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Compound Detail

CHEMBL404271

ACARBOSE
💊 Approved Drug
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💊 Approved Drug
C[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O[C@H]3[C@H](O)[C@@H](O)C(O)O[C@@H]3CO)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1N[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O

Basic Information

ChEMBL ID CHEMBL404271
Name ACARBOSE
Phase Approved
Structure Type MOL
InChI Key XUFXOAAUWZOOIT-UGEKTDRHSA-N
Therapeutic ✓ Yes

Known Names

Acarbosa Acarbose BAY G 5421 BAY-G 5421 BAY-G-5421 Glucobay NSC-758915 Precose
14
Targets
386
Activities
2
Assay Types
7
PK Parameters
20
Publications
8
Known Names
15
Indications
2
Mechanisms

Molecular Properties

645.6
MW (Da)
-8.56
ALogP
19
HBA
14
HBD
321.2
PSA (Ų)
0.10
QED
3
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Oligosaccharide
First Approval 1995
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product
USAN Year 1983

Extended Properties

Molecular Formula C25H43NO18
MW 645.61
Aromatic Rings 0
Heavy Atoms 44
NP-Likeness 1.83

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Pancreatic alpha-amylase inhibitor INHIBITOR Pancreatic alpha-amylase
Maltase-glucoamylase inhibitor INHIBITOR Maltase-glucoamylase

Indications

Diabetes Mellitus Diabetes Mellitus, Type 2 Atherosclerosis Coronary Disease Diabetes, Gestational Hypercholesterolemia Hypertension Metabolic Diseases Metabolic Syndrome Aging Kidney Neoplasms Non-alcoholic Fatty Liver Disease Hypotension, Orthostatic Nesidioblastosis Obesity

ATC Classification

A10BF01
acarbose
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: DRUGS USED IN DIABETES

Activity Summary

IC50 366 meas. best 7.48
Ki 20 meas. best 8.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
Ki 8.05 5.65 9.0 9
Unchecked
CHEMBL612545
IC50 7.48 5.0252 33.0 87
Alpha amylase
CHEMBL6066863
IC50 6.92 5.5393 120.0 15
Acidic alpha-glucosidase
CHEMBL3513
IC50 6.8 5.7359 160.0 17
Alpha-glucosidase
CHEMBL4412
Ki 6.47 6.47 340.0 1
Sucrase-isomaltase, intestinal
CHEMBL3114
IC50 6.4 5.5647 400.0 17
Maltase-glucoamylase
CHEMBL2074
IC50 6.38 4.7438 421.0 8
Alpha-amylase 1A
CHEMBL2478
IC50 6.37 6.2233 430.0 3
Alpha glucosidase
CHEMBL3833502
Ki 6.36 6.36 440.0 1
Alpha-glucosidase
CHEMBL5291954
IC50 5.97 4.8259 1060.3 22
Pancreatic alpha-amylase
CHEMBL5730
IC50 5.87 5.0657 1353.0 7
Alpha glucosidase
CHEMBL3833502
IC50 5.7 4.9375 2000.0 4
Acidic alpha-glucosidase
CHEMBL3513
Ki 5.46 5.46 3500.0 1
Lysosomal alpha-glucosidase
CHEMBL2608
IC50 5.3 4.84 5000.0 2
Alpha-amylase
CHEMBL3308960
IC50 5.29 4.8775 5080.0 4
SARS-CoV-2
CHEMBL4303835
IC50 4.66 4.66 21980.0 1
Oligo-1,6-glucosidase IMA1
CHEMBL5848
IC50 4.42 4.42 38250.0 1
Alpha-amylase
CHEMBL3308960
Ki 4.21 4.21 62400.0 1
Alpha amylase
CHEMBL6066863
Ki 4.21 4.21 62000.0 1
Alpha-glucosidase
CHEMBL5291954
Ki 4.04 4.04 90700.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 3343000.0 ng.hr.mL-1 Mus musculus
AUC 2232000.0 ng.hr.mL-1 Mus musculus
CL 2.2 mL.min-1.kg-1 Homo sapiens
CL 0.1 mL.min-1.kg-1 Homo sapiens
CL 2.2 mL.min-1.kg-1 Homo sapiens
MRT 2.4 hr Homo sapiens
T1/2 2.7 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 9.0 nM 8.05 Inhibition of mouse his-tagged ctMGAM-N2 expressed in Sf9 cells assessed as amou... 21669536
Unchecked Ki = 28.0 nM 7.55 Inhibition of mouse his-tagged ctMGAM-N20 expressed in Sf9 cells assessed as amo... 21669536
Unchecked IC50 = 33.0 nM 7.48 Inhibition of Bacillus stearothermophilus alpha-glucosidase 25999202
Unchecked IC50 = 33.0 nM 7.48 Inhibition of Bacillus stearothermophilus alpha-glucosidase type IV 19719245
Unchecked IC50 = 34.0 nM 7.47 Inhibition of Bacillus stearothermophilus alpha-glucosidase type 4 23025417
Unchecked IC50 = 36.0 nM 7.44 Inhibition of alpha-glucosidase (unknown origin) using pNPG as substrate by spec... 36680985
Unchecked IC50 = 49.0 nM 7.31 Inhibition of Bacillus stearothermophilus alpha glucosidase-4 20568785
Unchecked IC50 = 100.0 nM 7.0 Inhibition of Bacillus stearothermophilus alpha-glucosidase 18783210
Unchecked IC50 = 100.0 nM 7.0 Inhibition of Saccharomyces cerevisiae alpha-glucosidase 18783210
Alpha amylase IC50 = 120.0 nM 6.92 Inhibition of alpha-amylase (unknown origin) by HPLC analysis 32711292
Unchecked IC50 = 126.0 nM 6.9 Property Evaluation 3: Using the samples prepared according to Example 1 and Com... -
Acidic alpha-glucosidase IC50 = 160.0 nM 6.8 Inhibition of Wistar rat small intestine maltase after 30 mins 21185187
Acidic alpha-glucosidase IC50 = 180.0 nM 6.75 Inhibition of Wistar rat intestinal maltase assessed as inhibition of D-glucose ... 24973028
Acidic alpha-glucosidase IC50 = 180.0 nM 6.75 Inhibition of rat intestinal maltase using moltose as substrate 23106358
Alpha amylase IC50 = 210.0 nM 6.68 Inhibition of alpha-amylase (unknown origin) using starch as substrate preincuba... 37122544
Unchecked IC50 = 213.7 nM 6.67 Inhibition of porcine pancreatic alpha-amylase preincubated for 10 mins followed... 35694689
Unchecked Ki = 246.0 nM 6.61 Inhibition of mouse his-tagged ctSI expressed in Sf9 cells assessed as amount of... 21669536
Unchecked IC50 = 300.0 nM 6.52 Inhibition of alpha-glucosidase (unknown origin) using p-nitrophenyl-alpha-D-glu... 36680985
Alpha-glucosidase Ki = 340.0 nM 6.47 Competitive inhibition of Bacillus stearothermophilus alpha-glucosidase assessed... 21397496
Acidic alpha-glucosidase IC50 = 350.0 nM 6.46 Inhibition of rat intestinal brush border membrane maltase 18595718

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1431
- 10.6019/CHEMBL3885881 Rattus norvegicus 320
36680985 10.1016/j.ejmech.2023.115119 Alpha-glucosidase 30
36680985 10.1016/j.ejmech.2023.115119 Unchecked 27
28964635 10.1016/j.bmcl.2017.09.027 Pancreatic alpha-amylase 20
32280435 10.1039/C9MD00301K Molecular identity unknown 20
16472241 10.2174/1570163043334794 Hepatotoxicity 18
28964635 10.1016/j.bmcl.2017.09.027 Unchecked 17
29866516 10.1016/j.bmcl.2018.05.034 Unchecked 16
30031655 10.1016/j.bmc.2018.07.021 Unchecked 14
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
21669536 10.1016/j.bmc.2011.05.033 Unchecked 13
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
28343876 10.1016/j.bmcl.2017.03.013 Unchecked 10
30282319 10.1016/j.ejmech.2018.07.073 Alpha-glucosidase 9
23993676 10.1016/j.bmc.2013.07.048 Mus musculus 8
32280435 10.1039/C9MD00301K Phocaeicola dorei 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
20070106 10.1021/jm901371v Homo sapiens 8
32008883 10.1016/j.bmc.2019.115263 Unchecked 7

Data from ChEMBL 36 via Core Engine