Details
| Stereochemistry | UNKNOWN |
| Molecular Formula | C11H13ClN2O2 |
| Molecular Weight | 240.686 |
| Optical Activity | UNSPECIFIED |
| Additional Stereochemistry | Yes |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
ClC1=CC=C(O1)C(=O)N2C[C@@H]3CNC[C@@H]3C2
InChI
InChIKey=GTUIQNHJSXQMKW-OCAPTIKFSA-N
InChI=1S/C11H13ClN2O2/c12-10-2-1-9(16-10)11(15)14-5-7-3-13-4-8(7)6-14/h1-2,7-8,13H,3-6H2/t7-,8+
| Molecular Formula | C11H13ClN2O2 |
| Molecular Weight | 240.686 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Approval Year
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:47:56 UTC 2023
by
admin
on
Fri Dec 15 19:47:56 UTC 2023
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| Record UNII |
P6W82N7VYO
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| Record Status |
Validated (UNII)
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| Record Version |
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1690074-15-7
Created by
admin on Fri Dec 15 19:47:56 UTC 2023 , Edited by admin on Fri Dec 15 19:47:56 UTC 2023
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P6W82N7VYO
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CHEMBL2179529
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1025007-04-8
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admin on Fri Dec 15 19:47:56 UTC 2023 , Edited by admin on Fri Dec 15 19:47:56 UTC 2023
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96568204
Created by
admin on Fri Dec 15 19:47:56 UTC 2023 , Edited by admin on Fri Dec 15 19:47:56 UTC 2023
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| Related Record | Type | Details | ||
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ACTIVE MOIETY |
Originator: Targacept; Developer: AstraZeneca; Class: Antidementia, Small molecule; Mechanism of Action: Alpha4 beta2 nicotinic receptor agonist; Highest Development Phases: Discontinued for Alzheimer's disease, Attention-deficit hyperactivity disorder; Most Recent Events: 30 Jun 2013 Discontinued - Phase-I for Alzheimer's disease in Japan and Sweden (PO, Liquid), 30 Jun 2013 Discontinued - Phase-I for Alzheimer's disease in Japan and Sweden (PO, Capsule), 30 Jun 2013 Discontinued - Phase-II for Alzheimer's disease in Czech Republic, Hungary, Slovakia, Russia and Ukraine (PO, Capsule)
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ACTIVE MOIETY |
A novel potent and highly selective .ALPHA.4.BETA.2 nAChR agonist 3-(5-chloro-2-furoyl)-3,7-diazabicyclo(3.3.0)octane (56, TC-6683, AZD1446) with favorable pharmaceutical properties and in vivo efficacy in animal models has been identified as a potential treatment for cognitive deficits associated with psychiatric or neurological conditions and is currently being progressed to phase 2 clinical trials as a treatment for Alzheimer's disease.
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ACTIVE MOIETY |
AZD1446 selectively activates the .ALPHA.4.BETA.2 subtype of nicotinic acetylcholine receptor. Acute administration of nicotine to AD patients improved accuracy of delayed recall, as well as deficits in attention and information processing. However, nicotine has significant side effects, including tachycardia, elevated blood pressure, and gastrointestinal distress. Agonists with better selectivity for nAChR subtypes that mediate the beneficial effects could be useful. Agonist binding to the .ALPHA.4.BETA.2 nAChR has been shown promote sAPP.ALPHA. secretion and attenuate A.BETA. production.
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