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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H23FN2O2
Molecular Weight 318.3858
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ROBALZOTAN

SMILES

NC(=O)C1=CC=C(F)C2=C1C[C@H](CO2)N(C3CCC3)C4CCC4

InChI

InChIKey=MQTUXRKNJYPMCG-CYBMUJFWSA-N
InChI=1S/C18H23FN2O2/c19-16-8-7-14(18(20)22)15-9-13(10-23-17(15)16)21(11-3-1-4-11)12-5-2-6-12/h7-8,11-13H,1-6,9-10H2,(H2,20,22)/t13-/m1/s1

HIDE SMILES / InChI

Molecular Formula C18H23FN2O2
Molecular Weight 318.3858
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
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/18775020| https://www.ncbi.nlm.nih.gov/pubmed/9851589

AstraZeneca (formerly Astra) is developing robalzotan (NAD-299, AZD-7371), a 5-HT1A antagonist, for the potential treatment of depression and anxiety. The compound has entered phase II trials but was discontinued. Then it investigated for the treatment of irritable bowel syndrome, but the study was prematurely terminated. The same final has expected the development of robalzotan in phase II to treat overactive bladder, this investigation was terminated in July 2005.

CNS Activity

Curator's Comment: Known to be CNS penetrant in monkey. Human data not available.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.6 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
PubMed

PubMed

TitleDatePubMed
The pharmacological characterization of a novel selective 5-hydroxytryptamine1A receptor antagonist, NAD-299.
1997 Oct
Positron emission tomographic analysis of dose-dependent NAD-299 binding to 5-hydroxytryptamine-1A receptors in the human brain.
2003 Apr
Selective 5-HT1A antagonists WAY 100635 and NAD-299 attenuate the impairment of passive avoidance caused by scopolamine in the rat.
2003 Feb
Effect of different 5-HT1A receptor antagonists in combination with paroxetine on expression of the immediate-early gene Arc in rat brain.
2003 Jun
Studies of drug binding to plasma proteins using a variant of equilibrium dialysis.
2005 Jul 1
Analysis of the role of 5-HT1A receptors in spatial and aversive learning in the rat.
2005 May
Bidirectional modulation of classical fear conditioning in mice by 5-HT(1A) receptor ligands with contrasting intrinsic activities.
2009 Oct-Nov
Selective serotonin reuptake inhibitors potentiate the rapid antidepressant-like effects of serotonin4 receptor agonists in the rat.
2010 Feb 16
The selective 5-HT(1A) receptor antagonist NAD-299 increases acetylcholine release but not extracellular glutamate levels in the frontal cortex and hippocampus of awake rat.
2010 Jul
Patents

Patents

Sample Use Guides

20 mg or 5 mg or matching placebo tablets twice daily for 12 wk
Route of Administration: Oral
In Vitro Use Guide
[3H]NAD-299 (Robalzotan) binding displayed a Kd value of 0.17 nM and a Bmax value of 26.7 pmol/g wet weight of rat hippocampus. Same binding affinity (Kd = 0.16 nM) was found to cloned human 5-HT1A receptors. Addition of the nonhydrolyzable GTP analog guanylylimidodiphosphate had no effect on the binding characteristics of [3H]NAD-299, while it significantly decreased both the affinity and density of receptors labeled with [3H]8-OH-DPAT. The rank order of potency of various compounds to inhibit [3H]NAD-299 binding is consistent with the labeling of 5-HT1A receptors.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:38:28 UTC 2023
Edited
by admin
on Sat Dec 16 17:38:28 UTC 2023
Record UNII
I18M56OGME
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ROBALZOTAN
INN  
INN  
Official Name English
robalzotan [INN]
Common Name English
AZD7371
Common Name English
AZD-7371
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1509
Created by admin on Sat Dec 16 17:38:29 UTC 2023 , Edited by admin on Sat Dec 16 17:38:29 UTC 2023
Code System Code Type Description
CAS
169758-66-1
Created by admin on Sat Dec 16 17:38:29 UTC 2023 , Edited by admin on Sat Dec 16 17:38:29 UTC 2023
PRIMARY
INN
7591
Created by admin on Sat Dec 16 17:38:29 UTC 2023 , Edited by admin on Sat Dec 16 17:38:29 UTC 2023
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WIKIPEDIA
ROBALZOTAN
Created by admin on Sat Dec 16 17:38:29 UTC 2023 , Edited by admin on Sat Dec 16 17:38:29 UTC 2023
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EVMPD
SUB10347MIG
Created by admin on Sat Dec 16 17:38:29 UTC 2023 , Edited by admin on Sat Dec 16 17:38:29 UTC 2023
PRIMARY
MESH
C108607
Created by admin on Sat Dec 16 17:38:29 UTC 2023 , Edited by admin on Sat Dec 16 17:38:29 UTC 2023
PRIMARY
EPA CompTox
DTXSID30168743
Created by admin on Sat Dec 16 17:38:29 UTC 2023 , Edited by admin on Sat Dec 16 17:38:29 UTC 2023
PRIMARY
FDA UNII
I18M56OGME
Created by admin on Sat Dec 16 17:38:29 UTC 2023 , Edited by admin on Sat Dec 16 17:38:29 UTC 2023
PRIMARY
ChEMBL
CHEMBL1628569
Created by admin on Sat Dec 16 17:38:29 UTC 2023 , Edited by admin on Sat Dec 16 17:38:29 UTC 2023
PRIMARY
SMS_ID
100000080266
Created by admin on Sat Dec 16 17:38:29 UTC 2023 , Edited by admin on Sat Dec 16 17:38:29 UTC 2023
PRIMARY
DRUG BANK
DB06538
Created by admin on Sat Dec 16 17:38:29 UTC 2023 , Edited by admin on Sat Dec 16 17:38:29 UTC 2023
PRIMARY
NCI_THESAURUS
C74143
Created by admin on Sat Dec 16 17:38:29 UTC 2023 , Edited by admin on Sat Dec 16 17:38:29 UTC 2023
PRIMARY
PUBCHEM
3055171
Created by admin on Sat Dec 16 17:38:29 UTC 2023 , Edited by admin on Sat Dec 16 17:38:29 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
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