Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C18H20ClNO2.BrH |
| Molecular Weight | 398.722 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Br.CN1CCC2=C(C=C(O)C(O)=C2Cl)C(C1)C3=CC(C)=CC=C3
InChI
InChIKey=FHYWNBUFNGHNCP-UHFFFAOYSA-N
InChI=1S/C18H20ClNO2.BrH/c1-11-4-3-5-12(8-11)15-10-20(2)7-6-13-14(15)9-16(21)18(22)17(13)19;/h3-5,8-9,15,21-22H,6-7,10H2,1-2H3;1H
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/12675914 | https://www.ncbi.nlm.nih.gov/pubmed/17553535 | https://www.ncbi.nlm.nih.gov/pubmed/23892272
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/12675914 | https://www.ncbi.nlm.nih.gov/pubmed/17553535 | https://www.ncbi.nlm.nih.gov/pubmed/23892272
SKF83959 is a benzodiazepine derivative which acts as an agonist of D1 receptor. Activation of D1 receptors by SKF83959 fails to stimulate adenylyl cyclase and inhibits the stimulation of adenylyl cyclase induced by dopamine but stimulates phosphatidylinositol 4,5-biphosphate hydrolysis in membranes of frontal cortex. SKF83959 was identified as a specific agonist for the heteromer D1/D2 complex. SKF83959 elicit anti-parkinsonism effects in monkeys and rodents. In lower concentrations, SKF83959 inhibits serotonin, norepinephrine and dopamine transporters and is an allosteric regulator of sigma 1 receptor. The compound has demonstrated activity in a preclinical model of depression.
CNS Activity
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P21728 Gene ID: 1812.0 Gene Symbol: DRD1 Target Organism: Homo sapiens (Human) |
0.66 nM [IC50] | ||
Target ID: Q99720|||Q7Z653 Gene ID: 10280.0 Gene Symbol: SIGMAR1 Target Organism: Homo sapiens (Human) |
|||
Target ID: P23975 Gene ID: 6530.0 Gene Symbol: SLC6A2 Target Organism: Homo sapiens (Human) |
0.6 µM [Ki] | ||
Target ID: P31645 Gene ID: 6532.0 Gene Symbol: SLC6A4 Target Organism: Homo sapiens (Human) |
1.43 µM [Ki] | ||
Target ID: Q01959 Gene ID: 6531.0 Gene Symbol: SLC6A3 Target Organism: Homo sapiens (Human) |
9.01 µM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Topographical assessment and pharmacological characterization of orofacial movements in mice: dopamine D(1)-like vs. D(2)-like receptor regulation. | 2001 Apr 20 |
|
| Ventral striatal vs. accumbal (shell) mechanisms and non-cyclase-coupled dopamine D(1)-like receptors in jaw movements. | 2001 Jul 6 |
|
| Prefrontal, accumbal [shell] and ventral striatal mechanisms in jaw movements and non-cyclase-coupled dopamine D1-like receptors. | 2003 Jul 18 |
|
| Effects of dopamine D1 ligands on eye blinking in monkeys: efficacy, antagonism, and D1/D2 interactions. | 2004 Dec |
|
| Regulation of cyclin-dependent kinase 5 and calcium/calmodulin-dependent protein kinase II by phosphatidylinositol-linked dopamine receptor in rat brain. | 2004 Dec |
|
| Modification by dopaminergic drugs of choice behavior under concurrent schedules of intravenous saline and food delivery in monkeys. | 2004 Jan |
|
| Differential activation of adenylate cyclase and receptor internalization by novel dopamine D1 receptor agonists. | 2005 Oct |
|
| Dopamine profoundly suppresses excitatory transmission in neonatal rat hippocampus via phosphatidylinositol-linked D1-like receptor. | 2006 |
|
| Activity-dependent modulation of limbic dopamine D3 receptors by CaMKII. | 2009 Feb 12 |
|
| D5 dopamine receptors are required for dopaminergic activation of phospholipase C. | 2009 Mar |
|
| Activation of phosphatidylinositol-linked novel D1 dopamine receptors inhibits high-voltage-activated Ca2+ currents in primary cultured striatal neurons. | 2009 May |
|
| Identification of G protein-biased agonists that fail to recruit β-arrestin or promote internalization of the D1 dopamine receptor. | 2015 Apr 15 |
Patents
Sample Use Guides
In a rat model of Parkinson's disease, SKF83959 was administered intraperitoneally at 0.5 mg/kg.
Route of Administration:
Intraperitoneal
[3H]SCH 23390 (72-80 Ci/mmol) was used as a radioligand to label dopamine D1 receptor. Rat striatal membranes were isolated in 50 mM K-phosphate buffer at pH 7.4 by homogenization and centrifugation. Membrane suspensions were incubated with 0.2 nM [3H]SCH23390 in a volume of 2.2 ml (1 mg original tissue) at 30°C for 60 min. After incubation, the samples were filtered through Whatman GF/F filters. Specific binding was defined as the difference in radioactivity obtained in the absence and the presence of 0.1 uM of cis(Z)-flupentixol. SKF83959 displaced [3H]SCH 23390 with IC50 of 0.66 nM.
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67287-95-0
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DTXSID9042629
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11957685
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ACTIVE MOIETY
SUBSTANCE RECORD
