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Session ID: 428841b3245df9e4f062dc0e9b58bb2a

Search Type: drug

Started at: 2009-10-15 11:31:38

Finished at: 2009-10-15 11:33:53

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Field Result Source
Name
ACARBOSE External
Drugbank ID
DB00284 DrugBank
Description
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. DrugBank
Chemical Kingdom
Organic BioSpider
Chemical Class
Not Available Not Applicable
Chemical Species
1,2-aminoalcohol Checkmol
1,2-diol Checkmol
acetal Checkmol
alkene Checkmol
hemiacetal Checkmol
heterocyclic compound Checkmol
primary alcohol Checkmol
secondary alcohol Checkmol
secondary aliphatic amine (dialkylamine) Checkmol
secondary amine Checkmol
Synonym
Acarbose (jan/usan/inn) Pubchem
Glucobay DPD
Precose Pubchem
Precose (TN) Pubchem
Brand Mixture
Not Available Not Applicable
CAS
56180-94-0 DrugBank
InChI Identifier 
InChI=1/C25H43NO18/c1-6-11(26-8-2-7(3-27)12(30)15(33)13(8)31)14(3
2)19(37)24(40-6)43-22-10(5-29)42-25(20(38)17(22)35)44-21-9(4-28)4
1-23(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
 World Wide Molecular Matrix
IUPAC
(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)-1-cyclohex-2-enyl]amino]oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,4-triol DrugBank
Chemical Formula
C25H43NO18 PubChem
Chemical Structure
Chemical Structure PubChem
Average Molecular Weight (g/mol)
645.604820 BioSpider
Monoisotopic Molecular Weight (g/mol)
645.248010 BioSpider
SMILES (Isomeric) 
O([C@H]1[C@H](O)[C@@H](O)C(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
 ChemSpider
SMILES (Canonical) 
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
 PubChem
Kegg Drug
D00216 DrugBank
Kegg Compound
C06802 DrugBank
Pubchem Compound ID
441184 DrugBank
Pubchem Substance ID
10940188 Pubchem
36885082 Pubchem
46508248 Pubchem
50752735 Pubchem
57403574 Pubchem
7847283 Pubchem
8148213 Pubchem
9021 Kegg
OMIM ID
Not Available Not Applicable
ChEBI
2376 DrugBank
BioCyc
Not Available Not Applicable
PharmGKB
PA448010 DrugBank
HET ID
Not Available Not Applicable
DPD ID
02190885 DPD
02190893 DPD
Rxlist Link
http://www.rxlist.com/cgi/generic/acarbose.htm DrugBank
Wikipedia
Not Available Not Applicable
Pdr Health Link
http://www.pdrhealth.com/drugs/altmed/altmed-mono.aspx?contentFileName=ame0337.xml&contentName=Pancreatin&contentId=493 PDRHealth
Melting Point
Not Available Not Applicable
State
Not Available Not Applicable
MSDS Link
Not Available Not Applicable
FDA Label
1255627965.pdf FDA
Experimental Water Solubility
Not Available Not Applicable
Predicted Water Solubility
1000 mg/mL at 25 oC [MEYLAN,WM et al. (1996)] PhysProp
148 mg/mL [Predicted by ALOGPS] Alogps
Experimental LogP
Not Available Not Applicable
Predicted LogP
-2.66 [Predicted by ALOGPS] Alogps
-8.08 [MEYLAN,WM & HOWARD,PH (1995)] PhysProp
pKa
Not Available Not Applicable
SDF File
1255627906.sdf Pubchem
Mol File
1255627900.mol Molconvert
Pdb File
1255627927.pdb Molconvert
Mass Spec File
Not Available Not Applicable
Associated Disorder
Not Available Not Applicable
Pathway
Not Available Not Applicable
Category
Not Available Not Applicable
ATC Code
A10BF01 DPD
AHFS Code
68:20.02 DPD
Schedule
SCHEDULE F (Canada) DPD
Indication
For treatment and management of diabetes type II (used in combination therapy as a second or third line agent) DrugBank
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. DrugBank
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. DrugBank
PRECOSE® (acarbose tablets) is an oral alpha-glucosidase inhibitor for use in the management of type 2 diabetes mellitus. Acarbose is an oligosaccharide which is obtained from fermentation processes of a microorganism, Actinoplanes utahensis, and is chemically known as O-4,6-dideoxy- 4-[[(1S,4R,5S,6S)-4,5,6­trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]- α-D-glucopyranosyl-(1 → 4)-O-α-D-glucopyranosyl­ (1→ 4)-D-glucose. It is a white to off-white powder with a molecular weight of 645.6. Acarbose is soluble in water and has a pKa of 5.1. Its empirical formula is C25H43NO18 and its chemical structure is as follows: RxList
Absorption
Extremely low bioavailability. DrugBank
Protein Binding
Not Available Not Applicable
Half Life
2 hours DrugBank
Biotransformation
Not Available Not Applicable
Toxicity
Not Available Not Applicable
Dosage
Tablet (Oral) DPD
Patient Information
1255628026.html RxList
Interactions
Not Available Not Applicable
Contraindications
Not Available Not Applicable
Targets 
O43451
[ UniProt | Analyze ]		 DrugBank 
P04746
[ UniProt | Analyze ]		 DrugBank 
P10253
[ UniProt | Analyze ]		 DrugBank 
P14410
[ UniProt | Analyze ]		 DrugBank