Dapagliflozin
- CAS No.
- 461432-26-8
- Chemical Name:
- Dapagliflozin
- Synonyms
- Dapagliflozin Propanediol Monohydrate;Dapagliflozin propanediol;Farxiga;DAPAGLIFLOZIN BASE;Dapagliflozi;(1S)-1,5-Anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol;D-Glucitol, 1,5-anhydro-1-C-(4-chloro-3-((4-ethoxyphenyl)methyl)phenyl)-, (1S)-;2-(3-(4-Ethoxybenzyl)-4-chlorophenyl)-6-hydroxymethyltetrahydro-2H-pyran-3,4,5-triol;(2S,4R,5R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxyMethyl)tetrahydro-2H-pyran-3,4,5-triol;CS-179
- CBNumber:
- CB91011730
- Molecular Formula:
- C21H25ClO6
- Molecular Weight:
- 408.88
- MOL File:
- 461432-26-8.mol
- Modify Date:
- 2025/3/6 17:06:57
| Melting point | 55-58°C |
|---|---|
| Boiling point | 609.0±55.0 °C(Predicted) |
| Density | 1.349 |
| storage temp. | 2-8°C |
| solubility | DMSO (Slightly), Methanol (Slightly) |
| pka | 13.23±0.70(Predicted) |
| form | Solid |
| color | White to Pale Yellow |
| optical activity | [α]/D (+7.0° to +13.0°, c = 0.2 in methanol) |
| Stability | Hygroscopic |
| InChIKey | JVHXJTBJCFBINQ-JNTNYNDRNA-N |
| SMILES | O[C@@H]1[C@H]([C@H](O)[C@@H](CO)O[C@H]1C1C=CC(Cl)=C(CC2C=CC(OCC)=CC=2)C=1)O |&1:1,2,3,5,9,r| |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |    GHS08,GHS07,GHS05 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H302-H372-H318 | |||||||||
| Precautionary statements | P264-P270-P301+P312-P330-P501-P260-P264-P270-P314-P501-P280-P305+P351+P338-P310 | |||||||||
| NFPA 704 |
|
Dapagliflozin Chemical Properties,Uses,Production
Description
The Australian Therapeutic Goods Administration (TGA) and the European Commission approved dapagliflozin in October and November 2012, respectively, as an adjunct to diet and exercise for the treatment of type 2 diabetes. Dapagliflozin is a potentially attractive therapy due to its glucosesensitive and insulin-independent mechanism of action. It is a first-in-class selective SGLT2 inhibitor (IC50=1.1 nM; selectivity vs. SGLT1 >1000) that lowers the renal threshold for reabsorption of glucose, allowing excess glucose to be eliminated via the kidneys. In normal rats, administration of dapagliflozin promotes dose-dependent excretion of up to 1900 mg of glucose over a 24 h period, with amaximal effect at 3 mg/kg. In a ratmodel of diabetes, pretreatment with the pancreatic toxin streptozotocin results in hyperglycemia that is reduced 55% by administration of a single 0.1 mg/kg dose of dapagliflozin compared with vehicle. Aryl O-glucoside SGLT2 inhibitors were early entrants into the clinic, but the aryl C-glucoside linkage found in dapagliflozin confers resistance to glucosidase-mediated metabolism leading to improved clinical utility relative to aryl O-glucosides. The modified carbohydrate–aglycone linkage required concomitant adjustment from an ortho- to a meta-substituted arylglucoside to achieve potent SGLT2 inhibition. Dapagliflozin was synthesized in several steps via reaction of an aryllithium with per-silylated gluconolactone to form the key C-glucoside linkage. An alpha-selective reduction of the resultant anomeric glycoside gave the desired beta-Carylglucoside. The main circulating (inactive) metabolite is the result of 3-O-glucuronidation of the glucosylmoiety. Of the minority metabolites, the main oxidative species result from O-dealkylation of the ethoxy-group and hydroxylation of the biarylmethane moiety.
Chemical Properties
White Solid
Uses
A sodium-glucose transporter 2 inhibitor.
Definition
ChEBI: A C-glycosyl comprising beta-D-glucose in which the anomeric hydroxy group is replaced by a 4-chloro-3-(4-ethoxybenzyl)phenyl group. Used (in the formo f its propanediol monohydrate) to improve glycemic ontrol, along with diet and exercise, in adults with type 2 diabetes.
Dapagliflozin Preparation Products And Raw materials
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| TAGOOR LABORATORIES PVT LTD | +919700187008 | AndhraPradesh, India | 90 | 58 | Inquiry |
| HEMA PHARMACEUTICALS PVT LTD | +91-9537936912 +91-9537936912 | Gujarat, India | 48 | 58 | Inquiry |
| Dr. Reddy's Laboratories Ltd | +91-4049002900 +91-4049002900 | Hyderabad, India | 165 | 58 | Inquiry |
| SGMR PHARMACEUTICALS PVT LTD | +91-9032001889 +91-9032001889 | Telangana, India | 83 | 58 | Inquiry |
| SKVen Technologies Pvt.Ltd. | +91-7032295152 +91-7032295152 | Hyderabad, India | 81 | 58 | Inquiry |
| Flax Laboratories | +91-9867665132 +91-9867665132 | Maharashtra, India | 44 | 58 | Inquiry |
| AARTIA KEM SCIENCE | +91-8291072530 +91-8291072530 | Maharashtra, India | 70 | 58 | Inquiry |
| Metrochem API Private Limited | +91-4069069999 +91-4069069999 | Telangana, India | 78 | 58 | Inquiry |
| Meenaakshi Molecules Pvt Ltd | +91-9121311126 +91-9121311126 | Telangana, India | 45 | 58 | Inquiry |
| Sekhment pharmaventures | +91-9030088669 +91-9030088669 | Mumbai, India | 105 | 58 | Inquiry |
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