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106128-89-6,MFCD00076799
Catalog No.:AA00842I

106128-89-6 | (5S,8S,14S,17S,20S)-14,17-Dibenzyl-5-carbamoyl-20-(carboxymethyl)-8-isobutyl-15-methyl-7,10,13,16,19,22-hexaoxo-2-thia-6,9,12,15,18,21-hexaazapentacosan-25-oic acid

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1mg
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5mg
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10mg
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00842I
Chemical Name:
(5S,8S,14S,17S,20S)-14,17-Dibenzyl-5-carbamoyl-20-(carboxymethyl)-8-isobutyl-15-methyl-7,10,13,16,19,22-hexaoxo-2-thia-6,9,12,15,18,21-hexaazapentacosan-25-oic acid
CAS Number:
106128-89-6
Molecular Formula:
C40H55N7O11S
Molecular Weight:
841.9700
MDL Number:
MFCD00076799
SMILES:
CSCC[C@@H](C(=O)N)NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](N(C(=O)[C@@H](NC(=O)[C@@H](NC(=O)CCC(=O)O)CC(=O)O)Cc1ccccc1)C)Cc1ccccc1)CC(C)C
Properties
Computed Properties
 
Complexity:
1450  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Heavy Atom Count:
59  
Hydrogen Bond Acceptor Count:
12  
Hydrogen Bond Donor Count:
8  
Rotatable Bond Count:
26  
XLogP3:
1.1  

Literature

Title: Neurokinin B and the control of the gonadotropic axis in the rat: developmental changes, sexual dimorphism, and regulation by gonadal steroids.

Journal: Endocrinology 20121001

Title: The NK3 receptor agonist senktide ameliorates scopolamine-induced deficits in memory for object, place and temporal order.

Journal: Neurobiology of learning and memory 20120201

Title: Kisspeptin signaling is indispensable for neurokinin B, but not glutamate, stimulation of gonadotropin secretion in mice.

Journal: Endocrinology 20120101

Title: Activation of neurokinin 3 receptors in the median preoptic nucleus decreases core temperature in the rat.

Journal: Endocrinology 20111201

Title: NK3 receptors mediate an increase in firing rate of midbrain dopamine neurons of the rat and the guinea pig.

Journal: Synapse (New York, N.Y.) 20110801

Title: Neurokinin3-R agonism in aged rats has anxiolytic-, antidepressant-, and promnestic-like effects and stimulates ACh release in frontal cortex, amygdala and hippocampus.

Journal: European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology 20110601

Title: Interactions between kisspeptin and neurokinin B in the control of GnRH secretion in the female rat.

Journal: American journal of physiology. Endocrinology and metabolism 20110101

Title: Blockade of tachykinin NK3 receptor reverses hypertension through a dopaminergic mechanism in the ventral tegmental area of spontaneously hypertensive rats.

Journal: British journal of pharmacology 20101201

Title: Bronchoconstrictor effect of the tachykinin NK₃-receptor agonists [MePhe⁷]-neurokinin B and senktide in the isolated guinea pig lung.

Journal: Experimental lung research 20101101

Title: Neurokinin B acts via the neurokinin-3 receptor in the retrochiasmatic area to stimulate luteinizing hormone secretion in sheep.

Journal: Endocrinology 20100801

Title: In vitro and in vivo comparison of two non-peptide tachykinin NK3 receptor antagonists: Improvements in efficacy achieved through enhanced brain penetration or altered pharmacological characteristics.

Journal: European journal of pharmacology 20100210

Title: Pharmacological characterization of senktide-induced tail whips.

Journal: Neuropharmacology 20100101

Title: Hypogonadotropic hypogonadism due to a novel missense mutation in the first extracellular loop of the neurokinin B receptor.

Journal: The Journal of clinical endocrinology and metabolism 20091001

Title: Activation of neurokinin 3 receptor increases Na(v)1.9 current in enteric neurons.

Journal: The Journal of physiology 20090401

Title: The tachykinin NK3 receptor agonist senktide induces locomotor activity in male Mongolian gerbils.

Journal: European journal of pharmacology 20081214

Title: Localization and function of NK(3) subtype tachykinin receptors of layer V pyramidal neurons of the guinea-pig medial prefrontal cortex.

Journal: Neuroscience 20081028

Title: Characterization of behavioral response to amphetamine, tyrosine hydroxylase levels, and dopamine receptor levels in neurokinin 3 receptor knockout mice.

Journal: Behavioural pharmacology 20080901

Title: Neurokinin B/NK3 receptors exert feedback inhibition on L-DOPA actions in the 6-OHDA lesion rat model of Parkinson's disease.

Journal: Neuropharmacology 20080601

Title: Neurokinin receptor modulation of respiratory activity in the rabbit.

Journal: The European journal of neuroscience 20080601

Title: Stimulation of the neurokinin 3 receptor activates protein kinase C epsilon and protein kinase D in enteric neurons.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20080501

Title: Neurokinin-3 peptide instead of neurokinin-1 synergistically exacerbates kainic acid-inducing degeneration of neurons in the substantia nigra of mice.

Journal: Journal of neurochemistry 20080401

Title: Expression and coupling of neurokinin receptor subtypes to inositol phosphate and calcium signaling pathways in human airway smooth muscle cells.

Journal: American journal of physiology. Lung cellular and molecular physiology 20080301

Title: Contractile effect of tachykinins on Suncus murinus (house musk shrew) isolated ileum.

Journal: Neuropeptides 20080101

Title: Senktide-induced gerbil foot tapping behaviour is blocked by selective tachykinin NK1 and NK3 receptor antagonists.

Journal: European journal of pharmacology 20071222

Title: Inflammation and inflammatory agents activate protein kinase C epsilon translocation and excite guinea-pig submucosal neurons.

Journal: Gastroenterology 20071001

Title: Neurokinin 3 receptor activation potentiates the psychomotor and nucleus accumbens dopamine response to cocaine, but not its place conditioning effects.

Journal: The European journal of neuroscience 20070401

Title: N',2-diphenylquinoline-4-carbohydrazide based NK3 receptor antagonists II.

Journal: Bioorganic & medicinal chemistry letters 20061115

Title: Interaction of the tachykinin NK3 receptor agonist senktide with behavioral effects of cocaine in marmosets (Callithrix penicillata).

Journal: Peptides 20060901

Title: The role of tachykinins in circular muscle contractility of the murine ileum: a functional investigation.

Journal: Autonomic neuroscience : basic & clinical 20060630

Title: Upregulation of tachykinin NK-1 and NK-3 receptor binding sites in the spinal cord of spontaneously hypertensive rat: impact on the autonomic control of blood pressure.

Journal: British journal of pharmacology 20060501

Title: Increased substance P content in nerve fibers associated with mesenteric veins from deoxycorticosterone acetate (DOCA)-salt hypertensive rats.

Journal: Regulatory peptides 20060115

Title: Intraventricular injections of tachykinin NK3 receptor agonists suppress the intake of 'salty' tastes by sodium deficient rats.

Journal: Behavioural brain research 20060106

Title: The ventral tegmental area as a putative target for tachykinins in cardiovascular regulation.

Journal: British journal of pharmacology 20050701

Title: Loperamide inhibits tachykinin NK3-receptor-triggered serotonin release without affecting NK2-receptor-triggered serotonin release from guinea pig colonic mucosa.

Journal: Journal of pharmacological sciences 20050601

Title: Intraventricular injections of tachykinin NK3 receptor agonist reduce the gain of the baroreflex in unrestrained rats.

Journal: Experimental neurology 20050501

Title: A novel role for tachykinin neurokinin-3 receptors in regulation of human bronchial Ganglia neurons.

Journal: American journal of respiratory and critical care medicine 20050201

Title: Slow excitatory post-synaptic potentials in myenteric AH neurons of the guinea-pig ileum are reduced by the 5-hydroxytryptamine7 receptor antagonist SB 269970.

Journal: Neuroscience 20050101

Title: Role of neurokinin 3 receptors in supraoptic vasopressin and oxytocin neurons.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20041110

Title: Involvement of enhanced neurokinin NK3 receptor expression in the severe asthma guinea pig model.

Journal: European journal of pharmacology 20040913

Title: GABAergic basal forebrain neurons that express receptor for neurokinin B and send axons to the cerebral cortex.

Journal: The Journal of comparative neurology 20040517

Title: Effects of TAK-637 on NK(1) receptor-mediated mechanisms regulating colonic secretion.

Journal: Toxicology and applied pharmacology 20040415

Title: NK-3 receptor activation depolarizes and induces an after-depolarization in pyramidal neurons in gerbil cingulate cortex.

Journal: Brain research bulletin 20040315

Title: Effects of neuropeptides on the sumatriptan-disturbed circulation in the optic nerve head of rabbits.

Journal: Pharmacology 20040301

Title: Neurokinin-1 and -3 receptor blockade inhibits slow excitatory synaptic transmission in myenteric neurons and reveals slow inhibitory input.

Journal: Neuroscience 20040101

Title: Neurokinin type-3 receptor stimulation impairs ethanol-associated appetitive behavior in Wistar rats.

Journal: Alcoholism, clinical and experimental research 20031201

Title: Central neurokinin 3 receptors increase systemic oxytocin release: interaction with norepinephrine.

Journal: Experimental neurology 20031201

Title: 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: Journal of neurochemistry 20031001

Title: Tachykinin receptor (NK(1), NK(2), NK(3)) binding sites in the rat caudal brainstem following neonatal capsaicin administration.

Journal: Brain research 20030725

Title: Action of tachykinins in the rat hippocampus: modulation of inhibitory synaptic transmission.

Journal: The European journal of neuroscience 20030601

Title: Estrogen-dependent regulation of neurokinin 3 receptor-mediated uterine contractility in the rat.

Journal: Biology of reproduction 20021101

Title: Neurokinin-receptor-mediated depolarization of cortical neurons elicits an increase in glutamate release at excitatory synapses.

Journal: The European journal of neuroscience 20021101

Title: Neurokinins activate local glutamatergic inputs to serotonergic neurons of the dorsal raphe nucleus.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20020901

Title: Endogenous neurokinins facilitate synaptic transmission in guinea pig airway parasympathetic ganglia.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20020801

Title: Biochemical and pharmacological activities of SSR 146977, a new potent nonpeptide tachykinin NK3 receptor antagonist.

Journal: Canadian journal of physiology and pharmacology 20020501

Title: Selective tachykinin NK3-receptor agonists stimulate in vitro exocrine pancreatic secretion in the guinea pig.

Journal: Peptides 20020501

Title: Peripheral activity of a new NK1 receptor antagonist TAK-637 in the gastrointestinal tract.

Journal: The Journal of pharmacology and experimental therapeutics 20020301

Title: Facilitation by endogenous tachykinins of the NMDA-evoked release of acetylcholine after acute and chronic suppression of dopaminergic transmission in the matrix of the rat striatum.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20020301

Title: Permissive role of neurokinin NK(3) receptors in NK(1) receptor-mediated activation of the locus coeruleus revealed by SR 142801.

Journal: Synapse (New York, N.Y.) 20020101

Title: Nonpeptide tachykinin receptor antagonists. III. SB 235375, a low central nervous system-penetrant, potent and selective neurokinin-3 receptor antagonist, inhibits citric acid-induced cough and airways hyper-reactivity in guinea pigs.

Journal: The Journal of pharmacology and experimental therapeutics 20020101

Title: Neuronal bursting induced by NK3 receptor activation in the neonatal rat spinal cord in vitro.

Journal: Journal of neurophysiology 20011201

Title: Modulation of cardiac activity by tachykinins in the rat substantia nigra.

Journal: British journal of pharmacology 20011201

Title: Radioligand binding and functional characterisation of tachykinin receptors in chicken small intestine.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20011001

Title: Tachykinins mediate slow excitatory postsynaptic transmission in guinea pig sphincter of Oddi ganglia.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20010801

Title: Peripheral inflammation reduces the response of spinal dorsal horn neurons to an NK3 receptor agonist.

Journal: Neuroscience letters 20010727

Title: Pharmacological characterization of ZD6021: a novel, orally active antagonist of the tachykinin receptors.

Journal: The Journal of pharmacology and experimental therapeutics 20010701

Title: Priming effects of substance P on calcium changes evoked by interleukin-8 in human neutrophils.

Journal: Journal of leukocyte biology 20010601

Title: Contribution of NK3 tachykinin receptors to propulsion in the rabbit isolated distal colon.

Journal: Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society 20010601

Title: Differential expression of functionally identified and immunohistochemically identified NK(1) receptors on sympathetic neurons.

Journal: Journal of neurophysiology 20010501

Title: Potent NK1 antagonism by SR-140333 reduces rat colonic secretory response to immunocyte activation.

Journal: American journal of physiology. Cell physiology 20010401

Title: Molecular and pharmacological characterization of the murine tachykinin NK(3) receptor.

Journal: European journal of pharmacology 20010216

Title: NK2 tachykinin receptors mediate contraction of the pig intravesical ureter: tachykinin-induced enhancement of non-adrenergic non-cholinergic excitatory neurotransmission.

Journal: Neurourology and urodynamics 20010101

Title: Nonpeptide tachykinin receptor antagonists. II. Pharmacological and pharmacokinetic profile of SB-222200, a central nervous system penetrant, potent and selective NK-3 receptor antagonist.

Journal: The Journal of pharmacology and experimental therapeutics 20001001

Title: Nonpeptide tachykinin receptor antagonists: I. Pharmacological and pharmacokinetic characterization of SB 223412, a novel, potent and selective neurokinin-3 receptor antagonist.

Journal: The Journal of pharmacology and experimental therapeutics 19970601

Title: The unpredicted high affinities of a large number of naturally occurring tachykinins for chimeric NK1/NK3 receptors suggest a role for an inhibitory domain in determining receptor specificity.

Journal: The Journal of biological chemistry 19960823

Title: 2-Phenyl-4-quinolinecarboxamides: a novel class of potent and selective non-peptide competitive antagonists for the human neurokinin-3 receptor.

Journal: Journal of medicinal chemistry 19960607

Title: Use of a dipeptide chemical library in the development of non-peptide tachykinin NK3 receptor selective antagonists.

Journal: Journal of medicinal chemistry 19960412

Title: GR138676, a novel peptidic tachykinin antagonist which is potent at NK3 receptors.

Journal: Neuropeptides 19941201

Title: Molecular characterisation, expression and localisation of human neurokinin-3 receptor.

Journal: FEBS letters 19920324

Title: Highly selective agonists for substance P receptor subtypes.

Journal: The EMBO journal 19861101

Title: Characterization of a neurokinin B receptor site in rat brain using a highly selective radioligand.

Journal: The Journal of biological chemistry 19860805

Title: Nordquist RE, et al. The tachykinin NK3 receptor agonist senktide induces locomotor activity in male Mongolian gerbils. Eur J Pharmacol. 2008 Dec 14;600(1-3):87-92.

Title: Keegan KD, et al. The selective NK3 receptor agonist senktide excites a subpopulation of dopamine-sensitiveneurones in the rat substantia nigra pars compacta in vitro. Br J Pharmacol. 1992 Jan;105(1):3-5.

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SDS
Tags:106128-89-6 Molecular Formula|106128-89-6 MDL|106128-89-6 SMILES|106128-89-6 (5S,8S,14S,17S,20S)-14,17-Dibenzyl-5-carbamoyl-20-(carboxymethyl)-8-isobutyl-15-methyl-7,10,13,16,19,22-hexaoxo-2-thia-6,9,12,15,18,21-hexaazapentacosan-25-oic acid