Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C15H20Cl2N2O3.C4H6O6 |
Molecular Weight | 497.324 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@H]([C@@H](O)C(O)=O)C(O)=O.CCN1CCC[C@H]1CNC(=O)C2=C(O)C(Cl)=CC(Cl)=C2OC
InChI
InChIKey=QULBVRZTKPQGCR-NDAAPVSOSA-N
InChI=1S/C15H20Cl2N2O3.C4H6O6/c1-3-19-6-4-5-9(19)8-18-15(21)12-13(20)10(16)7-11(17)14(12)22-2;5-1(3(7)8)2(6)4(9)10/h7,9,20H,3-6,8H2,1-2H3,(H,18,21);1-2,5-6H,(H,7,8)(H,9,10)/t9-;1-,2-/m01/s1
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/3131792 | https://www.ncbi.nlm.nih.gov/pubmed/3873656 | https://www.ncbi.nlm.nih.gov/pubmed/27286237 | https://www.ncbi.nlm.nih.gov/pubmed/21678422https://www.ncbi.nlm.nih.gov/pubmed/2975809Curator's Comment: the description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/24848155 | https://www.ncbi.nlm.nih.gov/pubmed/17765546 | https://www.drugs.com/mmx/raclopride-c-11.html
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3131792 | https://www.ncbi.nlm.nih.gov/pubmed/3873656 | https://www.ncbi.nlm.nih.gov/pubmed/27286237 | https://www.ncbi.nlm.nih.gov/pubmed/21678422https://www.ncbi.nlm.nih.gov/pubmed/2975809
Curator's Comment: the description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/24848155 | https://www.ncbi.nlm.nih.gov/pubmed/17765546 | https://www.drugs.com/mmx/raclopride-c-11.html
Raclopride is a salicylamide neuroleptic, that acts as a selective antagonist of D2 dopamine receptors both in vitro and in vivo. Tritium-labelled raclopride has properties that demonstrate its usefulness as a radioligand for the labelling of dopamine-D2 receptors : 3H-Raclopride has a high affinity for the rat and human dopamine-D2 receptors, the non-specific binding of 3H-raclopride is very low, not exceeding 5% of the total binding and the distribution of the 3H-raclopride binding sites in the brain closely correlates with the dopaminergic innervation. The binding of 3H-raclopride is blocked by dopamine-D2 agonists and antagonists, while the D1 agonist SKF 38393 and the Dl antagonist SCH 23390 have much less potency. The interaction of dopamine with 3H-raclopride binding results in a shallow competition curve, which suggests that 3H-raclopride, similar to other dopamine-D2 radioligands, labels both high and low agonist affinity states of the dopamine-D2 receptor. The in vivo receptor binding studies performed with 3H-raclopride also demonstrate its favorable properties as a dopamine-D2 receptor marker in vivo In contrast to some other compounds used as radioligands, raclopride enters the brain readily and binds with a low component of non-specific binding in all dopamine-rich brain areas. A saturation curve may be achieved in vivo binding studies since injections of increasing concentrations of 3H-raclopride appears to be saturated at concentrations above 25 mkCi (corresponding to approximately 5 nmol/kg). Raclopride antagonizes apomorphine-induced hyperactivity in the rat at low doses (ED50 = 130 nM/kg i.p.) but induces catalepsy only at much higher doses (ED50 = 27 mkM/kg i.p.). Radiolabelled raclopride has been used as a ligand for in vitro and in vivo autoradiography in rat and primate brains. Raclopride C 11 is used with positron emission tomography (PET) as a clinical research tool to determine dopamine type 2 (D 2) receptor density in the human brain under normal and pathological conditions. For example, raclopride C 11 used in PET studies has served to confirm the age-related decrease in striatal dopamine D2 receptor density, which may be associated with a decline in the motor as well as cognitive functions. In patients with Alzheimer's disease, raclopride C 11 may be used to examine neuroreceptor distribution and quantities, which may help in the analysis of degenerative alterations of neuron populations and neuroreceptor systems in patients with this disease. In Huntington's disease, in which degeneration of neostriatal interneurons occurs (postsynaptic to the dopaminergic input), specific binding of raclopride C 11 to D 2 receptors may serve as one of the parameters in predicting performance in cognitive tasks.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24848155 |
12.7 nM [Ki] | ||
Target ID: CHEMBL234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24848155 |
13.4 nM [Ki] | ||
Target ID: CHEMBL219 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17765546 |
3100.0 nM [Ki] | ||
Target ID: CHEMBL2096905 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2391685 |
8.7 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Stereoselective binding of 11C-raclopride in living human brain--a search for extrastriatal central D2-dopamine receptors by PET. | 1988 |
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Effects of the atypical neuroleptic clozapine on micturition parameters in anesthetized rats. | 2001 |
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A consideration of the dopamine D2 receptor monomer-dimer equilibrium and the anomalous binding properties of the dopamine D2 receptor ligand, N-methyl spiperone. | 2001 |
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Nigral neurotensin receptor regulation of nigral glutamate and nigroventral thalamic GABA transmission: a dual-probe microdialysis study in intact conscious rat brain. | 2001 |
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D1 but not D2 dopamine receptor antagonism blocks the acquisition of a flavor preference conditioned by intragastric carbohydrate infusions. | 2001 Apr |
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The role of D2-like dopamine receptors in the locomotor stimulant effects of cocaine in mice. | 2001 Apr |
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D2 dopamine receptor-G protein coupling. Cross-regulation of agonist and guanosine nucleotide binding sites. | 2001 Apr 13 |
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beta-Phenylethylamine modulates acetylcholine release in the rat striatum: involvement of a dopamine D(2) receptor mechanism. | 2001 Apr 20 |
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Effect of endogenous dopamine on extrastriatal [¹¹C]FLB 457 binding measured by PET. | 2001 Aug |
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Repetitive transcranial magnetic stimulation of the human prefrontal cortex induces dopamine release in the caudate nucleus. | 2001 Aug 1 |
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Functional neuroanatomy of the ventral striopallidal GABA pathway. New sites of intervention in the treatment of schizophrenia. | 2001 Aug 15 |
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Facilitation of dopaminergic neural transmission does not affect [(11)C]SCH23390 binding to the striatal D(1) dopamine receptors, but the facilitation enhances phosphodiesterase type-IV activity through D(1) receptors: PET studies in the conscious monkey brain. | 2001 Dec 15 |
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A PET study with [11-C]raclopride in Parkinson's disease: preliminary results on the effect of amantadine on the dopaminergic system. | 2001 Feb |
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Dinapsoline: characterization of a D1 dopamine receptor agonist in a rat model of Parkinson's disease. | 2001 Feb |
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Increased dopamine d(2) receptor occupancy and elevated prolactin level associated with addition of haloperidol to clozapine. | 2001 Feb |
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Effects of acute and repeated treatment with a novel dopamine D2 receptor ligand on L-DOPA-induced dyskinesias in MPTP monkeys. | 2001 Feb 2 |
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Negative interaction of dopamine D2 receptor antagonists and GBR 12909 and GBR 12935 dopamine uptake inhibitors in the nucleus accumbens. | 2001 Feb 23 |
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Receptor-mediated regulation of serotonin output in the rat dorsal raphe nucleus: effects of risperidone. | 2001 Jan |
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Kinetics of the metabolism of four PET radioligands in living minipigs. | 2001 Jan |
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A Peltier thermal cycling unit for radiopharmaceutical synthesis. | 2001 Jan |
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Biochemical and immunohistological changes in the brain of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-treated mouse. | 2001 Jan |
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Pharmacology of [3H]R(+)-7-OH-DPAT binding in the rat caudate-putamen. | 2001 Jan |
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Studies on the involvement of the dopaminergic system in the 5-HT2 agonist (DOI)-induced premature responding in a five-choice serial reaction time task. | 2001 Jan 1 |
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Prepulse inhibition deficits and perseverative motor patterns in dopamine transporter knock-out mice: differential effects of D1 and D2 receptor antagonists. | 2001 Jan 1 |
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Therapeutic doses of oral methylphenidate significantly increase extracellular dopamine in the human brain. | 2001 Jan 15 |
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Antipsychotic drugs classified by their effects on the release of dopamine and noradrenaline in the prefrontal cortex and striatum. | 2001 Jan 26 |
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Delta 9-tetrahydrocannabinol-induced MAPK/ERK and Elk-1 activation in vivo depends on dopaminergic transmission. | 2001 Jul |
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Additive hypothermic effects of the 5-HT1A receptor agonist 8-OH-DPAT and the dopamine D2/3 receptor agonist 7-OH-DPAT in the rat. | 2001 Jul |
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A simple loop method for the automated preparation of (11C)raclopride from (11C)methyl triflate. | 2001 Jul |
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Atropine acts in the ventral striatum to reduce raclopride-induced catalepsy. | 2001 Jul 27 |
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D1 or D2 antagonism in nucleus accumbens core or dorsomedial shell suppresses lever pressing for food but leads to compensatory increases in chow consumption. | 2001 Jul-Aug |
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Vulnerability of positron emission tomography radiotracers to endogenous competition. New insights. | 2001 Jun |
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No support for regional selectivity in clozapine-treated patients: a PET study with [(11)C]raclopride and [(11)C]FLB 457. | 2001 Jun |
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Effects of dopamine antagonists with different receptor blockade profiles on morphine-induced place preference in male mice. | 2001 Jun |
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Dopamine, but not glutamate, receptor blockade in the basolateral amygdala attenuates conditioned reward in a rat model of relapse to cocaine-seeking behavior. | 2001 Mar |
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Interactions of histogranin and related peptides with dopamine D2 receptor in rat brain membranes. | 2001 Mar 1 |
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The imidazoline receptor ligand 2-(2-benzofuranyl)-2-imidazoline is a dopamine-releasing agent in the rat striatum in vivo. | 2001 Mar 23 |
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Dopaminergic retinal cell differentiation in culture: modulation by forskolin and dopamine. | 2001 May |
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Dopamine-dependent inhibition of glycine release in the nucleus accumbens of the rat brain during food consumption. | 2001 May-Jun |
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[11C]Raclopride binding was reduced in vivo by sigma(1) receptor ligand SA4503 in the mouse brain, while [11C]SA4503 binding was not by raclopride. | 2001 Oct |
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Imaging human mesolimbic dopamine transmission with positron emission tomography: I. Accuracy and precision of D(2) receptor parameter measurements in ventral striatum. | 2001 Sep |
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Positron emission tomography of dopamine pathways in familial Parkinsonian syndromes. | 2001 Sep |
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Demonstration of competition between endogenous dopamine and [11C]raclopride binding in in vitro brain slices using a dynamic autoradiography technique. | 2002 Apr |
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Amphetamine-induced dopamine release and post-synaptic specific binding in patients with mild tardive dyskinesia. | 2002 Mar |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22886761
Primary cultures of rat neonatal ventricular cardiac myocytes were prepared by enzymatic digestion of ventricle tissue with 0.25% trypsin. The cardiomyocytes were first plated for 2 h to reduce non-myocyte contamination. The cells were then washed to remove erythrocytes, replated at a density of 2.0x10^6 cells in culture flasks and incubated at 37C in the presence of 5% CO2 in a humidified incubator. 2.0x10^6 neonatal rat ventricular myocytes were treated with 40 mkM of Raclopride for 24 h.
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98185-20-7
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ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD