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Identification
NameGlucosamine
Accession NumberDB01296  (EXPT01563)
TypeSmall Molecule
GroupsApproved
Description

Glucosamine is commonly used as a treatment for osteoarthritis, although its acceptance as a medical therapy varies. It is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylated proteins and lipids. Since glucosamine is a precursor for glycosaminoglycans, and glycosaminoglycans are a major component of joint cartilage, supplemental glucosamine may help to rebuild cartilage and treat arthritis.

Structure
Thumb
Synonyms
SynonymLanguageCode
2-Amino-2-deoxy-D-glucoseNot AvailableNot Available
ChitosamineNot AvailableNot Available
D-GlucosamineNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number3416-24-8
WeightAverage: 179.1711
Monoisotopic: 179.079372531
Chemical FormulaC6H13NO5
InChI KeyMSWZFWKMSRAUBD-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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as amino sugars. These are sugars having one alcoholic hydroxy group replaced by an amino group; systematically known as x-amino-x-deoxymonosaccharides. These compounds do not include Glycosylamines.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassAminosaccharides
Direct ParentAmino sugars
Alternative Parents
Substituents
  • Glucosamine
  • Amino sugar
  • Oxane
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Hemiacetal
  • 1,2-diol
  • 1,2-aminoalcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationGlucosamine is usually used in the treatment of osteoarthritis, although its efficacy is still in question.
PharmacodynamicsOsteoarthritis is characterized by the progressive degeneration of cartilage glycosaminoglycans. The formation of glucosamine is the rate limiting step in glycosaminoglycans synthesis thus the addition is glucosamine, would in theory provide a building block towards the synthesis of glycosaminoglycans and thus slow down the progression of osteoarthritis. Thus far however, the results have not been conclusive.
Mechanism of actionGlucosamine is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylated proteins and lipids. Oral glucosamine is commonly used for the treatment of osteoarthritis. Since glucosamine is a precursor for glycosaminoglycans, and glycosaminoglycans are a major component of joint cartilage, supplemental glucosamine may help to rebuild cartilage and treat arthritis. Its use as a therapy for osteoarthritis appears safe, but there is conflicting evidence as to its effectiveness with more recent studies showing limited to no clinical benefit of use. In the United States, glucosamine is not approved by the Food and Drug Administration for medical use in humans. Since glucosamine is classified as a dietary supplement, safety and formulation are solely the responsibility of the manufacturer; evidence of safety and efficacy is not required as long as it is not advertised as a treatment for a medical condition.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityAdverse effects are generally mild: itching, diarrhea, heartburn, nausea and vomiting.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.9347
CYP450 2D6 substrateNon-inhibitor0.9494
CYP450 2C19 substrateNon-inhibitor0.9115
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point88 °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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
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 Reference
  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. Pubmed
  2. Roseman S: Reflections on glycobiology. J Biol Chem. 2001 Nov 9;276(45):41527-42. Epub 2001 Sep 11. Pubmed
  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. Pubmed
  4. Buse MG: Hexosamines, insulin resistance, and the complications of diabetes: current status. Am J Physiol Endocrinol Metab. 2006 Jan;290(1):E1-E8. Pubmed
  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. Pubmed
  6. Lexicomp [Internet]. Glucosamine (Natural Products Database). 2014. Available from: http://online.lexi.com.login.ezproxy.library.ualberta.ca/lco/action/doc/retrieve/docid/fc_rnp2/3750166#
External Links
ATC CodesM01AX05
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (73.2 KB)
Interactions
Drug Interactions
Drug
AbciximabMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
Acetylsalicylic acidMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
AnagrelideMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
CilostazolMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
CitalopramMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
ClopidogrelMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
DesvenlafaxineMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
DiflunisalMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
DipyridamoleMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
DuloxetineMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
EptifibatideMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
EscitalopramMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
EtodolacMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
FenoprofenMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
FloctafenineMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
FluoxetineMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
FluvoxamineMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
IbuprofenMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
IndomethacinMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
KetoprofenMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
KetorolacMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
LevomilnacipranMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
Mefenamic acidMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
MeloxicamMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
MilnacipranMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
NabumetoneMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
NaproxenMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
OxaprozinMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
ParoxetineMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
PiroxicamMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
PrasugrelMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
SertralineMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
SulindacMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
Tiaprofenic acidMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
TicagrelorMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
TiclopidineMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
TirofibanMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
TolmetinMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
VenlafaxineMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
VilazodoneMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
VorapaxarMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
Food InteractionsNot Available

Targets

1. Matrix metalloproteinase-9

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Matrix metalloproteinase-9 P14780 Details

References:

  1. Fenton JI, Chlebek-Brown KA, Caron JP, Orth MW: Effect of glucosamine on interleukin-1-conditioned articular cartilage. Equine Vet J Suppl. 2002 Sep;(34):219-23. Pubmed
  2. Mendis E, Kim MM, Rajapakse N, Kim SK: Carboxy derivatized glucosamine is a potent inhibitor of matrix metalloproteinase-9 in HT1080 cells. Bioorg Med Chem Lett. 2006 Jun 15;16(12):3105-10. Epub 2006 Apr 17. Pubmed
  3. Chu SC, Yang SF, Lue KH, Hsieh YS, Lee CY, Chou MC, Lu KH: Glucosamine sulfate suppresses the expressions of urokinase plasminogen activator and inhibitor and gelatinases during the early stage of osteoarthritis. Clin Chim Acta. 2006 Oct;372(1-2):167-72. Epub 2006 Jun 6. Pubmed
  4. Rajapakse N, Mendis E, Kim MM, Kim SK: Sulfated glucosamine inhibits MMP-2 and MMP-9 expressions in human fibrosarcoma cells. Bioorg Med Chem. 2007 Jul 15;15(14):4891-6. Epub 2007 Apr 29. Pubmed
  5. Dodge GR, Jimenez SA: Glucosamine sulfate modulates the levels of aggrecan and matrix metalloproteinase-3 synthesized by cultured human osteoarthritis articular chondrocytes. Osteoarthritis Cartilage. 2003 Jun;11(6):424-32. Pubmed

2. Nuclear factor NF-kappa-B p100 subunit

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Nuclear factor NF-kappa-B p100 subunit Q00653 Details

References:

  1. Largo R, Alvarez-Soria MA, Diez-Ortego I, Calvo E, Sanchez-Pernaute O, Egido J, Herrero-Beaumont G: Glucosamine inhibits IL-1beta-induced NFkappaB activation in human osteoarthritic chondrocytes. Osteoarthritis Cartilage. 2003 Apr;11(4):290-8. Pubmed

3. Tumor necrosis factor

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Tumor necrosis factor P01375 Details

References:

  1. Delcommenne M, Kannagi R, Johnson P: TNF-alpha increases the carbohydrate sulfation of CD44: induction of 6-sulfo N-acetyl lactosamine on N- and O-linked glycans. Glycobiology. 2002 Oct;12(10):613-22. Pubmed
  2. Bitler CM, Viale TM, Damaj B, Crea R: Hydrolyzed olive vegetation water in mice has anti-inflammatory activity. J Nutr. 2005 Jun;135(6):1475-9. Pubmed
  3. 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. Pubmed
  4. Yi HA, Yi SD, Jang BC, Song DK, Shin DH, Mun KC, Kim SP, Suh SI, Bae JH: Inhibitory effects of glucosamine on lipopolysaccharide-induced activation in microglial cells. Clin Exp Pharmacol Physiol. 2005 Dec;32(12):1097-103. Pubmed
  5. Lapaque N, Takeuchi O, Corrales F, Akira S, Moriyon I, Howard JC, Gorvel JP: Differential inductions of TNF-alpha and IGTP, IIGP by structurally diverse classic and non-classic lipopolysaccharides. Cell Microbiol. 2006 Mar;8(3):401-13. Pubmed

4. Interferon gamma

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Interferon gamma P01579 Details

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. Pubmed
  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. Pubmed
  3. Lortat-Jacob H: Interferon and heparan sulphate. Biochem Soc Trans. 2006 Jun;34(Pt 3):461-4. Pubmed
  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. Pubmed

5. Chitosanase

Kind: protein

Organism: Bacillus circulans

Pharmacological action: unknown

Components

Name UniProt ID Details
Chitosanase P33673 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Kurakake M, Yo-u S, Nakagawa K, Sugihara M, Komaki T: Properties of chitosanase from Bacillus cereus S1. Curr Microbiol. 2000 Jan;40(1):6-9. Pubmed
  4. Kimoto H, Kusaoke H, Yamamoto I, Fujii Y, Onodera T, Taketo A: Biochemical and genetic properties of Paenibacillus glycosyl hydrolase having chitosanase activity and discoidin domain. J Biol Chem. 2002 Apr 26;277(17):14695-702. Epub 2002 Feb 19. Pubmed
  5. Shimono K, Shigeru K, Tsuchiya A, Itou N, Ohta Y, Tanaka K, Nakagawa T, Matsuda H, Kawamukai M: Two glutamic acids in chitosanase A from Matsuebacter chitosanotabidus 3001 are the catalytically important residues. J Biochem (Tokyo). 2002 Jan;131(1):87-96. Pubmed

Enzymes

1. Cytochrome P450 2C19

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C19 P33261 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 2E1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2E1 P05181 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on December 29, 2014 19:54