Glucosamine

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Glucosamine
Stereo structural formula of glucosamine ((2S,6R)-6-meth,-2-ol) Glucosamine Structural Formulae V.1.svg
Stereo structural formula of glucosamine ((2S,6R)-6-meth,-2-ol)
Ball and stick model of glucosamine ((2R,6R)-6-meth,-2-ol) Beta-D-glucosamine-3D-balls.png
Ball and stick model of glucosamine ((2R,6R)-6-meth,-2-ol)
Names
IUPAC name
2-Amino-2-deoxy-glucose
Systematic IUPAC name
(3R,4R,5S)-3-Amino-6-(hydroxymethyl)oxane-2,4,5-triol
Other names
Chitosamine
Identifiers
3D model (JSmol)
1723616
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.020.284 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 222-311-2
720725
KEGG
MeSH Glucosamine
PubChem CID
UNII
  • 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 X mark.svgN
    Key: MSWZFWKMSRAUBD-SPZCMYQFSA-N X mark.svgN
  • N[C@H]1C(O)OC(CO)[C@@H](O)[C@@H]1O
Properties
C6H13NO5
Molar mass 179.172 g·mol−1
Density 1.563 g/mL
Melting point 150 °C (302 °F; 423 K)
log P −2.175
Acidity (pKa)7.5
Basicity (pKb)4.5
Pharmacology
M01AX05 ( WHO )
Legal status
  • EU:Authorized [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Glucosamine (C6H13NO5) is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylated proteins and lipids. Glucosamine is part of the structure of two polysaccharides, chitosan and chitin. Glucosamine is one of the most abundant monosaccharides. [2] It is produced commercially by the hydrolysis of shellfish exoskeletons or, less commonly, by fermentation of a grain such as corn or wheat. Glucosamine has various names depending on the country and its intended use. [3]

Although a common dietary supplement, there is little clinical evidence that it is effective for relief of arthritis or pain, and is not an approved prescription drug in most countries, [4] [5] [6] although it is listed as a medicinal product in Europe. [1] Worldwide, there are no clinical organizations that recommend use of glucosamine as a treatment for arthritis. [6]

Absence of clinical recommendations

No national clinical organizations recommend use of glucosamine for relief from arthritis. These include medical associations in Australia, [7] Canada, [8] the European Society for Clinical and Economic Aspects of Osteoporosis and Osteoarthritis, [9] the United Kingdom National Institute for Health and Care Excellence, [10] the United States National Center for Complementary and Integrative Health, [5] and the American College of Rheumatology and American Arthritis Foundation. [11]

Recommendations against use

Several clinical organizations have explicitly recommended against use of glucosamine to treat arthritis, stating that it has not been proven to be effective, that it may have negative interactions with prescription drugs, and that it may cause allergic reactions in people sensitive to shellfish, [7] [8] [10] a common starting material in glucosamine manufacturing. [4] The American College of Rheumatology and American Arthritis Foundation stated that "glucosamine is strongly recommended against in patients with knee, hip, and/or hand osteoarthritis". [11]

Dietary supplement

Oral glucosamine is a dietary supplement and is not a prescription drug in the United States. [4] [5] [6] Glucosamine is marketed as a supplement to support the structure and function of joints, and the marketing is targeted to people with osteoarthritis. [4] [5] [6] [11] Commonly sold forms of glucosamine are glucosamine sulfate, [4] glucosamine hydrochloride, and N-acetylglucosamine. [4] [3] Of the three commonly available forms of glucosamine, only glucosamine sulfate is given a "likely effective" rating for treating osteoarthritis. [4] Glucosamine is often sold in combination with other supplements such as chondroitin sulfate and methylsulfonylmethane. [4] [5] [6]

Glucosamine, along with commonly used chondroitin, is not routinely prescribed to treat people who have symptomatic osteoarthritis of the knee, as there is insufficient evidence that this treatment is helpful. [4] [5] [12]

As is common with heavily promoted dietary supplements, the claimed benefits of glucosamine are based principally on individual clinical and laboratory studies. Clinical studies on glucosamine efficacy are divided, [4] [5] with some reporting relief from arthritic pain and stiffness, while most studies report no conclusive benefit above placebo. [4] [5] [12] [13] [14]

Adverse effects and drug interactions

Glucosamine with or without chondroitin elevates the international normalized ratio (INR) in individuals who are taking the anticoagulant warfarin. [4]

Adverse effects are mild and infrequent, including stomach upset, constipation, diarrhea, headache, and rash. [4] [15]

Since glucosamine is usually derived from the shells of shellfish, it may be unsafe for those with shellfish allergy. [4] [5] [16] Many manufacturers of glucosamine derived from shellfish include a warning that those with a seafood allergy should consult a healthcare professional before taking the product. [4] Alternatively, non-shellfish-derived forms of glucosamine are available. [17]

Another concern has been that the extra glucosamine could contribute to incident diabetes by interfering with the normal regulation of the hexosamine biosynthesis pathway. [18]

Biochemistry

Glucosamine is naturally present in the shells (exoskeletons) of shellfish, animal bones, bone marrow, and fungi. [4] [19] D-Glucosamine is made naturally in the form of glucosamine-6-phosphate, and is the biochemical precursor of all nitrogen-containing sugars. [20] Specifically in humans, glucosamine-6-phosphate is synthesized from fructose 6-phosphate and glutamine by glutamine—fructose-6-phosphate transaminase as the first step of the hexosamine biosynthesis pathway. [21] The end-product of this pathway is uridine diphosphate N-acetylglucosamine (UDP-GlcNAc), which is then used for making glycosaminoglycans, proteoglycans, and glycolipids.

As the formation of glucosamine-6-phosphate is the first step for the synthesis of these products, glucosamine may be important in regulating their production; however, the way that the hexosamine biosynthesis pathway is actually regulated, and whether this could be involved in contributing to human disease remains unclear. [18]

Manufacturing

Most glucosamine is manufactured by processing chitin from the exoskeletons of shellfish, including shrimp, lobsters, and crabs. [4] [22] To meet the demands of vegetarians and others with objections to shellfish, manufacturers have brought glucosamine products to market made using fungus Aspergillus niger and from fermenting corn. [17]

History

Glucosamine was first prepared in 1876 by Georg Ledderhose by the hydrolysis of chitin with concentrated hydrochloric acid. [23] [24] [25] The stereochemistry was not fully determined until the 1939 work of Walter Haworth. [2] [26]

United States

In the United States, glucosamine is not approved by the Food and Drug Administration (FDA) for medical use in humans. [4] [6] [27] Because glucosamine is classified as a dietary supplement in the United States, the FDA requires evidence of its safety, but not its effectiveness, as long as it is not marketed as a treatment for any medical condition. [28]

In 2004, the FDA declared there was insufficient evidence for supplement manufacturers to state that glucosamine was effective for treating arthritis, joint degeneration, or cartilage deterioration, a position remaining in effect, as of 2025. [4] [27] [29]

Europe

In most of Europe, glucosamine is approved as a medical drug and is sold in the form of glucosamine sulfate. [1] [30]

The Task Force of the European League Against Rheumatism (EULAR) committee has granted glucosamine sulfate a level of toxicity of 5 on a 0–100 scale. [30] By 2014, OARSI no longer recommended glucosamine for disease modification and deemed its effectiveness for symptom relief in knee osteoarthritis as "uncertain." [31] A 2016 review concluded that only the formulated prescription-only patented crystalline glucosamine sulfate had efficacy in the treatment of arthritis. [9]

Class-action lawsuits

In 2013, without admitting fault, manufacturer Rexall Sundown and NBTY agreed to pay up to US$2 million to settle consumer claims related to the wording of certain claims on the packaging of glucosamine bottles sold at Costco under the Kirkland label. [32]

In August 2012, a class-action lawsuit was filed in New York claiming that 21st Century Healthcare, Inc. had falsely advertised that its "Glucosamine 750 Chondroitin 600 Triple Strength" dietary supplements would restore lost cartilage. [33] In April 2013, a San Diego man launched a proposed class-action lawsuit in the United States District Court for the Central District of California accusing Nutramax Laboratories, Walmart, and Rite Aid of falsely advertising the effectiveness of glucosamine. [34]

Research

Humans

Because glucosamine is a precursor for glycosaminoglycans, and glycosaminoglycans are a major component of cartilage, research has focused on the potential for supplemental glucosamine to improve cartilage structure and alleviate arthritis, but there is little evidence from clinical trials that it is effective for alleviating arthritis pain. [4] [5]

A 2023 review concluded that there was weak evidence from clinical studies that glucosamine and chondroitin when combined were effective in relieving the pain of knee osteoarthritis, with most results not attaining statistical significance. [35]

Bioavailability

Two studies measured the concentrations of glucosamine in the synovial fluid and plasma after oral administration of glucosamine sulfate to both healthy volunteers and people with osteoarthritis. [36] [37]

In the first study, glucosamine sulfate was given to healthy volunteers in doses of 750, 1,500, or 3,000 mg once daily. In the second study, oral glucosamine sulfate capsules (1,500 mg) were given daily for two weeks to 12 people with osteoarthritis. Glucosamine concentrations in plasma and synovial fluid increased significantly from baseline levels, and the levels in the two fluids were highly correlated. The authors interpreted that these levels could be biologically advantageous to articular cartilage, but the levels are still ten to one hundred times lower than required to positively influence the cartilage (chondrocytes) to build new tissue. [38] Glucosamine sulfate uptake in synovial fluid may be as much as 20%, or it could be negligible, indicating no biological significance. [39]

Veterinary medicine

Dogs

Some studies have demonstrated efficacy of glucosamine supplementation for dogs with osteoarthritis pain, particularly in combination with other nutraceuticals like chondroitin, [40] [41] while others have not. [42] A trial of oral combination capsules (glucosamine, chondroitin, and manganese ascorbate) in dogs with osteoarthritis found no benefit on either gait analysis or subjective assessments by the veterinarian or owner. [42]

Horses

The use of glucosamine in equine medicine is recognized; however, a meta-analysis deemed the existing research too flawed to effectively guide the treatment of horses. [43]

Several studies have measured the bioavailability of glucosamine after oral administration to horses. When given as a single oral dose (9 g) with or without chondroitin sulfate (3 g) to ten horses, glucosamine (hydrochloride) was detected in the blood with a maximum level of 10.6±6.9 μg/mL at two hours after dosing. [44] Another study examined both the serum and the joint synovial fluid after nasogastric (oral) or intravenous administration of 20 mg/kg glucosamine hydrochloride to eight adult horses. [45] Although joint fluid concentrations of glucosamine reached 9–15 μmol/L following intravenous dosing, it was only 0.3–0.7 μmol/L with nasogastric dosing. The authors calculated that these glucosamine synovial fluid levels achieved by the oral route were 500 times lower than required to positively affect the metabolism of cartilage cells. A follow-up study by the same research group compared glucosamine sulfate with glucosamine hydrochloride at the same dose (20 mg/kg) in eight horses and found a higher fluid concentration with the sulfate preparation (158 ng/mL compared to 89 ng/mL one hour post oral dose). [46] They concluded that these higher synovial fluid levels obtained with the sulfate derivative were still too low to have a relevant biological effect on articular cartilage.

A three-month trial of an oral dosage regime of a commercial preparation of glucosamine sulfate, chondroitin sulfate, and methylsulfonylmethane was performed in veteran horses with no effect on gait stiffness, with exercise alone in the control group being effective. [47] The intravenous use of a combination of N-acetylglucosamine, pentosan polysulfate, and sodium hyaluronate in horses with surgically-induced osteoarthritis saw improvements in X-ray changes to the cartilage but not histologically or in biochemical outcomes, [48] suggesting more evidence is needed for this combination and route of administration.

See also

References

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  2. 1 2 Pigman WW, Horton D, Wander JD (1980). The Carbohydrates. Vol. IB. New York: Academic Press. pp. 727–728. ISBN   978-0-12-556351-2.
  3. 1 2 "Glucosamine". Drugs.com. 31 July 2019. Retrieved 14 September 2019.
  4. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 "Glucosamine: Natural Products Monograph". Drugs.com. 11 November 2025. Retrieved 24 January 2026.
  5. 1 2 3 4 5 6 7 8 9 10 "Glucosamine and Chondroitin for Osteoarthritis: What You Need To Know". National Center for Complementary and Integrative Health, US National Institutes of Health. October 2023. Retrieved 24 January 2026.
  6. 1 2 3 4 5 6 Williams C, Ampat G (22 July 2023). "Glucosamine sulfate". StatPearls, US National Library of Medicine. Retrieved 24 January 2026.
  7. 1 2 "Glucosamine". Australian Rheumatology Association. February 2020. Retrieved 24 January 2026.
  8. 1 2 "Using Supplements to Treat Arthritis". Arthritis Society Canada. 2026. Retrieved 24 January 2026.
  9. 1 2 Bruyère O, Cooper C, Pelletier JP, et al. (February 2016). "A consensus statement on the European Society for Clinical and Economic Aspects of Osteoporosis and Osteoarthritis (ESCEO) algorithm for the management of knee osteoarthritis-From evidence-based medicine to the real-life setting". Seminars in Arthritis and Rheumatism. 45 (4 Suppl): S3–11. doi:10.1016/j.semarthrit.2015.11.010. PMID   26806188.
  10. 1 2 "NICE Guideline: Osteoarthritis in over 16s: diagnosis and management". UK National Institute for Health and Care Excellence. 19 October 2022. Retrieved 24 January 2026.
  11. 1 2 3 Kolasinski SL, Neogi T, Hochberg MC, et al. (February 2020). "2019 American College of Rheumatology/Arthritis Foundation Guideline for the Management of Osteoarthritis of the Hand, Hip, and Knee". Arthritis Care & Research. 72 (2): 149–162. doi:10.1002/acr.24131. PMC   11488261 . PMID   31908149.
  12. 1 2 Zhu X, Sang L, Wu D, et al. (July 2018). "Effectiveness and safety of glucosamine and chondroitin for the treatment of osteoarthritis: a meta-analysis of randomized controlled trials". Journal of Orthopedic Surgery and Research. 13 (1) 170. doi: 10.1186/s13018-018-0871-5 . PMC   6035477 . PMID   29980200.
  13. ↑ Towheed, T. E.; Maxwell, L; Anastassiades, T. P.; et al. (2005). "Glucosamine for osteoarthritis". The Cochrane Database of Systematic Reviews. 2005 (2) CD002946. doi:10.1002/14651858.CD002946.pub2. PMC   8459392 . PMID   15846645.
  14. ↑ DiNubile N (July 2018). "Glucosamine and Chondroitin Sulfate: What Has Been Learned Since the Glucosamine/chondroitin Arthritis Intervention Trial". Orthopedics. 41 (4): 200–207. doi:10.3928/01477447-20180511-06. PMID   29771395. S2CID   21707977.
  15. ↑ "Complementary and alternative medicines for the treatment of rheumatoid arthritis, osteoarthritis and fibromyalgia". Arthritis Research UK. October 2012. pp. 34–5. Archived from the original on 18 February 2017. Retrieved 17 February 2017.
  16. ↑ Gray HC; Hutcheson PS; Slavin RG (August 2004). "Is glucosamine safe in patients with seafood allergy?". The Journal of Allergy and Clinical Immunology . 114 (2): 459–60. doi: 10.1016/j.jaci.2004.05.050 . PMID   15341031.
  17. 1 2 "Another vegetarian glucosamine launched in US". NutraIngredients-USA.com. 25 January 2008. Archived from the original on 17 April 2009.
  18. 1 2 Buse MG (2006). "Hexosamines, insulin resistance, and the complications of diabetes: current status". Am. J. Physiol. Endocrinol. Metab. 290 (1): E1–E8. doi:10.1152/ajpendo.00329.2005. PMC   1343508 . PMID   16339923.
  19. ↑ "Scientific Opinion of the Panel on Dietetic Products Nutrition and Allergies on a request from the European Commission on the safety of glucosamine hydrochloride from Aspergillus niger as food ingredient". The EFSA Journal. 1099: 1–19. 2009.
  20. ↑ Roseman S (2001). "Reflections on glycobiology". Journal of Biological Chemistry. 276 (45): 41527–42. doi: 10.1074/jbc.R100053200 . PMID   11553646.
  21. ↑ "UDP-N-acetylglucosamine Biosynthesis". Recommendations of the Nomenclature Committee of the International Union of Biochemistry and Molecular Biology on the Nomenclature and Classification of Enzymes by the Reactions they Catalyse. International Union of Biochemistry and Molecular Biology. 2002. Retrieved 10 September 2012.
  22. ↑ Murray, Michael T. (2012). "Chapter 94: Glucosamine". In Pizzorno, Joseph E. Jr.; Murray, Michael T. (eds.). Textbook of natural medicine (4th ed.). Edinburgh: Churchill Livingstone. p. 790. ISBN   978-1-4377-2333-5.
  23. ↑ Georg Ledderhose (1876). "Über salzsaures Glycosamin" [On glucosamine hydrochloride]. Berichte der Deutschen Chemischen Gesellschaft. 9 (2): 1200–1201. doi:10.1002/cber.18760090251.
  24. ↑ Ledderhose G (1879). "Über Chitin und seine Spaltungs-produkte" [On chitin and its hydrolysis products]. Zeitschrift für Physiologische Chemie. ii: 213–227.
  25. ↑ Ledderhose G (1880). "Über Glykosamin". Zeitschrift für Physiologische Chemie. iv: 139–159.
  26. ↑ W. N. Haworth; W. H. G. Lake; S. Peat (1939). "The configuration of glucosamine (chitosamine)". Journal of the Chemical Society: 271–274. doi:10.1039/jr9390000271.
  27. 1 2 Hubbard, W. K. (7 October 2004). "Letter Regarding the Relationship Between the Consumption of Glucosamine and/or Chondroitin Sulfate and a Reduced Risk of: Osteoarthritis; Osteoarthritis-related Joint Pain, Joint Tenderness, and Joint Swelling; Joint Degeneration; and Cartilage Deterioration (Docket No. 2004P-0059)". U.S. Food and Drug Administration. Archived from the original on 21 April 2025. Retrieved 12 January 2026. FDA concludes that there is no credible evidence to support qualified health claims for glucosamine or chondroitin sulfate and reduced risk of osteoarthritis (OA), joint degeneration (JD), or cartilage deterioration (CD).
  28. ↑ "Dietary Supplements". U.S. Food and Drug Administration. Archived from the original on 12 May 2009. Retrieved 10 December 2009.
  29. ↑ "Qualified Health Claims: Letters of Denial, Osteoarthritis". U.S. Food and Drug Administration. 13 December 2018. Archived from the original on 14 December 2025. Retrieved 12 January 2026.
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  31. ↑ McAlindon TE, Bannuru RR, Sullivan MC, et al. (March 2014). "OARSI guidelines for the non-surgical management of knee osteoarthritis". Osteoarthritis and Cartilage. 22 (3): 363–88. doi: 10.1016/j.joca.2014.01.003 . PMID   24462672.
  32. ↑ "Glucosamine Settlement". www.glucosaminesettlement.com. Archived from the original on 10 July 2013. Retrieved 17 June 2013.
  33. ↑ "21st Century Glucosamine/Chondroitin Triple Strength Class Action Lawsuit". www.topclassactions.com. 14 September 2012. Retrieved 17 June 2013.
  34. ↑ "Wal-Mart, Rite Aid Face Suit Over Glucosamine Promises". www.law360.com. Retrieved 17 June 2013.
  35. ↑ Meng Z, Liu J, Zhou N (January 2023). "Efficacy and safety of the combination of glucosamine and chondroitin for knee osteoarthritis: a systematic review and meta-analysis". Archives of Orthopaedic and Trauma Surgery. 143 (1): 409–421. doi:10.1007/s00402-021-04326-9. PMID   35024906.
  36. ↑ Persiani S; Rotini R; Trisolino G; et al. (July 2007). "Synovial and plasma glucosamine concentrations in osteoarthritic patients following oral crystalline glucosamine sulphate at therapeutic dose". Osteoarthritis and Cartilage. 15 (7): 764–72. doi: 10.1016/j.joca.2007.01.019 . PMID   17353133.
  37. ↑ Persiani S; Roda E; Rovati LC; et al. (December 2005). "Glucosamine oral bioavailability and plasma pharmacokinetics after increasing doses of crystalline glucosamine sulfate in man". Osteoarthritis and Cartilage. 13 (12): 1041–9. doi: 10.1016/j.joca.2005.07.009 . PMID   16168682.
  38. ↑ Mroz PJ, Silbert JE (2004). "Use of 3H-glucosamine and 35S-sulfate with cultured human chondrocytes to determine the effect of glucosamine concentration on formation of chondroitin sulfate". Arthritis Rheum. 50 (11): 3574–9. doi:10.1002/art.20609. PMID   15529373.
  39. ↑ Cohen MJ, Braun L (2007). Herbs & natural supplements: an evidence-based guide. Marrickville, New South Wales: Elsevier Australia. ISBN   978-0-7295-3796-4.
  40. ↑ Gupta, R. C.; Canerdy, T. D.; Lindley, J; et al. (2012). "Comparative therapeutic efficacy and safety of type-II collagen (UC-II), glucosamine and chondroitin in arthritic dogs: Pain evaluation by ground force plate". Journal of Animal Physiology and Animal Nutrition. 96 (5): 770–7. doi:10.1111/j.1439-0396.2011.01166.x. PMID   21623931.
  41. ↑ d'Altilio, M; Peal, A; Alvey, M; et al. (2007). "Therapeutic Efficacy and Safety of Undenatured Type II Collagen Singly or in Combination with Glucosamine and Chondroitin in Arthritic Dogs". Toxicology Mechanisms and Methods. 17 (4): 189–96. doi:10.1080/15376510600910469. PMID   20020968. S2CID   36796044.
  42. 1 2 Moreau, M; Dupuis, J; Bonneau, N. H.; Desnoyers, M (2003). "Clinical evaluation of a nutraceutical, carprofen and meloxicam for the treatment of dogs with osteoarthritis". The Veterinary Record. 152 (11): 323–9. doi:10.1136/vr.152.11.323. PMID   12665145. S2CID   40196882.
  43. ↑ Pearson, W; Lindinger, M (2009). "Low quality of evidence for glucosamine-based nutraceuticals in equine joint disease: Review of in vivo studies". Equine Veterinary Journal. 41 (7): 706–12. doi:10.2746/042516409X424153. PMID   19927591.
  44. ↑ Du, J; White, N; Eddington, N. D. (2004). "The bioavailability and pharmacokinetics of glucosamine hydrochloride and chondroitin sulfate after oral and intravenous single dose administration in the horse". Biopharmaceutics & Drug Disposition. 25 (3): 109–16. doi: 10.1002/bdd.392 . PMID   15083499. S2CID   39668131.
  45. ↑ Laverty, S; Sandy, J. D.; Celeste, C; et al. (2005). "Synovial fluid levels and serum pharmacokinetics in a large animal model following treatment with oral glucosamine at clinically relevant doses". Arthritis and Rheumatism. 52 (1): 181–91. doi:10.1002/art.20762. PMID   15641100.
  46. ↑ Meulyzer, M; Vachon, P; Beaudry, F; et al. (2008). "Comparison of pharmacokinetics of glucosamine and synovial fluid levels following administration of glucosamine sulphate or glucosamine hydrochloride". Osteoarthritis and Cartilage. 16 (9): 973–9. doi: 10.1016/j.joca.2008.01.006 . PMID   18295513.
  47. ↑ Higler, M. H.; Brommer, H; l'Ami, J. J.; et al. (2013). "The effects of three-month oral supplementation with a nutraceutical and exercise on the locomotor pattern of aged horses". Equine Veterinary Journal. 46 (5): 611–7. doi:10.1111/evj.12182. PMID   24011144.
  48. ↑ Koenig, T. J.; Dart, A. J.; McIlwraith, C. W.; et al. (2014). "Treatment of Experimentally Induced Osteoarthritis in Horses Using an Intravenous Combination of Sodium Pentosan Polysulfate, N-Acetyl Glucosamine, and Sodium Hyaluronan". Veterinary Surgery. 43 (5): 612–22. doi:10.1111/j.1532-950X.2014.12203.x. PMID   24819506.
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