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SML2804

Sigma-Aldrich

Dapagliflozin

≥98% (HPLC), powder, SGLT2 inhibitor

Synonym(s):

(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

Empirical Formula (Hill Notation):
C21H25ClO6
CAS Number:
461432-26-8
Molecular Weight:
408.87
MDL number:
MFCD13182359
UNSPSC Code:
51111800
NACRES:
NA.77

product name

Dapagliflozin, ≥98% (HPLC)

Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

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

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−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

InChI key

JVHXJTBJCFBINQ-ADAARDCZSA-N

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.

Signal Word

Danger

Hazard Statements

H302,H319,H372,H411

Hazard Classifications

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

Target Organs

Kidney

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
Ryo Shibusawa et al.
Scientific reports, 9(1), 9887-9887 (2019-07-10)
The new type 2 diabetes drug, dapagliflozin, reduces blood glucose levels and body weight by inhibiting sodium glucose transporter 2 (SGLT2) in proximal tubular cells. SGLT2 inhibitors might modulate glucose influx into renal tubular cells, thereby regulating the metabolic conditions
Hiroki Yoshioka et al.
Obesity research & clinical practice, 13(5), 505-510 (2019-08-31)
Chronopharmacology is the study of the varying responses of drugs to changes in biological timing and endogenous periodicities. The selective sodium-glucose cotransporter 2 inhibitor, dapagliflozin, is a globally prescribed antihyperglycemic drug. Although dapagliflozin is usually administered once a day, the
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