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[ CAS No. 461432-26-8 ] {[proInfo.proName]}

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Chemical Structure| 461432-26-8
Chemical Structure| 461432-26-8
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Ahasanul Hasan ; Sreelakshmi N. Menon ; Farzana Zerin , et al. DOI: PubMed ID:

Abstract: Dapagliflozin is a sodium-glucose cotransporter 2 (SGLT2) inhibitor that, in addition to glucose reduction, lowers systemic blood pressure. Here, we investigated if dapagliflozin could directly relax small mesenteric arteries that control peripheral vascular resistance and blood pressure, and the underlying molecular mechanism. We used pressurized arterial myography, pharmacological inhibition and Western blotting to investigate the direct effect of dapagliflozin on the contractility of freshly isolated, resistance-size rat mesenteric arteries. Our pressure myography data unveiled that dapagliflozin relaxed small mesenteric arteries in a concentration-dependent manner. Non-selective inhibition of KV channels and selective inhibition of smooth muscle cell voltage-gated K+ channels KV7 attenuated dapagliflozin-induced vasorelaxation. Inhibition of other major KV isoforms such as KV1.3, KV1.5 channels as well as large-conductance Ca2+-activated K+ (BKCa) channels, ATP-sensitive (KATP) channels did not abolish vasodilation. Dapagliflozin-evoked vasodilation remained unaltered by pharmacological inhibition of endothelium-derived nitric oxide (NO) signaling, prostacyclin (PGI2), as well as by endothelium denudation. Our Western blotting data revealed that SGLT2 protein is expressed in rat mesenteric arteries. However, non-selective inhibition of SGLTs did not induce vasodilation, demonstrating that the vasodilatory action is independent of SGLT2 inhibition. Overall, our data suggests that dapagliflozin directly and selectively stimulates arterial smooth muscle cells KV7 channels, leading to vasodilation in resistance-size mesenteric arteries. These findings are significant as it uncovers for the first time a direct vasodilatory action of dapagliflozin in resistance mesenteric arteries, which may lower systemic blood pressure.

Keywords: Dapagliflozin ; Vascular resistance ; Mesenteric arteries ; Vasodilation ; Voltage-gated K+ channels

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Product Details of [ 461432-26-8 ]

CAS No. :461432-26-8 MDL No. :MFCD13182359
Formula : C21H25ClO6 Boiling Point : -
Linear Structure Formula :- InChI Key :JVHXJTBJCFBINQ-ADAARDCZSA-N
M.W : 408.87 Pubchem ID :9887712
Synonyms :
BMS-512148
Chemical Name :(2S,3R,4R,5S,6R)-2-(4-Chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Calculated chemistry of [ 461432-26-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 28
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.43
Num. rotatable bonds : 6
Num. H-bond acceptors : 6.0
Num. H-bond donors : 4.0
Molar Refractivity : 104.82
TPSA : 99.38 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.13 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.12
Log Po/w (XLOGP3) : 2.35
Log Po/w (WLOGP) : 1.52
Log Po/w (MLOGP) : 1.07
Log Po/w (SILICOS-IT) : 2.77
Consensus Log Po/w : 2.17

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.78
Solubility : 0.0684 mg/ml ; 0.000167 mol/l
Class : Soluble
Log S (Ali) : -4.08
Solubility : 0.0343 mg/ml ; 0.0000838 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.46
Solubility : 0.0141 mg/ml ; 0.0000344 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 4.52

Safety of [ 461432-26-8 ]

Signal Word:Danger Class:9
Precautionary Statements:P260-P264-P270-P273-P280-P301+P312+P330-P305+P351+P338-P314-P337+P313-P391-P501 UN#:3077
Hazard Statements:H302-H319-H372-H411 Packing Group:
GHS Pictogram:
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