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Substance Name: Acarbose [USAN:USP:INN:BAN:JAN]
RN: 56180-94-0
UNII: T58MSI464G
InChIKey: CEMXHAPUFJOOSV-XGWNLRGSSA-N

Note

  • An inhibitor of ALPHA-GLUCOSIDASES that retards the digestion and absorption of DIETARY CARBOHYDRATES in the SMALL INTESTINE.

Molecular Formula

  • C25-H43-N-O18

Molecular Weight

  • 645.6037
 

Classification Codes

  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Glycoside Hydrolase Inhibitors
  • Human Data
  • Hypoglycemic Agents
  • Inhibitor (alpha-Glucosidase)

Names and Synonyms

Name of Substance

  • Acarbose
  • Acarbose [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Acarbose

Synonyms

  • Acarbosa
  • Acarbosa [INN-Spanish]
  • Acarbose
  • Acarbosum
  • Acarbosum [INN-Latin]
  • Bay g 5421
  • BAY-g 5421
  • BAYG5421
  • D-Glucose, O-4,6-dideoxy-4-(((1S-(1alpha,4alpha,5beta,6alpha))-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl)amino)-alpha-D-glucopyranosyl-(1-4)-O-alpha-D-glucopyranosyl-(1-4)-
  • EINECS 260-030-7
  • Glucobay
  • HSDB 7984
  • O-4,6-Dideoxy-4-(((1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl)amino)-alpha-D-glucopyranosyl-(1-4)-O-alpha-D-glucopyranosyl-(1-4)-D-glucose
  • Precose
  • UNII-T58MSI464G

Systematic Names

  • Acarbose
  • D-Glucose, O-4,6-dideoxy-4-(((1S-(1-alpha,4-alpha,5-beta,6-alpha))-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl)amino)-alpha-D-glucopyranosyl-(1-4)-O-alpha-D-glucopyranosyl-(1-4)-
  • O-4,6-Dideoxy-4-(((1S-(1alpha,4alpha,5beta,6alpha))-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl)amino)-alpha-D-glucopyranosyl-(1-4)-O-alpha-D-glucopyranosyl-(1-4)-D-glucose

Registry Numbers

CAS Registry Number

  • 56180-94-0

FDA UNII

  • T58MSI464G

System Generated Number

  • 0056180940

Structure Descriptors

InChI

1S/C25H43NO18/c1-7-13(26-9-2-8(3-27)14(33)18(37)15(9)34)17(36)20(39)24(41-7)44-23-12(6-30)42-25(21(40)19(23)38)43-22(11(32)5-29)16(35)10(31)4-28/h2,4,7,9-27,29-40H,3,5-6H2,1H3/t7-,9+,10+,11-,12-,13-,14-,15+,16-,17+,18+,19-,20-,21-,22-,23-,24-,25-/m1/s1

InChIKey

CEMXHAPUFJOOSV-XGWNLRGSSA-N

Smiles

C[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1N[C@H]3C=C(CO)[C@@H](O)[C@H](O)[C@H]3O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo oral 10gm/kg (10000mg/kg)   Pharmaceutical Chemistry Journal Vol. 23, Pg. 82, 1989.
man TDLo oral 56mg/kg/13D-I (56mg/kg) BLOOD: EOSINOPHILIA

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Lancet. Vol. 354, Pg. 396, 1999.
mouse LD50 intravenous 12gm/kg (12000mg/kg)   Drugs in Japan Vol. -, Pg. 2, 1995.
mouse LD50 oral 24gm/kg (24000mg/kg)   Drugs in Japan Vol. -, Pg. 2, 1995.
rat LD50 intravenous 6gm/kg (6000mg/kg)   Drugs in Japan Vol. -, Pg. 2, 1995.
rat LD50 oral 24gm/kg (24000mg/kg)   Drugs in Japan Vol. -, Pg. 2, 1995.
rat LD50 subcutaneous 12gm/kg (12000mg/kg)   Drugs in Japan Vol. -, Pg. 2, 1995.
women TDLo oral 360mg/kg/60D- (360mg/kg) LIVER: LIVER FUNCTION TESTS IMPAIRED

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Annals of Internal Medicine. Vol. 124, Pg. 931, 1996.
women TDLo oral 378mg/kg/9W-I (378mg/kg) LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"

GASTROINTESTINAL: NAUSEA OR VOMITING

LIVER: LIVER FUNCTION TESTS IMPAIRED
Lancet. Vol. 349, Pg. 698, 1997.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -8.080 (none)   EST
Atmospheric OH Rate Constant 4.58E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.