Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C28H30N4O |
| Molecular Weight | 438.564 |
| Optical Activity | NONE |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O=C(N[C@H]1CC[C@H](CCN2CCC3=C(C2)C=CC(=C3)C#N)CC1)C4=CC=NC5=CC=CC=C45
InChI
InChIKey=OLWRVVHPJFLNPW-LSNLESRRSA-N
InChI=1S/C28H30N4O/c29-18-21-5-8-23-19-32(16-13-22(23)17-21)15-12-20-6-9-24(10-7-20)31-28(33)26-11-14-30-27-4-2-1-3-25(26)27/h1-5,8,11,14,17,20,24H,6-7,9-10,12-13,15-16,19H2,(H,31,33)/t20-,24-
| Molecular Formula | C28H30N4O |
| Molecular Weight | 438.564 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| 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/18329700 | https://www.ncbi.nlm.nih.gov/pubmed/12645041 | https://www.ncbi.nlm.nih.gov/pubmed/15083257 | https://www.ncbi.nlm.nih.gov/pubmed/21466803 | https://www.ncbi.nlm.nih.gov/pubmed/17303116 | https://www.ncbi.nlm.nih.gov/pubmed/17407496 | https://www.ncbi.nlm.nih.gov/pubmed/20142301
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/18329700 | https://www.ncbi.nlm.nih.gov/pubmed/12645041 | https://www.ncbi.nlm.nih.gov/pubmed/15083257 | https://www.ncbi.nlm.nih.gov/pubmed/21466803 | https://www.ncbi.nlm.nih.gov/pubmed/17303116 | https://www.ncbi.nlm.nih.gov/pubmed/17407496 | https://www.ncbi.nlm.nih.gov/pubmed/20142301
SB-277011 is a potent and selective dopamine D(3) receptor antagonist. SB-277011 attenuates reinforcing propertes of drugs of abuse incluting opiates, cocaine, methamphetamine, nicotine and ethanol. SB-277011A produced a significant decrease in food intake in obese rats. Clinical development of SB-277011A has been halted by GlaxoSmithKline Pharmaceuticals, due to poor bioavailability (~2%) and a very short half-life (<20 min) in primates.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Implication of dorsostriatal D3 receptors in motivational processes: a potential target for neuropsychiatric symptoms in Parkinson's disease. | 2017-01-30 |
|
| Examining the role of dopamine D2 and D3 receptors in Pavlovian conditioned approach behaviors. | 2016-05-15 |
|
| The selective dopamine D3 receptor antagonist SB-277011A significantly accelerates extinction to environmental cues associated with cocaine-induced place preference in male Sprague-Dawley rats. | 2015-10 |
|
| Alcohol enhances the psychostimulant and conditioning effects of mephedrone in adolescent mice; postulation of unique roles of D3 receptors and BDNF in place preference acquisition. | 2015-10 |
|
| The selective dopamine D₃ receptor antagonist SB-277011A attenuates drug- or food-deprivation reactivation of expression of conditioned place preference for cocaine in male Sprague-Dawley rats. | 2015-06 |
|
| Implication of dopamine D3 receptor activation in the reversion of Parkinson's disease-related motivational deficits. | 2014-06-17 |
|
| The selective D₃ receptor antagonist SB-277011A attenuates morphine-triggered reactivation of expression of cocaine-induced conditioned place preference. | 2013-08 |
|
| Blockade of dopamine D3 receptors in the nucleus accumbens and central amygdala inhibits incubation of cocaine craving in rats. | 2013-07 |
|
| In vivo occupancy of dopamine D3 receptors by antagonists produces neurochemical and behavioral effects of potential relevance to attention-deficit-hyperactivity disorder. | 2013-02 |
|
| The effects of the preferential dopamine D(3) receptor antagonist S33138 on ethanol binge drinking in C57BL/6J mice. | 2012-11 |
|
| Dopamine agonist-induced penile erection and yawning: differential role of D₂-like receptor subtypes and correlation with nitric oxide production in the paraventricular nucleus of the hypothalamus of male rats. | 2012-05-01 |
|
| YQA14: a novel dopamine D3 receptor antagonist that inhibits cocaine self-administration in rats and mice, but not in D3 receptor-knockout mice. | 2012-03 |
|
| The acute administration of the selective dopamine D(3) receptor antagonist SB-277011A reverses conditioned place aversion produced by naloxone precipitated withdrawal from acute morphine administration in rats. | 2012-01 |
|
| Roles of BDNF, dopamine D(3) receptors, and their interactions in the expression of morphine-induced context-specific locomotor sensitization. | 2011-11 |
|
| Dopamine D(3) receptor antagonist SB-277011A inhibits methamphetamine self-administration and methamphetamine-induced reinstatement of drug-seeking in rats. | 2011-06-01 |
|
| The effects of two highly selective dopamine D3 receptor antagonists (SB-277011A and NGB-2904) on food self-administration in a rodent model of obesity. | 2008-06 |
|
| The selective dopamine D3 receptor antagonists SB-277011A and NGB 2904 and the putative partial D3 receptor agonist BP-897 attenuate methamphetamine-enhanced brain stimulation reward in rats. | 2008-03 |
|
| Role of dopamine D3 receptors in the expression of conditioned fear in rats. | 2008-01-28 |
|
| Dopamine D2 receptor stimulation inhibits cold-initiated thermogenesis in brown adipose tissue in conscious rats. | 2007-06-15 |
|
| Effects of the selective dopamine D3 receptor antagonist SB-277011A on the reinforcing effects of nicotine as measured by a progressive-ratio schedule in rats. | 2007-03-22 |
|
| Evidence for the role of dopamine D3 receptors in oral operant alcohol self-administration and reinstatement of alcohol-seeking behavior in mice. | 2007-03 |
|
| Habituation deficits induced by metabotropic glutamate receptors 2/3 receptor blockade in mice: reversal by antipsychotic drugs. | 2007-02 |
|
| The selective dopamine D3 receptor antagonist SB-277011A reduces nicotine-enhanced brain reward and nicotine-paired environmental cue functions. | 2006-10 |
|
| Acute administration of SB-277011A, NGB 2904, or BP 897 inhibits cocaine cue-induced reinstatement of drug-seeking behavior in rats: role of dopamine D3 receptors. | 2005-07 |
|
| Selective dopamine D3 receptor antagonism by SB-277011A attenuates cocaine reinforcement as assessed by progressive-ratio and variable-cost-variable-payoff fixed-ratio cocaine self-administration in rats. | 2005-06 |
|
| Blockade of mesolimbic dopamine D3 receptors inhibits stress-induced reinstatement of cocaine-seeking in rats. | 2004-10 |
|
| Acute administration of the selective D3 receptor antagonist SB-277011A blocks the acquisition and expression of the conditioned place preference response to heroin in male rats. | 2003-06-01 |
|
| Pharmacokinetics of the novel, high-affinity and selective dopamine D3 receptor antagonist SB-277011 in rat, dog and monkey: in vitro/in vivo correlation and the role of aldehyde oxidase. | 2001-09-25 |
|
| SB-277011 GlaxoSmithKline. | 2001-07 |
|
| Design and synthesis of trans-N-[4-[2-(6-cyano-1,2,3, 4-tetrahydroisoquinolin-2-yl)ethyl]cyclohexyl]-4-quinolinecarboxamide (SB-277011): A potent and selective dopamine D(3) receptor antagonist with high oral bioavailability and CNS penetration in the rat. | 2000-05-04 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 13:12:55 GMT 2025
by
admin
on
Wed Apr 02 13:12:55 GMT 2025
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CHW57ND47C
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Validated (UNII)
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CHW57ND47C
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DTXSID10944188
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