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SML2804

Sigma-Aldrich

Dapagliflozin

≥98% (HPLC), powder, SGLT2 inhibitor

Synonyme(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

Formule empirique (notation de Hill):
C21H25ClO6
Numéro CAS:
461432-26-8
Poids moléculaire :
408.87
Numéro MDL:
MFCD13182359
Code UNSPSC :
51111800
Nomenclature NACRES :
NA.77

product name

Dapagliflozin, ≥98% (HPLC)

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Activité optique

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

Couleur

white to beige

Solubilité

DMSO: 2 mg/mL, clear

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

JVHXJTBJCFBINQ-ADAARDCZSA-N

Actions biochimiques/physiologiques

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.

Pictogrammes

Health hazardExclamation markEnvironment
GHS08,GHS07,GHS09

Mention d'avertissement

Danger

Mentions de danger

H302,H319,H372,H411

Classification des risques

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

Organes cibles

Kidney

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Consulter la Bibliothèque de documents

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
Ying-Ying Chen et al.
International journal of molecular sciences, 20(18) (2019-09-08)
Cataracts in patients with diabetes mellitus (DM) are a major cause of blindness in developed and developing countries. This study aims to examine whether the generation of reactive oxygen species (ROS) via the increased expression of glucose transporters (GLUTs) and
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
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
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