SML2804

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

Properties

• 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

Description

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.

Safety Information

• Pictograms: GHS08,GHS07,GHS09
• Signal Word: Danger
• Hazard Statements: H302,H319,H372,H411
• Precautionary Statements: P260 - P264 - P273 - P301 + P312 - P305 + P351 + P338 - P314
• 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