Acarbose

Identification

Summary

Acarbose is an alpha-glucosidase inhibitor used in adjunctly with diet and exercise for the management of glycemic control in patients with type 2 diabetes mellitus.

Brand Names
Precose
Generic Name
Acarbose
DrugBank Accession Number
DB00284
Background

Acarbose is a complex oligosaccharide that acts as an inhibitor of several enzymes responsible for the breakdown of complex carbohydrates in the intestines. It inhibits both pancreatic alpha-amylase and membrane-bound alpha-glucosidases - including intestinal glucoamylase, sucrase, maltase, and isomaltase - which are responsible for the metabolism of complex starches and oligo-, tri-, and disaccharides into absorbable simple sugars.7,4 By inhibiting the activity of these enzymes, acarbose limits the absorption of dietary carbohydrates and the subsequent postprandial increase in blood glucose and insulin levels. Acarbose is therefore used in conjunction with diet, exercise, and other pharmacotherapies for the management of blood sugar levels in patients with type 2 diabetes.6,7

Acarbose is one of only two approved alpha-glucosidase inhibitors (the other being miglitol), receiving its first FDA approval in 1995 under the brand name Precose (since discontinued).9 This class of antidiabetic therapy is not widely used due to their relatively modest impact on A1c, their requirement for thrice-daily dosing, and the potential for significant gastrointestinal adverse effects.9

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 645.608
Monoisotopic: 645.248013549
Chemical Formula
C25H43NO18
Synonyms
  • Acarbosa
  • Acarbose
  • Acarbosum
External IDs
  • Bay g 5421
  • BAY-g 5421
  • BAY-G-5421
  • BAYG5421
  • HSDB 7984

Pharmacology

Indication

Acarbose is indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus.6

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Adjunct therapy in management ofType 2 diabetes mellitus••••••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Acarbose is a complex oligosaccharide that competitively inhibits the ability of brush-border alpha-glucosidase enzymes to break down ingested carbohydrates into absorbable monosaccharides, reducing carbohydrate absorption and subsequent postprandial insulin levels.4 Acarbose requires the co-administration of carbohydrates in order to exert its therapeutic effect, and as such should be taken with the first bite of a meal three times daily.7

Given its mechanism of action, acarbose in isolation poses little risk of contributing to hypoglycemia - this risk is more pronounced, however, when acarbose is used in conjunction with other antidiabetic therapies (e.g. sulfonylureas, insulin).7 Patients maintained on acarbose in addition to other antidiabetic agents should be aware of the symptoms and risks of hypoglycemia and how to treat hypoglycemic episodes. There have been rare post-marketing reports of the development of pneumatosis cystoides intestinalis following treatment with alpha-glucosidase inhibitors - patients experiencing significant diarrhea/constipation, mucus discharge, and/or rectal bleeding should be investigated and, if pneumatosis cystoides intestinalis is suspected, should discontinue therapy.6

Mechanism of action

Alpha-glucosidase enzymes are located in the brush-border of the intestinal mucosa and serve to metabolize oligo-, tri-, and disaccharides (e.g. sucrose) into smaller monosaccharides (e.g. glucose, fructose) which are more readily absorbed.4 These work in conjunction with pancreatic alpha-amylase, an enzyme found in the intestinal lumen that hydrolyzes complex starches to oligosaccharides.7

Acarbose is a complex oligosaccharide that competitively and reversibly inhibits both pancreatic alpha-amylase and membrane-bound alpha-glucosidases - of the alpha-glucosidases, inhibitory potency appears to follow a rank order of glucoamylase > sucrase > maltase > isomaltase.7 By preventing the metabolism and subsequent absorption of dietary carbohydrates, acarbose reduces postprandial blood glucose and insulin levels.

TargetActionsOrganism
AMaltase-glucoamylase, intestinal
inhibitor
Humans
ASucrase-isomaltase, intestinal
inhibitor
Humans
APancreatic alpha-amylase
inhibitor
Humans
ULysosomal alpha-glucosidase
inhibitor
Humans
Absorption

The oral bioavailability of acarbose is extremely minimal, with less than 1-2% of orally administered parent drug reaching the systemic circulation. Despite this, approximately 35% of the total radioactivity from a radiolabeled and orally administered dose of acarbose reaches the systemic circulation, with peak plasma radioactivity occurring 14-24 hours after dosing - this delay is likely reflective of metabolite absorption rather than absorption of the parent drug. As acarbose is intended to work within the gut, its minimal degree of oral bioavailability is therapeutically desirable.6

Volume of distribution

Not Available

Protein binding

As only 1-2% of an orally administered dose is absorbed into the circulation, acarbose is unlikely to be subject to clinically relevant protein binding.7

Metabolism

Acarbose is extensively metabolized within the gastrointestinal tract, primarily by intestinal bacteria and to a lesser extent by digestive enzymes, into at least 13 identified metabolites. Approximately 1/3 of these metabolites are absorbed into the circulation where they are subsequently renally excreted. The major metabolites appear to be methyl, sulfate, and glucuronide conjugates of 4-methylpyrogallol.6

Only one metabolite - resulting from the cleavage of a glucose molecule from acarbose - has been identified as having alpha-glucosidase inhibitory activity.6

Route of elimination

Roughly half of an orally administered dose is excreted in the feces within 96 hours of administration.7 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.7

Half-life

In healthy volunteers, the plasma elimination half-life of acarbose is approximately 2 hours.6

Clearance

Not Available

Adverse Effects
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Toxicity

The symptoms of acarbose overdose are likely to be consistent with its adverse effect profile and may therefore include significant gastrointestinal (GI) symptoms (flatulence, distension, etc), although an overdose on an empty stomach (i.e. when not co-administered with food) is less likely to result in these GI symptoms.6 In the event of an overdose, patients should be instructed to avoid carbohydrate-containing foods for 4-6 hours following administration as these can precipitate the aforementioned GI symptoms.6

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcebutololThe therapeutic efficacy of Acarbose can be increased when used in combination with Acebutolol.
AcetazolamideThe therapeutic efficacy of Acarbose can be increased when used in combination with Acetazolamide.
AcetohexamideThe risk or severity of hypoglycemia can be increased when Acarbose is combined with Acetohexamide.
Acetyl sulfisoxazoleThe therapeutic efficacy of Acarbose can be increased when used in combination with Acetyl sulfisoxazole.
Acetylsalicylic acidThe risk or severity of hypoglycemia can be increased when Acetylsalicylic acid is combined with Acarbose.
Food Interactions
  • Take with food. Each dose should be taken with the first bite of a main meal.

Products

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Product Images
International/Other Brands
Glucobay / Prandase (Bayer AG) / Precose
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Acarbose TabletsTablet100 mgOralStrides Pharma Canada Inc2020-05-28Not applicableCanada flag
Acarbose TabletsTablet50 mgOralStrides Pharma Canada Inc2020-05-28Not applicableCanada flag
GlucobayTablet100 mgOralBayer1996-02-022023-07-10Canada flag
GlucobayTablet50 mgOralBayer1996-02-022023-07-10Canada flag
PrecoseTablet100 mg/1OralBayer HealthCare Pharmaceuticals Inc.2008-01-30Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AcarboseTablet50 mg/1OralAvKARE2013-12-242023-06-30US flag
AcarboseTablet50 mg/1OralChartwell Rx, Llc2021-04-16Not applicableUS flag
AcarboseTablet100 mg/1Oralbryant ranch prepack2009-05-142016-05-30US flag
AcarboseTablet25 mg/1OralActavis Pharma, Inc.2008-05-082018-07-31US flag
AcarboseTablet100 mg/1OralA-S Medication Solutions2008-01-30Not applicableUS flag

Categories

ATC Codes
A10BD17 — Metformin and acarboseA10BF01 — Acarbose
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as aminocyclitol glycosides. These are organic compounds containing an amicocyclitol moiety glycosidically linked to a carbohydrate moiety. There are two major classes of aminoglycosides containing a 2-streptamine core. They are called 4,5- and 4,6-disubstituted 2-deoxystreptamines.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Aminocyclitol glycosides
Alternative Parents
Oligosaccharides / Alkyl glycosides / O-glycosyl compounds / Beta-hydroxy aldehydes / Cyclitols and derivatives / Oxanes / Alpha-hydroxyaldehydes / 1,2-aminoalcohols / Secondary alcohols / Polyols
show 7 more
Substituents
1,2-aminoalcohol / Acetal / Alcohol / Aldehyde / Aliphatic heteromonocyclic compound / Alkyl glycoside / Alpha-hydroxyaldehyde / Amine / Amino cyclitol glycoside / Beta-hydroxy aldehyde
show 20 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
T58MSI464G
CAS number
56180-94-0
InChI Key
CEMXHAPUFJOOSV-XGWNLRGSSA-N
InChI
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
IUPAC Name
(2R,3R,4R,5R)-4-{[(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}-2,3,5,6-tetrahydroxyhexanal
SMILES
[H]C(=O)[C@H](O)[C@@H](O)[C@]([H])(O[C@@]1([H])O[C@H](CO)[C@@]([H])(O[C@H]2O[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)[C@H](O)CO

References

Synthesis Reference

Anneliese Crueger, Wolfgang Piepersberg, Jurgen Distler, Ansgar Stratmann, "Acarbose biosynthesis genes from actinoplanes sp., process for the isolation thereof and the use thereof." U.S. Patent US5753501, issued December, 1977.

US5753501
General References
  1. Clissold SP, Edwards C: Acarbose. A preliminary review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential. Drugs. 1988 Mar;35(3):214-43. [Article]
  2. McIver LA, Tripp J: Acarbose . [Article]
  3. Everett JA: Use of oral antidiabetic agents during breastfeeding. J Hum Lact. 1997 Dec;13(4):319-21. doi: 10.1177/089033449701300418. [Article]
  4. Martin AE, Montgomery PA: Acarbose: an alpha-glucosidase inhibitor. Am J Health Syst Pharm. 1996 Oct 1;53(19):2277-90; quiz 2336-7. doi: 10.1093/ajhp/53.19.2277. [Article]
  5. White JR Jr: A Brief History of the Development of Diabetes Medications. Diabetes Spectr. 2014 May;27(2):82-6. doi: 10.2337/diaspect.27.2.82. [Article]
  6. DailyMed: Acarbose oral tablets [Link]
  7. Health Canada Product Monograph: Acarbose oral tablets [Link]
  8. CaymanChem: Acarbose MSDS [Link]
  9. FDA Approved Drug Products: Precose (acarbose) oral tablets [discontinued] [Link]
KEGG Drug
D00216
KEGG Compound
C06802
PubChem Compound
9811704
PubChem Substance
46508248
ChemSpider
23264314
RxNav
16681
ChEBI
2376
ChEMBL
CHEMBL1566
ZINC
ZINC000096309558
Therapeutic Targets Database
DCL000309
PharmGKB
PA448010
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Acarbose
FDA label
Download (268 KB)

Clinical Trials

Clinical Trials

Pharmacoeconomics

Manufacturers
  • Impax laboratories inc
  • Roxane laboratories inc
  • Watson laboratories inc
  • Bayer healthcare pharmaceuticals inc
Packagers
  • Arrow Pharm Malta Ltd.
  • A-S Medication Solutions LLC
  • Bayer Healthcare
  • Cobalt Pharmaceuticals Inc.
  • Global Pharmaceuticals
  • Impax Laboratories Inc.
  • Kaiser Foundation Hospital
  • Murfreesboro Pharmaceutical Nursing Supply
  • PD-Rx Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Roxane Labs
Dosage Forms
FormRouteStrength
TabletOral100 mg/1
TabletOral25 mg/1
TabletOral
TabletOral50.000 mg
TabletOral100 mg
TabletOral50 mg
TabletOral50 mg/1
TabletOral100.0000 mg
Prices
Unit descriptionCostUnit
Acarbose 100 100 mg tablet Bottle120.62USD bottle
Acarbose 100 50 mg tablet Bottle100.71USD bottle
Acarbose 100 25 mg tablet Bottle93.54USD bottle
Precose 100 mg tablet1.28USD tablet
Acarbose 100 mg tablet1.17USD tablet
Precose 50 mg tablet1.11USD tablet
Precose 25 mg tablet1.01USD tablet
Acarbose 25 mg tablet0.91USD tablet
Acarbose 50 mg tablet0.88USD tablet
Glucobay 100 mg Tablet0.4USD tablet
Glucobay 50 mg Tablet0.29USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP-6.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility108.0 mg/mLALOGPS
logP-2.7ALOGPS
logP-8.3Chemaxon
logS-0.78ALOGPS
pKa (Strongest Acidic)11.83Chemaxon
pKa (Strongest Basic)7.03Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count19Chemaxon
Hydrogen Donor Count14Chemaxon
Polar Surface Area329.01 Å2Chemaxon
Rotatable Bond Count13Chemaxon
Refractivity139.02 m3·mol-1Chemaxon
Polarizability60.87 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.8467
Blood Brain Barrier-0.9723
Caco-2 permeable-0.725
P-glycoprotein substrateSubstrate0.5316
P-glycoprotein inhibitor IInhibitor0.5421
P-glycoprotein inhibitor IINon-inhibitor0.8656
Renal organic cation transporterNon-inhibitor0.8647
CYP450 2C9 substrateNon-substrate0.7581
CYP450 2D6 substrateNon-substrate0.8505
CYP450 3A4 substrateNon-substrate0.5683
CYP450 1A2 substrateNon-inhibitor0.8791
CYP450 2C9 inhibitorNon-inhibitor0.8677
CYP450 2D6 inhibitorNon-inhibitor0.8974
CYP450 2C19 inhibitorNon-inhibitor0.8392
CYP450 3A4 inhibitorNon-inhibitor0.986
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7163
Ames testNon AMES toxic0.8054
CarcinogenicityNon-carcinogens0.967
BiodegradationNot ready biodegradable0.6447
Rat acute toxicity1.4610 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8586
hERG inhibition (predictor II)Non-inhibitor0.8288
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0yea-0105409000-0ef74c0a7d6f4189d307
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fr6-4007089000-621566a63568558cfcf6
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-1119022000-09894bcb933c0fc2511a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0w91-2519313000-a2ad084610ebbc20038f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-9554043000-f53142b2111b3911ea62
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-1913002000-d309be695a388922112b
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-208.43285
predicted
DeepCCS 1.0 (2019)
[M+H]+210.15656
predicted
DeepCCS 1.0 (2019)
[M+Na]+216.48552
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Maltose alpha-glucosidase activity
Specific Function
May serve as an alternate pathway for starch digestion when luminal alpha-amylase activity is reduced because of immaturity or malnutrition. May play a unique role in the digestion of malted dietar...
Gene Name
MGAM
Uniprot ID
O43451
Uniprot Name
Maltase-glucoamylase, intestinal
Molecular Weight
209850.8 Da
References
  1. Zhang H, Kallwass H, Young SP, Carr C, Dai J, Kishnani PS, Millington DS, Keutzer J, Chen YT, Bali D: Comparison of maltose and acarbose as inhibitors of maltase-glucoamylase activity in assaying acid alpha-glucosidase activity in dried blood spots for the diagnosis of infantile Pompe disease. Genet Med. 2006 May;8(5):302-6. [Article]
  2. Yamagishi S, Matsui T, Ueda S, Fukami K, Okuda S: Clinical utility of acarbose, an alpha-glucosidase inhibitor in cardiometabolic disorders. Curr Drug Metab. 2009 Feb;10(2):159-63. [Article]
  3. Martin AE, Montgomery PA: Acarbose: an alpha-glucosidase inhibitor. Am J Health Syst Pharm. 1996 Oct 1;53(19):2277-90; quiz 2336-7. doi: 10.1093/ajhp/53.19.2277. [Article]
  4. Health Canada Product Monograph: Acarbose oral tablets [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Sucrose alpha-glucosidase activity
Specific Function
Plays an important role in the final stage of carbohydrate digestion. Isomaltase activity is specific for both alpha-1,4- and alpha-1,6-oligosaccharides.
Gene Name
SI
Uniprot ID
P14410
Uniprot Name
Sucrase-isomaltase, intestinal
Molecular Weight
209451.49 Da
References
  1. Juretic D, Bernik S, Cop L, Hadzija M, Petlevski R, Lukac-Bajalo J: Short-term effect of acarbose on specific intestinal disaccharidase activities and hyperglycaemia in CBA diabetic mice. J Anim Physiol Anim Nutr (Berl). 2003 Aug;87(7-8):263-8. [Article]
  2. Samulitis BK, Goda T, Lee SM, Koldovsky O: Inhibitory mechanism of acarbose and 1-deoxynojirimycin derivatives on carbohydrases in rat small intestine. Drugs Exp Clin Res. 1987;13(8):517-24. [Article]
  3. Martin AE, Montgomery PA: Acarbose: an alpha-glucosidase inhibitor. Am J Health Syst Pharm. 1996 Oct 1;53(19):2277-90; quiz 2336-7. doi: 10.1093/ajhp/53.19.2277. [Article]
  4. Health Canada Product Monograph: Acarbose oral tablets [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Chloride ion binding
Specific Function
Not Available
Gene Name
AMY2A
Uniprot ID
P04746
Uniprot Name
Pancreatic alpha-amylase
Molecular Weight
57706.51 Da
References
  1. Martin AE, Montgomery PA: Acarbose: an alpha-glucosidase inhibitor. Am J Health Syst Pharm. 1996 Oct 1;53(19):2277-90; quiz 2336-7. doi: 10.1093/ajhp/53.19.2277. [Article]
  2. Health Canada Product Monograph: Acarbose oral tablets [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Maltose alpha-glucosidase activity
Specific Function
Essential for the degradation of glygogen to glucose in lysosomes.
Gene Name
GAA
Uniprot ID
P10253
Uniprot Name
Lysosomal alpha-glucosidase
Molecular Weight
105322.935 Da
References
  1. Salehi A, Fan BG, Ekelund M, Nordin G, Lundquist I: TPN-evoked dysfunction of islet lysosomal activity mediates impairment of glucose-stimulated insulin release. Am J Physiol Endocrinol Metab. 2001 Jul;281(1):E171-9. [Article]
  2. Zhang H, Kallwass H, Young SP, Carr C, Dai J, Kishnani PS, Millington DS, Keutzer J, Chen YT, Bali D: Comparison of maltose and acarbose as inhibitors of maltase-glucoamylase activity in assaying acid alpha-glucosidase activity in dried blood spots for the diagnosis of infantile Pompe disease. Genet Med. 2006 May;8(5):302-6. [Article]
  3. Gelb MH, Turecek F, Scott CR, Chamoles NA: Direct multiplex assay of enzymes in dried blood spots by tandem mass spectrometry for the newborn screening of lysosomal storage disorders. J Inherit Metab Dis. 2006 Apr-Jun;29(2-3):397-404. [Article]
  4. Bourbon JR, Doucet E, Rieutort M: Role of alpha-glucosidase in fetal lung maturation. Biochim Biophys Acta. 1987 Jan 13;917(1):203-10. [Article]
  5. Calder PC, Geddes R: Acarbose is a competitive inhibitor of mammalian lysosomal acid alpha-D-glucosidases. Carbohydr Res. 1989 Aug 1;191(1):71-8. doi: 10.1016/0008-6215(89)85047-5. [Article]
  6. Wang M, Wang M, Zhang F, Su X: A ratiometric fluorescent biosensor for the sensitive determination of alpha-glucosidase activity and acarbose based on N-doped carbon dots. Analyst. 2020 Aug 24;145(17):5808-5815. doi: 10.1039/d0an01065k. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48