| Identification | Back Directory | [Name]
(R)-SLV 319 | [CAS]
656827-86-0 | [Synonyms]
(R)-SLV 319
SLV 319, (R)-(+)-
(4R)-5-(4-chlorophenyl)-N-(4-chlorophenyl)sulfonyl-N'-methyl-4-phenyl-3,4-dihydropyrazole-2-carboximidamide
4-chloro-N-{[3-(4-chloro-phenyl)-4-phenyl-4,5-dihydro-pyrazol-1-yl]-methylamino-methylene}-benzenesulfonamide
1H-Pyrazole-1-carboximidamide, 3-(4-chlorophenyl)-N-[(4-chlorophenyl)sulfonyl]-4,5-dihydro-N'-methyl-4-phenyl-, (4R)- | [Molecular Formula]
C23H20Cl2N4O2S | [MDL Number]
MFCD09951896 | [MOL File]
656827-86-0.mol | [Molecular Weight]
487.4 |
| Chemical Properties | Back Directory | [Boiling point ]
623.2±65.0 °C(Predicted) | [density ]
1.38±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
≤30mg/ml in ethanol;30mg/ml in DMSO;30mg/ml in dimethyl formamide | [form ]
crystalline solid | [pka]
11?+-.0.60(Predicted) |
| Hazard Information | Back Directory | [Description]
Central cannabinoid (CB1) receptor antagonists may have potential in the treatment of a number of diseases such as neuroinflammatory disorders, cognitive disorders, septic shock, obesity, psychosis, addiction, and gastrointestinal disorders. (R)-SLV 319 is the inactive enantiomer of SLV 319 with 100-fold less affinity for the CB1 receptor. SLV 319 is a potent and selective CB1 receptor antagonist with Ki values of 7.8 and 7,943 nM for CB1 and peripheral cannabinoid (CB2) receptors, respectively. SLV 319 is less lipophilic (log P = 5.1) and therefore more water soluble than other known CB1 receptor ligands. | [in vitro]
(r)-slv 319 is the inactive enantiomer of slv 319 with 100-fold less affinity for the cb1 receptor. slv 319 was identified as a potent and selective cb1 receptor antagonist with ki values of 7.8 and 7,943 nm for cb1 and peripheral cannabinoid (cb2) receptors, respectively. slv 319 was found to be less lipophilic and thus more water soluble than other known cb1 receptor ligands [1,2]. | [in vivo]
a previous animal study examined the chronic effects of slv 319 in hyperinsulinemic zucker rats to determine their chronic effects on insulinemia. results showed that r slv 319 at 10 mg·kg-1·day-1 elicited body weight-independent improvements in insulinemia and glycemia during 10 wk of chronic treatment. moreover, slv 319 treatment caused glucose intolerance in cb1 but not sur1-ko mice [3]. | [References]
[1] lange, j. h.m.,coolen, h.k.a.c.,van stuivenberg, h.h., et al. synthesis, biological properties, and molecular modeling investigations of novel 3,4-diarylpyrazolines as potent and selective cb1 cannabinoid receptor antagonists. journal of medicinal chemistry 47(3), 627-643 (2004).
[2] lange, j. h.m.,van stuivenberg, h.h.,veerman, w., et al. novel 3,4-diarylpyrazolines as potent cannabinoid cb1 receptor antagonists with lower lipophilicity. bioorganic & medicinal chemistry letters 15, 4794-4798 (2005).
[3] lynch cj, zhou q, shyng sl, heal dj, cheetham sc, dickinson k, gregory p, firnges m, nordheim u, goshorn s, reiche d, turski l, antel j. some cannabinoid receptor ligands and their distomers are direct-acting openers of sur1 k(atp) channels. am j physiol endocrinol metab. 2012 mar 1;302(5):e540-51. |
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