Ipragliflozin

ChemicalBook > CAS DataBase List > Ipragliflozin

Product Name: Ipragliflozin
CAS No.: 761423-87-4
Chemical Name: Ipragliflozin
Synonyms: Suglat;CS-1580;Igliazine;Ipragliflozin;Iprag iflozin;Ipragliflozin-002;Ipragliflozin, >=98%;Ipragliflozin impuity;Ipragliflozin （Suglat）;IpragliflozinL-Proline
CBNumber: CB02589633
Molecular Formula: C21H21FO5S
Formula Weight: 404.45
MOL File: 761423-87-4.mol

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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

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 22287
Product name: Ipragliflozin
Purity: ≥98%
Packaging: 10mg
Price: $32
Updated: 2024/03/01

Cayman Chemical

Product number: 22287
Product name: Ipragliflozin
Purity: ≥98%
Packaging: 50mg
Price: $139
Updated: 2024/03/01

Cayman Chemical

Product number: 22287
Product name: Ipragliflozin
Purity: ≥98%
Packaging: 100mg
Price: $199
Updated: 2024/03/01

Cayman Chemical

Product number: 22287
Product name: Ipragliflozin
Purity: ≥98%
Packaging: 250mg
Price: $456
Updated: 2024/03/01

TRC

Product number: I739475
Product name: Ipragliflozin
Packaging: 500mg
Price: $620
Updated: 2021/12/16

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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

Baoji Guokang Bio-Technology Co., Ltd.

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

Cangzhou Kangrui Pharma Tech Co. Ltd.,

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

Nanjing Fred Technology Co., Ltd

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

761423-87-4, IpragliflozinRelated Search:

Methyl 1-C-[3-(benzo[b]thien-2-ylMethyl)-4-fluorophenyl]- Capecitabine Rivaroxaban Benzo[b]thiophene-2-Methanol, α-(5-broMo-2-fluorophenyl)- 2-(5-BroMo-2-Methylbenzyl)-5-(4-fluorophenyl)thiophene 5-bromo-2-chloro-4’-ethoxydiphenylmethane (2S,3R,4S,5S,6R)-2-(3-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)-4-chlorophenyl)-tetrahydro-6-(hydroxyMethyl)-2-Methoxy-2H-pyran-3,4,5-triol 2-(4-Fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene Canagliflozin heMihydrate 2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone PF-04971729 1-Chloro-2-(4-ethoxybenzyl)-4-iodobenzene 2,3,4,6-TETRA-O-PIVALOYL-ALPHA-D-GLUCOPYRANOSYL BROMIDE Dapagliflozin Empagliflozin D-Glucitol, 1,5-dideoxy-1,5-epithio-1-C-[5-[(4-ethoxyphenyl)Methyl]-2-Methoxy-4-Methylphenyl]-, (1S)- Tofogliflozin LX-4211

Ipragliflozin, >=98%

IpragliflozinL-Proline

Ipragliflozin (ASP1941)

Ipragliflozin impuity

(1S)-1,5-Anhydro-1-C-[3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl]-D-glucitol

Ipragliflozin

ASP-1941/D-Glucitol, 1,5-anhydro-1-C-[3-(benzo[b]thien-2-ylMethyl)-4-fluorophenyl]-, (1S)-

Ipragliflozin, (1S)-1,5-Anhydro-1-C-[3-[(1-benzothiophen-2-yl)Methyl]-4-fluorophenyl]-D-glucitol

(2S,3R,4R,5S,6R)-2-[3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl]-6-(hydroxymethyl)oxane-3,4,5-triol

Ipragliflozin （Suglat）

IpragliflozinL-Proline int

Ipragliflozin-002

Ipragliflozin Impurity

CS-1580

D-Glucitol, 1,5-anhydro-1-C-[3-(benzo[b]thien-2-ylmethyl)-4-fluorophenyl]-, (1S)-

Suglat

Iprag iflozin

Igliazine

761423-87-4

C21H21FO5S

Inhibitors