Details
| 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
| Molecular Formula | C21H24O10 |
| Molecular Weight | 436.4093 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| Characterization of glucose transport by cultured rabbit kidney proximal convoluted and proximal straight tubule cells. | 2002 Apr |
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| Electrogenic ion transport in the intestine of the Australian common brushtail possum, Trichosurus vulpecula: indications of novel transport patterns in a marsupial. | 2002 Aug |
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| Mechanisms by which bis(maltolato)oxovanadium(IV) normalizes phosphoenolpyruvate carboxykinase and glucose-6-phosphatase expression in streptozotocin-diabetic rats in vivo. | 2002 Dec |
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| pH dependence of Na+/myo-inositol cotransporters in rat thick limb cells. | 2002 Dec |
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| Mobility of ions, sugar, and water in the cytoplasm of Xenopus oocytes expressing Na(+)-coupled sugar transporters (SGLT1). | 2002 Jul 1 |
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| The antioxidant activity of phloretin: the disclosure of a new antioxidant pharmacophore in flavonoids. | 2002 Jul 5 |
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| Functional activities of the colon of the desert gerbil (Gerbillus cheesmani). | 2002 Jun |
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| Glucose uptake via SGLT-1 is stimulated by beta(2)-adrenoceptors in the ruminal epithelium of sheep. | 2002 Jun |
|
| Functional expression of the Vibrio parahaemolyticus Na+/galactose (vSGLT) cotransporter in Xenopus laevis oocytes. | 2002 May 1 |
|
| 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 Nov |
|
| AICAR and phlorizin reverse the hypoglycemia-specific defect in glucagon secretion in the diabetic BB rat. | 2002 Nov |
|
| Influence of food deprivation on the transport of 3-O-methyl-alpha-D-glucose across the isolated ruminal epithelium of sheep. | 2002 Oct |
|
| Glucagon-like peptide 2 enhances maltase-glucoamylase and sucrase-isomaltase gene expression and activity in parenterally fed premature neonatal piglets. | 2002 Oct |
|
| Sodium glucose-linked transport in the ruminal epithelium of fallow deer -- comparison to sheep. | 2002 Oct |
|
| Three-dimensional structure of the inclusion complex between phloridzin and beta-cyclodextrin. | 2002 Oct 11 |
|
| Glucose-induced beta cell production of IL-1beta contributes to glucotoxicity in human pancreatic islets. | 2002 Sep |
|
| Intrahepatic bile ducts transport water in response to absorbed glucose. | 2002 Sep |
|
| Identification of a novel Na+/myo-inositol cotransporter. | 2002 Sep 20 |
|
| Exploring levels of hexosamine biosynthesis pathway intermediates and protein kinase C isoforms in muscle and fat tissue of Zucker Diabetic Fatty rats. | 2003 Apr |
|
| Inositol transport in preimplantation rabbit embryos: effects of embryo stage, sodium, osmolality and metabolic inhibitors. | 2003 Apr |
|
| Loss of nucleotide regulation of epithelial chloride transport in the jejunum of P2Y4-null mice. | 2003 Apr |
|
| 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 Apr 1 |
|
| Functional asymmetry of the human Na+/glucose transporter (hSGLT1) in bacterial membrane vesicles. | 2003 Aug 5 |
|
| Absorption of sugars and amino acids by the epidermis of Aphidius ervi larvae. | 2003 Dec |
|
| 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 Dec 1 |
|
| A role for Ca(v)1.3 in rat intestinal calcium absorption. | 2003 Dec 12 |
|
| Phlorizin recognition in a C-terminal fragment of SGLT1 studied by tryptophan scanning and affinity labeling. | 2003 Dec 5 |
|
| An enhancer activates the pig lactase phlorizin hydrolase promoter in intestinal cells. | 2003 Feb 13 |
|
| Inositol transport in mouse oocytes and preimplantation embryos: effects of mouse strain, embryo stage, sodium and the hexose transport inhibitor, phloridzin. | 2003 Jan |
|
| Synthesis and biologic evaluation of (11)c-methyl-d-glucoside, a tracer of the sodium-dependent glucose transporters. | 2003 Jul |
|
| Expression of Na(+) / D-glucose cotransport in Xenopus laevis oocytes by injection of poly(A)(+) RNA isolated from lobster (Homarus americanus) hepatopancreas. | 2003 Jul |
|
| 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 Jun |
|
| The monosaccharide transporter gene, AtSTP4, and the cell-wall invertase, Atbetafruct1, are induced in Arabidopsis during infection with the fungal biotroph Erysiphe cichoracearum. | 2003 Jun |
|
| Tubular reabsorption of myo-inositol vs. that of D-glucose in rat kidney in vivo et situ. | 2003 Jun |
|
| Non-nutritive bioactive food constituents of plants: bioavailability of flavonoids. | 2003 Mar |
|
| Hydrolysis by lactase phlorizin hydrolase is the first step in the uptake of daidzein glucosides by rat small intestine in vitro. | 2003 Mar |
|
| High blood glucose and osmolality, but not high urinary glucose and osmolality, affect neuronal nitric oxide synthase expression in diabetic rat kidney. | 2003 Mar |
|
| A novel glucose-sensing mechanism contributing to glucagon-like peptide-1 secretion from the GLUTag cell line. | 2003 May |
|
| Binding of phlorizin to the isolated C-terminal extramembranous loop of the Na+/glucose cotransporter assessed by intrinsic tryptophan fluorescence. | 2003 May 27 |
|
| Detection of phloridzin in strawberries (Fragaria x ananassa Duch.) by HPLC-PDA-MS/MS and NMR spectroscopy. | 2003 May 7 |
|
| Increase in adenosine A1 receptor gene expression in the liver of streptozotocin-induced diabetic rats. | 2003 May-Jun |
|
| 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 Nov |
|
| Genomic organization and functional characterization of the human concentrative nucleoside transporter-3 isoform (hCNT3) expressed in mammalian cells. | 2003 Nov |
|
| Differential expression of Na+/D-glucose cotransport in isolated cells of Marsupenaeus japonicus hepatopancreas. | 2003 Nov |
|
| In vivo sugar diffusion in the ileal epithelium of spontaneously hypertensive rats. | 2003 Sep |
|
| Evidence for rapid "metabolic switching" through lipoprotein lipase occupation of endothelial-binding sites. | 2003 Sep |
|
| Response of scab-susceptible (McIntosh) and scab-resistant (Liberty) apple tissues to treatment with yeast extract and Venturia inaequalis. | 2003 Sep |
|
| Prior exercise enhances passive absorption of intraduodenal glucose. | 2003 Sep |
|
| Aminoglycoside antibiotics reduce glucose reabsorption in kidney through down-regulation of SGLT1. | 2003 Sep 5 |
|
| A new sweet dihydrochalcone-glucoside from leaves of Lithocarpus pachyphyllus (Kurz) Rehd. (Fagaceae). | 2003 Sep-Oct |
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:45:36 GMT 2023
by
admin
on
Fri Dec 15 16:45:36 GMT 2023
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| Record UNII |
CU9S17279X
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| Record Status |
Validated (UNII)
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| Record Version |
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4325 (Number of products:2)
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1362735
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8113
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200-487-1
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60-81-1
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D010695
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6072
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PHLORIZIN
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2833
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m8708
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CU9S17279X
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CU9S17279X
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DTXSID3075339
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| Related Record | Type | Details | ||
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SOLVATE->ANHYDROUS |
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ACTIVE MOIETY |
