Ipragliflozin
- Product Name
- Ipragliflozin
- CAS No.
- 761423-87-4
- Chemical Name
- Ipragliflozin
- Synonyms
- Suglat;CS-1580;Ipragliflozin;Iprag iflozin;Ipragliflozin-002;Ipragliflozin, >=98%;Ipragliflozin impuity;Ipragliflozin （Suglat）;IpragliflozinL-Proline;Ipragliflozin Impurity
- CBNumber
- CB02589633
- Molecular Formula
- C21H21FO5S
- Formula Weight
- 404.45
- MOL File
- 761423-87-4.mol
Ipragliflozin Property
- Melting point:
- 155-157°C
- Boiling point:
- 628.8±55.0 °C(Predicted)
- Density
- 1.452
- storage temp.
- Refrigerator
- solubility
- DMSO (Slightly), Methanol (Slightly)
- pka
- 13.27±0.70(Predicted)
- form
- Solid
- color
- White to Off-White
N-Bromosuccinimide Price
- Product number
- 22287
- Product name
- Ipragliflozin
- Purity
- ≥98%
- Packaging
- 10mg
- Price
- $32
- Updated
- 2024/03/01
- Product number
- 22287
- Product name
- Ipragliflozin
- Purity
- ≥98%
- Packaging
- 50mg
- Price
- $139
- Updated
- 2024/03/01
- Product number
- 22287
- Product name
- Ipragliflozin
- Purity
- ≥98%
- Packaging
- 100mg
- Price
- $199
- Updated
- 2024/03/01
- Product number
- 22287
- Product name
- Ipragliflozin
- Purity
- ≥98%
- Packaging
- 250mg
- Price
- $456
- Updated
- 2024/03/01
- Product number
- I739475
- Product name
- Ipragliflozin
- Packaging
- 500mg
- Price
- $620
- Updated
- 2021/12/16
Ipragliflozin Chemical Properties,Usage,Production
Description
Ipragliflozin is a sodium-glucose cotransporter 2 (SGLT2) inhibitor (IC50 = 7.4 nM in CHO cells expressing the human cotransporter). It is selective for SGLT2 over SGLT1, SGLT3, SGLT4, SGLT5, and SGLT6 (IC50s = 1.9, 30.4, 15.9, 0.46, and 10.4 μM, respectively). Ipragliflozin (0.1-3 mg/kg) decreases plasma levels of insulin and glucose in an oral glucose tolerance test in a mouse model of diabetes induced by high-fat diet, streptozotocin (STZ; ), and nicotinamide . It decreases plasma and hepatic IL-6, TNF-α, chemokine (C-C motif) ligand 2 (CCL2), and C-reactive protein (CRP) levels in the same model when administered at a dose of 3 mg/kg per day for 28 days.
History
Ipragliflozin L-proline was approved in Japan in January 2014 for the treatment of type 2 diabetes. The drug was discovered by Astellas Pharma and co-developed and marketed with Kotobuki Pharmaceutical and Merck Sharp Dohme as Suglat?. Similar to empagliflozin (XIII), ipragliflozin L-proline is a sodium-glucose 1956 A. C. Flick et al. / Bioorg. Med. Chem. 24 (2016) 1937–1980 co-transporter-2 inhibitor which prevents glucose reabsorption by excreting excess glucose in the urine. Ipragliflozin exhibits remarkable selectivity over SLGT-1 (>250x).
Uses
Ipragliflozin is a potent and selective inhibitor of sodium-glucose cotransporter-2 (SGLT2) and can serve as a potential agent for the treatment of type 1 and type 2 diabetes.
Definition
ChEBI: Ipragliflozin is a glycoside.
Trade name
Suglat
Synthesis
Commercial 5-bromo-2-fluorobenzaldehyde (123) was subjected to nucleophilic attack upon subjection to lithiated benzo[b]thiophene (124) to afford the dibenzylic alcohol 125 in 85% yield. This alcohol was then halogenated by means of thionyl chloride in acetonitrile to give 126, which was followed by treatment with sodium borohydride to give rise to 2-(5-bromo-2-fluorophenyl)- 1-benzothiophene (127), which was isolated by crystallization from 2-propanol and methanol in 81% yield across the two steps. Bromide 127 then underwent lithium¨Chalogen exchange prior to exposure to 2,3,4,6-tetrakis-O-(trimethylsilyl)- D-glucono-1,5-lactone (128) in toluene. Without workup, the resulting mixture was treated with a solution of methanol and HCl at 0 C to give a globally desilylated a-glucopyranoside intermediate. Subjection to acetic anhydride and 4-dimethylaminopyridine furnished tetra-O-acetyl ipragliflozin (129) in 75% yield for the 3 steps. Polyacetate 129 was then saponified using aqueous sodium hydroxide and the product was crystallized from methanol and water and subsequently treated with D-proline in ethanol to furnish the desired product ipragliflozin D-proline (XVI) in 68% yield.
Mode of action
Ipragliflozin is a selective SGLT2 (sodium-glucose co-transporter 2) inhibitor discovered through research collaboration with Kotobuki Pharmaceutical Co., Ltd. SGLTs are membrane proteins that exist on the cell surface and transfer glucose into cells. SGLT2 is a subtype of the sodium-glucose co-transporters and plays a key role in the reuptake of glucose in the proximal tubule of the kidneys. Ipragliflozin reduces blood glucose levels by inhibiting the reuptake of glucose.
Ipragliflozin Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Ipragliflozin manufacturers
- Product
- ipragliflozin 761423-87-4
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 99%，single impurity＜0.1
- Supply Ability
- 1 ton
- Release date
- 2024-01-04
- Product
- (1S)-1,5-Anhydro-1-C-[3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl]-D-glucitol 761423-87-4
- Price
- US $166.00/g/Bag
- Min. Order
- 5g
- Purity
- 99%
- Supply Ability
- 100kg
- Release date
- 2021-06-04
- Product
- Ipragliflozin 761423-87-4
- Price
- US $10.00/Kg/Drum
- Min. Order
- 1KG
- Purity
- 98%
- Supply Ability
- 10 ton
- Release date
- 2021-08-24