Pharmakon1600-01504273

Base Information

• Chemical Name: Pharmakon1600-01504273
• CAS No.: 72432-03-2
• Molecular Formula: C8H17NO5
• Molecular Weight: 207.227
• Hs Code.: 29333990
• NSC Number: 758702
• ChEMBL ID: CHEMBL3039370
• Mol file: 72432-03-2.mol

Synonyms:Spectrum_001632;Spectrum2_000507;Spectrum3_001000;Spectrum4_001128;Spectrum5_001470;BSPBio_002699;KBioGR_001615;KBioSS_002112;SPECTRUM1504273;SPBio_000433;SCHEMBL7862967;CHEMBL3039370;KBio2_002112;KBio2_004680;KBio2_007248;KBio3_001919;HMS1922J17;HMS2093G08;Pharmakon1600-01504273;CCG-39595;NSC758702;NCGC00178523-01;SBI-0206794.P001;AB01563021_01;SR-05000001994;SR-05000001994-1

Chemical Property of Pharmakon1600-01504273

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 3.87E-10mmHg at 25°C
• Melting Point: 114 °C
• Refractive Index: 1.597
• Boiling Point: 453.7 °C at 760 mmHg
• PKA: 5.9(at 25℃)
• Flash Point: 284.3 °C
• PSA: 104.39000
• Density: 1.458 g/cm³
• LogP: -3.32420
• Storage Temp.: -20°C Freezer
• Solubility.: Soluble in DMSO (up to 50 mg/ml with warming), or in Water (up to 60 mg/ml).
• Water Solubility.: Soluble
• XLogP3: -2.6
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 207.11067264
• Heavy Atom Count: 14
• Complexity: 179

Purity/Quality:

99.9% ^*data from raw suppliers

Miglitol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C(N1CCO)CO)O)O)O
• Isomeric SMILES: C1[C@H]([C@H](C(C(N1CCO)CO)O)O)O
• Description: Miglitol was introduced in Germany as an auxiliary treatment for non-insulin dependent diabetes (NIDDM). A simple two-step synthesis of Miglitol consists of converting 6-desoxy-6-aminosorbose into desoxynojirimycin by reductive cyclization, then selectively hydroxyethylating the cyclic nitrogen. Miglitol is a short-acting intestinal alpha-D-glucosidase inhibitor, reducing postprandial glucose excursions by helping to delay absorption of complex carbohydrates. Acarbose and voglibose are the previous compounds marketed in this class. At low doses, orally administered miglitol was shown to be rapidly and completely absorbed then removed by renal excretion.
• Uses: An inhibitor of alpha-glucosidases. A potent α-glucosidase inhibitor. A new antidiabetic drug. antibacterial
• Indications: Miglitol [Glyset] is the second alpha-glucosidase inhibitor approved in the United States. Like acarbose, miglitol delays conversion of oligosaccharides and complex carbohydrates to glucose and other monosaccharides, and thereby reduces the postprandial rise in blood glucose. In clinical trials, the drug was especially effective among Latinos and African Americans. Hypoglycemia does not occur with miglitol monotherapy, but may occur if the drug is combined with insulin or a sulfonylurea. Like acarbose, miglitol causes flatulence, abdominal discomfort, and other GI effects. In contrast to acarbose, miglitol has not been associated with liver dysfunction. As with acarbose therapy, oral sucrose cannot be used to treat hypoglycemia. Rather, oral glucose must be given. Miglitol is available in 25-, 50-, and 100-mg tablets. The initial dosage is 25 mg 3 times daily before meals. The maintenance dosage is 50 or 100 mg 3 times a day.
• Therapeutic Function: Glucosidase inhibitor
• Clinical Use: One of the widely used a-glucosidase inhibitors for treatment of Type II diabetes is miglitol (C8H17NO5; IUPAC name (2R,3R,4R,5S)-1-(2-hydroxyethyl)- 2-(hydroxymethyl)piperidine-3,4,5-triol; molecular weight 207.2). Miglitol is a second-generation a-glucosidase inhibitor derived from 1-deoxynojirimycin, which is yet another a-glucosidase inhibitor and is structurally similar to glucose (Tan, 1997). It is a white to pale yellow powder and is soluble in water (Campbell et al., 2000). Miglitol was approved by the U.S. Food and Drug Administration (FDA) in 1996 as an additional therapy to diet alone therapy or diet plus sulfonylurea therapy in patients with Type II diabetes. Miglitol’s story begins with the successful attempts for identifying new compounds with inhibitory properties, which initially resulted in the discovery of nojirimycin, deoxynojirimycin, and their derivatives from various Bacillus and Streptomyces strains (Schmidt et al., 1979). During initial attempts, 1-deoxynojirimycin was successfully obtained (Schmidt et al., 1979); however, its N-hydroxyethyl analog (miglitol) later proved to possess better inhibitory activities. It is currently being manufactured by Bayer AG under the trade name of Glysetò in USA and as Diastabolò in Europe. Miglitol is considered to be a good choice for the therapy of patients who have the relative risk of developing hypoglycemia, weight gain, or lactic acidosis (Campbell et al., 2000). It is observed to have the same efficacy as acarbose at lesser dosages (50 and 100 mg tid). Miglitol therapy provides better reduction on fasting and postprandial plasma glucose levels in patients in comparison with sulfonylureas (Scott and Spencer, 2000), whereas voglibose, another a-glucosidase inhibitor, could achieve reduction only for postprandial glucose levels.

Technology Process of Pharmakon1600-01504273

There total 24 articles about Pharmakon1600-01504273 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

[(2R,3R,4R,5S)-3,4,5-Tris-benzyloxy-1-(2-benzyloxy-ethyl)-piperidin-2-yl]-methanol (308273-87-2) → migitol (72432-03-2,132310-34-0,149302-58-9)

Guidance literature:

DOI:10.1016/S0040-4039(00)01229-6

Reference yield: 97.5%

C10H21NO4 → migitol (72432-03-2,132310-34-0,149302-58-9)

Guidance literature:

With palladium on activated charcoal; acetic acid; In tetrahydrofuran; water; at 35 - 40 ℃; for 6h; under 45004.5 Torr; Reagent/catalyst; Temperature; Solvent; Pressure; Autoclave;

Reference yield: 95.0%

N-(2-benzyloxyethyl)-1-deoxynojirimycin (1203659-54-4) → migitol (72432-03-2,132310-34-0,149302-58-9)

Guidance literature:

With hydrogenchloride; palladium 10% on activated carbon; hydrogen; In methanol; water; at 20 ℃; for 20h; under 3000.3 Torr; pH=Ca. 3;

DOI:10.1021/jm901281m

upstream raw materials:

[(2R,3R,4R,5S)-3,4,5-Tris-benzyloxy-1-(2-benzyloxy-ethyl)-piperidin-2-yl]-methanol

1,5-dideoxy-1,5-imino-D-glucitol

2-bromoethanol

[(2S,3R,4R,5S)-3,4,5-Tris-benzyloxy-1-(2-benzyloxy-ethyl)-piperidin-2-yl]-methanol

Downstream raw materials:

2,3,4-tri-O-acetyl-N-(2-acetyloxyethyl)-6-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol

2,3-di-O-acetyl-6-O-benzyl-1,5-dideoxy-N-(2-acetyloxyethyl)-1,5-imino-D-glucitol

2,3-di-O-acetyl-N-(2-acetyloxyethyl)-4,6-O-benzylidene-1,5-dideoxy-1,5-imino-D-glucitol

2,3-di-O-acetyl-4,6-O-benzylidene-1,5-dideoxy-N-(2-fluoroethyl)-1,5-imino-D-glucitol

Refernces

• 1、 Zamoner, Luís O. B.,Arag?o-Leoneti, Valquiria,Carvalho, Ivone. "Iminosugars: Effects of stereochemistry, ring size, and n-substituents on glucosidase activities". . . Retrieved 2019/09/03.
• 2、 Khobare, Sandip R.,Gajare, Vikas,Reddy, E. Vishnuvardhan,Datrika, Rajender,Banda, Malavika,Siddaiah, Vidavalur,Pachore, Sharad S.,Timanna, Upadhya,Dahanukar, Vilas H.,Syam Kumar. "One pot oxidative dehydration - oxidation of polyhydroxyhexanal oxime to polyhydroxy oxohexanenitrile: A versatile methodology for the facile access of azasugar alkaloids". . p. 1 - 6. Retrieved 2016/09/28.