Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H24O10.2H2O |
| Molecular Weight | 472.4398 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.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=XQWBNXSENPTIDY-YXMARJSJSA-N
InChI=1S/C21H24O10.2H2O/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;2*1H2/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.
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
4.5 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30806398/ |
5 mg/kg single, intravenous dose: 5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PHLORIZIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
25.4 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30806398/ |
10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PHLORIZIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
44.2 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30806398/ |
20 mg/kg single, intravenous dose: 20 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PHLORIZIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
39.5 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30806398/ |
10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PHLORIZIN plasma | Rattus norvegicus population: UNHEALTHY age: ADULT sex: MALE food status: FASTED |
|
7.4 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30806398/ |
10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PHLORETIN plasma | Rattus norvegicus population: UNHEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.86 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30806398/ |
10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PHLORETIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2.97 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30806398/ |
20 mg/kg single, intravenous dose: 20 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PHLORETIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
0.48 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30806398/ |
5 mg/kg single, intravenous dose: 5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PHLORETIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
450.9 mg × min/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30806398/ |
5 mg/kg single, intravenous dose: 5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PHLORIZIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
777.7 mg × min/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30806398/ |
10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PHLORIZIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1197.5 mg × min/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30806398/ |
20 mg/kg single, intravenous dose: 20 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PHLORIZIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1338.2 mg × min/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30806398/ |
10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PHLORIZIN plasma | Rattus norvegicus population: UNHEALTHY age: ADULT sex: MALE food status: FASTED |
|
200 mg × min/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30806398/ |
10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PHLORETIN plasma | Rattus norvegicus population: UNHEALTHY age: ADULT sex: MALE food status: FASTED |
|
147 mg × min/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30806398/ |
10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PHLORETIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
294.6 mg × min/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30806398/ |
20 mg/kg single, intravenous dose: 20 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PHLORETIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
106.1 mg × min/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30806398/ |
5 mg/kg single, intravenous dose: 5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PHLORETIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
192.2 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30806398/ |
5 mg/kg single, intravenous dose: 5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PHLORIZIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
209.1 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30806398/ |
10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PHLORIZIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
171 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30806398/ |
20 mg/kg single, intravenous dose: 20 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PHLORIZIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
155.9 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30806398/ |
10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PHLORIZIN plasma | Rattus norvegicus population: UNHEALTHY age: ADULT sex: MALE food status: FASTED |
|
57.9 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30806398/ |
10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PHLORETIN plasma | Rattus norvegicus population: UNHEALTHY age: ADULT sex: MALE food status: FASTED |
|
113.7 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30806398/ |
10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PHLORETIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
121.4 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30806398/ |
20 mg/kg single, intravenous dose: 20 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PHLORETIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
353.6 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30806398/ |
5 mg/kg single, intravenous dose: 5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PHLORETIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
PubMed
| Title | Date | PubMed |
|---|---|---|
| A role for Ca(v)1.3 in rat intestinal calcium absorption. | 2003-12-12 |
|
| Phlorizin recognition in a C-terminal fragment of SGLT1 studied by tryptophan scanning and affinity labeling. | 2003-12-05 |
|
| Synthesis of photoaffinity probes [2(')-iodo-4(')-(3(")-trifluoromethyldiazirinyl)phenoxy]-D-glucopyranoside and [(4(')-benzoyl)phenoxy]-D-glucopyranoside for the identification of sugar-binding and phlorizin-binding sites in the sodium/D-glucose cotransporter protein. | 2003-12-01 |
|
| Absorption of sugars and amino acids by the epidermis of Aphidius ervi larvae. | 2003-12 |
|
| The beta-D-glucoside and sodium-dependent glucose transporter 1 (SGLT1)-inhibitor phloridzin is transported by both SGLT1 and multidrug resistance-associated proteins 1/2. | 2003-11 |
|
| Genomic organization and functional characterization of the human concentrative nucleoside transporter-3 isoform (hCNT3) expressed in mammalian cells. | 2003-11 |
|
| Differential expression of Na+/D-glucose cotransport in isolated cells of Marsupenaeus japonicus hepatopancreas. | 2003-11 |
|
| A new sweet dihydrochalcone-glucoside from leaves of Lithocarpus pachyphyllus (Kurz) Rehd. (Fagaceae). | 2003-10-28 |
|
| Aminoglycoside antibiotics reduce glucose reabsorption in kidney through down-regulation of SGLT1. | 2003-09-05 |
|
| In vivo sugar diffusion in the ileal epithelium of spontaneously hypertensive rats. | 2003-09 |
|
| Evidence for rapid "metabolic switching" through lipoprotein lipase occupation of endothelial-binding sites. | 2003-09 |
|
| Response of scab-susceptible (McIntosh) and scab-resistant (Liberty) apple tissues to treatment with yeast extract and Venturia inaequalis. | 2003-09 |
|
| Prior exercise enhances passive absorption of intraduodenal glucose. | 2003-09 |
|
| Functional asymmetry of the human Na+/glucose transporter (hSGLT1) in bacterial membrane vesicles. | 2003-08-05 |
|
| Synthesis and biologic evaluation of (11)c-methyl-d-glucoside, a tracer of the sodium-dependent glucose transporters. | 2003-07 |
|
| Expression of Na(+) / D-glucose cotransport in Xenopus laevis oocytes by injection of poly(A)(+) RNA isolated from lobster (Homarus americanus) hepatopancreas. | 2003-07 |
|
| Alteration of alpha(1A)-adrenoceptor gene expression in the prostate of streptozotocin-induced diabetic rats. | 2003-07 |
|
| Increase in adenosine A1 receptor gene expression in the liver of streptozotocin-induced diabetic rats. | 2003-06-06 |
|
| Phlorizin treatment prevents the decrease in plasma insulin levels but not the progressive histopathological changes in the pancreatic islets during aging of Zucker diabetic fatty rats. | 2003-06 |
|
| The monosaccharide transporter gene, AtSTP4, and the cell-wall invertase, Atbetafruct1, are induced in Arabidopsis during infection with the fungal biotroph Erysiphe cichoracearum. | 2003-06 |
|
| Tubular reabsorption of myo-inositol vs. that of D-glucose in rat kidney in vivo et situ. | 2003-06 |
|
| Binding of phlorizin to the isolated C-terminal extramembranous loop of the Na+/glucose cotransporter assessed by intrinsic tryptophan fluorescence. | 2003-05-27 |
|
| Detection of phloridzin in strawberries (Fragaria x ananassa Duch.) by HPLC-PDA-MS/MS and NMR spectroscopy. | 2003-05-07 |
|
| A novel glucose-sensing mechanism contributing to glucagon-like peptide-1 secretion from the GLUTag cell line. | 2003-05 |
|
| Absorption of quercetin-3-glucoside and quercetin-4'-glucoside in the rat small intestine: the role of lactase phlorizin hydrolase and the sodium-dependent glucose transporter. | 2003-04-01 |
|
| Exploring levels of hexosamine biosynthesis pathway intermediates and protein kinase C isoforms in muscle and fat tissue of Zucker Diabetic Fatty rats. | 2003-04 |
|
| Inositol transport in preimplantation rabbit embryos: effects of embryo stage, sodium, osmolality and metabolic inhibitors. | 2003-04 |
|
| Loss of nucleotide regulation of epithelial chloride transport in the jejunum of P2Y4-null mice. | 2003-04 |
|
| Non-nutritive bioactive food constituents of plants: bioavailability of flavonoids. | 2003-03 |
|
| Hydrolysis by lactase phlorizin hydrolase is the first step in the uptake of daidzein glucosides by rat small intestine in vitro. | 2003-03 |
|
| High blood glucose and osmolality, but not high urinary glucose and osmolality, affect neuronal nitric oxide synthase expression in diabetic rat kidney. | 2003-03 |
|
| An enhancer activates the pig lactase phlorizin hydrolase promoter in intestinal cells. | 2003-02-13 |
|
| Inositol transport in mouse oocytes and preimplantation embryos: effects of mouse strain, embryo stage, sodium and the hexose transport inhibitor, phloridzin. | 2003-01 |
|
| Mechanisms by which bis(maltolato)oxovanadium(IV) normalizes phosphoenolpyruvate carboxykinase and glucose-6-phosphatase expression in streptozotocin-diabetic rats in vivo. | 2002-12 |
|
| pH dependence of Na+/myo-inositol cotransporters in rat thick limb cells. | 2002-12 |
|
| Abnormal expression of pancreatic islet exocytotic soluble N-ethylmaleimide-sensitive factor attachment protein receptors in Goto-Kakizaki rats is partially restored by phlorizin treatment and accentuated by high glucose treatment. | 2002-11 |
|
| AICAR and phlorizin reverse the hypoglycemia-specific defect in glucagon secretion in the diabetic BB rat. | 2002-11 |
|
| Three-dimensional structure of the inclusion complex between phloridzin and beta-cyclodextrin. | 2002-10-11 |
|
| Influence of food deprivation on the transport of 3-O-methyl-alpha-D-glucose across the isolated ruminal epithelium of sheep. | 2002-10 |
|
| Glucagon-like peptide 2 enhances maltase-glucoamylase and sucrase-isomaltase gene expression and activity in parenterally fed premature neonatal piglets. | 2002-10 |
|
| Sodium glucose-linked transport in the ruminal epithelium of fallow deer -- comparison to sheep. | 2002-10 |
|
| Identification of a novel Na+/myo-inositol cotransporter. | 2002-09-20 |
|
| Glucose-induced beta cell production of IL-1beta contributes to glucotoxicity in human pancreatic islets. | 2002-09 |
|
| Intrahepatic bile ducts transport water in response to absorbed glucose. | 2002-09 |
|
| Electrogenic ion transport in the intestine of the Australian common brushtail possum, Trichosurus vulpecula: indications of novel transport patterns in a marsupial. | 2002-08 |
|
| The antioxidant activity of phloretin: the disclosure of a new antioxidant pharmacophore in flavonoids. | 2002-07-05 |
|
| Mobility of ions, sugar, and water in the cytoplasm of Xenopus oocytes expressing Na(+)-coupled sugar transporters (SGLT1). | 2002-07-01 |
|
| Functional activities of the colon of the desert gerbil (Gerbillus cheesmani). | 2002-06 |
|
| Glucose uptake via SGLT-1 is stimulated by beta(2)-adrenoceptors in the ruminal epithelium of sheep. | 2002-06 |
|
| Characterization of glucose transport by cultured rabbit kidney proximal convoluted and proximal straight tubule cells. | 2002-04 |
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
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Preferred Name | English | ||
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9912668
Created by
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CRK54BIJ5D
Created by
admin on Mon Mar 31 18:09:22 GMT 2025 , Edited by admin on Mon Mar 31 18:09:22 GMT 2025
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7061-54-3
Created by
admin on Mon Mar 31 18:09:22 GMT 2025 , Edited by admin on Mon Mar 31 18:09:22 GMT 2025
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m8708
Created by
admin on Mon Mar 31 18:09:22 GMT 2025 , Edited by admin on Mon Mar 31 18:09:22 GMT 2025
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PRIMARY | Merck Index | ||
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DTXSID70990828
Created by
admin on Mon Mar 31 18:09:22 GMT 2025 , Edited by admin on Mon Mar 31 18:09:22 GMT 2025
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PRIMARY |
SUBSTANCE RECORD
