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SML2758

Dapagliflozin propanediol monohydrate

Name: Dapagliflozin propanediol monohydrate
Brand: SIGMA

≥98% (HPLC), SGLT2 inhibitor, powder

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

UNSPSC Code:

12352200

NACRES:

NA.77

MDL number:

MFCD28167768

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

Storage condition:

desiccated

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Product Name

Dapagliflozin propanediol monohydrate, ≥98% (HPLC)

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

Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Discovery of dapagliflozin: a potent, selective renal sodium-dependent glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.

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

Dapagliflozin - a breakthrough in the search for drugs to treat HFrEF.

Karina Huynh

Nature reviews. Cardiology, 16(12), 700-700 (2019-10-04)

Chronopharmacology of dapagliflozin-induced antihyperglycemic effects in C57BL/6J mice.

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

Effects of dapagliflozin and/or insulin glargine on beta cell mass and hepatic steatosis in db/db mice.

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

Dapagliflozin rescues endoplasmic reticulum stress-mediated cell death.

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

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Global Trade Item Number

SKU	GTIN
SML2758-10MG	04061841396741
SML2758-50MG	04061841396758

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