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Dapagliflozin propanediol monohydrate

Product Name
Dapagliflozin propanediol monohydrate
CAS No.
960404-48-2
Chemical Name
Dapagliflozin propanediol monohydrate
Synonyms
Dapagliflozin propylene glycolate hydrate;Dapagliflozin propanediol hydrate;Forxiga;(2S,3R,4R,5S,6R)-2-(4-CHLORO-3-(4-ETHOXYBENZYL)PHENYL)-6-(HYDROXYMETHYL)TETRAHYDRO-2H-PYRAN-3,4,5-TRIOL COMPOUND WITH (S)-PROPANE-1,2-DIOL (1:1) HYDRATE;CS-1307;Dapaglilozin;Enzymes Pepsase;Dapagliflozin Hydrate;Dapagliflozin SC crystal;Dapagliflozin Impurity 67
CBNumber
CB62705080
Molecular Formula
C24H33ClO8
Formula Weight
484.97
MOL File
960404-48-2.mol
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Dapagliflozin propanediol monohydrate Property

Melting point:
74 - 78°C
storage temp. 
-20°C Freezer
solubility 
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
form 
Solid
color 
White to Off-White
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TRC
Product number
D185398
Product name
DapagliflozinPropanediolHydrate
Packaging
100mg
Price
$640
Updated
2021/12/16
Biosynth Carbosynth
Product number
MD45346
Product name
Dapagliflozin propanediol monohydrate
Packaging
500mg
Price
$85
Updated
2021/12/16
Biosynth Carbosynth
Product number
MD45346
Product name
Dapagliflozin propanediol monohydrate
Packaging
1g
Price
$140
Updated
2021/12/16
ChemScene
Product number
CS-3077
Product name
Dapagliflozin((2S)-1,2-propanediol,hydrate)
Purity
99.99%
Packaging
1g
Price
$180
Updated
2021/12/16
Medical Isotopes, Inc.
Product number
73598
Product name
Dapagliflozinpropyleneglycolatehydrate
Packaging
10mg
Price
$190
Updated
2021/12/16
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Dapagliflozin propanediol monohydrate Chemical Properties,Usage,Production

Description

Dapagliflozin propanediol monohydrate is the first approved sodium-glucose cotransporter protein 2 (SGLT2) inhibitor. It is indicated for the treatment of type 2 diabetes. When combined with diet and exercise in adults, dagliflozin helps improve glycaemic control by inhibiting glucose reabsorption in the proximal tubules of renal units and causing glycosuria. Dagliflozin can be given alone or in combination with insulin or other oral hypoglycaemic agents as adjunctive therapy.
Dagliflozin was originally approved by the FDA on 8 January 2014 for use in combination with diet and exercise to improve glycemic control in adults with type 2 diabetes. It was later approved in April 2021 to reduce the risk of declining kidney function, kidney failure, cardiovascular death and hospitalisation for heart failure in adults with chronic kidney disease.

Uses

Dapagliflozin Propanediol Hydrate is an SGLT2 inhibitor, which can be used for the treatment of diabetes.

Definition

ChEBI: A hydrate that consists of dapagliflozin compounded with (S)-propylene glycol and hydrate in a (1:1:1) ratio. Used to improve glycemic control, along with diet and exercise, in adults with type 2 diabetes.

Clinical Use

The most likely process-scale synthesis has been described in a literature publication and patent, and this is summarized in the scheme below. The synthesis began with global silylation glucolactone 63 to form tetrasiloxide 64. In parallel, commercial 5-bromo-2-chlorobenzoyl acid (65) was converted to the corresponding acid chloride with oxalyl chloride. Subsequently, this acid chloride was subjected to Friedel-Crafts acylation with ethyl phenyl ether (“phenetole”) in the presence of aluminum trichloride at low temperature to give benzophenone 66 in 91% yield. Next, the carbonyl functionality within 66 was removed upon treatment with triethylsilane and boron trifluoride-etherate, producing 5-bromo-2-chloro- 4'-ethoxydiphenylmethane 67 in 75% yield as the aglycon partner. Aryl bromide 67 was subjected to lithium halogen exchange conditions and subsequent exposure to lactone 64, which gave a mixture of lactols which were then immediately subjected to methanesulfonic acid to provide glucol 68 in 85% yield. The anomeric methoxy group of 68 was reduced with triethylsilane and boron trifluoride-etherate followed by peracetylation to deliver α-C-glycoside tetra-acetate 69 in 55% (two steps) after recrystalliaztion in ethanol. Hydrolysis of polyacetate 69 with lithium hydroxide gave dapagliflozin in quantitative yield, and upon treatment with propanediol in water, dapagliflozin propanediol hydrate (X) was produced.

Synthesis

Dapagliflozin propanediol hydrate, an orally active sodium glucose cotransporter type 2 (SGLT-2) inhibitor, was developed by Bristol-Myers Squibb (BMS) and AstraZeneca for the once-daily treatment of type 2 diabetes. As opposed to competitor SGLT-2 inhibitors, dapagliflozin was not associated with renal toxicity or long-term deterioration of renal function in phase III clinical trials. The drug exhibits excellent SGLT2 potency with more than 1200 fold selectivity over the SGLT1 enzyme.

Dapagliflozin propanediol monohydrate Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Dapagliflozin propanediol monohydrate manufacturers

Nanjing Fred Technology Co., Ltd
Product
Dapagliflozin propanediol monohydrate 960404-48-2
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
BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
Product
Dapagliflozin Propanediol Monohydrate 960404-48-2
Price
US $0.00/g
Min. Order
1g
Purity
More Than 99%
Supply Ability
100kg/Month
Release date
2024-09-06
Hangzhou Hyper Chemicals Limited
Product
Dapagliflozin propanediol monohydrate 960404-48-2
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
150kg
Release date
2024-05-10

960404-48-2, Dapagliflozin propanediol monohydrateRelated Search:

Dapagliflozin Impurity 4 (Mixture of Diastereomers) Dapagliflozin Impurity D Dapagliflozin Impurity 1 Dagliflozin (S)-propylene glycol hydrate (2R,3R,4R,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxyMethyl)tetrahydro-2H-pyran-3,4,5-triol Ortho-Isomer of Dapagliflozin 4,4'-dichloro-3,3'-bis(4-ethoxybenzyl)-1,1'-biphenyl Dapagliflozin Impurity 21 Dapagliflozin Open Ring Dapagliflozin Impurity G 4,4''-Diethoxybenzil 2-Propanone, 1-(2-hydroxypropoxy)- (9CI) Dapagliflozin Impurity 46 (2,5-dibromophenyl)(4-ethoxyphenyl)methanone Dapagliflozin Impurity (MW:423Da) (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3- (4-methoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4- hydroxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate Dapagliflozin Impurity 28

  • (2S,3R,4R,5S,6R)-2-(4-CHLORO-3-(4-ETHOXYBENZYL)PHENYL)-6-(HYDROXYMETHYL)TETRAHYDRO-2H-PYRAN-3,4,5-TRIOL COMPOUND WITH (S)-PROPANE-1,2-DIOL (1:1) HYDRATE
  • BMS 512148 (2S)-1,2-propanediol
  • CS-1307
  • Dapagliflozin (S)-Propylene Glycol Hydrate
  • Dag column net a water glycol
  • Dapagliflozin propanediol hydrate
  • Dapagliflozin,(2S)-1,2-propanediol, hydrate (1:1:1)
  • Dapagliflozin ((2S)-1,2-propanediol, hydrate)###461432-26-8###Dapagliflozin
  • Dapagliflozin ((2S)-1,2-propanediol, hydrate)
  • Dapagliflozin propylene glycolate hydrate
  • Forxiga
  • Dapragliflozin Propanediol Monohydrate
  • (1S)-1,5-Anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol compound with (2S)-1,2-Propanediol (1:1), Monohydrate (9CI)
  • (1S)-1,5-Anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl
  • Dapagliflozin Impurity 67
  • BMS-512148 (2S)-1,2-propanediol, hydrate
  • Enzymes Pepsase
  • Dapagliflozin (API)
  • (1S)-1,5-Anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol, compounded with (2S)-1,2-propanediol, hydrate (1:1:1)
  • (2S)-propane-1,2-diol (2S,3R,4R,5S,6R)-2-{4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl}-6-(hydroxymethyl)oxane-3,4,5-triol hydrate
  • Dapagliflozin (2S)-1,2-Propanediol Monohydrate
  • Dapaglilozin
  • Dapagliflozin Hydrate
  • Dapagliflozin Monohydrate In-House
  • Dapagliflozin SC crystal
  • (2S,3R,4R,5S,6R)-2-(4-Chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (S)-propane-1,2-diol hydrate
  • 960404-48-2
  • 496040-08-2
  • C3H8O2C21H25ClO6H2O
  • C21H25ClO6C3H8O2H2O
  • C24H35ClO9
  • API
  • 960404-48-2