3D Mol Similar

Voglibose

Iupac Name：(1S,2S,3R,4S,5S)-5-(1,3-dihydroxypropan-2-ylamino)-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol

CAS No.: 83480-29-9

Molecular Weight：267.278

Modify Date.: 2022-11-29 06:02

Introduction: 1. It is used for treating diabetes.2. Anti-diabetic drug. View more+

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1. Names and Identifiers

1.1 Name: Voglibose
1.2 Synonyms: (1S,2S,3R,4S,5S)-5-((1,3-Dihydroxypropan-2-yl)amino)-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetraol (1S,2S,3R,4S,5S)-5-[(1,3-Dihydroxypropan-2-yl)amino]-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetraol 2,3-Dideoxy-2-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-4-C-(hydroxymethyl)-epi-inositol 3,4-Dideoxy-4-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-2-C-(hydroxymethyl)-D-epi-inositol 3,4-Dideoxy-4-{[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-2-D-epi-inositol A 71100 AO 128 Basen Beigrace D-epi-Inositol, 3,4-dideoxy-4-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-2-C-(hydroxymethyl)- epi-Inositol, 2,3-dideoxy-2-((2-hydroxy-1-(hydroxymethyl)ethyl)amino)-4-C-(hydroxymethyl)- Glustat Jumeal N-(1,3-Dihydroxy-2-propyl)valiolamine N-(1,3-Dihydroxyprop-2-yl)valiolamine Voglistat

1.3 CAS No.: 83480-29-9

1.4 CID: 444020

1.5 EINECS(EC#): 1312995-182-4

1.6 Molecular Formula: C10H21NO7 (isomer)

1.7 Inchi: InChI=1S/C10H21NO7/c12-2-5(3-13)11-6-1-10(18,4-14)9(17)8(16)7(6)15/h5-9,11-18H,1-4H2/t6-,7-,8+,9-,10-/m0/s1

1.8 InChkey: FZNCGRZWXLXZSZ-CIQUZCHMSA-N

1.9 Canonical Smiles: C1C(C(C(C(C1(CO)O)O)O)O)NC(CO)CO

1.10 Isomers Smiles: C1[C@@H]([C@@H]([C@H]([C@@H]([C@]1(CO)O)O)O)O)NC(CO)CO

2. Properties

2.1 Density: 1.58

2.1 Melting point: 162-163℃

2.1 Boiling point: 601.9oC at 760 mmHg

2.1 Refractive index: 1.635

2.1 Flash Point: 274.1oC

2.1 Precise Quality: 267.13200

2.1 PSA: 153.64000

2.1 logP: -4.10150

2.1 Appearance: Solid

2.2 Storage: Store at -20°C

2.3 Chemical Properties: Colourless Crystalline Solid

2.4 Physical: Solid

2.5 pKa: 13.26±0.70(Predicted)

2.6 Water Solubility: 1.90e+02 g/L

2.7 StorageTemp: Store in original container in a cool dark place.

3. Use and Manufacturing

3.1 Methods of Manufacturing: III (0.2 g, 0.001 mmol) was added to DMF (8 mL), stirred and dissolved, followed by the addition of 1, 3-dihydroxyacetone (0.3 g, 0.03 mmol), 2N HCl (0.15 mL) and NaBH3CN (0.22 g, 0.004 mol) at 60 °C for 24 h cooled to room temperature, add water (3mL), adjusted to pH=4.0 with 2 Ν HCl, stirred for 30min, 1N NaOH was added to adjust PH = 7.0, the solvent was distilled off under reduced pressure through the UBK resin, followed by elution with water, 2N ammonia, and the eluate was collected and concentrated. After passing through CG50, water: ethanol (6: 4) was eluted and the eluate was collected, and then decolorized by Dowex1 x 2 to give 0.24 g of white powder voglibose, 85percent.To a solution of 6 (483mg, 2.5mmol) in DMF (30mL), 1, 3-dihydroxyacetone (900mg, 10.0mmol) and 2.0M hydrochloric acid (0.50mL) and NaBHThe synthesis of voglibose from the starting material, d-glucose, to compound 1 referred to the previous reports.

3.2 Usage: 1. It is used for treating diabetes.2. Anti-diabetic drug.

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: R20/21/22

4.1 Safety Statements: S36/37

4.1 RIDADR: HAZARD

4.1 WGK Germany: 3

4.1 RTECS: NM7524600

4.1 Safety: Hazard Codes:?Xi
Risk Statements: 20/21/22-36/37/38?
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed
R36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 36/37-37/39-26?
S36/37: Wear suitable protective clothing and gloves
S37/39: Wear suitable gloves and eye/face protection
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
RTECS: NM7524600

4.2 Specification: ?Voglibose?(CAS NO.83480-29-9) is also called as?Voglibose [USAN:INN]?; 3,4-Dideoxy-4-((2-hydroxy-1-(hydroxymethyl)ethyl)amino)-2-C-(hydroxymethyl)-D-epi-inositol ; Voglibosa ; Voglibosa [INN-Spanish] ; Voglibose ; Voglibosum ; Voglibosum [INN-Latin] ; 3,4-Dideoxy-4-((2-hydroxy-1-(hydroxymethyl)ethyl)amino)-2-C-(hydroxymethyl)-D-epi-inositol .There are three molecules which belong to this class namely, Acarbose, Miglitol and Voglibose?(CAS NO.83480-29-9). Voglibose?(CAS NO.83480-29-9) is the latest molecule in this class. Voglibose?(CAS NO.83480-29-9) scores over both Acarbose and MIglitol in terms of side effect profile. But Acarbose has an edge over Voglibose?(CAS NO.83480-29-9) in terms of efficacy(FBG , PPBG , HBA1C).

4.3 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LD50	oral	> 2gm/kg (2000mg/kg)	?	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 25, Pg. 815, 1994.
mouse	LD50	intravenous	7820mg/kg (7820mg/kg)	?	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 25, Pg. 815, 1994.
mouse	LD50	oral	14700mg/kg (14700mg/kg)	?	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 25, Pg. 815, 1994.
rat	LD50	intravenous	6300mg/kg (6300mg/kg)	?	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 25, Pg. 815, 1994.
rat	LD50	oral	20gm/kg (20000mg/kg)	?	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 25, Pg. 815, 1994.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s)	no data available
Signal word	no data available
Hazard statement(s)	no data available
Precautionary statement(s)
Prevention	no data available
Response	no data available
Storage	no data available
Disposal	no data available

2.3 Other hazards which do not result in classification

no data available

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6. NMR Spectrum

Predict 1H proton NMR

7. Synthesis Route

83480-29-9Total: 4 Synthesis Route

115250-39-0 69 Suppliers

83480-29-9 307 Suppliers

Literatures:
Fukase; Horii Journal of Organic Chemistry, 1992 , vol. 57, # 13 p. 3651 - 3658
Yield: ~91%

115250-38-9 39 Suppliers

83480-29-9 307 Suppliers

Literatures:
Journal of Organic Chemistry, , vol. 57, # 13 p. 3651 - 3658
Yield: null

849419-34-7

83480-29-9 307 Suppliers

Literatures:
WO2005/30698 A1, ; Page/Page column 9-10 ;
Yield: null

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8. Precursor and Product

precursor:

115250-39-0

96-26-4

83465-22-9

115250-38-9

849419-34-7

9. Other Information

9.0 Storage Conditions: III (0.2 g, 0.001 mmol) was added to DMF (8 mL), stirred and dissolved, followed by the addition of 1, 3-dihydroxyacetone (0.3 g, 0.03 mmol), 2N HCl (0.15 mL) and NaBH3CN (0.22 g, 0.004 mol) at 60 °C for 24 h cooled to room temperature, add water (3mL), adjusted to pH=4.0 with 2 Ν HCl, stirred for 30min, 1N NaOH was added to adjust PH = 7.0, the solvent was distilled off under reduced pressure through the UBK resin, followed by elution with water, 2N ammonia, and the eluate was collected and concentrated. After passing through CG50, water: ethanol (6: 4) was eluted and the eluate was collected, and then decolorized by Dowex1 x 2 to give 0.24 g of white powder voglibose, 85percent.To a solution of 6 (483mg, 2.5mmol) in DMF (30mL), 1, 3-dihydroxyacetone (900mg, 10.0mmol) and 2.0M hydrochloric acid (0.50mL) and NaBHThe synthesis of voglibose from the starting material, d-glucose, to compound 1 referred to the previous reports.

9.1 Mesh: Substances which lower blood glucose levels. (See all compounds classified as Hypoglycemic Agents.)|Compounds that inhibit or block the activity of GLYCOSIDE HYDROLASES such as ALPHA-AMYLASES and ALPHA-GLUCOSIDASES. (See all compounds classified as Glycoside Hydrolase Inhibitors.)

9.2 Absorption: Slowly and poorly absorbed. The reported pharmacokinetic parameters of voglibose with metformin are Cmax corresponds to 1.38 mcg/ml while AUC is 8.17 mcg.h/ml and tmax is of 2.5 hours.

9.3 Metabolism: Little metabolism occurs and no metabolites have as yet been identified.

9.4 Biological Half Life: The half-life of voglibose is very similar to the one found for metformin and it is reported to be of 4.08 hours.

9.5 Mesh Entry Terms: 3,4-dideoxy-4-((2-hydroxy-1-(hydroxymethyl)ethyl)amino)-2-C-(hydroxymethyl)-D-epi-inositol

10. Computational chemical data

Molecular Weight: 267.278g/mol
Molecular Formula: C₁₀H₂₁NO₇
Compound Is Canonicalized: True
XLogP3-AA: -4.1
Exact Mass: 267.13180201
Monoisotopic Mass: 267.13180201
Complexity: 263
Rotatable Bond Count: 5
Hydrogen Bond Donor Count: 8
Hydrogen Bond Acceptor Count: 8
Topological Polar Surface Area: 154
Heavy Atom Count: 18
Defined Atom Stereocenter Count: 5
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceByOAAAAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAAAAAAAHgAQCAAADHzhgAYAAALAAgAAAAAAAAAAAAAAAAAAAIAIAAADEAIAgAAEQAAHEACRAAHw8DcOAAAAAAAAAABCgAKUABCgAAAAAAAAAA==

11. Question & Answer

Role of voglibose in prevention of type 2 diabetes May 16 2021
Description Voglibose (INN and USAN, trade name Voglib, marketed by Mascot Health Series) is an alpha-glucosidase inhibitor used for lowering post-prandial blood glucose levels in people with diabetes mellitus. Voglibose delays the absorption of glucose thereby reducing the risk of macrovascular co...

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