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targets (5) enzymes (2)
for drugs
Identification
Name Glucosamine
Accession Number DB01296 (EXPT01563)
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names Not Available
Brand mixtures Not Available
Categories Not Available
CAS number 3416-24-8
Weight Average: 179.1711
Monoisotopic: 179.079372531
Chemical Formula C6H13NO5
InChI Key InChIKey=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
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Aminoglycosides
Substructures
  • Aminoglycosides
  • Glycerol and Derivatives
  • Hydroxy Compounds
  • Pyrans
  • Acetals and Derivatives
  • Aliphatic and Aryl Amines
  • Ethers
  • Alcohols and Polyols
  • Amino Alcohols
  • Heterocyclic compounds
Pharmacology
Indication Not Available
Pharmacodynamics Not Available
Mechanism of action Glucosamine 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.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms Not Available
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers
Dosage forms Not Available
Prices
Unit description Cost Unit
Glucosamine hcl (d) powder 1.05 USD g
Cidatrine 500 mg tablet 0.81 USD tablet
Glucosamine 500 mg tablet 0.23 USD tablet
Glucosamine hcl 500 mg tablet 0.21 USD tablet
Sm glucosamine hcl 1500 mg tablet 0.2 USD tablet
Eql glucosamine 1000 mg tablet 0.17 USD tablet
Glucosamine sulf 750 mg cplt 0.16 USD caplet
Glucosamine 500 mg caplet 0.12 USD tablet
Glucosamine relief 1000 mg tablet 0.09 USD tablet
Glucosamine 750 mg caplet 0.08 USD caplet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 88 °C PhysProp
Predicted Properties
Property Value Source
water solubility 5.51e+02 g/l ALOGPS
logP -2.7 ALOGPS
logP -3 ChemAxon
logS 0.49 ALOGPS
pKa (strongest acidic) 11.73 ChemAxon
pKa (strongest basic) 8.23 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 6 ChemAxon
hydrogen donor count 5 ChemAxon
polar surface area 116.17 ChemAxon
rotatable bond count 1 ChemAxon
refractivity 37.58 ChemAxon
polarizability 16.87 ChemAxon
References
Synthesis Reference Not Available
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
External Links
Resource Link
PubChem Compound 439213 Link_out
PubChem Substance 46506420 Link_out
ChemSpider 388352 Link_out
ChEBI 5417 Link_out
ChEMBL 5417 Link_out
Therapeutic Targets Database DAP001097 Link_out
PharmGKB PA164747613 Link_out
Drugs.com http://www.drugs.com/cdi/glucosamine.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Glucosamine Link_out
ATC Codes
  • M01AX05
AHFS Codes Not Available
PDB Entries
FDA label Not Available
MSDS show (73.2 KB)
Interactions
Drug Interactions
Drug Interaction
Chlorpropamide Possible hyperglycemia
Gliclazide Possible hyperglycemia
Glimepiride Possible hyperglycemia
Glyburide Possible hyperglycemia
Insulin Possible hyperglycemia
Metformin Possible hyperglycemia
Miglitol Possible hyperglycemia
Nateglinide Possible hyperglycemia
Pioglitazone Possibly hyperglycemia
Repaglinide Possible hyperglycemia
Food Interactions Not Available
Targets

1. Matrix metalloproteinase-9

Pharmacological action: yes
Actions: antagonist

May play an essential role in local proteolysis of the extracellular matrix and in leukocyte migration. Could play a role in bone osteoclastic resorption. Cleaves KiSS1 at a Gly-|-Leu bond

Organism class: human
UniProt ID: P14780 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA

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

Pharmacological action: unknown
Actions: antagonist

Appears to have dual functions such as cytoplasmic retention of attached NF-kappa-B proteins and generation of p52 by a cotranslational processing. The proteasome-mediated process ensures the production of both p52 and p100 and preserves their independent function. p52 binds to the kappa-B consensus sequence 5'-GGRNNYYCC-3', located in the enhancer region of genes involved in immune response and acute phase reactions. p52 and p100 are respectively the minor and major form; the processing of p100 being relatively poor. Isoform p49 is a subunit of the NF-kappa-B protein complex, which stimulates the HIV enhancer in synergy with p65

Organism class: human
UniProt ID: Q00653 Link_out
Gene: NFKB2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: unknown

Cytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct action or by stimulation of interleukin 1 secretion and is implicated in the induction of cachexia, Under certain conditions it can stimulate cell proliferation and induce cell differentiation

Organism class: human
UniProt ID: P01375 Link_out
Gene: TNF Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: unknown

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 macrophages, it has antiproliferative effects on transformed cells and it can potentiate the antiviral and antitumor effects of the type I interferons

Organism class: human
UniProt ID: P01579 Link_out
Gene: IFNG Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: unknown

Aids in the defense against invading fungal pathogens by degrading their cell wall chitosan

Organism class: bacterial
UniProt ID: P33673 Link_out
Gene: csn
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: substrate

Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine

UniProt ID: P33261 Link_out
Gene: CYP2C19 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: substrate

Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms

UniProt ID: P05181 Link_out
Gene: CYP2E1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:20