Details
Stereochemistry | ACHIRAL |
Molecular Formula | C23H20FN3O2 |
Molecular Weight | 389.4222 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1C2=CC=C(F)C=C2C3=C1C(=O)N(C=C3C(=O)N4CCCC4)C5=CC=CC=C5
InChI
InChIKey=QQWHWWDIFGNCLV-UHFFFAOYSA-N
InChI=1S/C23H20FN3O2/c1-25-19-10-9-15(24)13-17(19)20-18(22(28)26-11-5-6-12-26)14-27(23(29)21(20)25)16-7-3-2-4-8-16/h2-4,7-10,13-14H,5-6,11-12H2,1H3
Molecular Formula | C23H20FN3O2 |
Molecular Weight | 389.4222 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/12595909 | https://www.ncbi.nlm.nih.gov/pubmed/11454940 | https://en.wikipedia.org/wiki/SL-651,498
Curator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/12595909 | https://www.ncbi.nlm.nih.gov/pubmed/11454940 | https://en.wikipedia.org/wiki/SL-651,498
SL651498 was identified as a drug development candidate from a research program designed to discover subtype-selective GABA(A) receptor agonists for the treatment of generalized anxiety disorder and muscle spasms. SL651498 displayed high affinity for GABA(A) receptors containing alpha(1) and alpha(2 subunits, and weaker affinity for alpha5-containing GABA(A) receptors, it behaved as a full agonist at recombinant t GABA(A) receptors containing alpha(2) and alpha(3) subunits, and as a partial agonist at recombinant GABA(A) receptors expressing alpha(1) and alpha(5) subunits. It was shown, that SL651498 represented a promising alternative to agents currently used for the treatment of anxiety disorders and muscle spasms without the major side effects seen with classical benzodiazepines).
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2095172 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11454940 |
17.0 nM [Ki] | ||
Target ID: CHEMBL2111413 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11454940 |
73.0 nM [Ki] | ||
Target ID: CHEMBL2094122 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11454940 |
117.0 nM [Ki] | ||
Target ID: CHEMBL2095167 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12595909 |
17.0 nM [Ki] | ||
Target ID: CHEMBL2111374 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12595909 |
215.0 nM [Ki] | ||
Target ID: CHEMBL2111343 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12595909 |
80.3 nM [Ki] | ||
Target ID: CHEMBL2111327 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12595909 |
73.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
375 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18635696 |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
SL651498 plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
11 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18635696 |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
SL651498 plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12595909
minimal effective dose: 30 to 100 mg/kg
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12595909
Studies of [3H]flumazenil binding to native rat GABAA receptor subtypes showed that SL651498 was more potent at displacing [3H]flumazenil binding to membranes from cerebellum (Ki = 6.8 nM) and spinal cord (Ki = 12.3 nM) than from hippocampus
(Ki = 117 nM).
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 11:04:58 GMT 2023
by
admin
on
Sat Dec 16 11:04:58 GMT 2023
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Record UNII |
082VH54RF1
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Record Status |
Validated (UNII)
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Record Version |
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Systematic Name | English | ||
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Systematic Name | English | ||
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Code | English |
Code System | Code | Type | Description | ||
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9908378
Created by
admin on Sat Dec 16 11:04:58 GMT 2023 , Edited by admin on Sat Dec 16 11:04:58 GMT 2023
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SL-651498
Created by
admin on Sat Dec 16 11:04:58 GMT 2023 , Edited by admin on Sat Dec 16 11:04:58 GMT 2023
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PRIMARY | Sanofi-Synthlabo (Originator), Anxiolytics, PSYCHOPHARMACOLOGIC DRUGS, GABA(A) BZ Site Receptor Agonists and compound synthesis | ||
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205881-86-3
Created by
admin on Sat Dec 16 11:04:58 GMT 2023 , Edited by admin on Sat Dec 16 11:04:58 GMT 2023
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PRIMARY | |||
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DTXSID401045803
Created by
admin on Sat Dec 16 11:04:58 GMT 2023 , Edited by admin on Sat Dec 16 11:04:58 GMT 2023
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SL-651,498
Created by
admin on Sat Dec 16 11:04:58 GMT 2023 , Edited by admin on Sat Dec 16 11:04:58 GMT 2023
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PRIMARY | SL-651,498 is an anxiolytic and anticonvulsant drug used in scientific research, with a chemical structure most closely related to .BETA.-carboline derivatives such as abecarnil and gedocarnil. It has similar effects to benzodiazepine drugs, but is structurally distinct and so is classed as a nonbenzodiazepine anxiolytic. | ||
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082VH54RF1
Created by
admin on Sat Dec 16 11:04:58 GMT 2023 , Edited by admin on Sat Dec 16 11:04:58 GMT 2023
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PRIMARY |
Related Record | Type | Details | ||
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TARGET -> AGONIST |
SL651498 is a subtype-selective GABAA agonist, which acts as a full agonist at α2 and α3 subtypes, and as a partial agonist at α1 and α5 (although its action at α5 subtypes is much weaker than at the others).
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
SL651498 was identified as a drug development candidate from a research program designed to discover subtype-selective GABA(A) receptor agonists for the treatment of generalized anxiety disorder and muscle spasms. The drug displays high affinity for rat native GABA(A) receptors containing alpha(1) (K(i) = 6.8 nM) and alpha(2) (K(i) = 12.3 nM) subunits, and weaker affinity for alpha5-containing GABA(A) receptors (K(i) = 117 nM).
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ACTIVE MOIETY |
New benzo analogue under development(2014). Very selective for a2 and a3 it has very small affinities for a1 and virtually none for a5. This is now postulated as the site responsible for physical dependance and early trials are reporting no tolerance/dependance.
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