Glucosamine

Identification

Summary

Glucosamine is a common ingredient in nutritional supplements used for the relief of joint pain.

Generic Name
Glucosamine
DrugBank Accession Number
DB01296
Background

Osteoarthritis (OA) is a progressive and degenerative joint disease marked by loss of cartilage, bone changes, and synovial membrane inflammation.14 Treatment with chondroprotective drugs, such as glucosamine sulfate may offer additional benefits to nonsteroidal anti-inflammatory drugs treating the painful symptoms of OA. Glucosamine is commonly used over the counter as a treatment for arthritic joint pain, although its acceptance as a medical therapy varies due to contradictory and findings with unclear clinical significance during clinical trials.6,14 It is currently not approved as a prescription product by the FDA, but is widely available over the counter.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 179.1711
Monoisotopic: 179.079372531
Chemical Formula
C6H13NO5
Synonyms
  • 2-amino-2-deoxy-D-glucose
  • Chitosamine
  • D-Glucosamine
  • Glucosamina
  • Glucosamine

Pharmacology

Indication

Glucosamine is generally used over the counter in the symptomatic treatment of osteoarthritis and joint pain,1 frequently combined with chondroitin sulfate and/or ibuprofen.27

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

The administration of glucosamine, in theory, provides a building block towards the synthesis of glycosaminoglycans, slowing the progression of osteoarthritis and relieving symptoms of joint pain. Studies to this date examining the efficacy of glucosamine sulfate have been inconclusive. Glycosaminoglycans contribute to joint cartilage elasticity, strength, and flexibility.11 A systematic review of various studies and guidelines determined that modest improvements were reported for joint pain and function in patients taking glucosamine. A consistent joint space narrowing was observed, but with an unclear clinical significance.6

Mechanism of action

The mechanism of action of glucosamine in joint health is unclear,6 however there are several possible mechanisms that contribute to its therapeutic effects. Because glucosamine is a precursor for glycosaminoglycans, and glycosaminoglycans are a major component of joint cartilage,14 glucosamine supplements may help to rebuild cartilage and treat the symptoms of arthritis. Some in vitro studies show evidence that glucosamine reduces inflammation via inhibition of interferon gamma15,16,17 and Nuclear factor kappa B subunit 65 (NF-κB p65),16,18 improving the symptoms of arthritis and joint pain. Clinical relevance is unknown at this time.

TargetActionsOrganism
UInterferon gamma
inhibitor
Humans
UTranscription factor p65
inhibitor
Humans
Absorption

In a pharmacokinetic study, glucosamine was 88.7% absorption by the gastrointestinal tract. Absolute oral bioavailability was 44%, likely due to the hepatic first-pass effect.12 In a pharmacokinetic study of 12 healthy adults receiving oral crystalline glucosamine, plasma levels increased up to 30 times the baseline levels and Cmax was 10 microM with a 1,500 mg once-daily dose. Tmax was about 3 hours. AUC was 20,216 ± 5021 after a 15,000 mg dose.13

Volume of distribution

Results of a pharmacokinetic study of 12 healthy volunteers receiving three daily consecutive oral administrations of glucosamine sulfate soluble powder demonstrated glucosamine distribution to extravascular compartments.13 Human pharmacokinetic data for glucosamine is limited in the literature, however, a large animal model study of horses revealed a mean apparent volume of distribution of 15.4 L/kg. Concentrations of glucosamine ranged from 9-15 microM after an intravenous dose, and 0.3-0.7 microM after nasogastric dosing. These concentrations remained in the range of 0.1-0.7 microM in the majority of horses 12 hours after dosing,5 suggesting effectiveness of a once-daily dose. In rats and dogs, radioactivity from a C-14 labeled dose of glucosamine is detected in the liver, kidneys, articular cartilage, and other areas.12

Protein binding

Not Available

Metabolism

Glucosamine undergoes metabolism in the liver.12 Metabolism information for glucosamine is limited in the literature.

Route of elimination

Fecal excretion of glucosamine in a pharmacokinetic study was 11.3% within 120 hours after administration.13 Urinary elimination was found to be 1.19% within the first 8 hours post-administration.12

Half-life

The estimated half-life for glucosamine is 15 hours after an oral dose.13 After a bolus intravenous injection of 1005 mg crystalline glucosamine sulfate, the parent drug has an apparent half life of 1.11 hours.12

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

The oral LD50 of glucosamine in rats is >5000 mg/kg.24 Symptoms of an overdose with glucosamine may include nausea, vomiting, abdominal pain, and diarrhea (common side effects of this drug). Severe and life-threatening hypersensitivity reactions to glucosamine may occur in patients with a shellfish allergy or asthma.28

Pathways
PathwayCategory
Amino Sugar MetabolismMetabolic
G(M2)-Gangliosidosis: Variant B, Tay-Sachs DiseaseDisease
Sialuria or French Type SialuriaDisease
Sialuria or French Type SialuriaDisease
Salla Disease/Infantile Sialic Acid Storage DiseaseDisease
Tay-Sachs DiseaseDisease
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
AbciximabGlucosamine may increase the antiplatelet activities of Abciximab.
AcenocoumarolGlucosamine may increase the anticoagulant activities of Acenocoumarol.
Acetylsalicylic acidGlucosamine may increase the antiplatelet activities of Acetylsalicylic acid.
AnagrelideGlucosamine may increase the antiplatelet activities of Anagrelide.
CangrelorGlucosamine may increase the antiplatelet activities of Cangrelor.
CaplacizumabGlucosamine may increase the antiplatelet activities of Caplacizumab.
CilostazolGlucosamine may increase the antiplatelet activities of Cilostazol.
ClopidogrelGlucosamine may increase the antiplatelet activities of Clopidogrel.
DefibrotideGlucosamine may increase the antiplatelet activities of Defibrotide.
DipyridamoleGlucosamine may increase the antiplatelet activities of Dipyridamole.
Interactions
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Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Glucosamine hydrochloride750W5330FY66-84-2QKPLRMLTKYXDST-NSEZLWDYSA-N
Glucosamine sulfate1FW7WLR73114999-43-0WLNBMPZUVDTASE-HXIISURNSA-N
Glucosamine sulfate potassium chloride15VQ11I66N1296149-08-0UOUQWMJTBOYJTE-YZJMRIMCSA-M
Glucosamine sulfate sodium chloride7RI65CXJ9SNot AvailableNot applicable
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Appeton Essentials Glucosamine-500mg TabletTabletOralKOTRA PHARMA (M) SDN. BHD.2020-09-08Not applicableMalaysia flag
ArthroflexCapsuleOralALLPAC SOLUTIONS SDN. BHD.2020-09-08Not applicableMalaysia flag
Artricap 250 mgCapsuleOralAV MANUFACTURING SDN.BHD2020-09-08Not applicableMalaysia flag
ArtriForte 500 mgCapsuleOralAV MANUFACTURING SDN.BHD2020-09-08Not applicableMalaysia flag
Artrisa Sachet for Oral Solution 1500 mgPowder, for solutionOralAV MANUFACTURING SDN.BHD2020-09-08Not applicableMalaysia flag
Axcel Glucosamine-500mg TabletTabletOralKOTRA PHARMA (M) SDN. BHD.2020-09-08Not applicableMalaysia flag
BIO-LIFE GLUCOSAMINE 500MG TABLETSTabletOralBIO-LIFE MARKETING SDN BHD2020-09-08Not applicableMalaysia flag
BiO-LiFE Glucosamine 750mg TabletTablet, film coatedOralMEGA LIFESCIENCES SDN. BHD.2020-09-08Not applicableMalaysia flag
Blackmores Glucosamine 1500 TabletTablet, film coatedOralBLACKMORES (MALAYSIA) SDN. BHD.2020-09-08Not applicableMalaysia flag
BLACKMORES GLUCOSAMINE 500 TABLETTablet, film coatedOralBLACKMORES (MALAYSIA) SDN. BHD.2020-09-082020-12-17Malaysia flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AdaxilGlucosamine sulfate (750 mg) + Chondroitin sulfate sodium (bovine) (600 mg)PowderOralMYLAN HEALTHCARE SDN. BHD.2020-09-08Not applicableMalaysia flag
Appeton Essentials Glucosamine 500 + Chondroitin 400 TabletGlucosamine sulfate potassium chloride (500 mg) + Chondroitin sulfate sodium (bovine) (400 mg)TabletOralKOTRA PHARMA (M) SDN. BHD.2020-09-08Not applicableMalaysia flag
Arthro CapsuleGlucosamine sulfate (375 mg) + Chondroitin sulfate sodium (bovine) (200 mg)CapsuleOralSTERILINE SDN. BHD.2020-09-08Not applicableMalaysia flag
ARTHRO-S Powder for Oral SolutionGlucosamine sulfate potassium chloride (1500 mg) + Chondroitin sulfate sodium (bovine) (1200 mg)PowderOralNoripharma Sdn. Bhd.2020-09-08Not applicableMalaysia flag
ARTROFORT(R) COMPLEXGlucosamine (750 mg) + Chondroitin sulfate (bovine) (600 mg)PowderOralบริษัท เมด้า ฟาม่าร์ (ประเทศไทย) จำกัด2011-11-04Not applicableThailand flag
Avance JOINT COMFORT TABLETGlucosamine (250 mg) + Chondroitin sulfate (200 mg)TabletOralBEST WORLD LIFESTYLE SDN. BHD.2020-09-08Not applicableMalaysia flag
Axcel Glucosatin Dry Powder for Oral SolutionGlucosamine sulfate potassium chloride (1500 mg) + Chondroitin sulfate sodium (bovine) (1200 mg)Powder, for solutionOralKOTRA PHARMA (M) SDN. BHD.2020-09-08Not applicableMalaysia flag
Axcel GLUCOSATIN TABLETGlucosamine sulfate potassium chloride (500 mg) + Chondroitin sulfate sodium (bovine) (400 mg)TabletOralKOTRA PHARMA (M) SDN. BHD.2020-09-08Not applicableMalaysia flag
Bio-Life Glucosamine 500mg tabletGlucosamine hydrochloride (500 mg) + Chondroitin sulfate (bovine) (400 mg)TabletOralBIO-LIFE MARKETING SDN BHD2020-09-08Not applicableMalaysia flag
BiO-LiFE Glucosamine 500mg with Chondroitin Sulfate 400mg TabletGlucosamine hydrochloride (500 mg) + Chondroitin sulfate (shark) (400 mg)TabletOralMEGA LIFESCIENCES SDN. BHD.2020-09-08Not applicableMalaysia flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Medi-flexx Rx Joint Support FormulaGlucosamine sulfate (500 mg/1) + Chondroitin sulfate (chicken) (400 mg/1) + Dimethyl sulfone (200 mg/1)TabletOralTwo Hip Consulting, Llc2014-12-052016-04-11US flag
Remaxazon External PatchGlucosamine (5 g/100g) + Capsaicin (.0285 g/100g) + Chondroitin sulfate sodium (bovine) (3 g/100g) + Lidocaine (4 g/100g)PatchTopicalHome Aide Diganostics, Inc.2015-03-09Not applicableUS flag

Categories

ATC Codes
M01AX05 — Glucosamine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Hexoses
Alternative Parents
Aminosaccharides / Oxanes / Secondary alcohols / Hemiacetals / 1,2-aminoalcohols / Polyols / Oxacyclic compounds / Primary alcohols / Organopnictogen compounds / Monoalkylamines
show 1 more
Substituents
1,2-aminoalcohol / Alcohol / Aliphatic heteromonocyclic compound / Amine / Amino saccharide / Hemiacetal / Hexose monosaccharide / Hydrocarbon derivative / Organic nitrogen compound / Organoheterocyclic compound
show 9 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
D-glucosamine (CHEBI:47977) / Amino sugars (C00329)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
N08U5BOQ1K
CAS number
3416-24-8
InChI Key
MSWZFWKMSRAUBD-IVMDWMLBSA-N
InChI
InChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4-,5-,6?/m1/s1
IUPAC Name
(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol
SMILES
N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O

References

Synthesis Reference

Yuichi Yamamura, Ichiro Azuma, Shigeru Kobayashi, "Glucosamine peptide derivatives, their production and use." U.S. Patent US4369178, issued July, 1978.

US4369178
General References
  1. Towheed TE, Maxwell L, Anastassiades TP, Shea B, Houpt J, Robinson V, Hochberg MC, Wells G: Glucosamine therapy for treating osteoarthritis. Cochrane Database Syst Rev. 2005 Apr 18;(2):CD002946. [Article]
  2. Roseman S: Reflections on glycobiology. J Biol Chem. 2001 Nov 9;276(45):41527-42. Epub 2001 Sep 11. [Article]
  3. GHOSH S, BLUMENTHAL HJ, DAVIDSON E, ROSEMAN S: Glucosamine metabolism. V. Enzymatic synthesis of glucosamine 6-phosphate. J Biol Chem. 1960 May;235:1265-73. [Article]
  4. Buse MG: Hexosamines, insulin resistance, and the complications of diabetes: current status. Am J Physiol Endocrinol Metab. 2006 Jan;290(1):E1-E8. [Article]
  5. Laverty S, Sandy JD, Celeste C, Vachon P, Marier JF, Plaas AH: Synovial fluid levels and serum pharmacokinetics in a large animal model following treatment with oral glucosamine at clinically relevant doses. Arthritis Rheum. 2005 Jan;52(1):181-91. [Article]
  6. Black C, Clar C, Henderson R, MacEachern C, McNamee P, Quayyum Z, Royle P, Thomas S: The clinical effectiveness of glucosamine and chondroitin supplements in slowing or arresting progression of osteoarthritis of the knee: a systematic review and economic evaluation. Health Technol Assess. 2009 Nov;13(52):1-148. doi: 10.3310/hta13520. [Article]
  7. Vasiliadis HS, Tsikopoulos K: Glucosamine and chondroitin for the treatment of osteoarthritis. World J Orthop. 2017 Jan 18;8(1):1-11. doi: 10.5312/wjo.v8.i1.1. eCollection 2017 Jan 18. [Article]
  8. Adebowale A, Du J, Liang Z, Leslie JL, Eddington ND: The bioavailability and pharmacokinetics of glucosamine hydrochloride and low molecular weight chondroitin sulfate after single and multiple doses to beagle dogs. Biopharm Drug Dispos. 2002 Sep;23(6):217-25. doi: 10.1002/bdd.315. [Article]
  9. Setnikar I, Palumbo R, Canali S, Zanolo G: Pharmacokinetics of glucosamine in man. Arzneimittelforschung. 1993 Oct;43(10):1109-13. [Article]
  10. Persiani S, Matthews A, Larger P, Hall M, Rotini R, Trisolino G, Antonioli D, Zaccarelli L, Rovati LC: Glucosamine binding to proteins in plasma and synovial fluid and blood cell/plasma partitioning in mouse and man in vitro. Drug Metabol Drug Interact. 2009;24(2-4):211-27. doi: 10.1515/dmdi.2009.24.2-4.211. [Article]
  11. Williams C, Ampat G: Glucosamine Sulfate . [Article]
  12. Setnikar I, Rovati LC: Absorption, distribution, metabolism and excretion of glucosamine sulfate. A review. Arzneimittelforschung. 2001 Sep;51(9):699-725. doi: 10.1055/s-0031-1300105. [Article]
  13. Persiani S, Roda E, Rovati LC, Locatelli M, Giacovelli G, Roda A: Glucosamine oral bioavailability and plasma pharmacokinetics after increasing doses of crystalline glucosamine sulfate in man. Osteoarthritis Cartilage. 2005 Dec;13(12):1041-9. doi: 10.1016/j.joca.2005.07.009. Epub 2005 Sep 13. [Article]
  14. Jerosch J: Effects of Glucosamine and Chondroitin Sulfate on Cartilage Metabolism in OA: Outlook on Other Nutrient Partners Especially Omega-3 Fatty Acids. Int J Rheumatol. 2011;2011:969012. doi: 10.1155/2011/969012. Epub 2011 Aug 2. [Article]
  15. Sarrazin S, Bonnaffe D, Lubineau A, Lortat-Jacob H: Heparan sulfate mimicry: a synthetic glycoconjugate that recognizes the heparin binding domain of interferon-gamma inhibits the cytokine activity. J Biol Chem. 2005 Nov 11;280(45):37558-64. Epub 2005 Sep 9. [Article]
  16. Chen JT, Liang JB, Chou CL, Chien MW, Shyu RC, Chou PI, Lu DW: Glucosamine sulfate inhibits TNF-alpha and IFN-gamma-induced production of ICAM-1 in human retinal pigment epithelial cells in vitro. Invest Ophthalmol Vis Sci. 2006 Feb;47(2):664-72. [Article]
  17. Chen JT, Chen CH, Horng CT, Chien MW, Lu DW, Liang JB, Tai MC, Chang YH, Chen PL, Chen YH: Glucosamine sulfate inhibits proinflammatory cytokine-induced icam-1 production in human conjunctival cells in vitro. J Ocul Pharmacol Ther. 2006 Dec;22(6):402-16. [Article]
  18. Chen JT, Chen PL, Chang YH, Chien MW, Chen YH, Lu DW: Glucosamine sulfate inhibits leukocyte adhesion in response to cytokine stimulation of retinal pigment epithelial cells in vitro. Exp Eye Res. 2006 Nov;83(5):1052-62. doi: 10.1016/j.exer.2006.05.010. Epub 2006 Jul 5. [Article]
  19. Dahmer S, Schiller RM: Glucosamine. Am Fam Physician. 2008 Aug 15;78(4):471-6. [Article]
  20. Fox BA, Stephens MM: Glucosamine hydrochloride for the treatment of osteoarthritis symptoms. Clin Interv Aging. 2007;2(4):599-604. doi: 10.2147/cia.s1632. [Article]
  21. National Research Council; Institute of Medicine; Food and Nutrition Board; Board on Life Sciences; Committee on the Framework for Evaluating the Safety of the Dietary Supplements (2005). Dietary Supplements A Framework for Evaluating Safety:. National Academies Press (US). [ISBN:0-309-09110-1]
  22. TITCK Product Information: Dona (crystalline glucosamine sulfate) for intramuscular injection [Link]
  23. TITCK Product Information: Dona Plus (chondroitin sulfate/glucosamine sulfate) powder for oral use [Link]
  24. Zoetisus Safety Data Sheet: Glucosamine sulfate [Link]
  25. AAFP (American Family Physician): Glucosamine [Link]
  26. NIH MedlinePlus: Glucosamine [Link]
  27. DailyMed: Theraflex advance (ibuprofen, glucosamine sulfate, Chondroitin sulfate) oral tablet [Link]
  28. National Capital Poison Center: What you need to know about glucosamine [Link]
Human Metabolome Database
HMDB0001514
KEGG Drug
D04334
KEGG Compound
C00329
PubChem Compound
439213
PubChem Substance
46506420
ChemSpider
388352
RxNav
4845
ChEBI
47977
ChEMBL
CHEMBL493287
Therapeutic Targets Database
DAP001097
PharmGKB
PA164747613
Drugs.com
Drugs.com Drug Page
Wikipedia
Glucosamine
MSDS
Download (73.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceOsteoarthritis of the Knee1
4CompletedTreatmentBack pain1
4CompletedTreatmentBack Pain Lower Back1
4CompletedTreatmentDiacerein / Glucosamine / Osteoarthritis (OA)1
4CompletedTreatmentOral Lichen Planus1
4CompletedTreatmentOsteoarthritis (OA)1
4CompletedTreatmentOsteoarthritis of the Knee3
4RecruitingTreatmentRotator Cuff Tears1
3CompletedTreatmentOsteoarthritis (OA)1
3CompletedTreatmentOsteoarthritis of the Knee4

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • 21st Century Healthcare Inc.
  • Equaline Vitamins
  • Freeda Vitamins
  • Janssen-Ortho Inc.
  • LeaderPharma
  • Mckesson Corp.
  • Mericon
  • Nexgen Pharma Inc.
  • Professional Co.
  • Sunmark
  • Walgreen Co.
  • Zylera Pharmaceuticals LLC
Dosage Forms
FormRouteStrength
TabletOral
CapsuleOral
Powder, for solutionOral1884 mg
Powder, for solutionOral
GranuleOral
Injection, solution, concentrateIntramuscular
Tablet, coatedOral250 MG
Tablet, film coatedOral750 MG
Powder, for solutionOral
SolutionIntramuscular
Powder, for suspensionOral
SolutionIntramuscular400 mg
Powder, for solutionOral1500.14 mg
Capsule, coatedOral500 mg
Tablet, coatedOral
Capsule, liquid filledOral
Powder, for solutionOral1200 mg
Tablet, effervescentOral
Capsule, coatedOral250 mg
CapsuleOral
Powder, for solutionOral49.69 g
Capsule, liquid filledOral250 mg
Powder, for solutionOral1500 mg
Capsule, coatedOral
Tablet, effervescentOral
PowderOral
PowderOral
Tablet, film coated
TabletOral
GranuleOral
Tablet, film coatedOral
PatchTopical
Tablet, film coatedOral
Injection, solutionIntramuscular
Tablet, delayed releaseOral
Tablet, coatedOral750 mg
CapsuleOral550 mg
TabletOral250 mg
TabletOral500 mg
CapsuleOral375 mg
Tablet, film coatedOral500 mg
CapsuleOral250 mg
CapsuleOral500 mg
Granule, for solutionOral1500 mg/1sachet
PowderOral1500 mg/1sachet
GranuleOral1500 mg/1sachet
Tablet, film coatedOral1500 mg
Tablet, coatedOral500 mg
Powder, for solutionOral1500 mg/1sachet
Prices
Unit descriptionCostUnit
Glucosamine hcl (d) powder1.05USD g
Cidatrine 500 mg tablet0.81USD tablet
Glucosamine 500 mg tablet0.23USD tablet
Glucosamine hcl 500 mg tablet0.21USD tablet
Sm glucosamine hcl 1500 mg tablet0.2USD tablet
Eql glucosamine 1000 mg tablet0.17USD tablet
Glucosamine sulf 750 mg cplt0.16USD caplet
Glucosamine 500 mg caplet0.12USD tablet
Glucosamine relief 1000 mg tablet0.09USD tablet
Glucosamine 750 mg caplet0.08USD caplet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)88 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility551.0 mg/mLALOGPS
logP-2.7ALOGPS
logP-3ChemAxon
logS0.49ALOGPS
pKa (Strongest Acidic)11.73ChemAxon
pKa (Strongest Basic)8.23ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area116.17 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.58 m3·mol-1ChemAxon
Polarizability16.87 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.8589
Blood Brain Barrier-0.9143
Caco-2 permeable-0.8221
P-glycoprotein substrateNon-substrate0.7833
P-glycoprotein inhibitor INon-inhibitor0.9452
P-glycoprotein inhibitor IINon-inhibitor0.976
Renal organic cation transporterNon-inhibitor0.9261
CYP450 2C9 substrateNon-substrate0.8377
CYP450 2D6 substrateNon-substrate0.8469
CYP450 3A4 substrateNon-substrate0.7168
CYP450 1A2 substrateNon-inhibitor0.9503
CYP450 2C9 inhibitorNon-inhibitor0.9347
CYP450 2D6 inhibitorNon-inhibitor0.9494
CYP450 2C19 inhibitorNon-inhibitor0.9115
CYP450 3A4 inhibitorNon-inhibitor0.9777
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9769
Ames testNon AMES toxic0.7558
CarcinogenicityNon-carcinogens0.9716
BiodegradationReady biodegradable0.8286
Rat acute toxicity1.2287 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9659
hERG inhibition (predictor II)Non-inhibitor0.969
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Data supported by in vitro studies only. Clinical relevance is unknown.
General Function
Interferon-gamma receptor binding
Specific Function
Produced by lymphocytes activated by specific antigens or mitogens. IFN-gamma, in addition to having antiviral activity, has important immunoregulatory functions. It is a potent activator of macrop...
Gene Name
IFNG
Uniprot ID
P01579
Uniprot Name
Interferon gamma
Molecular Weight
19348.165 Da
References
  1. Sarrazin S, Bonnaffe D, Lubineau A, Lortat-Jacob H: Heparan sulfate mimicry: a synthetic glycoconjugate that recognizes the heparin binding domain of interferon-gamma inhibits the cytokine activity. J Biol Chem. 2005 Nov 11;280(45):37558-64. Epub 2005 Sep 9. [Article]
  2. Chen JT, Liang JB, Chou CL, Chien MW, Shyu RC, Chou PI, Lu DW: Glucosamine sulfate inhibits TNF-alpha and IFN-gamma-induced production of ICAM-1 in human retinal pigment epithelial cells in vitro. Invest Ophthalmol Vis Sci. 2006 Feb;47(2):664-72. [Article]
  3. Lortat-Jacob H: Interferon and heparan sulphate. Biochem Soc Trans. 2006 Jun;34(Pt 3):461-4. [Article]
  4. Chen JT, Chen CH, Horng CT, Chien MW, Lu DW, Liang JB, Tai MC, Chang YH, Chen PL, Chen YH: Glucosamine sulfate inhibits proinflammatory cytokine-induced icam-1 production in human conjunctival cells in vitro. J Ocul Pharmacol Ther. 2006 Dec;22(6):402-16. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Data supported by in vitro studies only. Clinical relevance is unknown.
General Function
Ubiquitin protein ligase binding
Specific Function
NF-kappa-B is a pleiotropic transcription factor present in almost all cell types and is the endpoint of a series of signal transduction events that are initiated by a vast array of stimuli related...
Gene Name
RELA
Uniprot ID
Q04206
Uniprot Name
Transcription factor p65
Molecular Weight
60218.53 Da
References
  1. Chen JT, Liang JB, Chou CL, Chien MW, Shyu RC, Chou PI, Lu DW: Glucosamine sulfate inhibits TNF-alpha and IFN-gamma-induced production of ICAM-1 in human retinal pigment epithelial cells in vitro. Invest Ophthalmol Vis Sci. 2006 Feb;47(2):664-72. [Article]
  2. Chen JT, Chen PL, Chang YH, Chien MW, Chen YH, Lu DW: Glucosamine sulfate inhibits leukocyte adhesion in response to cytokine stimulation of retinal pigment epithelial cells in vitro. Exp Eye Res. 2006 Nov;83(5):1052-62. doi: 10.1016/j.exer.2006.05.010. Epub 2006 Jul 5. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Hexose transmembrane transporter activity
Specific Function
Facilitative glucose transporter. This isoform likely mediates the bidirectional transfer of glucose across the plasma membrane of hepatocytes and is responsible for uptake of glucose by the beta c...
Gene Name
SLC2A2
Uniprot ID
P11168
Uniprot Name
Solute carrier family 2, facilitated glucose transporter member 2
Molecular Weight
57488.955 Da
References
  1. Uldry M, Ibberson M, Hosokawa M, Thorens B: GLUT2 is a high affinity glucosamine transporter. FEBS Lett. 2002 Jul 31;524(1-3):199-203. doi: 10.1016/s0014-5793(02)03058-2. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic transporter activity
Specific Function
Facilitative glucose transporter. This isoform may be responsible for constitutive or basal glucose uptake. Has a very broad substrate specificity; can transport a wide range of aldoses including b...
Gene Name
SLC2A1
Uniprot ID
P11166
Uniprot Name
Solute carrier family 2, facilitated glucose transporter member 1
Molecular Weight
54083.325 Da
References
  1. Mueckler M, Thorens B: The SLC2 (GLUT) family of membrane transporters. Mol Aspects Med. 2013 Apr-Jun;34(2-3):121-38. doi: 10.1016/j.mam.2012.07.001. [Article]
  2. Chopra A: cypate-d: -(+)-glucosamine (cyp-GlcN), and d: -(+)-glucosamine-cypate-d: -(+)-glucosamine (cyp-2GlcN) . [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Glucose transmembrane transporter activity
Specific Function
Insulin-regulated facilitative glucose transporter.
Gene Name
SLC2A4
Uniprot ID
P14672
Uniprot Name
Solute carrier family 2, facilitated glucose transporter member 4
Molecular Weight
54786.79 Da
References
  1. Mueckler M, Thorens B: The SLC2 (GLUT) family of membrane transporters. Mol Aspects Med. 2013 Apr-Jun;34(2-3):121-38. doi: 10.1016/j.mam.2012.07.001. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Glucose transmembrane transporter activity
Specific Function
Facilitative glucose transporter that can also mediate the uptake of various other monosaccharides across the cell membrane (PubMed:9477959, PubMed:26176916). Mediates the uptake of glucose, 2-deox...
Gene Name
SLC2A3
Uniprot ID
P11169
Uniprot Name
Solute carrier family 2, facilitated glucose transporter member 3
Molecular Weight
53923.785 Da
References
  1. Chopra A: cypate-d: -(+)-glucosamine (cyp-GlcN), and d: -(+)-glucosamine-cypate-d: -(+)-glucosamine (cyp-2GlcN) . [Article]

Drug created on June 13, 2005 13:24 / Updated on March 27, 2021 17:16