-09
Patents

Patents

JP2006516976A
30
JP2006516977A
31
JP2011525180A
180
JP2011528275A
456

Sample Use Guides

In Vivo Use Guide
Nausea and vomiting: itasetron hydrochloride is effective in the dose range 35-280 microg/kg in preventing cisplatin-induced emesis.
Route of Administration: Intravenous
In Vitro Use Guide
DA 6215 (Itasetron ) has been synthesized and evaluated for 5-HT3 antagonistic activity in a radioligand binding assay. DA 6215 showed a Ki = 3.8 nM in the binding test
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:27:54 GMT 2025
Edited
by admin
on Mon Mar 31 18:27:54 GMT 2025
Record UNII
00S0D0OEKR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ITASETRON
INN   MI   USAN  
INN   USAN  
Official Name English
DA-6215
Preferred Name English
2-Oxo-N-1?H,5?H-tropan-3?-yl-1-benzimidazoline-1-carboxamide
Systematic Name English
U98079A
Code English
ITASETRON [USAN]
Common Name English
DA6215
Code English
1H-BENZIMIDAZOLE-1-CARBOXAMIDE, 2,3-DIHYDRO-N-(8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL)-2-OXO, ENDO-
Systematic Name English
ITASETRON [MI]
Common Name English
itasetron [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C94726
Created by admin on Mon Mar 31 18:27:54 GMT 2025 , Edited by admin on Mon Mar 31 18:27:54 GMT 2025
NCI_THESAURUS C267
Created by admin on Mon Mar 31 18:27:54 GMT 2025 , Edited by admin on Mon Mar 31 18:27:54 GMT 2025
Code System Code Type Description
USAN
HH-62
Created by admin on Mon Mar 31 18:27:54 GMT 2025 , Edited by admin on Mon Mar 31 18:27:54 GMT 2025
PRIMARY
ChEMBL
CHEMBL2105109
Created by admin on Mon Mar 31 18:27:54 GMT 2025 , Edited by admin on Mon Mar 31 18:27:54 GMT 2025
PRIMARY
SMS_ID
100000082841
Created by admin on Mon Mar 31 18:27:54 GMT 2025 , Edited by admin on Mon Mar 31 18:27:54 GMT 2025
PRIMARY
MERCK INDEX
m1199
Created by admin on Mon Mar 31 18:27:54 GMT 2025 , Edited by admin on Mon Mar 31 18:27:54 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID9048803
Created by admin on Mon Mar 31 18:27:54 GMT 2025 , Edited by admin on Mon Mar 31 18:27:54 GMT 2025
PRIMARY
CAS
123258-84-4
Created by admin on Mon Mar 31 18:27:54 GMT 2025 , Edited by admin on Mon Mar 31 18:27:54 GMT 2025
PRIMARY
INN
6983
Created by admin on Mon Mar 31 18:27:54 GMT 2025 , Edited by admin on Mon Mar 31 18:27:54 GMT 2025
PRIMARY
FDA UNII
00S0D0OEKR
Created by admin on Mon Mar 31 18:27:54 GMT 2025 , Edited by admin on Mon Mar 31 18:27:54 GMT 2025
PRIMARY
NCI_THESAURUS
C65990
Created by admin on Mon Mar 31 18:27:54 GMT 2025 , Edited by admin on Mon Mar 31 18:27:54 GMT 2025
PRIMARY
MESH
C070191
Created by admin on Mon Mar 31 18:27:54 GMT 2025 , Edited by admin on Mon Mar 31 18:27:54 GMT 2025
PRIMARY
EVMPD
SUB08350MIG
Created by admin on Mon Mar 31 18:27:54 GMT 2025 , Edited by admin on Mon Mar 31 18:27:54 GMT 2025
PRIMARY
Related Record Type Details
Structure of ITASETRON HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Structure of ITASETRON HYDROCHLORIDE MONOHYDRATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of ITASETRON
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