SML2758

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
• 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

Properties

• 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

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

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable