Bexagliflozin
- Product Name
- Bexagliflozin
- CAS No.
- 1118567-05-7
- Chemical Name
- Bexagliflozin
- Synonyms
- CS-250;CS-2165;EGT1442;THR1442;THR 1442;THR-1442;EGT0001442;EGT-0001442;EGT 0001442;Bexgliflozin
- CBNumber
- CB92650633
- Molecular Formula
- C24H29ClO7
- Formula Weight
- 464.94
- MOL File
- 1118567-05-7.mol
Bexagliflozin Property
- Boiling point:
- 671.0±55.0 °C(Predicted)
- Density
- 1.41
- storage temp.
- Store at -20°C
- solubility
- DMSO:100.0(Max Conc. mg/mL);215.08(Max Conc. mM)
- form
- A crystalline solid
- pka
- 13.23±0.70(Predicted)
- InChIKey
- BTCRKOKVYTVOLU-IZSIRFNDNA-N
- SMILES
- [C@H]1(C2C=C(CC3C=CC(OCCOC4CC4)=CC=3)C(Cl)=CC=2)[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 |&1:0,22,24,26,28,r|
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
- Precautionary statements
-
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P270Do not eat, drink or smoke when using this product.
P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P330Rinse mouth.
P501Dispose of contents/container to..…
N-Bromosuccinimide Price
- Product number
- 21359
- Product name
- EGT-1442
- Purity
- ≥95%
- Packaging
- 1mg
- Price
- $32
- Updated
- 2024/03/01
- Product number
- 21359
- Product name
- EGT-1442
- Purity
- ≥95%
- Packaging
- 5mg
- Price
- $139
- Updated
- 2024/03/01
- Product number
- 21359
- Product name
- EGT-1442
- Purity
- ≥95%
- Packaging
- 10mg
- Price
- $243
- Updated
- 2024/03/01
- Product number
- 21359
- Product name
- EGT-1442
- Purity
- ≥95%
- Packaging
- 25mg
- Price
- $533
- Updated
- 2024/03/01
- Product number
- B336785
- Product name
- Bexagliflozin3
- Packaging
- 10mg
- Price
- $310
- Updated
- 2021/12/16
Bexagliflozin Chemical Properties,Usage,Production
Description
EGT-1442 is a potent, selective sodium glucose co-transporter 2 (SGLT2) inhibitor with IC50 values of 5.6 μM and 2 nM for human SGLT1 and SGLT2, respectively. It produces a stable urinary excretion of glucose in rats and dogs with ED50 values of 0.38 and 0.09 mg/kg, respectively, and reduces HbA(1c) and blood glucose in db/db mice in a concentration dependent manner.
Uses
Bexagliflozin, also known as EGT1442, is a potent and selective SGLT2 inhibitor, attenuates blood glucose and HbA(1c) levels in db/db mice and prolongs the survival of stroke-prone rats. EGT1442 showed favorable properties both in vitro and in vivo and could be beneficial to the management of type 2 diabetic patients.
Definition
ChEBI: Bexagliflozin is a C-glycosyl comprising of beta-D-glucose in which the anomeric hydroxy group is replaced by a 4-chloro-3-({4-[2-(cyclopropyloxy)ethoxy]phenyl}methyl)phenyl group. It is a sodium-glucose co-transporter 2 (SGLT2) inhibitor indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus. It has a role as a sodium-glucose transport protein subtype 2 inhibitor, a hypoglycemic agent and an antihypertensive agent. It is a C-glycosyl compound, an aromatic ether, a member of monochlorobenzenes, a diether and a member of cyclopropanes.
Mechanism of action
Bexagliflozin is a highly selective inhibitor of sodium-glucose cotransporter protein 2 (SGLT2), which cotransports sodium and glucose from the filtrate to the epithelium of the proximal renal tubule, thereby lowering the tubular glucose reabsorption threshold, reducing renal glucose reabsorption, and increasing urinary glucose excretion without affecting insulin levels.
Synthesis
1459754-30-3
1118567-05-7
Example 5: Preparation of (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(2-cyclopropoxyethoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol [0236] This embodiment describes the preparation of (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(2-cyclopropoxyethoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol by reduction of end-isomers OMe and/or OH. Procedure. 1. Add (3R,4S,5S,6R)-2-(4-chloro-3-(4-(2-cyclopropoxyethoxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol crude (2.7 kg), dichloromethane (5.4 kg), and acetonitrile (3.2 kg) to a 30L glass reactor under nitrogen protection with magnetic stirred until complete dissolution. 2. In another vessel, boron trifluoride ethyl ether complex (2.34 kg) was added dropwise to a mixture of dichloromethane (5.4 kg) and acetonitrile (3.2 kg) of triethylsilane (2.55 kg) at -21 to -15 °C, maintaining a nitrogen atmosphere. 3. The feedstock solution prepared in step 1 was slowly added to the cold solution in step 2, and the addition rate was controlled to maintain the reaction temperature between -20 and -25°C (about 3 hours). After addition, the reaction continues to be stirred at -22 to -25°C for 4 hours. 4. Upon completion of the reaction, the reaction was quenched by the slow addition of 7.4% w/w aqueous sodium bicarbonate (18.3 kg), controlling the internal temperature to no more than -10°C. The reaction was then quenched by the addition of solid sodium bicarbonate (18.3 kg). Subsequently, solid sodium bicarbonate (1.35 kg) was added to adjust the pH to 7.5. 5. The solvent was removed by depressurized concentration (temperature < 40 °C) and the residue was partitioned with ethyl acetate (18 kg) and water (9.2 kg). The organic phase was separated and the aqueous phase was extracted with ethyl acetate (2 x 9 kg). The organic layers were combined and washed with saturated brine (2 x 9 kg). 6. The organic phase was concentrated to near dryness (temperature < 40 °C) under pressure, added anhydrous ethanol (9 kg) and concentrated again to give the crude product (2.5 kg, yield 90%, HPLC purity 90.8%, method HPLC-0001) as a foamy solid.
References
[1] Patent: US2013/267694, 2013, A1. Location in patent: Paragraph 0236; 0237; 0238; 0239; 0240; 0241
[2] Tetrahedron Letters, 2016, vol. 57, # 42, p. 4684 - 4687
[3] Patent: WO2013/152476, 2013, A1. Location in patent: Paragraph 0206; 0207; 0208; 0209; 0210
[4] Patent: WO2013/152654, 2013, A1. Location in patent: Paragraph 0212-0216
Bexagliflozin Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Bexagliflozin manufacturers
- Product
- Bexagliflozin 1118567-05-7
- Price
- US $2.20-8.80/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- g-kg-tons
- Release date
- 2025-07-08
- Product
- Bexagliflozin 1118567-05-7
- Price
- US $2.00/kg
- Min. Order
- 0.10000000149011612kg
- Purity
- 99%
- Supply Ability
- 200KG
- Release date
- 2023-09-11
- Product
- Bexagliflozin 1118567-05-7
- Price
- US $0.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 10000KGS
- Release date
- 2025-03-15