Precose

Base Information

• Chemical Name: Precose
• CAS No.: 56180-94-0
• Molecular Formula: C25H43NO18
• Molecular Weight: 645.612
• Hs Code.: 29400090
• European Community (EC) Number: 260-030-7
• Nikkaji Number: J1.629.106D
• Wikipedia: Acarbose
• Wikidata: Q338005
• NCI Thesaurus Code: C983
• RXCUI: 16681
• Pharos Ligand ID: 2GHRKRPZGFS5
• ChEMBL ID: CHEMBL1566
• Mol file: 56180-94-0.mol

Synonyms:Acarbose;Bay g 5421;Glucobay;Glucor;Glumida;Prandase;Precose

Chemical Property of Precose

Chemical Property:

• Appearance/Colour: Off-white solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 165-170 °C
• Refractive Index: 1.689
• Boiling Point: 971.6 °C at 760 mmHg
• PKA: 12.39±0.20(Predicted)
• Flash Point: 541.4 °C
• PSA: 321.17000
• Density: 1.74 g/cm³
• LogP: -8.17360
• Storage Temp.: Store at RT
• Solubility.: Very soluble in water, soluble in methanol, practically insoluble in methylene chloride.
• Water Solubility.: Soluble in water.
• XLogP3: -8.5
• Hydrogen Bond Donor Count: 14
• Hydrogen Bond Acceptor Count: 19
• Rotatable Bond Count: 9
• Exact Mass: 645.24801352
• Heavy Atom Count: 44
• Complexity: 962

Purity/Quality:

99% ^*data from raw suppliers

Acarbose ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Antidiabetic Agents
• Canonical SMILES: CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OC3C(OC(C(C3O)O)O)CO)CO)O)O)NC4C=C(C(C(C4O)O)O)CO
• Isomeric SMILES: C[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@H]2[C@H](O[C@@H]([C@@H]([C@H]2O)O)O[C@@H]3[C@H](O[C@H]([C@@H]([C@H]3O)O)O)CO)CO)O)O)N[C@H]4C=C([C@H]([C@@H]([C@H]4O)O)O)CO
• Recent ClinicalTrials: The Efficacy and Tolerability of Acarbose in Healthy Individuals
• Recent EU Clinical Trials: HypoBar I: Delaying intestinal glucose absorption to ameliorate post-bariatric hypoglycaemia. A randomized cross-over clinical trial.
• Recent NIPH Clinical Trials: Comparison of effects of a DPP-4 inhibitor and an alpha-glucosidase inhibitor on visceral fat and oxidative stress in type 2 diabetes mellitus
• Description: Acarbose, a complex oligosaccharide isolated from Actinoplanes, is reportedly useful as an adjuvant therapy in diabetes. By inhibiting alpha-glucosidase, acarbose delays carbohydrate metabolism in the gastrointestinal tract and modulates changes in food induced blood sugar levels.
• Uses: A reversible alpha-glucosidase inhibitorAcarbose is used as a reversible alfa-glucosidase inhibitor. It acts as an anti-diabetic drug, which finds useful application to treat type 2 diabetes mellitus and prediabetes. It is also employed for Hepatitis. It also acts as a beta glucosidase inhibitor, antihyperlipidaemia and antiobesity. antipsychotic: 5HT antagonist, dopamine antagonist, H1-antihistamine, alpha adrenergic blocker Acarbose is pseudo-oligosaccharide with a terminal C7-cyclitol patented in 1975 by Bayer. Acarbose is a component of the amylostatin complex produced by a species of Actinoplanes and Streptomyces. Acarbose acts as a potent inhibitor of alpha-glucosidases and saccharases. Since 1990, acarbose has been used therapeutically for the treatment of type 2 diabetes.
• Therapeutic Function: Antidiabetic
• Clinical Use: Based on the structure of acarbose, it should come as nosurprise that little intact acarbose reaches the systemic circulation;instead, acarbose is extensively biotransformed by the actionof microbes and digestive enzymes in the gut. Only about35% of the radioactivity in a dose of 14C-labeled acarbose administeredorally to men was excreted in the urine, appearingas several metabolites, some of which are phase II conversionproducts of 4-methylpyrogallol (O-methyl, O-sulfate, orO-glucuronide conjugates); the methylpyrogallol fragmentarises from the terminal valienamine pseudosugar. That thesebiotransformation products are mostly formed in the gut isshown by the fact that nearly 90% of an intravenously administereddose of acarbose is excreted intact in urine.
• Drug interactions: Potentially hazardous interactions with other drugs Antibacterials: hypoglycaemic effect possibly enhanced and increased gastrointestinal side effects with neomycin. Lipid lowering agents: hypoglycaemic effect possibly enhanced by colestyramine.

Technology Process of Precose

There total 4 articles about Precose 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: 59.0%

1,2,3,6,2',3',6',2'',3''-nona-O-acetyl-4'',6''-dideoxy-4''-<(1S)-(1,4,6/5)-4,5,6-triacetoxy-3-acetoxymethyl-2-cyclohexenylamino>-α-maltotriose (68107-35-7,117065-98-2) → acarbose (56180-94-0,68107-33-5,106864-09-9)

Guidance literature:

With sodium methylate; In methanol; for 2h; Ambient temperature;

DOI:10.1016/0008-6215(89)84107-2

Reference yield: 59.0%

acarbose trideca-acetate → acarbose (56180-94-0,68107-33-5,106864-09-9)

Guidance literature:

DOI:10.1039/c39880000605

Reference yield:

2,3,2',3',6',2'',3''-hepta-O-acetyl-1,6-anhydro-4'',6''-dideoxy-4''-<(1S)-(1,4,6/5)-4,5,6-triacetoxy-3-acetoxymethyl-2-cyclohexenylamino>-β-maltotriose (117011-93-5) → acarbose (56180-94-0,68107-33-5,106864-09-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / conc. sulphuric acid / acetic acid / Ambient temperature

2: 59 percent

With sulfuric acid; In acetic acid;

DOI:10.1039/c39880000605

upstream raw materials:

1,2,3,6,2',3',6',2'',3''-nona-O-acetyl-4'',6''-dideoxy-4''-<(1S)-(1,4,6/5)-4,5,6-triacetoxy-3-acetoxymethyl-2-cyclohexenylamino>-α-maltotriose

2,3,2',3',6',2'',3''-hepta-O-acetyl-1,6-anhydro-4'',6''-dideoxy-4''-<(1S)-(1,4,6/5)-4,5,6-triacetoxy-3-acetoxymethyl-2-cyclohexenylamino>-β-maltotriose

Downstream raw materials:

β-D-glucose pentaacetate

α-D-glucopyranose peracetylate

Methyl-4-<(1S)-(1,4,6/5)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexen-1-yl>amino-D-glucopyranosid

Refernces

• 1、 Shibata, Yasushi,Ogawa, Seiichiro. "TOTAL SYNTHESIS OF ACARBOSE AND ADIPOSIN-2". . p. 309 - 322. Retrieved 2007/10/02.