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SLV-319

CAS No.
362519-49-1
Chemical Name:
SLV-319
Synonyms
(±)-BMS6462);(+/-)-SLV319;SLV 319;SLV-319;rac-(±)-SLV 319;(±)-SLV319(Ibipinabant);(±)-Ibipinabant((±)-SLV319;Inhibitor,(±)-Ibipinabant,Cannabinoid Receptor,(±) Ibipinabant,inhibit,(±)Ibipinabant;3-(4-Chlorophenyl)-N-((4-chlorophenyl)sulfonyl)-N'-methyl-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboximidamide;3-(4-Chlorophenyl)-N-[(4-Chlorophenyl)sulfonyl]-4,5-dihydro-N'-methyl-4-phenyl-1H-pyrazole-1-carboximidamide;1H-Pyrazole-1-carboximidamide, 3-(4-chlorophenyl)-N-[(4-chlorophenyl)sulfonyl]-4,5-dihydro-N'-methyl-4-phenyl-
CBNumber:
CB61463426
Molecular Formula:
C23H20Cl2N4O2S
Molecular Weight:
487.4
MDL Number:
MFCD12912330
MOL File:
362519-49-1.mol
MSDS File:
SDS
Last updated:2023-05-18 11:31:04

SLV-319 Properties

Boiling point 623.2±65.0 °C(Predicted)
Density 1.38±0.1 g/cm3(Predicted)
storage temp. 2-8°C
solubility Soluble in DMSO
form crystalline solid
pka 11?+-.0.60(Predicted)

SLV-319 price More Price(29)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Cayman Chemical 10009226 (±)-SLV 319 ≥98% 362519-49-1 1mg $32 2024-03-01 Buy
Cayman Chemical 10009226 (±)-SLV 319 ≥98% 362519-49-1 5mg $116 2024-03-01 Buy
Cayman Chemical 10009226 (±)-SLV 319 ≥98% 362519-49-1 10mg $214 2024-03-01 Buy
Cayman Chemical 10009226 (±)-SLV 319 ≥98% 362519-49-1 50mg $836 2024-03-01 Buy
Tocris 4605 (+/-)-SLV319 ≥98%(HPLC) 362519-49-1 50 $933 2021-12-16 Buy
Product number Packaging Price Buy
10009226 1mg $32 Buy
10009226 5mg $116 Buy
10009226 10mg $214 Buy
10009226 50mg $836 Buy
4605 50 $933 Buy

SLV-319 Chemical Properties,Uses,Production

Uses

(+/-)-SLV 319 is a mixture of the CB1 antagonist SLV 319 and its distomer.

Biological Activity

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.

SLV-319 Preparation Products And Raw materials

Raw materials

Preparation Products

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SLV-319 Spectrum

rac-(±)-SLV 319 (±)-SLV319(Ibipinabant) (±)-BMS6462) (±)-Ibipinabant((±)-SLV319 3-(4-Chlorophenyl)-N-[(4-Chlorophenyl)sulfonyl]-4,5-dihydro-N'-methyl-4-phenyl-1H-pyrazole-1-carboximidamide SLV 319;SLV-319 3-(4-Chlorophenyl)-N-((4-chlorophenyl)sulfonyl)-N'-methyl-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboximidamide (E)-3-(4-chlorophenyl)-N-((4-chlorophenyl)sulfonyl)-N'-methyl-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboximidamide 1H-Pyrazole-1-carboximidamide, 3-(4-chlorophenyl)-N-[(4-chlorophenyl)sulfonyl]-4,5-dihydro-N'-methyl-4-phenyl- (+/-)-SLV319 Inhibitor,(±)-Ibipinabant,Cannabinoid Receptor,(±) Ibipinabant,inhibit,(±)Ibipinabant 362519-49-1