ChemicalBook > CAS DataBase List > Bexagliflozin

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

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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|

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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..…

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 21359
Product name: EGT-1442
Purity: ≥95%
Packaging: 1mg
Price: $32
Updated: 2024/03/01

Cayman Chemical

Product number: 21359
Product name: EGT-1442
Purity: ≥95%
Packaging: 5mg
Price: $139
Updated: 2024/03/01

Cayman Chemical

Product number: 21359
Product name: EGT-1442
Purity: ≥95%
Packaging: 10mg
Price: $243
Updated: 2024/03/01

Cayman Chemical

Product number: 21359
Product name: EGT-1442
Purity: ≥95%
Packaging: 25mg
Price: $533
Updated: 2024/03/01

TRC

Product number: B336785
Product name: Bexagliflozin3
Packaging: 10mg
Price: $310
Updated: 2021/12/16

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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

ZHENGZHOU JIUYI TIME NEW MATERIALS CO,.LTD

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

Jinan Million Pharmaceutical Co., Ltd

Product: Bexagliflozin 1118567-05-7
Price: US $2.00/kg
Min. Order: 0.10000000149011612kg
Purity: 99%
Supply Ability: 200KG
Release date: 2023-09-11

Shaanxi Dideu New Materials Co. Ltd

Product: Bexagliflozin 1118567-05-7
Price: US $0.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 10000KGS
Release date: 2025-03-15

1118567-05-7, BexagliflozinRelated Search:

EGT1442

(1S)-1,5-Anhydro-1-C-[4-chloro-3-[[4-[2-(cyclopropyloxy)ethoxy]phenyl]methyl]phenyl]-D-glucitol

Bexagliflozin

EGT1442(Bexagliflozin,THR1442)

Bexagliflozin，EGT1442

CS-2165

EGT 0001442

EGT0001442

EGT-0001442

EGT1442; THR1442; EGT0001442; EGT-1442; THR-1442; EGT-0001442; EGT 1442; THR 1442; EGT 0001442

THR 1442

THR1442

THR-1442

CS-250

Bexagliflozin(THR1442,EGT1442)|

BEXAGLIFLOZIN;EGT-1442;THR1442;EGT0001442;EGT-1442;THR-1442;EGT-0001442;EGT 1442;THR 1442;EGT 0001442

Bexagliflozin (THR1442)

D-Glucitol, 1,5-anhydro-1-C-[4-chloro-3-[[4-[2-(cyclopropyloxy)ethoxy]phenyl]methyl]phenyl]-, (1S)-

Bexagliflozin3

Bexgliflozin

(2S,3R,4R,5S,6R)-2-(4-Chloro-3-(4-(2-cyclopropoxyethoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Bexagliflozin Impurity 1

Bexgliflozin (EGT1442)

Bexgliflozin Impurity 1

Bexagliflozin, 10 mM in DMSO

Bexagliflozin (EGT1442) ，E0141

Beisha Gelejing

1118567-05-7

118567-05-7