EBALZOTAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H30N2O2
Molecular Weight	318.4537
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCN(C(C)C)[C@H]1COC2=C(C1)C(=CC=C2)C(=O)NC(C)C

InChI

InChIKey=UEAKCKJAKUFIQP-OAHLLOKOSA-N

InChI=1S/C19H30N2O2/c1-6-10-21(14(4)5)15-11-17-16(19(22)20-13(2)3)8-7-9-18(17)23-12-15/h7-9,13-15H,6,10-12H2,1-5H3,(H,20,22)/t15-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C19H30N2O2
Molecular Weight	318.4537
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11714872 | https://adisinsight.springer.com/drugs/800006909 | https://www.ncbi.nlm.nih.gov/pubmed/12904815

Ebalzotan is a selective serotonin (5-HT1A) receptor agonist, was chosen by Astra in the early 1990s as a candidate drug for the treatment of depression and anxiety. It has a modest affinity for the 5-HT(7). In vivo, ebalzotan induced all the typical effects of a 5-HT(1A) receptor agonist in rats: it decreased 5-HT synthesis (5-HTP accumulation) and 5-HT turnover (measured as the ratio of 5-hydroxyindoleacetic acid/5-HT), increased corticosterone secretion, induced the 5-HT(1A) syndrome (flat body posture and forepaw treading), inhibited the cage-leaving response, and caused hypothermia. Ebalzotan had been in phase I clinical trial for the treatment of major depressive disorder. However, this study was discontinued.

Approval Year

PubMed

Title	Date	PubMed
Synthesis of robalzotan, ebalzotan, and rotigotine precursors via the stereoselective multienzymatic cascade reduction of α,β-unsaturated aldehydes.	2013-05-17	23611252
Logistics of process R&D: transforming laboratory methods to manufacturing scale.	2003-08	12904815
The pharmacological profile of (R)-3,4-dihydro-N-isopropyl-3-(N-isopropyl-N-propylamino)-2H-1-benzopyran-5-carboxamide, a selective 5-hydroxytryptamine(1A) receptor agonist.	2001-12	11714872

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:58:46 GMT 2025` Edited by `admin` on `Mon Mar 31 17:58:46 GMT 2025`
Record UNII	WV4B56N49H
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

ebalzotan [INN]

Preferred Name

English

EBALZOTAN

Official Name

English

(R)-N-ISOPROPYL-3-(ISOPROPYLPROPYLAMINO)-5-CHROMANCARBOXAMIDE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1509