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SML2804

Sigma-Aldrich

Dapagliflozin

≥98% (HPLC), powder, SGLT2 inhibitor

Synonym(e):

(1S)-1,5-Anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol, (2S,3R,4R,5S,6R)-2-(3-(4-Ethoxybenzyl)-4-chlorophenyl)-6-hydroxymethyl-tetrahydro-2H-pyran-3,4,5-triol, BMS 512148, BMS-512148

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About This Item

Empirische Formel (Hill-System):
C21H25ClO6
CAS-Nummer:
461432-26-8
Molekulargewicht:
408.87
MDL-Nummer:
MFCD13182359
UNSPSC-Code:
51111800
NACRES:
NA.77
Preise und Verfügbarkeit sind derzeit nicht verfügbar.

Produktbezeichnung

Dapagliflozin, ≥98% (HPLC)

Qualitätsniveau

100

Assay

≥98% (HPLC)

Form

powder

Optische Aktivität

[α]/D (+7.0° to +13.0°, c = 0.2 in methanol)

Farbe

white to beige

Löslichkeit

DMSO: 2 mg/mL, clear

Lagertemp.

−20°C

SMILES String

CCOC1=CC=C(C=C1)CC2=C(C=CC([C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)=C2)Cl

InChI

1S/C21H25ClO6/c1-2-27-15-6-3-12(4-7-15)9-14-10-13(5-8-16(14)22)21-20(26)19(25)18(24)17(11-23)28-21/h3-8,10,17-21,23-26H,2,9,11H2,1H3/t17-,18-,19+,20-,21+/m1/s1

InChIKey

JVHXJTBJCFBINQ-ADAARDCZSA-N

Biochem./physiol. Wirkung

Dapagliflozin (BMS-512148) is an orally active, potent and selective renal sodium-dependent glucose cotransporter 2 (SGLT2; SLC5A2) inhibitor (human/rat SGLT2 IC50 = 1.1/3 nM vs. human/rat SGLT1 IC50 = 1.39/0.6 μM; R-methyl-D-glucopyranoside (AMG) uptake assay with respective CHO transfectants). Dapagliflozin reduces blood glucose levels (by 55% in streptozotocin (STZ)-induced hyperglycemic rats 5 hrs post 0.1 mg/kg p.o.) by preventing the renal glucose reabsorption process and promoting glucose excretion in urine with good pharmacokinetic properties and oral availability (84% in rats and 83% in dogs, respectively, post 1 mg/kg and 6.6 mg/kg p.o.) in vivo.
Orally active, potent and selective renal sodium-dependent glucose cotransporter 2 (SGLT2; SLC5A2) inhibitor with blood sugar-lowering efficacy in vivo.

Signalwort

Danger

Gefahreneinstufungen

Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - STOT RE 1

Zielorgane

Kidney

Lagerklassenschlüssel

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
0000425774
0000425774
0000418350
0000418350
0000366519

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Die Dokumentenbibliothek aufrufen

Dapagliflozin - a breakthrough in the search for drugs to treat HFrEF.
Karina Huynh
Nature reviews. Cardiology, 16(12), 700-700 (2019-10-04)
Wei Meng et al.
Journal of medicinal chemistry, 51(5), 1145-1149 (2008-02-12)
The C-aryl glucoside 6 (dapagliflozin) was identified as a potent and selective hSGLT2 inhibitor which reduced blood glucose levels in a dose-dependent manner by as much as 55% in hyperglycemic streptozotocin (STZ) rats. These findings, combined with a favorable ADME
Kazuno Omori et al.
Metabolism: clinical and experimental, 98, 27-36 (2019-06-17)
To explore the beneficial effects of dapagliflozin and/or insulin glargine on the pancreatic beta cell mass and hepatic steatosis in db/db mice. Six-week-old db/db mice were assigned to one of four groups: untreated (Placebo), treated with dapagliflozin (Dapa), treated with
Nannan Zhang et al.
Cardiovascular diabetology, 18(1), 107-107 (2019-08-21)
Heart failure with preserved ejection fraction (HFpEF) is a difficult disease with high morbidity and mortality rates and lacks an effective treatment. Here, we report the therapeutic effect of dapagliflozin, a sodium-glucose cotransporter 2 inhibitor (SGLT2i), on hypertension + hyperlipidemia-induced HFpEF in a
Fengjuan Huang et al.
Frontiers in endocrinology, 10, 441-441 (2019-07-25)
Tubulointerstitial fibrosis (TIF) plays an important role in the progression of renal fibrosis in diabetic nephropathy (DN). Accumulating evidence supports a crucial inhibitory effect of dapagliflozin, a SGLT2 inhibitor, on TIF, but the underlying mechanisms remain largely unknown. This study
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