(2R,3R,4R,5S,6R)-5-{[(2R,3R,4R,5S,6R)-5-{[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-{[(1S,4S,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: 169
• Molecular Formular: C25H43NO18
• Molecular Mass: 645.60482
• Monoisotopic Mass: 645.24801354
• SMILES: [C@H]1([C@H](O[C@@H]([C@@H]([C@H]1O)O)O[C@@H]1[C@H](O[C@H]([C@@H]([C@H]1O)O)O)CO)CO)O[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)C)N[C@H]1C=C([C@@H]([C@@H]([C@H]1O)O)O)CO)O)O
• 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-JMPDRRIHSA-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,4S,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
• Brand Name: Precose; Glucobay; Prandase
• Synonyms: Acarbose

Database IDs

• CAS Number: 56180-94-0
• PubChem SID: 46508248; 160963632
• PubChem CID: 441184

CALCULATED PROPERTIES

JChem

• 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
• Polar Surface Area: 321.17 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -2.66
• LOG S: -0.64
• Solubility (Water): 1.48e+02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): -6.8

DETAILS

DrugBank - DB00284

• Drug Groups: approved; investigational
• Description: An inhibitor of alpha glucosidase that retards the digestion and absorption of carbohydrates in the small intestine and hence reduces the increase in blood-glucose concentrations after a carbohydrate load. It is given orally to non-insulin dependent diabetes mellitus patients where diet modification or oral hypoglycemic agents do not control their condition. (From Martindale The Extra Pharmacopoeia, 31st ed)
• Indication: For treatment and management of diabetes type II (used in combination therapy as a second or third line agent)
• Pharmacology: Used to reduce blood gluose in patients with type 2 diabetes. Acarbose is a complex oligosaccharide that delays the digestion of ingested carbohydrates, thereby resulting in a smaller rise in blood glucose concentration following meals. Acarbose binds to and inhibits alpha amylase and alpha-gluocside hydrolases. In diabetic patients, this enzyme inhibition results in a delayed glucose absorption and a lowering of postprandial hyperglycemia.
• Affected Organisms: Humans and other mammals
• Absorption: Extremely low bioavailability.
• Half Life: 2 hours
• Elimination: The fraction of acarbose that is absorbed as intact drug is almost completely excreted by the kidneys.
• References: Clissold SP, Edwards C: Acarbose. A preliminary review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential. Drugs. 1988 Mar;35(3):214-43. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Clissold SP, Edwards C: Acarbose. A preliminary review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential. Drugs. 1988 Mar;35(3):214-43. Pubmed