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Identification
Name Acarbose
Accession Number DB00284 (APRD00656)
Type small molecule
Groups approved
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)
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Glucobay
Prandase
Precose
Brand mixtures Not Available
Categories
  • Hypoglycemic Agents
  • Enzyme Inhibitors
CAS number 56180-94-0
Weight Average: 645.6048
Monoisotopic: 645.248013577
Chemical Formula C25H43NO18
InChI Key InChIKey=XUFXOAAUWZOOIT-JMPDRRIHSA-N
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
Plain Text
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
SMILES
C[C@H]1O[C@H](O[C@@H]2[C@@H](CO)O[C@H](O[C@@H]3[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1N[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Glycolipids
Substructures
  • Glycolipids
  • Glycerol and Derivatives
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Pyrans
  • Acetals and Derivatives
  • Aliphatic and Aryl Amines
  • Carbohydrates
  • Ethers
  • Alcohols and Polyols
  • Amino Alcohols
  • Heterocyclic compounds
  • Cyclohexenes and Derivatives
Pharmacology
Indication For treatment and management of diabetes type II (used in combination therapy as a second or third line agent)
Pharmacodynamics 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.
Mechanism of action Acarbose reversibly bind to pancreatic alpha-amylase and membrane-bound intestinal alpha-glucoside hydrolases. These enzymes inhibit hydrolysis of complex starches to oligosaccharides in the lumen of the small intestine and hydrolysis of oligosaccharides, trisaccharides, and disaccharides to glucose and other monosaccharides in the brush border of the small intestine.
Absorption Extremely low bioavailability.
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination The fraction of acarbose that is absorbed as intact drug is almost completely excreted by the kidneys.
Half life 2 hours
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Impax laboratories inc
  • Roxane laboratories inc
  • Watson laboratories inc
  • Bayer healthcare pharmaceuticals inc
Packagers
Dosage forms
Form Route Strength
Tablet Oral
Prices
Unit description Cost Unit
Acarbose 100 100 mg tablet Bottle 120.62 USD bottle
Acarbose 100 50 mg tablet Bottle 100.71 USD bottle
Acarbose 100 25 mg tablet Bottle 93.54 USD bottle
Precose 100 mg tablet 1.28 USD tablet
Acarbose 100 mg tablet 1.17 USD tablet
Precose 50 mg tablet 1.11 USD tablet
Precose 25 mg tablet 1.01 USD tablet
Acarbose 25 mg tablet 0.91 USD tablet
Acarbose 50 mg tablet 0.88 USD tablet
Glucobay 100 mg Tablet 0.4 USD tablet
Glucobay 50 mg Tablet 0.29 USD tablet
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Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
logP -6.8 Not Available
Predicted Properties
Property Value Source
water solubility 1.48e+02 g/l ALOGPS
logP -2.7 ALOGPS
logP -7.6 ChemAxon
logS -0.64 ALOGPS
pKa (strongest acidic) 11.23 ChemAxon
pKa (strongest basic) 7.03 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 19 ChemAxon
hydrogen donor count 14 ChemAxon
polar surface area 321.17 ChemAxon
rotatable bond count 9 ChemAxon
refractivity 137.6 ChemAxon
polarizability 62.39 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. 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
Resource Link
KEGG Drug D00216 Link_out
KEGG Compound C06802 Link_out
PubChem Compound 441184 Link_out
PubChem Substance 46508248 Link_out
ChemSpider 389971 Link_out
ChEBI 2376 Link_out
ChEMBL 2376 Link_out
Therapeutic Targets Database DCL000309 Link_out
PharmGKB PA448010 Link_out
Drug Product Database 2190893 Link_out
RxList http://www.rxlist.com/cgi/generic/acarbose.htm Link_out
Drugs.com http://www.drugs.com/cdi/acarbose.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Acarbose Link_out
ATC Codes
  • A10BF01
AHFS Codes
  • 68:20.02
PDB Entries Not Available
FDA label show (268 KB)
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Digoxin Acarbose may decrease the serum levels of digoin. It is thought that acarbose reduces digoin absorption. Monitor for changes in digoxin serum levels and therapeutic and adverse effects if acarbose is initiated, discontinued or dose changed.
Somatropin recombinant Somatropin may antagonize the hypoglycemic effect of acarbose. Monitor for changes in fasting and postprandial blood sugars.
Food Interactions
  • Take with food, at beginning of each meal.
Targets

1. Maltase-glucoamylase, intestinal

Pharmacological action: yes
Actions: inhibitor

May serve as an alternate pathway for starch digestion when luminal alpha-amylase activity is reduced because of immaturity or malnutrition. May play a unique role in the digestion of malted dietary oligosaccharides used in food manufacturing

Organism class: human
UniProt ID: O43451 Link_out
Gene: MGAM Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Okumiya T, Keulemans JL, Kroos MA, Van der Beek NM, Boer MA, Takeuchi H, Van Diggelen OP, Reuser AJ: A new diagnostic assay for glycogen storage disease type II in mixed leukocytes. Mol Genet Metab. 2006 May;88(1):22-8. Epub 2005 Dec 15. Pubmed
  2. Zhang H, Kallwass H, Young SP, Carr C, Dai J, Kishnani PS, Millington DS, Keutzer J, Chen YT, Bali D: Comparison of maltose and acarbose as inhibitors of maltase-glucoamylase activity in assaying acid alpha-glucosidase activity in dried blood spots for the diagnosis of infantile Pompe disease. Genet Med. 2006 May;8(5):302-6. Pubmed
  3. Gelb MH, Turecek F, Scott CR, Chamoles NA: Direct multiplex assay of enzymes in dried blood spots by tandem mass spectrometry for the newborn screening of lysosomal storage disorders. J Inherit Metab Dis. 2006 Apr-Jun;29(2-3):397-404. Pubmed
  4. Yamagishi S, Matsui T, Ueda S, Fukami K, Okuda S: Clinical utility of acarbose, an alpha-glucosidase inhibitor in cardiometabolic disorders. Curr Drug Metab. 2009 Feb;10(2):159-63. Pubmed
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Pancreatic alpha-amylase

Pharmacological action: yes
Actions: inhibitor

Endohydrolysis of 1,4-alpha-D-glucosidic linkages in oligosaccharides and polysaccharides

Organism class: human
UniProt ID: P04746 Link_out
Gene: AMY2A
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Jonas L, Mikkat U, Lehmann R, Schareck W, Walzel H, Schroder W, Lopp H, Pussa T, Toomik P: Inhibitory effects of human and porcine alpha-amylase on CCK-8-stimulated lipase secretion of isolated rat pancreatic acini. Pancreatology. 2003;3(4):342-8. Pubmed

3. Lysosomal alpha-glucosidase

Pharmacological action: yes
Actions: inhibitor

Essential for the degradation of glygogen to glucose in lysosomes

Organism class: human
UniProt ID: P10253 Link_out
Gene: GAA Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Salehi A, Fan BG, Ekelund M, Nordin G, Lundquist I: TPN-evoked dysfunction of islet lysosomal activity mediates impairment of glucose-stimulated insulin release. Am J Physiol Endocrinol Metab. 2001 Jul;281(1):E171-9. Pubmed
  2. Li Y, Scott CR, Chamoles NA, Ghavami A, Pinto BM, Turecek F, Gelb MH: Direct multiplex assay of lysosomal enzymes in dried blood spots for newborn screening. Clin Chem. 2004 Oct;50(10):1785-96. Epub 2004 Aug 3. Pubmed
  3. Lundquist I, Panagiotidis G: The relationship of islet amyloglucosidase activity and glucose-induced insulin secretion. Pancreas. 1992;7(3):352-7. Pubmed
  4. Zhang H, Kallwass H, Young SP, Carr C, Dai J, Kishnani PS, Millington DS, Keutzer J, Chen YT, Bali D: Comparison of maltose and acarbose as inhibitors of maltase-glucoamylase activity in assaying acid alpha-glucosidase activity in dried blood spots for the diagnosis of infantile Pompe disease. Genet Med. 2006 May;8(5):302-6. Pubmed
  5. Gelb MH, Turecek F, Scott CR, Chamoles NA: Direct multiplex assay of enzymes in dried blood spots by tandem mass spectrometry for the newborn screening of lysosomal storage disorders. J Inherit Metab Dis. 2006 Apr-Jun;29(2-3):397-404. Pubmed
  6. Lullmann-Rauch R, Watermann D: Fusion of storage lysosomes in experimental lipidosis and glycogenosis. Exp Mol Pathol. 1987 Feb;46(1):136-43. Pubmed
  7. Bourbon JR, Doucet E, Rieutort M: Role of alpha-glucosidase in fetal lung maturation. Biochim Biophys Acta. 1987 Jan 13;917(1):203-10. Pubmed
  8. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

4. Sucrase-isomaltase, intestinal

Pharmacological action: yes
Actions: inhibitor

Plays an important role in the final stage of carbohydrate digestion

Organism class: human
UniProt ID: P14410 Link_out
Gene: SI Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Juretic D, Bernik S, Cop L, Hadzija M, Petlevski R, Lukac-Bajalo J: Short-term effect of acarbose on specific intestinal disaccharidase activities and hyperglycaemia in CBA diabetic mice. J Anim Physiol Anim Nutr (Berl). 2003 Aug;87(7-8):263-8. Pubmed
  2. Meyer H, Wieczorek H, Zeiske W: K+ transport in the caterpillar intestine epithelium: role of osmolytes for the K+-secretory capacity of the tobacco hornworm midgut. J Comp Physiol [B]. 2004 Oct;174(7):527-39. Epub 2004 Aug 20. Pubmed
  3. Karley AJ, Ashford DA, Minto LM, Pritchard J, Douglas AE: The significance of gut sucrase activity for osmoregulation in the pea aphid, Acyrthosiphon pisum. J Insect Physiol. 2005 Dec;51(12):1313-9. Epub 2005 Sep 15. Pubmed
  4. Samulitis BK, Goda T, Lee SM, Koldovsky O: Inhibitory mechanism of acarbose and 1-deoxynojirimycin derivatives on carbohydrases in rat small intestine. Drugs Exp Clin Res. 1987;13(8):517-24. Pubmed
  5. Newbrun E, Hoover CI, Walker GJ: Inhibition by acarbose, nojirimycin and 1-deoxynojirimycin of glucosyltransferase produced by oral streptococci. Arch Oral Biol. 1983;28(6):531-6. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19