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GR 205171

CAS No.:
168266-90-8
Catalog Number:
AG00AP1U
Molecular Formula:
C21H23F3N6O
Molecular Weight:
432.4421
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
99%
1 week
United States
$543
- +
10mg
99%
1 week
United States
$821
- +
50mg
99%
1 week
United States
$2348
- +
100mg
99%
1 week
United States
$3182
- +
Product Description
Catalog Number:
AG00AP1U
Chemical Name:
GR 205171
CAS Number:
168266-90-8
Molecular Formula:
C21H23F3N6O
Molecular Weight:
432.4421
MDL Number:
MFCD06199014
IUPAC Name:
(2S,3S)-N-[[2-methoxy-5-[5-(trifluoromethyl)tetrazol-1-yl]phenyl]methyl]-2-phenylpiperidin-3-amine
InChI:
InChI=1S/C21H23F3N6O/c1-31-18-10-9-16(30-20(21(22,23)24)27-28-29-30)12-15(18)13-26-17-8-5-11-25-19(17)14-6-3-2-4-7-14/h2-4,6-7,9-10,12,17,19,25-26H,5,8,11,13H2,1H3/t17-,19-/m0/s1
InChI Key:
XILNRORTJVDYRH-HKUYNNGSSA-N
SMILES:
COc1ccc(cc1CNC1CCCNC1c1ccccc1)n1nnnc1C(F)(F)F
UNII:
K08BK043YS
Properties
Complexity:
562  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Defined Bond Stereocenter Count:
0
Exact Mass:
432.189g/mol
Formal Charge:
0
Heavy Atom Count:
31  
Hydrogen Bond Acceptor Count:
9  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
432.451g/mol
Monoisotopic Mass:
432.189g/mol
Rotatable Bond Count:
6  
Topological Polar Surface Area:
76.9A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3.1  
Literature
Title Journal
A pharmacokinetic PET study of NK₁ receptor occupancy. European journal of nuclear medicine and molecular imaging 20120201
Discovery and biological characterization of (2R,4S)-1'-acetyl-N-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}-2-(4-fluoro-2-methylphenyl)-N-methyl-4,4'-bipiperidine-1-carboxamide as a new potent and selective neurokinin 1 (NK1) receptor antagonist clinical candidate. Journal of medicinal chemistry 20110224
Potentiation of the anticonvulsant efficacy of sodium channel inhibitors by an NK1-receptor antagonist in the rat. Epilepsia 20100801
Discovery process and pharmacological characterization of 2-(S)-(4-fluoro-2-methylphenyl)piperazine-1-carboxylic acid [1-(R)-(3,5-bis-trifluoromethylphenyl)ethyl]methylamide (vestipitant) as a potent, selective, and orally active NK1 receptor antagonist. Journal of medicinal chemistry 20090528
Inhibition of the bradycardic component of the von Bezold-Jarisch reflex and carotid chemoreceptor reflex by periaqueductal gray stimulation: involvement of medullary receptors. The European journal of neuroscience 20090501
Neurokinin1 antagonists potentiate antidepressant properties of serotonin reuptake inhibitors, yet blunt their anxiogenic actions: a neurochemical, electrophysiological, and behavioral characterization. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20090301
Differential effects of dexamethasone, ondansetron and a tachykinin NK1 receptor antagonist (GR205171) on cisplatin-induced changes in behaviour, food intake, pica and gastric function in rats. European journal of pharmacology 20070126
Synthesis of two potential NK1-receptor ligands using [1-11C]ethyl iodide and [1-11C]propyl iodide and initial PET-imaging. BMC medical imaging 20070101
A new application of pre-normalized principal component analysis for improvement of image quality and clinical diagnosis in human brain PET studies--clinical brain studies using [11C]-GR205171, [11C]-L-deuterium-deprenyl, [11C]-5-Hydroxy-L-Tryptophan, [11C]-L-DOPA and Pittsburgh Compound-B. NeuroImage 20061101
Proteomic analysis of rat hippocampus and frontal cortex after chronic treatment with fluoxetine or putative novel antidepressants: CRF1 and NK1 receptor antagonists. European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology 20061001
Blockade of tachykinin NK1 receptors attenuates stress-induced rise of extracellular noradrenaline and dopamine in the rat and gerbil medial prefrontal cortex. Journal of neuroscience research 20061001
Antidepressant-like activity of selective serotonin reuptake inhibitors combined with a NK1 receptor antagonist in the mouse forced swimming test. Behavioural brain research 20060925
[3H]GR205171 displays similar NK1 receptor binding profile in gerbil and human brain. British journal of pharmacology 20060501
Use of LC/MS to assess brain tracer distribution in preclinical, in vivo receptor occupancy studies: dopamine D2, serotonin 2A and NK-1 receptors as examples. Life sciences 20051212
Sustained pharmacological blockade of NK1 substance P receptors causes functional desensitization of dorsal raphe 5-HT 1A autoreceptors in mice. Journal of neurochemistry 20051201
Antidepressant-like effects of agomelatine, melatonin and the NK1 receptor antagonist GR205171 in impulsive-related behaviour in rats. Psychopharmacology 20051001
TRPV1 activation results in disruption of the blood-brain barrier in the rat. British journal of pharmacology 20051001
Cerebral blood flow changes after treatment of social phobia with the neurokinin-1 antagonist GR205171, citalopram, or placebo. Biological psychiatry 20050715
Functional interaction between nucleus tractus solitarius NK1 and 5-HT3 receptors in the inhibition of baroreflex in rats. Cardiovascular research 20050301
Blockade of substance P (neurokinin 1) receptors enhances extracellular serotonin when combined with a selective serotonin reuptake inhibitor: an in vivo microdialysis study in mice. Journal of neurochemistry 20040401
Stress-induced increase of cortical dopamine metabolism: attenuation by a tachykinin NK1 receptor antagonist. European journal of pharmacology 20040119
The new neurokinin 1-sensitive receptor mediates the facilitation by endogenous tachykinins of the NMDA-evoked release of acetylcholine after suppression of dopaminergic transmission in the matrix of the rat striatum. Journal of neurochemistry 20031001
Contribution of tachykinin receptor subtypes to micturition reflex in guinea pigs. European journal of pharmacology 20030923
Comparison of the functional blockade of rat substance P (NK1) receptors by GR205171, RP67580, SR140333 and NKP-608. Neuropharmacology 20030801
Effects of antidepressant drugs and GR 205171, an neurokinin-1 (NK1) receptor antagonist, on the response in the forced swim test and on monoamine extracellular levels in the frontal cortex of the mouse. Neuroscience letters 20030717
Control by tachykinin NK(2) receptors of CRF(1) receptor-mediated activation of hippocampal acetylcholine release in the rat and guinea-pig. Neuropeptides 20030401
The selective neurokinin (NK)(1) antagonist, GR205,171, stereospecifically enhances mesocortical dopaminergic transmission in the rat: a combined dialysis and electrophysiological study. Brain research 20020510
Stereospecific blockade of marble-burying behaviour in mice by selective, non-peptidergic neurokinin1 (NK1) receptor antagonists. Neuropharmacology 20020401
Permissive role of neurokinin NK(3) receptors in NK(1) receptor-mediated activation of the locus coeruleus revealed by SR 142801. Synapse (New York, N.Y.) 20020101
Role of tachykinin receptors in the central processing of afferent input from the acid-threatened rat stomach. Regulatory peptides 20011215
Comparison of the phenotype of NK1R-/- mice with pharmacological blockade of the substance P (NK1 ) receptor in assays for antidepressant and anxiolytic drugs. Behavioural pharmacology 20011101
Selective blockade of neurokinin (NK)(1) receptors facilitates the activity of adrenergic pathways projecting to frontal cortex and dorsal hippocampus in rats. Journal of neurochemistry 20010301
Nitric oxide and NK(1)-tachykinin receptors in cyclophosphamide-induced cystitis, in rats. The Journal of pharmacology and experimental therapeutics 20001101
Structural optimization affording 2-(R)-(1-(R)-3, 5-bis(trifluoromethyl)phenylethoxy)-3-(S)-(4-fluoro)phenyl-4- (3-oxo-1,2,4-triazol-5-yl)methylmorpholine, a potent, orally active, long-acting morpholine acetal human NK-1 receptor antagonist. Journal of medicinal chemistry 19981105
GR205171: a novel antagonist with high affinity for the tachykinin NK1 receptor, and potent broad-spectrum anti-emetic activity. Regulatory peptides 19960827
Properties