Ipragliflozin
- Product Name
- Ipragliflozin
- CAS No.
- 761423-87-4
- Chemical Name
- Ipragliflozin
- Synonyms
- Suglat;CS-1580;Igliazine;Yigelejing;Ipraglifozin;Ipragliflozin;Iprag iflozin;Ipragliflozin-002;Iglienet free base;Ipragliflozin, >=98%
- 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
- InChI
- InChI=1/C21H21FO5S/c22-15-6-5-12(21-20(26)19(25)18(24)16(10-23)27-21)7-13(15)9-14-8-11-3-1-2-4-17(11)28-14/h1-8,16,18-21,23-26H,9-10H2/t16-,18-,19+,20-,21+/s3
- InChIKey
- AHFWIQIYAXSLBA-OPUVIHLBNA-N
- SMILES
- O1[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1C1C=CC(F)=C(CC2=CC3C=CC=CC=3S2)C=1 |&1:1,4,6,8,10,r|
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H303May be harmfulif swallowed
H320Causes eye irritation
- Precautionary statements
-
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P312Call a POISON CENTER or doctor/physician if you feel unwell.
P337+P313IF eye irritation persists: Get medical advice/attention.
N-Bromosuccinimide Price
- Product number
- I1284
- Product name
- Ipragliflozin
- Packaging
- 200MG
- Price
- $115
- Updated
- 2025/07/31
- Product number
- I1284
- Product name
- Ipragliflozin
- Packaging
- 1G
- Price
- $345
- Updated
- 2025/07/31
- 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
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.
References
[1] Patent: EP2105442, 2009, A1. Location in patent: Page/Page column 13
[2] Patent: CN108276396, 2018, A. Location in patent: Paragraph 0041; 0052; 0053; 0068; 0083
[3] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 10, p. 3263 - 3279
[4] Patent: EP2009010, 2008, A1. Location in patent: Page/Page column 6-7
Ipragliflozin Preparation Products And Raw materials
Raw materials
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View Lastest Price from Ipragliflozin manufacturers
- Product
- Ipragliflozin 761423-87-4
- Price
- US $6.00/kg
- Min. Order
- 1kg
- Purity
- 0.99
- Supply Ability
- 1000
- Release date
- 2024-09-04
- Product
- Ipragliflozin 761423-87-4
- Price
- US $0.00-0.00/g
- Min. Order
- 50g
- Purity
- 99%
- Supply Ability
- 15kg
- Release date
- 2024-10-18
- 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