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SML2758

Sigma-Aldrich

Dapagliflozin propanediol monohydrate

≥98% (HPLC)

Synonym(s):

(1S)-1,5-Anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol (S)-propane-1,2-diol (1:1) monohydrate, (2S,3R,4R,5S,6R)-2-(3-(4-Ethoxybenzyl)-4-chlorophenyl)-6-hydroxymethyl-tetrahydro-2H-pyran-3,4,5-triol propanediol monohydrate, BMS 512148 propanediol hydrate, BMS-512148 propanediol hydrate, Dapagliflozin (S)-propylene glycol monohydrate, Dapagliflozin propanediol hydrate

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About This Item

Empirical Formula (Hill Notation):
C21H25ClO6·C3H8O2·H2O
CAS Number:
960404-48-2
Molecular Weight:
502.98
MDL number:
MFCD28167768
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +17 to +25, c = 1.0 in chloroform-d

storage condition

desiccated

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

Clc1c(cc(cc1)[C@@H]3O[C@@H]([C@H]([C@@H]([C@H]3O)O)O)CO)Cc2ccc(cc2)OCC.O[C@H](CO)C.O

InChI

1S/C21H25ClO6.C3H8O2.H2O/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;1-3(5)2-4;/h3-8,10,17-21,23-26H,2,9,11H2,1H3;3-5H,2H2,1H3;1H2/t17-,18-,19+,20-,21+;3-;/m10./s1

InChI key

GOADIQFWSVMMRJ-UPGAGZFNSA-N

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Biochem/physiol Actions

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000418344
0000418344
0000379679
0000303378
0000303378

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M Obermeier et al.
Drug metabolism and disposition: the biological fate of chemicals, 38(3), 405-414 (2009-12-10)
(2S,3R,4R,5S,6R)-2-(3-(4-Ethoxybenzyl)-4-chlorophenyl)-6-hydroxymethyl-tetrahydro-2H-pyran-3,4,5-triol (dapagliflozin; BMS-512148) is a potent sodium-glucose cotransporter type II inhibitor in animals and humans and is currently under development for the treatment of type 2 diabetes. The preclinical characterization of dapagliflozin, to allow compound selection and prediction of pharmacological
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
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
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
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