Details of the Drug

General Information of Drug (ID: DMRM3AW)

Drug Name
Acarbose
Synonyms
acarbose; 56180-94-0; Glucobay; Precose; Prandase; C25H43NO18; CHEBI:2376; CHEMBL3734896; BAY-g 5421; 4,6-dideoxy-4-{[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino}-alpha-D-glucopyranosyl-(1->4)-alpha-D-glucopyranosyl-(1->4)-D-glucopyranose; SMR000466376; SR-01000759407; Acarbose/; Acarbose [USAN:BAN:INN:JAN]; Acarbose,(S); Precose (TN); AC1L26GM; Acarbose (JAN/USAN/INN); MLS006011898; MLS000759506; MLS001424056; SPECTRUM1505172; SCHEMBL5316305; CHEMBL404271; BDBM23406; MolPort-002-507-369
Indication
Disease Entry ICD 11 Status REF
Diabetic complication 5A2Y Approved [1]
Non-insulin dependent diabetes 5A11 Approved [2]
Cardiovascular disease BA00-BE2Z Phase 3 [1]
Therapeutic Class
Hypoglycemic Agents
Affected Organisms
Humans and other mammals
ATC Code
A10BF01: Acarbose
A10BF: Alpha glucosidase inhibitors
A10B: BLOOD GLUCOSE LOWERING DRUGS, EXCL. INSULINS
A10: DRUGS USED IN DIABETES
A: ALIMENTARY TRACT AND METABOLISM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 4 Molecular Weight (mw) 645.6
Logarithm of the Partition Coefficient (xlogp) -8.5
Rotatable Bond Count (rotbonds) 9
Hydrogen Bond Donor Count (hbonddonor) 14
Hydrogen Bond Acceptor Count (hbondacc) 19
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [3]
Clearance
The drug present in the plasma can be removed from the body at the rate of 2.2 mL/min/kg [4]
Elimination
What little drug material is absorbed into the systemic circulation (approximately 34% of an orally administered dose) is excreted primarily by the kidneys, suggesting renal excretion would be a significant route of elimination if the parent drug was more readily absorbed - this is further supported by data in which approximately 89% of an intravenously administered dose of acarbose was excreted in the urine as active drug (in comparison to <2% following oral administration) within 48 hours [5]
Half-life
The concentration or amount of drug in body reduced by one-half in 2 hours [6]
Metabolism
The drug is metabolized via the intestinal bacteria and to a lesser extent by digestive enzymes [6]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 6.63816 micromolar/kg/day [7]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.32 L/kg [4]
Chemical Identifiers
Formula
C25H43NO18
IUPAC Name
(3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,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
Canonical SMILES
C[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@H]2[C@H](O[C@@H]([C@@H]([C@H]2O)O)O[C@@H]3[C@H](OC([C@@H]([C@H]3O)O)O)CO)CO)O)O)N[C@H]4C=C([C@H]([C@@H]([C@H]4O)O)O)CO
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-UGEKTDRHSA-N
Cross-matching ID
PubChem CID
41774
ChEBI ID
CHEBI:2376
CAS Number
56180-94-0
UNII
T58MSI464G
DrugBank ID
DB00284
TTD ID
D0AD5C
VARIDT ID
DR00978
ACDINA ID
D00007
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Intestinal maltase-glucoamylase (MGAM) TTXWASR MGA_HUMAN Modulator [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Diabetic complication
ICD Disease Classification 5A2Y
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Intestinal maltase-glucoamylase (MGAM) DTT MGAM 4.59E-01 -0.02 -0.24
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Acarbose (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Remdesivir DMBFZ6L Moderate Increased risk of hepatotoxicity by the combination of Acarbose and Remdesivir. 1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019] [9]
Thioguanine DM7NKEV Moderate Increased risk of hepatotoxicity by the combination of Acarbose and Thioguanine. Acute myeloid leukaemia [2A60] [10]
Clarithromycin DM4M1SG Moderate Decreased metabolism of Acarbose caused by Clarithromycin mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [11]
Pexidartinib DMS2J0Z Major Increased risk of hepatotoxicity by the combination of Acarbose and Pexidartinib. Bone/articular cartilage neoplasm [2F7B] [12]
Cannabidiol DM0659E Moderate Increased risk of hepatotoxicity by the combination of Acarbose and Cannabidiol. Epileptic encephalopathy [8A62] [13]
Digoxin DMQCTIH Moderate Decreased absorption of Acarbose due to adsorption of Digoxin. Heart failure [BD10-BD1Z] [14]
Digitoxin DMWVIGP Moderate Decreased absorption of Acarbose due to adsorption of Digitoxin. Heart failure [BD10-BD1Z] [14]
Brentuximab vedotin DMWLC57 Moderate Increased risk of hepatotoxicity by the combination of Acarbose and Brentuximab vedotin. Hodgkin lymphoma [2B30] [15]
Efavirenz DMC0GSJ Moderate Increased risk of hepatotoxicity by the combination of Acarbose and Efavirenz. Human immunodeficiency virus disease [1C60-1C62] [16]
Mipomersen DMGSRN1 Major Increased risk of hepatotoxicity by the combination of Acarbose and Mipomersen. Hyper-lipoproteinaemia [5C80] [17]
Teriflunomide DMQ2FKJ Major Increased risk of hepatotoxicity by the combination of Acarbose and Teriflunomide. Hyper-lipoproteinaemia [5C80] [18]
BMS-201038 DMQTAGO Major Increased risk of hepatotoxicity by the combination of Acarbose and BMS-201038. Hyper-lipoproteinaemia [5C80] [19]
Methotrexate DM2TEOL Moderate Increased risk of hepatotoxicity by the combination of Acarbose and Methotrexate. Leukaemia [2A60-2B33] [13]
Idelalisib DM602WT Moderate Increased risk of hepatotoxicity by the combination of Acarbose and Idelalisib. Mature B-cell leukaemia [2A82] [20]
Clofarabine DMCVJ86 Moderate Increased risk of hepatotoxicity by the combination of Acarbose and Clofarabine. Mature B-cell lymphoma [2A85] [21]
Gatifloxacin DMSL679 Major Antagonize the effect of Acarbose when combined with Gatifloxacin. Respiratory infection [CA07-CA4Z] [22]
Leflunomide DMR8ONJ Major Increased risk of hepatotoxicity by the combination of Acarbose and Leflunomide. Rheumatoid arthritis [FA20] [18]
Trabectedin DMG3Y89 Moderate Increased risk of hepatotoxicity by the combination of Acarbose and Trabectedin. Solid tumour/cancer [2A00-2F9Z] [13]
Epirubicin DMPDW6T Moderate Increased risk of hepatotoxicity by the combination of Acarbose and Epirubicin. Solid tumour/cancer [2A00-2F9Z] [9]
Naltrexone DMUL45H Moderate Increased risk of hepatotoxicity by the combination of Acarbose and Naltrexone. Substance abuse [6C40] [23]
Albiglutide DM1JEGF Minor Altered absorption of Acarbose due to GI dynamics variation caused by Albiglutide. Type 2 diabetes mellitus [5A11] [24]
Metformin DM89QE1 Minor Altered absorption of Acarbose due to GI dynamics variation caused by Metformin. Type 2 diabetes mellitus [5A11] [25]
Pramlintide DM0EZ9Q Moderate Altered absorption of Acarbose due to GI dynamics variation caused by Pramlintide. Type-1/2 diabete [5A10-5A11] [26]
⏷ Show the Full List of 23 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Carmellose sodium E00625 Not Available Disintegrant
Magnesium stearate E00208 11177 lubricant
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Acarbose 100 mg tablet 100 mg Oral Tablet Oral
Acarbose 25 mg tablet 25 mg Oral Tablet Oral
Acarbose 50 mg tablet 50 mg Oral Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6791).
2 Acarbose FDA Label
3 BDDCS applied to over 900 drugs
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 Health Canada Product Monograph: Acarbose oral tablets
6 DailyMed: Acarbose oral tablets
7 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
8 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
9 Cerner Multum, Inc. "Australian Product Information.".
10 Product Information. Aubagio (teriflunomide). Genzyme Corporation, Cambridge, MA.
11 Bussing R, Gende A "Severe hypoglycemia from clarithromycin-sulfonylurea drug interaction." Diabetes Care 25 (2002): 1659-61. [PMID: 12196446]
12 Product Information. Turalio (pexidartinib). Daiichi Sankyo, Inc., Parsippany, NJ.
13 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
14 Product Information. Precose (acarbose). Bayer, West Haven, CT.
15 Product Information. Adcetris (brentuximab vedotin). Seattle Genetics Inc, Bothell, WA.
16 Elsharkawy AM, Schwab U, McCarron B, et al. "Efavirenz induced acute liver failure requiring liver transplantation in a slow drug metaboliser." J Clin Virol 58 (2013): 331-3. [PMID: 23763943]
17 Product Information. Kynamro (mipomersen). Genzyme Corporation, Cambridge, MA.
18 Canadian Pharmacists Association.
19 Product Information. Juxtapid (lomitapide). Aegerion Pharmaceuticals Inc, Cambridge, MA.
20 Product Information. Zydelig (idelalisib). Gilead Sciences, Foster City, CA.
21 Product Information. Clolar (clofarabine). sanofi-aventis, Bridgewater, NJ.
22 Greenberg AL, Decerbo M, Fan J "Gatifloxacin therapy associated with hypoglycemia." Clin Infect Dis 40 (2005): 1210-1. [PMID: 15791528]
23 Product Information. ReVia (naltrexone). DuPont Pharmaceuticals, Wilmington, DE.
24 EMEA. European Medicines Agency "EPARs. European Union Public Assessment Reports.".
25 Scheen AJ, de Magalhaes AC, Salvatore T, Lefebvre PJ "Reduction of the acute bioavailability of metformin by the a-glucosidase inhibitor acarbose in normal man." Eur J Clin Invest 24 Suppl 3 (1994): 50-4. [PMID: 7818725]
26 Product Information. Symlin (pramlintide). Amphastar Pharmaceuticals Inc, South El Monte, CA.