U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C25H43NO18
Molecular Weight 645.6058
Optical Activity UNSPECIFIED
Defined Stereocenters 18 / 18
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACARBOSE

SMILES

C[C@]1([H])[C@]([H])([C@@]([H])([C@]([H])([C@]([H])(O1)O[C@]2([H])[C@@]([H])(CO)O[C@@]([H])([C@@]([H])([C@@]2([H])O)O)O[C@]([H])([C@@]([H])(CO)O)[C@@]([H])([C@]([H])(C=O)O)O)O)O)N[C@@]3([H])C=C(CO)[C@]([H])([C@@]([H])([C@@]3([H])O)O)O

InChI

InChIKey=CEMXHAPUFJOOSV-XGWNLRGSSA-N
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

HIDE SMILES / InChI
Acarbose is an anti-diabetic drug used to treat type 2 diabetes mellitus and, in some countries, prediabetes. 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)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]¬ α-D-glucopyranosyl-(1 → 4)-O-α-D-glucopyranosyl-(1 → 4)-D-glucose. Acarbose is a complex oligosaccharide that delays the digestion of ingested carbohydrates, thereby resulting in a smaller rise in blood glucose concentration following meals. As a consequence of plasma glucose reduction, PRECOSE (acarbose tablets) reduces levels of glycosylated hemoglobin in patients with type 2 diabetes mellitus. Systemic non-enzymatic protein glycosylation, as reflected by levels of glycosylated hemoglobin, is a function of average blood glucose concentration over time. In contrast to sulfonylureas, PRECOSE does not enhance insulin secretion. The antihyperglycemic action of acarbose results from a competitive, reversible inhibition of pancreatic alpha-amylase and membrane-bound intestinal alpha-glucoside hydrolase enzymes. Pancreatic alpha-amylase hydrolyzes complex starches to oligosaccharides in the lumen of the small intestine, while the membrane-bound intestinal alpha-glucosidases hydrolyze oligosaccharides, trisaccharides, and disaccharides to glucose and other monosaccharides in the brush border of the small intestine. In diabetic patients, this enzyme inhibition results in a delayed glucose absorption and a lowering of postprandial hyperglycemia. Because its mechanism of action is different, the effect of PRECOSE to enhance glycemic control is additive to that of sulfonylureas, insulin or metformin when used in combination. In addition, PRECOSE diminishes the insulinotropic and weight-increasing effects of sulfonylureas. Acarbose has no inhibitory activity against lactase and consequently would not be expected to induce lactose intolerance.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
PRECOSE

Approved Use

Acarbose Tablets are indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus.

Launch Date

8.1034563E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
49 ng/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ACARBOSE unknown
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
0.51 μg × h/mL
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ACARBOSE unknown
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
3.13 μg × h/mL
0.4 mg/kg single, intravenous
dose: 0.4 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ACARBOSE unknown
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
0.55 h
0.4 mg/kg single, intravenous
dose: 0.4 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ACARBOSE unknown
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
100 mg 3 times / day multiple, oral (max)
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
unhealthy, 57.2
n = 84
Health Status: unhealthy
Condition: diabetes mellitus
Age Group: 57.2
Sex: M+F
Population Size: 84
Sources:
Disc. AE: Flatulence, Diarrhea...
AEs leading to
discontinuation/dose reduction:
Flatulence (26%)
Diarrhea (17%)
Abdominal pain (7%)
Sources:
300 mg 1 times / day multiple, oral (max)
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 63
n = 1954
Health Status: unhealthy
Condition: diabetes mellitus, type 2
Age Group: 63
Sex: M+F
Population Size: 1954
Sources:
Other AEs: Flatulence, Diarrhea...
Other AEs:
Flatulence (68 patients)
Diarrhea (13 patients)
Loose stools (1 patient)
Abdominal pain (4 patients)
Nausea (3 patients)
Constipation (1 patient)
Hypoglycaemic episode (10 patients)
Appetite lost (2 patients)
Weight loss (1 patient)
Burning anal (1 patient)
Heartburn (1 patient)
Sources:
300 mg 1 times / day multiple, oral (max)
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 63
n = 27803
Health Status: unhealthy
Condition: diabetes mellitus
Age Group: 63
Sex: M+F
Population Size: 27803
Sources:
Other AEs: Flatulence, Diarrhoea...
Other AEs:
Flatulence (13.7%)
Diarrhoea (2.2%)
Hypoglycaemia (0.07%)
Function liver abnormal (0.01%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Diarrhea 17%
Disc. AE
100 mg 3 times / day multiple, oral (max)
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
unhealthy, 57.2
n = 84
Health Status: unhealthy
Condition: diabetes mellitus
Age Group: 57.2
Sex: M+F
Population Size: 84
Sources:
Flatulence 26%
Disc. AE
100 mg 3 times / day multiple, oral (max)
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
unhealthy, 57.2
n = 84
Health Status: unhealthy
Condition: diabetes mellitus
Age Group: 57.2
Sex: M+F
Population Size: 84
Sources:
Abdominal pain 7%
Disc. AE
100 mg 3 times / day multiple, oral (max)
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
unhealthy, 57.2
n = 84
Health Status: unhealthy
Condition: diabetes mellitus
Age Group: 57.2
Sex: M+F
Population Size: 84
Sources:
Burning anal 1 patient
300 mg 1 times / day multiple, oral (max)
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 63
n = 1954
Health Status: unhealthy
Condition: diabetes mellitus, type 2
Age Group: 63
Sex: M+F
Population Size: 1954
Sources:
Constipation 1 patient
300 mg 1 times / day multiple, oral (max)
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 63
n = 1954
Health Status: unhealthy
Condition: diabetes mellitus, type 2
Age Group: 63
Sex: M+F
Population Size: 1954
Sources:
Heartburn 1 patient
300 mg 1 times / day multiple, oral (max)
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 63
n = 1954
Health Status: unhealthy
Condition: diabetes mellitus, type 2
Age Group: 63
Sex: M+F
Population Size: 1954
Sources:
Loose stools 1 patient
300 mg 1 times / day multiple, oral (max)
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 63
n = 1954
Health Status: unhealthy
Condition: diabetes mellitus, type 2
Age Group: 63
Sex: M+F
Population Size: 1954
Sources:
Weight loss 1 patient
300 mg 1 times / day multiple, oral (max)
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 63
n = 1954
Health Status: unhealthy
Condition: diabetes mellitus, type 2
Age Group: 63
Sex: M+F
Population Size: 1954
Sources:
Hypoglycaemic episode 10 patients
300 mg 1 times / day multiple, oral (max)
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 63
n = 1954
Health Status: unhealthy
Condition: diabetes mellitus, type 2
Age Group: 63
Sex: M+F
Population Size: 1954
Sources:
Diarrhea 13 patients
300 mg 1 times / day multiple, oral (max)
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 63
n = 1954
Health Status: unhealthy
Condition: diabetes mellitus, type 2
Age Group: 63
Sex: M+F
Population Size: 1954
Sources:
Appetite lost 2 patients
300 mg 1 times / day multiple, oral (max)
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 63
n = 1954
Health Status: unhealthy
Condition: diabetes mellitus, type 2
Age Group: 63
Sex: M+F
Population Size: 1954
Sources:
Nausea 3 patients
300 mg 1 times / day multiple, oral (max)
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 63
n = 1954
Health Status: unhealthy
Condition: diabetes mellitus, type 2
Age Group: 63
Sex: M+F
Population Size: 1954
Sources:
Abdominal pain 4 patients
300 mg 1 times / day multiple, oral (max)
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 63
n = 1954
Health Status: unhealthy
Condition: diabetes mellitus, type 2
Age Group: 63
Sex: M+F
Population Size: 1954
Sources:
Flatulence 68 patients
300 mg 1 times / day multiple, oral (max)
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 63
n = 1954
Health Status: unhealthy
Condition: diabetes mellitus, type 2
Age Group: 63
Sex: M+F
Population Size: 1954
Sources:
Function liver abnormal 0.01%
300 mg 1 times / day multiple, oral (max)
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 63
n = 27803
Health Status: unhealthy
Condition: diabetes mellitus
Age Group: 63
Sex: M+F
Population Size: 27803
Sources:
Hypoglycaemia 0.07%
300 mg 1 times / day multiple, oral (max)
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 63
n = 27803
Health Status: unhealthy
Condition: diabetes mellitus
Age Group: 63
Sex: M+F
Population Size: 27803
Sources:
Flatulence 13.7%
300 mg 1 times / day multiple, oral (max)
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 63
n = 27803
Health Status: unhealthy
Condition: diabetes mellitus
Age Group: 63
Sex: M+F
Population Size: 27803
Sources:
Diarrhoea 2.2%
300 mg 1 times / day multiple, oral (max)
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 63
n = 27803
Health Status: unhealthy
Condition: diabetes mellitus
Age Group: 63
Sex: M+F
Population Size: 27803
Sources:
PubMed

PubMed

TitleDatePubMed
Altered expression of muscle glucose transporter GLUT-4 in diabetic fatty Zucker rats (ZDF/Drt-fa).
1991 Dec
Effect of acarbose on glucose homeostasis, lipogenesis and lipogenic enzyme gene expression in adipose tissue of weaned rats.
1993 Jun
Acarbose reduces blood pressure in sucrose-induced hypertension in rats.
1997 Mar
Piroxicam and acarbose as chemopreventive agents for spontaneous intestinal adenomas in APC gene 1309 knockout mice.
1998 Apr
[Acarbose-induced acute hepatitis. Report of two events in the same patient].
2000 Jun-Jul
Chronic acarbose-feeding increases GLUT1 protein without changing intestinal glucose absorption function.
2002 Jan 11
Treatment for hyperglycemia promotes pancreatic regeneration in rats without CCK-1 receptor gene expression.
2003 May
Acarbose attenuates experimental non-alcoholic steatohepatitis.
2004 Mar 12
Contribution of mucosal maltase-glucoamylase activities to mouse small intestinal starch alpha-glucogenesis.
2007 Jul
The alpha-glucosidase inhibitor acarbose prevents obesity and simple steatosis in sequestosome 1/A170/p62 deficient mice.
2009 May
Bioinformatic and biochemical studies point to AAGR-1 as the ortholog of human acid alpha-glucosidase in Caenorhabditis elegans.
2010 Aug
The α-glucosidase inhibitor miglitol decreases glucose fluctuations and inflammatory cytokine gene expression in peripheral leukocytes of Japanese patients with type 2 diabetes mellitus.
2010 Dec
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: There is no fixed dosage regimen for the management of diabetes mellitus with PRECOSE or any other pharmacologic agent
Dosage of PRECOSE must be individualized on the basis of both effectiveness and tolerance while not exceeding the maximum recommended dose of 100 mg t.i.d. PRECOSE should be taken three times daily at the start (with the first bite) of each main meal. PRECOSE should be started at a low dose,
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment:: an inhibition of two thirds of alpha-amylase activity can be expected from pharmacologically used doses of acarbose.
Unknown
Name Type Language
ACARBOSE
USAN  
Official Name English
ACARBOSE [MI]
Common Name English
ACARBOSE [ORANGE BOOK]
Common Name English
ACARBOSE [EP]
Common Name English
ACARBOSE [MART.]
Common Name English
ACARBOSE [VANDF]
Common Name English
ACARBOSE [USP MONOGRAPH]
Common Name English
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-GLUCOPYRANOSE
Common Name English
ACARBOSE [USAN]
Common Name English
ACARBOSE [EP MONOGRAPH]
Common Name English
NSC-758915
Code English
ACARBOSE [USP-RS]
Common Name English
BAY G 5421
Code English
ACARBOSE [JAN]
Common Name English
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)-
Common Name English
ACARBOSE [INN]
Common Name English
BAY-G-5421
Code English
ACARBOSE [WHO-DD]
Common Name English
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
Common Name English
PRECOSE
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C2846
Created by admin on Fri Jun 25 20:46:41 UTC 2021 , Edited by admin on Fri Jun 25 20:46:41 UTC 2021
NDF-RT N0000000166
Created by admin on Fri Jun 25 20:46:41 UTC 2021 , Edited by admin on Fri Jun 25 20:46:41 UTC 2021
WHO-VATC QA10BF01
Created by admin on Fri Jun 25 20:46:41 UTC 2021 , Edited by admin on Fri Jun 25 20:46:41 UTC 2021
NCI_THESAURUS C29711
Created by admin on Fri Jun 25 20:46:41 UTC 2021 , Edited by admin on Fri Jun 25 20:46:41 UTC 2021
LIVERTOX 6
Created by admin on Fri Jun 25 20:46:41 UTC 2021 , Edited by admin on Fri Jun 25 20:46:41 UTC 2021
WHO-ATC A10BF01
Created by admin on Fri Jun 25 20:46:41 UTC 2021 , Edited by admin on Fri Jun 25 20:46:41 UTC 2021
NDF-RT N0000175559
Created by admin on Fri Jun 25 20:46:41 UTC 2021 , Edited by admin on Fri Jun 25 20:46:41 UTC 2021
WHO-ATC A10BD17
Created by admin on Fri Jun 25 20:46:41 UTC 2021 , Edited by admin on Fri Jun 25 20:46:41 UTC 2021
Code System Code Type Description
MERCK INDEX
M1289
Created by admin on Fri Jun 25 20:46:41 UTC 2021 , Edited by admin on Fri Jun 25 20:46:41 UTC 2021
PRIMARY Merck Index
INN
4527
Created by admin on Fri Jun 25 20:46:41 UTC 2021 , Edited by admin on Fri Jun 25 20:46:41 UTC 2021
PRIMARY
EPA CompTox
56180-94-0
Created by admin on Fri Jun 25 20:46:41 UTC 2021 , Edited by admin on Fri Jun 25 20:46:41 UTC 2021
PRIMARY
DRUG CENTRAL
39
Created by admin on Fri Jun 25 20:46:41 UTC 2021 , Edited by admin on Fri Jun 25 20:46:41 UTC 2021
PRIMARY
WIKIPEDIA
ACARBOSE
Created by admin on Fri Jun 25 20:46:41 UTC 2021 , Edited by admin on Fri Jun 25 20:46:41 UTC 2021
PRIMARY
MESH
D020909
Created by admin on Fri Jun 25 20:46:41 UTC 2021 , Edited by admin on Fri Jun 25 20:46:41 UTC 2021
PRIMARY
NCI_THESAURUS
C983
Created by admin on Fri Jun 25 20:46:41 UTC 2021 , Edited by admin on Fri Jun 25 20:46:41 UTC 2021
PRIMARY
USP_CATALOG
1000521
Created by admin on Fri Jun 25 20:46:41 UTC 2021 , Edited by admin on Fri Jun 25 20:46:41 UTC 2021
PRIMARY USP-RS
FDA UNII
T58MSI464G
Created by admin on Fri Jun 25 20:46:41 UTC 2021 , Edited by admin on Fri Jun 25 20:46:41 UTC 2021
PRIMARY
CAS
56180-94-0
Created by admin on Fri Jun 25 20:46:41 UTC 2021 , Edited by admin on Fri Jun 25 20:46:41 UTC 2021
PRIMARY
ECHA (EC/EINECS)
260-030-7
Created by admin on Fri Jun 25 20:46:41 UTC 2021 , Edited by admin on Fri Jun 25 20:46:41 UTC 2021
PRIMARY
IUPHAR
6791
Created by admin on Fri Jun 25 20:46:41 UTC 2021 , Edited by admin on Fri Jun 25 20:46:41 UTC 2021
PRIMARY
LACTMED
Acarbose
Created by admin on Fri Jun 25 20:46:41 UTC 2021 , Edited by admin on Fri Jun 25 20:46:41 UTC 2021
PRIMARY
EVMPD
SUB07368MIG
Created by admin on Fri Jun 25 20:46:41 UTC 2021 , Edited by admin on Fri Jun 25 20:46:41 UTC 2021
PRIMARY
ChEMBL
CHEMBL1566
Created by admin on Fri Jun 25 20:46:41 UTC 2021 , Edited by admin on Fri Jun 25 20:46:41 UTC 2021
PRIMARY
DRUG BANK
DB00284
Created by admin on Fri Jun 25 20:46:41 UTC 2021 , Edited by admin on Fri Jun 25 20:46:41 UTC 2021
PRIMARY
PUBCHEM
9811704
Created by admin on Fri Jun 25 20:46:41 UTC 2021 , Edited by admin on Fri Jun 25 20:46:41 UTC 2021
PRIMARY
HSDB
56180-94-0
Created by admin on Fri Jun 25 20:46:41 UTC 2021 , Edited by admin on Fri Jun 25 20:46:41 UTC 2021
PRIMARY
RXCUI
16681
Created by admin on Fri Jun 25 20:46:41 UTC 2021 , Edited by admin on Fri Jun 25 20:46:41 UTC 2021
PRIMARY RxNorm