(±)-SLV 319

CB1 receptor antagonist,potent and selective CAS# 362519-49-1

(±)-SLV 319

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Chemical structure

(±)-SLV 319

3D structure

Chemical Properties of (±)-SLV 319

Cas No. 362519-49-1 SDF Download SDF
PubChem ID 11179267 Appearance Powder
Formula C23H20Cl2N4O2S M.Wt 487.4
Type of Compound N/A Storage Desiccate at -20°C
Synonyms (±)-Ibipinabant; (±)-BMS6462
Solubility DMSO : ≥ 31 mg/mL (63.60 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name 5-(4-chlorophenyl)-N-(4-chlorophenyl)sulfonyl-N'-methyl-4-phenyl-3,4-dihydropyrazole-2-carboximidamide
SMILES CN=C(NS(=O)(=O)C1=CC=C(C=C1)Cl)N2CC(C(=N2)C3=CC=C(C=C3)Cl)C4=CC=CC=C4
Standard InChIKey AXJQVVLKUYCICH-UHFFFAOYSA-N
Standard InChI InChI=1S/C23H20Cl2N4O2S/c1-26-23(28-32(30,31)20-13-11-19(25)12-14-20)29-15-21(16-5-3-2-4-6-16)22(27-29)17-7-9-18(24)10-8-17/h2-14,21H,15H2,1H3,(H,26,28)
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of (±)-SLV 319

DescriptionPotent and selective CB1 receptor antagonist (Ki = 7.8 nM). Exhibits 1000-fold selectivity for CB1 over CB2 receptors. Inhibits CP 55,940-induced hypotension and WIN 55,212-2-induced hypothermia in vivo. Orally active.

(±)-SLV 319 Dilution Calculator

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(±)-SLV 319 Molarity Calculator

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Preparing Stock Solutions of (±)-SLV 319

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.0517 mL 10.2585 mL 20.517 mL 41.0341 mL 51.2926 mL
5 mM 0.4103 mL 2.0517 mL 4.1034 mL 8.2068 mL 10.2585 mL
10 mM 0.2052 mL 1.0259 mL 2.0517 mL 4.1034 mL 5.1293 mL
50 mM 0.041 mL 0.2052 mL 0.4103 mL 0.8207 mL 1.0259 mL
100 mM 0.0205 mL 0.1026 mL 0.2052 mL 0.4103 mL 0.5129 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on (±)-SLV 319

SLV 319 is described here instead of (±)-SLV 319. SLV 319, also called ibipinabant, is a CB1 antagonist with an IC50 value of 22 nM [1, 2].

There are 2 types of cannabinoid receptors (CB1 and CB2). Their endogenous ligands are primarily anandamide and 2-AG. Cannabinoid receptors and their endogenous ligands together are prominent in the control of food intake and energy metabolism. Stimulation of this endocannabinoid system triggers metabolic processes and leads to lipogenesis, weight gain, insulin resistance, dyslipidemias and impaired glucose homeostasis [2].

C2C12 murine myoblasts were model cells. Exposure to increasing concentrations of ibipinabant at the highest concentration tested (100 μM) for 24 hours significantly decreased cell viability to 73 ± 5%. After 48 hours of exposure to the drug at this concentration only 33 ± 4% of cells remained viable. Cellular reactive oxygen species (ROS) generation is an index of mitochondrial function. A more than 2-fold increase in cellular ROS generation could already be observed after 8 hours exposure to ibipinabant at a concentration of 100 μM compared to the vehicle treated C2C12 myoblasts [3].

CB1 receptor occupancy was related to potencies to increase dopamine (DA) and norepinephrine (NE) releases. In the medial prefrontal cortex (mPFC), SLV 319 caused a significant increase in the extracellular DA level at 10 mg/kg. The time course of the effects of SLV 319 and SR141716A at the 10-mg/kg dose appeared to be similar with peak effects at 30 and 180 min. But SLV 319 showed a more pronounced biphasic effect on DA release. SLV319 administration caused significant increases in extracellular concentrations of 3,4-dihydroxyphenylacetic acid (DOPAC) and homovanillic acid (HVA), metabolites of DA and NE, after the 10-mg/kg dose in rat [4].

References:
[1].  Srivastava BK, Soni R, Joharapurkar A, et al. Bioisosteric replacement of dihydropyrazole of 4S-(-)-3-(4-chlorophenyl)-N-methyl-N’-[(4-chlorophenyl)-
sulfonyl]-4-phenyl-4,5-dihydro-1H-pyrazole-1-caboxamidine (SLV-319) a potent CB1 receptor antagonist by imidazole and oxazole.  Bioorganic & medicinal chemistry letters, 2008, 18(3): 963-968.
[2].  Chorvat RJ, Berbaum J, Seriacki K, et al. JD-5006 and JD-5037: peripherally restricted (PR) cannabinoid-1 receptor blockers related to SLV-319 (Ibipinabant) as metabolic disorder therapeutics devoid of CNS liabilities. Bioorganic & medicinal chemistry letters, 2012, 22(19): 6173-6180.
[3].  Schirris TJJ, Ritschel T, Renkema GH, et al. Mitochondrial ADP/ATP exchange inhibition: a novel off-target mechanism underlying ibipinabant-induced myotoxicity. Scientific reports, 2015, 5.
[4].  Need AB, Davis RJ, Alexander-Chacko JT, et al. The relationship of in vivo central CB1 receptor occupancy to changes in cortical monoamine release and feeding elicited by CB1 receptor antagonists in rats. Psychopharmacology, 2006, 184(1): 26-35.

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References on (±)-SLV 319

JD-5006 and JD-5037: peripherally restricted (PR) cannabinoid-1 receptor blockers related to SLV-319 (Ibipinabant) as metabolic disorder therapeutics devoid of CNS liabilities.[Pubmed:22959249]

Bioorg Med Chem Lett. 2012 Oct 1;22(19):6173-80.

Analogs of SLV-319 (Ibipinibant), a CB1 receptor inverse agonist, were synthesized with functionality intended to limit brain exposure while maintaining the receptor affinity and selectivity of the parent compound. Structure activity relationships of this series, and pharmacology of two lead compounds, 16 (JD-5006) and 23 (JD-5037) showing little brain presence as indicated by tissue distribution and receptor occupancy studies, are described. Effects with one of these compounds on plasma triglyceride levels, liver weight and enzymes, glucose tolerance and insulin sensitivity support the approach that blockade of peripheral CB(1) receptors is sufficient to produce many of the beneficial metabolic effects of globally active CB(1) blockers. Thus, PR CB(1) inverse agonists may indeed represent a safer alternative to highly brain-penetrant agents for the treatment of metabolic disorders, including diabetes, liver diseases, dyslipidemias, and obesity.

Bioisosteric replacement of dihydropyrazole of 4S-(-)-3-(4-chlorophenyl)-N-methyl-N'-[(4-chlorophenyl)-sulfonyl]-4-phenyl-4,5-di hydro-1H-pyrazole-1-caboxamidine (SLV-319) a potent CB1 receptor antagonist by imidazole and oxazole.[Pubmed:18207393]

Bioorg Med Chem Lett. 2008 Feb 1;18(3):963-8.

Design, synthesis and conformational analysis of few imidazole and oxazole as bioisosters of 4S-(-)-3-(4-chlorophenyl)-N-methyl-N'-[(4-chlorophenyl)-sulfonyl]-4-phenyl-4,5-di hydro-1H-pyrazole-1-caboxamidine (SLV-319) 2 is reported. Computer assisted conformational analysis gave a direct clue for the loss of CB1 antagonistic activity of the ligands without a fine docking simulation for the homology model.

Novel 3,4-diarylpyrazolines as potent cannabinoid CB1 receptor antagonists with lower lipophilicity.[Pubmed:16140010]

Bioorg Med Chem Lett. 2005 Nov 1;15(21):4794-8.

Novel 3,4-diarylpyrazolines 1 as potent CB1 receptor antagonists with lipophilicity lower than that of SLV319 are described. The key change is the replacement of the arylsulfonyl group in the original series by a dialkylaminosulfonyl moiety. The absolute configuration (4S) of eutomer 24 was established by X-ray diffraction analysis and 24 showed a close molecular fit with rimonabant in a CB1 receptor-based model. Compound 17 exhibited the highest CB1 receptor affinity (Ki = 24 nM) in this series, as well as very potent CB1 antagonistic activity (pA2 = 8.8) and a high CB1/CB2 subtype selectivity (approximately 147-fold).

Synthesis, biological properties, and molecular modeling investigations of novel 3,4-diarylpyrazolines as potent and selective CB(1) cannabinoid receptor antagonists.[Pubmed:14736243]

J Med Chem. 2004 Jan 29;47(3):627-43.

A series of novel 3,4-diarylpyrazolines was synthesized and evaluated in cannabinoid (hCB(1) and hCB(2)) receptor assays. The 3,4-diarylpyrazolines elicited potent in vitro CB(1) antagonistic activities and in general exhibited high CB(1) vs CB(2) receptor subtype selectivities. Some key representatives showed potent pharmacological in vivo activities after oral dosing in both a CB agonist-induced blood pressure model and a CB agonist-induced hypothermia model. Chiral separation of racemic 67, followed by crystallization and an X-ray diffraction study, elucidated the absolute configuration of the eutomer 80 (SLV319) at its C(4) position as 4S. Bioanalytical studies revealed a high CNS-plasma ratio for the development candidate 80. Molecular modeling studies showed a relatively close three-dimensional structural overlap between 80 and the known CB(1) receptor antagonist rimonabant (SR141716A). Further analysis of the X-ray diffraction data of 80 revealed the presence of an intramolecular hydrogen bond that was confirmed by computational methods. Computational models and X-ray diffraction data indicated a different intramolecular hydrogen bonding pattern in the in vivo inactive compound 6. In addition, X-ray diffraction studies of 6 revealed a tighter intermolecular packing than 80, which also may contribute to its poorer absorption in vivo. Replacement of the amidine -NH(2) moiety with a -NHCH(3) group proved to be the key change for gaining oral biovailability in this series of compounds leading to the identification of 80.

Description

(±)-Ibipinabant ((±)-SLV319) is the racemate of SLV319. (±)-Ibipinabant ((±)-SLV319) is a potent and selective cannabinoid-1 (CB-1) receptor antagonist with an IC50 of 22 nM.

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