| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H24O10 |
| Molecular Weight | 436.4093 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC[C@H]1O[C@@H](OC2=C(C(=O)CCC3=CC=C(O)C=C3)C(O)=CC(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O
InChI
InChIKey=IOUVKUPGCMBWBT-QNDFHXLGSA-N
InChI=1S/C21H24O10/c22-9-16-18(27)19(28)20(29)21(31-16)30-15-8-12(24)7-14(26)17(15)13(25)6-3-10-1-4-11(23)5-2-10/h1-2,4-5,7-8,16,18-24,26-29H,3,6,9H2/t16-,18-,19+,20-,21-/m1/s1
The flavonoid phlorizin was isolated from the bark of apple trees and shown to cause glucosuria. Phlorizin is an inhibitor of sodium glucose cotransporters (SGLT1 and SGLT2). With phlorizin as lead compound, specific inhibitors of SGLT2 were developed in the last decade and some of them have been approved for treatment mainly of type 2 diabetes. Inhibition of SGLT2 eliminates excess glucose via the urine. In recent times, the dual SGLT1/SGLT2 inhibitory activity of phlorizin has served as a model for the development and testing of new drugs exhibiting both activities.
Originator
Approval Year
PubMed
Patents
Sample Use Guides
The minimum intravenous dose of phlorizin required in man to produce complete phlorizination (i.e., to raise the glucose clearance to xylose clearance) was found to be in the neighborhood of 10 to 20 mgm. per kgm.
The oral administration of phlorizin in man produces a transient glycuresis, but the largest practical doses (approximately 400 mgm. per kgm. divided into four doses at 45 minute intervals) are inadequate to raise the glucose clearance to the level of the xylose clearance with any certainty, nor do they lower the creatinine clearance to the level of the glucose or xylose clearances. Oral administration of the drug is apparently much less efficient than intravenous injection in producing complete glycuresis.
Route of Administration:
Other
ACTIVE MOIETY
