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56180-94-0 molecular structure
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(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 and InChIs

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

Cite this record

CBID:169 http://www.chembase.cn/molecule-169.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
56180-94-0
PubChem SID
160963632
46508248
PubChem CID
441184

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
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 cm3 Polarizability 57.392616 Å3
Polar Surface Area 321.17 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P -2.66  LOG S -0.64 
Solubility (Water) 1.48e+02 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Hydrophobicity(logP)
-6.8 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00284 external link
Item Information
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

REFERENCES

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  • • 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
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PATENTS

PATENTS

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INTERNET

INTERNET

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