(2R,3R,4R,5S,6R)-5-{[(2R,3R,4R,5S,6R)-5-{[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-{[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino}oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-(hydroxymethyl)oxane-2,3,4-triol

• ChemBase ID: 72605
• Molecular Formular: C25H43NO18
• Molecular Mass: 645.60482
• Monoisotopic Mass: 645.24801354
• SMILES: [C@@H]1([C@@H]([C@H]([C@H](O[C@@H]1C)O[C@H]1[C@@H]([C@H]([C@H](O[C@@H]1CO)O[C@H]1[C@@H]([C@H]([C@@H](O[C@@H]1CO)O)O)O)O)O)O)O)N[C@H]1C=C([C@H]([C@@H]([C@H]1O)O)O)CO
• Canonical SMILES: OC[C@H]1O[C@H](O[C@@H]2[C@@H](CO)O[C@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O[C@H]1O[C@H](C)[C@H]([C@@H]([C@H]1O)O)N[C@H]1C=C(CO)[C@H]([C@@H]([C@H]1O)O)O)O)O
• InChI: InChI=1S/C25H43NO18/c1-6-11(26-8-2-7(3-27)12(30)15(33)13(8)31)14(32)19(37)24(40-6)43-22-10(5-29)42-25(20(38)17(22)35)44-21-9(4-28)41-23(39)18(36)16(21)34/h2,6,8-39H,3-5H2,1H3/t6-,8+,9-,10-,11-,12-,13+,14+,15+,16-,17-,18-,19-,20-,21-,22-,23-,24-,25-/m1/s1
• InChIKey: XUFXOAAUWZOOIT-SXARVLRPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6R)-5-{[(2R,3R,4R,5S,6R)-5-{[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-{[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino}oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-(hydroxymethyl)oxane-2,3,4-triol
• IUPAC Traditional name: acarbose; @acarbose
• Brand Name: Precose
• Synonyms: 4",6"-Dideoxy-4"-([1S]-[1,4,6/5]-4,5,6-trihydroxy-3-hydroxymethyl-2-yclohexenylamino)-maltotriose; Acarbose; Prandase; Precose; Glucobay; Bay-g 5421; Acarbose

Database IDs

• CAS Number: 56180-94-0
• EC Number: 260-030-7
• MDL Number: MFCD00869592
• PubChem SID: 162037530
• PubChem CID: 444254
• ATC CODE: A10BF01
• CHEMBL: 1566
• Chemspider ID: 392239
• DrugBank ID: DB00284
• KEGG ID: D00216
• Unique Ingredient Identifier: T58MSI464G
• Wikipedia Title: Acarbose
• Medline Plus: a696015

CALCULATED PROPERTIES

• Polar Surface Area: 321.17 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false
• Acid pKa: 11.225573
• H Acceptors: 19
• H Donor: 14
• LogD (pH = 5.5): -9.150389
• LogD (pH = 7.4): -7.7692995
• Log P: -7.6145587
• Molar Refractivity: 137.6024 cm^3
• Polarizability: 57.392616 Å^3

PROPERTIES

Safety Information

• Storage Condition: -20°C
• German water hazard class: 1
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: Extremely low
• Excretion: Renal (less than 2%)
• Half Life: 2 hours
• Metabolism: Gastrointestinal tract
• Legal Status: POM (UK); Rx-only (US)
• Pregnancy Category: B (US); B3 (Australia)
• US Licence: Precose

Product Information

• Purity: ≥95%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C25H43NO18

DETAILS

Selleck Chemicals - S1271

Research Area: Metabolic Disease
Biological Activity:
Acarbose is an anti-diabetic drug used to treat type 2 diabetes mellitus and, in some countries, prediabetes. It is an inhibitor of alpha glucosidase, an enteric enzyme that releases glucose from larger carbohydrates. [1]

Sigma Aldrich - A8980

Biochem/physiol Actions
Modified tetrasaccharide that acts as a reversible α -glucosidase inhibitor.
Application
Acarbose, a derivitized maltotriose antidiabetic drug, is a reversible α-glucosidase inhibitor used in medical studies to control the effects of Type II diabetes. Acarbose is often used as a reference to which other α-glucosidase inhibitors are compared.

REFERENCES

• http://en.wikipedia.org/wiki/Acarbose