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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H43NO18
Molecular Weight 645.6048
Optical Activity UNSPECIFIED
Defined Stereocenters 18 / 18
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACARBOSE

SMILES

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

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
Molecular Formula C25H43NO18
Molecular Weight 645.6048
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 18 / 18
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Unknown
86413
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:23:22 UTC 2023
Edited
by admin
on Fri Dec 15 16:23:22 UTC 2023
Record UNII
T58MSI464G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ACARBOSE
USAN  
Official Name English
ACARBOSE [MI]
Common Name English
ACARBOSE [ORANGE BOOK]
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
ACARBOSE [EP IMPURITY]
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 [WHO-DD]
Common Name English
acarbose [INN]
Common Name English
BAY-G-5421
Code 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 Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
NDF-RT N0000000166
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
WHO-VATC QA10BF01
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
NCI_THESAURUS C29711
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
LIVERTOX NBK548181
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
WHO-ATC A10BF01
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
NDF-RT N0000175559
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
WHO-ATC A10BD17
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
Code System Code Type Description
MERCK INDEX
m1289
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
PRIMARY Merck Index
CHEBI
84363
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
PRIMARY
INN
4527
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
PRIMARY
EPA CompTox
DTXSID8046034
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
PRIMARY
DRUG CENTRAL
39
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
PRIMARY
WIKIPEDIA
ACARBOSE
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
PRIMARY
MESH
D020909
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
PRIMARY
NCI_THESAURUS
C983
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
PRIMARY
FDA UNII
T58MSI464G
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
PRIMARY
RS_ITEM_NUM
1000521
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
PRIMARY
CAS
56180-94-0
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
PRIMARY
USAN
T-9
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
PRIMARY
ECHA (EC/EINECS)
260-030-7
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
PRIMARY
IUPHAR
6791
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
PRIMARY
LACTMED
Acarbose
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
PRIMARY
EVMPD
SUB07368MIG
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
PRIMARY
ChEMBL
CHEMBL1566
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
PRIMARY
DRUG BANK
DB00284
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
PRIMARY
SMS_ID
100000092276
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
PRIMARY
PUBCHEM
9811704
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
PRIMARY
HSDB
56180-94-0
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
PRIMARY
CHEBI
2376
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
PRIMARY
RXCUI
16681
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
PRIMARY RxNorm
DAILYMED
T58MSI464G
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
PRIMARY
NSC
758915
Created by admin on Fri Dec 15 16:23:22 UTC 2023 , Edited by admin on Fri Dec 15 16:23:22 UTC 2023
PRIMARY
Related Record Type Details
PANCREATIC ALPHA-AMYLASE
TARGET -> INHIBITOR
Acarbose acts locally within the gastrointestinal tract, this low systemic bioavailability of parent compound.
IC50
GLUCAGON-LIKE PEPTIDE 1
TARGET->ACTIVATOR OF EXPRESSION
Acarbose treatment stimulates postprandial GLP-1 secretion in patients with type 2 diabetes. Dependent on dose and saccharide or polysaccharide present. A single dose of 100 mg acarbose during an oral sucrose (disaccharide) load resulted in elevated GLP-1 levels compared to placebo (8, 10, 28, 29) whereas no effect was seen during oral glucose tolerance test (24), emphasizing that acarbose needs relevant carbohydrates to ‘act on’ in order to increase GLP-1 secretion. A single dose of 100 mg acarbose during an oral sucrose (disaccharide) load resulted in elevated GLP-1 levels compared to placebo (8, 10, 28, 29) whereas no effect was seen during oral glucose tolerance test (24), emphasizing that acarbose needs relevant carbohydrates to ‘act on’ in order to increase GLP-1 secretion.
Isomaltase, human intestinal
TARGET -> INHIBITOR
Sucrase, human intestinal
TARGET -> INHIBITOR
Related Record Type Details
Structure of ACARVIOSINE-GLUCOSE
METABOLITE ACTIVE -> PARENT
Acarbose is exclusively metabolized within the gastrointestinal tract, principally by intestinal bacteria.
MAJOR
URINE
Related Record Type Details
Structure of 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)-O-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-D-FRUCTOSE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
Structure of O-4,6-DIDEOXY-4-(((1S,4R,5S,6S)-4,5,6-TRIHYDROXY-3-(HYDROXYMETHYL)CYCLOHEX-2-ENYL)AMINO)-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-O-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-D-ARABINO-HEX-2-ULOPYRANOSE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
Structure of ACARBOSE IMPURITY F
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
Structure of D-GLUCOPYRANOSYL O-4,6-DIDEOXY-4-(((1S,4R,5S,6S)-4,5,6-TRIHYDROXY-3-(HYDROXYMETHYL)CYCLOHEX-2-ENYL)AMINO)-D-GLUCOPYRANOSYL-(1->4)-O-D-GLUCOPYRANOSYL-(1->4)-O-D-GLUCOPYRANOSIDE (D-GLUCOPYRANOSYL-ACARBOSIDE)
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
Structure of (1R,4R,5S,6R)-4,5,6-TRIHYDROXY-2-(HYDROXYMETHYL)CYCLOHEX-2-ENYL 4-O-(4,6-DIDEOXY-4-(((1S,4R,5S,6S)-4,5,6-TRIHYDROXY-3-(HYDROXYMETHYL)CYCLOHEX-2-ENYL)AMINO)-.ALPHA.-D-GLUCOPYRANOSYL)-.ALPHA.-D-GLUCOPYRANOSIDE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
Other
Structure of .ALPHA.-D-GLUCOPYRANOSYL 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)-.ALPHA.-D-GLUCOPYRANOSIDE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of ACARVIOSINE-GLUCOSE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
Structure of PSEUDOACARBOSE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of ACARBOSE
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
NIH
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