Acarbose

Title: Acarbose
CAS Registry Number: 56180-94-0
CAS Name: O-4,6-Dideoxy-4-[[[1S-(1a,4a,5b,6a)]-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-a-D-glucopyranosyl-(1®4)-O-a-D-glucopyranosyl-(1®4)-D-glucose
Additional Names: 4¢¢,6¢¢-dideoxy-4¢¢-[(1S)-(1,4,6/5)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenylamino]maltotriose
Manufacturers' Codes: Bay g 5421
Trademarks: Glucobay (Bayer); Prandase (Bayer); Precose (Bayer)
Molecular Formula: C25H43NO18
Molecular Weight: 645.60
Percent Composition: C 46.51%, H 6.71%, N 2.17%, O 44.61%
Literature References: Pseudotetrasaccharide containing an unsaturated cyclitol moiety. An a-glucosidase inhibitor that reduces sugar absorption in the gastrointestinal tract. Isoln from strains of Actinoplanes: W. Frommer et al., DE 2347782; eidem, US 4062950 (1975, 1977 both to Bayer). Total synthesis: S. Ogawa, Y. Shibata, Chem. Commun. 1988, 605; eidem, Carbohydr. Res. 189, 309 (1989). Biosynthetic studies: U. Degwert et al., J. Antibiot. 40, 855 (1987). Glucosidase inhibition studies: D. D. Schmidt et al., Naturwissenschaften 64, 535 (1977); W. Puls et al., ibid. 536. Use in treatment of diabetic adults: D. Sailor, G. Roder, Arzneim.-Forsch. 30, 2182 (1980); H. Laube et al., ibid. 1154. Long-term study in sulfonylurea-treated diabetics: H. Vierhapper et al., Diabetologia 20, 586 (1981). Potential use in prophylaxis of dental caries: N. E. Fiehn, D. Moe, Scand. J. Dent. Res. 90, 124 (1982). Review of pharmacodynamics, pharmacokinetics and therapeutic potential: S. P. Clissold, C. Edwards, Drugs 35, 214-243 (1988).
Properties: Amorphous powder. [a]D18 +165° (c = 0.4 in water).
Optical Rotation: [a]D18 +165° (c = 0.4 in water)
Therap-Cat: Antidiabetic.
Keywords: Antidiabetic; a-Glucosidase Inhibitor.
Acebutolol Acecainide Acecarbromal Aceclofenac Acedapsone

Acarbose
Acarbose structure.svg
Systematic (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} tetrahydro-2H-pyran-2-yl]oxy}-3,4-dihydroxy- 6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}- 6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4-triol
Clinical data
Trade names Precose
AHFS/Drugs.com monograph
MedlinePlus a696015
Licence data US FDA:link
Pregnancy cat. B3 (AU) B (US)
Legal status POM (UK) -only (US)
Routes Oral
Pharmacokinetic data
Bioavailability Extremely low
Metabolism Gastrointestinal tract
Half-life 2 hours
Excretion Renal (less than 2%)
Identifiers
CAS number 56180-94-0 YesY
ATC code A10BF01
PubChem CID 444254
DrugBank DB00284
ChemSpider 392239 YesY
UNII T58MSI464G YesY
KEGG D00216 YesY
ChEMBL CHEMBL1566 YesY
Chemical data
Formula C25H43NO18 
Mol. mass 645.605 g/mol
 YesY (what is this?)  (verify)

Acarbose is an anti-diabetic drug used to treat type 2 diabetes mellitus and, in some countries, prediabetes. It is a generic sold in Europe and China as Glucobay (Bayer AG), in North America as Precose (Bayer Pharmaceuticals), and in Canada as Prandase (Bayer AG). It is cheap and popular in China, but not in the U.S. One physician explains the use in the U.S. is limited because it is not potent enough to justify the side effects of diarrhea and flatulence.[1] However, a recent large study concludes "acarbose is effective, safe and well tolerated in a large cohort of Asian patients with type 2 diabetes."[2]A possible explanation for the differing opinions is an observation that acarbose is significantly more effective in patients eating a relatively high carbohydrate Eastern diet [3]

It is a starch blocker, and inhibits alpha glucosidase, an intestinal enzyme that releases glucose from larger carbohydrates. It is composed of an acarviosin moiety with a maltose at the reducing terminus.