acarbose

Also known as BAY-G 5421, BAY-G-5421, Glucobay®, Precose®

Acarbose (INN) is an anti-diabetic drug used to treat diabetes mellitus type 2 and (in some countries), prediabetes. It is sold in Europe and China as Glucobay (Bayer AG), in North America as Precose (Bayer Pharmaceuticals), and in Canada as Prandase (Bayer AG).

Key facts

Drug.Watchedfields: changed
Drug.verifiedrevid: 477237664
Drug.image: Haworth projection of acarbose.svg
Drug.image_class: skin-invert-image
Drug.alt: Haworth projection of acarbose
Drug.width: 300
Drug.image2: Acarbose-3D-balls.png
Drug.image_class2: bg-transparent
Drug.alt2: Ball-and-stick model of the acarbose molecule
Drug.width2: 200
Drug.tradename: Glucobay, Precose, Prandase
Drug.synonyms: (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
Drug.IUPAC_name: O-4,6-Dideoxy-4--α-D-glucopyranosyl-(1→4)-O-α-D-glucopyranosyl-(1→4)-D-glucopyranose
Drug.C: 25
Drug.H: 43
Drug.N: 1
Drug.O: 18
Drug.smiles: O([C@H]1[C@H](O)[C@@H](O)[C@H](O)O[C@@H]1CO)[C@H]4O[C@@H]([C@@H](O[C@H]3O[C@H](C)[C@@H](N[C@H]2/C=C(/CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]3O)[C@H](O)[C@H]4O)CO

via Wikipedia infobox

Chemical data

Formula: C25H43NO18
Molecular weight: 645.6 g/mol
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
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
InChIKey: XUFXOAAUWZOOIT-SXARVLRPSA-N
XLogP: -8.5
Polar surface area: 321 Å²
H-bond donors: 14
H-bond acceptors: 19
Formal charge: 0

via PubChem

Research

4,855 papers

Acarbose ameliorates podocyte injury and glomerular lesions in diabetic nephropathy through USP46 activation.Science translational medicine · 2026
Acarbose: an alpha-glucosidase inhibitor.American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists · 1996
Acarbose enhances the efficacy of immunotherapy against solid tumours by modulating the gut microbiota.Nature metabolism · 2024
Acarbose With Comparable Glucose-Lowering but Superior Weight-Loss Efficacy to Dipeptidyl Peptidase-4 Inhibitors: A Systematic Review and Network Meta-Analysis of Randomized Controlled Trials.Frontiers in endocrinology · 2020
Acarbose: oral anti-diabetes drug with additional cardiovascular benefits.Expert review of cardiovascular therapy · 2008

via PubMed

Wikidata facts

Mass: 645.248

Show 6 more facts

Commons category: Acarbose
chemical formula: C₂₅H₄₃NO₁₈
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]1O[C@H](O[C@@H]2[C@@H](CO)O[C@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1N[C@H]3C=C(CO)[C@@H](O)[C@H](O)[C@H]3O
defined daily dose: 0.3
NCI Thesaurus ID: C983

Sources (5)

via Wikidata · CC0

~10 min read

Article

11 sections

Contents

Medical uses
Efficacy
Combination therapy
Adverse effects
Pharmacology
Mechanism of action
Metabolism
Natural distribution
In molecular biology
Research
References

{{Infobox drug | Watchedfields = changed | verifiedrevid = 477237664 | image = Haworth projection of acarbose.svg | image_class = skin-invert-image | alt = Haworth projection of acarbose | width = 300 | image2 = Acarbose-3D-balls.png | image_class2 = bg-transparent | alt2 = Ball-and-stick model of the acarbose molecule | width2 = 200