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
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
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/11249580Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11249580
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10700661
Curator's Comment: Known to be CNS penetrant in monkey. Human data not available.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9851589 |
0.6 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator​
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
yes [IC50 10.684 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no |
PubMed
Title | Date | PubMed |
---|---|---|
Effects of NAD-299, a new, highly selective 5-HT1A receptor antagonist, on bladder function in rats. | 2002 Dec |
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Positron emission tomographic analysis of dose-dependent NAD-299 binding to 5-hydroxytryptamine-1A receptors in the human brain. | 2003 Apr |
|
Selective serotonin reuptake inhibitors potentiate the rapid antidepressant-like effects of serotonin4 receptor agonists in the rat. | 2010 Feb 16 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18775020
20 mg or 5 mg or matching placebo tablets twice daily for 12 wk
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9851589
[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.
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NCI_THESAURUS |
C1509
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169758-66-1
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7591
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ROBALZOTAN
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SUB10347MIG
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C108607
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DTXSID30168743
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I18M56OGME
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CHEMBL1628569
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100000080266
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DB06538
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C74143
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3055171
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ACTIVE MOIETY