Chemistry:Glucosamine

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Short description: Organic chemical compound
Glucosamine
Stereo structural formula of glucosamine ((2S,6R)-6-meth,-2-ol)
Ball and stick model of glucosamine ((2R,6R)-6-meth,-2-ol)
Names
IUPAC name
(3R,4R,5S)-3-Amino-6-(hydroxymethyl)oxane-2,4,5-triol
Other names
2-Amino-2-deoxy-glucose
Chitosamine
Identifiers
3D model (JSmol)
1723616
ChEBI
ChEMBL
ChemSpider
DrugBank
EC Number
  • 222-311-2
720725
KEGG
MeSH Glucosamine
UNII
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
1=ATC code }} 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).
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Infobox references

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] Produced commercially by the hydrolysis of shellfish exoskeletons or, less commonly, by fermentation of a grain such as corn or wheat, glucosamine has many names depending on country.[3]

Although a common dietary supplement, there is little evidence that it is effective for relief of arthritis or pain, and is not an approved prescription drug.[4][5][6]

Dietary supplement

Oral glucosamine is a dietary supplement and is not a prescription drug.[4][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][6]

Commonly sold forms of glucosamine are glucosamine sulfate,[4] glucosamine chondroitin, glucosamine hydrochloride,[5] 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.[citation needed]

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.[7][8]

As is common with heavily promoted dietary supplements, the claimed benefits of glucosamine are based principally on clinical and laboratory studies. Clinical studies on glucosamine efficacy are divided, with some reporting relief from arthritic pain and stiffness, while others report no benefit above placebo.[4][9][8][10]

(As of 2015), there is no evidence that consumption of glucosamine by sport participants prevents or limits joint damage after injury.[11]

Adverse effects and drug interactions

Glucosamine with or without chondroitin elevates the international normalized ratio (INR) in individuals who are taking the blood thinner, warfarin.[4][12] It may also interfere with the efficacy of chemotherapy for treating cancer symptoms.[4]

Adverse effects are mild and infrequent and may include stomach upset, constipation, diarrhea, headache, and rash.[13]

Since glucosamine is usually derived from the shells of shellfish, it may be unsafe for those with shellfish allergy.[14] 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.[15] Alternatively, non-shellfish-derived forms of glucosamine are available.[16]

Another concern has been that the extra glucosamine could contribute to diabetes by interfering with the normal regulation of the hexosamine biosynthesis pathway,[17] but several investigations found no evidence that this occurs.[18][19] Other studies conducted in lean or obese subjects concluded that oral glucosamine at standard doses does not affect insulin resistance.[20][21]

Biochemistry

Glucosamine is naturally present in the shells of shellfish, animal bones, bone marrow, and fungi.[22] D-Glucosamine is made naturally in the form of glucosamine-6-phosphate, and is the biochemical precursor of all nitrogen-containing sugars.[23] 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.[24] 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.[17]

Manufacturing

Most glucosamine is manufactured by processing chitin from the shells of shellfish including shrimp, lobsters, and crabs.[25] 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.[16]

History

Glucosamine was first prepared in 1876 by Georg Ledderhose by the hydrolysis of chitin with concentrated hydrochloric acid.[26][27][28] The stereochemistry was not fully determined until the 1939 work of Walter Haworth.[2][29]

Legal status

United States

In the United States, glucosamine is not approved by the Food and Drug Administration (FDA) for medical use in humans.[30] Since glucosamine is classified as a dietary supplement in the United States, evidence of safety is required by FDA regulations, but evidence of efficacy is not required so long as it is not advertised as a treatment for a medical condition.[31]

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 2018.[32][30]

Europe

In most of Europe, glucosamine is approved as a medical drug and is sold in the form of glucosamine sulfate.[33] In this case, evidence of safety and efficacy is required for the medical use of glucosamine and several guidelines have recommended its use as an effective and safe therapy for osteoarthritis.

The Task Force of the European League Against Rheumatism (EULAR) committee has granted glucosamine sulfate a level of toxicity of 5 in a 0-100 scale,[33] and recent OARSI (Osteoarthritis Research Society International) guidelines for hip and knee osteoarthritis indicate an acceptable safety profile.[34] By 2014, the OARSI did not recommend glucosamine for disease modification, and considered it "uncertain" for symptom relief, in knee osteoarthritis.[35]

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.[36]

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.[37] In April 2013, a San Diego man launched a proposed class-action lawsuit in California Federal Court accusing Nutramax Laboratories, Walmart and Rite Aid of falsely advertising the effectiveness of glucosamine.[38]

Research

Humans

Main page: Medicine:Clinical trials on glucosamine and chondroitin

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.[7][failed verification][9]

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.[39][40]

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.[41] Glucosamine sulfate uptake in synovial fluid may be as much as 20%, or it could be negligible, indicating no biological significance.[42]

Veterinary medicine

Dogs

Some studies have shown efficacy of glucosamine supplementation for dogs with osteoarthritis pain, particularly in combination with other nutraceuticals like chondroitin,[43][44] while others have not.[45] 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.[45]

Horses

The use of glucosamine in equine medicine exists, but one meta-analysis judged extant research too flawed to be of value in guiding treatment of horses.[46]

A number of 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.[47] 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.[48] 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 that required to have a positive effect on 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).[49] 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.[50] 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,[51] suggesting more evidence is needed for this combination and route of administration.

See also

References

  1. ↑ "List of nationally authorised medicinal products". European Medicines Agency. 1 December 2022. https://www.ema.europa.eu/documents/psusa/glucosamine-list-nationally-authorised-medicinal-products-psusa/00001539/202203_en.pdf. 
  2. ↑ 2.0 2.1 The Carbohydrates. IB. New York: Academic Press. 1980. pp. 727–728. ISBN 9780125563512. 
  3. ↑ 3.0 3.1 "Glucosamine". Drugs.com. 31 July 2019. https://www.drugs.com/international/glucosamine.html. 
  4. ↑ 4.0 4.1 4.2 4.3 4.4 4.5 4.6 4.7 4.8 "Glucosamine sulfate". MedlinePlus, US National Library of Medicine. 17 June 2019. https://www.nlm.nih.gov/medlineplus/druginfo/natural/807.html. 
  5. ↑ 5.0 5.1 "Glucosamine Hydrochloride". 8 January 2020. https://medlineplus.gov/druginfo/natural/747.html. 
  6. ↑ 6.0 6.1 6.2 "The latest on glucosamine/chondroitin supplements". Harvard Health Publishing, Harvard University Medical School. 17 October 2016. https://www.health.harvard.edu/blog/the-latest-on-glucosaminechondroitin-supplements-2016101710391. 
  7. ↑ 7.0 7.1 American Academy of Orthopaedic Surgeons (February 2013), "Five Things Physicians and Patients Should Question", Choosing Wisely: an initiative of the ABIM Foundation (American Academy of Orthopaedic Surgeons), http://www.choosingwisely.org/doctor-patient-lists/american-academy-of-orthopaedic-surgeons/, retrieved 19 May 2013 {{dead link|date=July 2024}}
  8. ↑ 8.0 8.1 "Effectiveness and safety of glucosamine and chondroitin for the treatment of osteoarthritis: a meta-analysis of randomized controlled trials". J Orthop Surg Res 13 (1): 170. July 2018. doi:10.1186/s13018-018-0871-5. PMID 29980200. 
  9. ↑ 9.0 9.1 Towheed, T. E.; Maxwell, L; Anastassiades, T. P.; Shea, B; Houpt, J; Robinson, V; Hochberg, M. C.; Wells, G (2005). "Glucosamine for osteoarthritis". The Cochrane Database of Systematic Reviews 2005 (2): CD002946. doi:10.1002/14651858.CD002946.pub2. PMID 15846645. 
  10. ↑ "Glucosamine and Chondroitin Sulfate: What Has Been Learned Since the Glucosamine/chondroitin Arthritis Intervention Trial". Orthopedics 41 (4): 200–207. July 2018. doi:10.3928/01477447-20180511-06. PMID 29771395. 
  11. ↑ Hespel, P; Maughan, R. J.; Greenhaff, P. L. (2006). "Dietary supplements for football". Journal of Sports Sciences 24 (7): 749–61. doi:10.1080/02640410500482974. PMID 16766503. 
  12. ↑ Knudsen, J. F.; Sokol, G. H. (April 2008). "Potential glucosamine-warfarin interaction resulting in increased international normalized ratio: case report and review of the literature and MedWatch database". Pharmacotherapy 28 (4): 540–8. doi:10.1592/phco.28.4.540. PMID 18363538. https://zenodo.org/record/1236349. 
  13. ↑ "Complementary and alternative medicines for the treatment of rheumatoid arthritis, osteoarthritis and fibromyalgia". Arthritis Research UK. October 2012. pp. 34–5. http://www.arthritisresearchuk.org/~/media/Files/Arthritis-information/Additional-items/CAM%20Report.ashx?la=en. 
  14. ↑ 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. 
  15. ↑ "Kirkland Signature Extra Strength Glucosamine with MSM". Dietary Supplements Labels Database. U.S. National Library of Medicine. 3 February 2010. http://dietarysupplements.nlm.nih.gov/dietary/detail.jsp?name=Kirkland+Signature+Extra+Strength+Glucosamine+with+MSM&contain=11001019&pageD=brand. 
  16. ↑ 16.0 16.1 "Another vegetarian glucosamine launched in US". NutraIngredients-USA.com. January 25, 2008. http://www.nutraingredients-usa.com/Industry/Another-vegetarian-glucosamine-launched-in-US. 
  17. ↑ 17.0 17.1 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. PMID 16339923. 
  18. ↑ Scroggie DA; Albright A; Harris MD (July 2003). "The effect of glucosamine-chondroitin supplementation on glycosylated hemoglobin levels in patients with type 2 diabetes mellitus: a placebo-controlled, double-blinded, randomized clinical trial". Archives of Internal Medicine 163 (13): 1587–90. doi:10.1001/archinte.163.13.1587. PMID 12860582. 
  19. ↑ Tannis AJ; Barban J; Conquer JA (June 2004). "Effect of glucosamine supplementation on fasting and non-fasting plasma glucose and serum insulin concentrations in healthy individuals". Osteoarthritis and Cartilage 12 (6): 506–11. doi:10.1016/j.joca.2004.03.001. PMID 15135147. 
  20. ↑ Muniyappa R; Karne RJ; Hall G et al. (November 2006). "Oral glucosamine for 6 weeks at standard doses does not cause or worsen insulin resistance or endothelial dysfunction in lean or obese subjects". Diabetes 55 (11): 3142–50. doi:10.2337/db06-0714. PMID 17065354. 
  21. ↑ Biggee BA; Blinn CM; Nuite M; Silbert JE; McAlindon TE (February 2007). "Effects of oral glucosamine sulphate on serum glucose and insulin during an oral glucose tolerance test of subjects with osteoarthritis". Annals of the Rheumatic Diseases 66 (2): 260–2. doi:10.1136/ard.2006.058222. PMID 16818461. 
  22. ↑ "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. http://www.efsa.europa.eu/en/efsajournal/pub/1099. 
  23. ↑ Roseman S (2001). "Reflections on glycobiology". J Biol Chem 276 (45): 41527–42. doi:10.1074/jbc.R100053200. PMID 11553646. http://www.jbc.org/content/276/45/41527.full. 
  24. ↑ "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. http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/polysacc/UDPGlcN.html. 
  25. ↑ Murray, Michael T. (2012). "Chapter 94: Glucosamine". in Pizzorno, Joseph E. Jr.; Murray, Michael T.. Textbook of natural medicine (4th ed.). Edinburgh: Churchill Livingstone. p. 790. ISBN 9781437723335. https://books.google.com/books?id=6cjgo1IixvEC&pg=PA790. 
  26. ↑ Georg Ledderhose (1876). "Über salzsaures Glycosamin". Berichte der Deutschen Chemischen Gesellschaft 9 (2): 1200–1201. doi:10.1002/cber.18760090251. https://zenodo.org/record/1425112/files/article.pdf. 
  27. ↑ Ledderhose G (1879). "Über Chitin und seine Spaltungs-produkte". Zeitschrift für Physiologische Chemie ii: 213–227. 
  28. ↑ Ledderhose G (1880). "Über Glykosamin". Zeitschrift für Physiologische Chemie iv: 139–159. 
  29. ↑ 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. 
  30. ↑ 30.0 30.1 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 (FDA). https://www.fda.gov/Food/IngredientsPackagingLabeling/LabelingNutrition/ucm073400.htm. "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)." 
  31. ↑ "Dietary Supplements". U.S. Food and Drug Administration (FDA). http://www.cfsan.fda.gov/~dms/supplmnt.html. 
  32. ↑ "Qualified Health Claims: Letters of Denial, Osteoarthritis". U.S. Food and Drug Administration (FDA). 13 December 2018. https://www.fda.gov/food/food-labeling-nutrition/qualified-health-claims-letters-denial. 
  33. ↑ 33.0 33.1 "EULAR Recommendations 2003: an evidence based approach to the management of knee osteoarthritis: Report of a Task Force of the Standing Committee for International Clinical Studies Including Therapeutic Trials (ESCISIT)". Ann. Rheum. Dis. 62 (12): 1145–55. December 2003. doi:10.1136/ard.2003.011742. PMID 14644851. 
  34. ↑ "OARSI recommendations for the management of hip and knee osteoarthritis, part I: critical appraisal of existing treatment guidelines and systematic review of current research evidence". Osteoarthr. Cartil. 15 (9): 981–1000. September 2007. doi:10.1016/j.joca.2007.06.014. PMID 17719803. 
  35. ↑ "OARSI guidelines for the non-surgical management of knee osteoarthritis". Osteoarthritis and Cartilage 22 (3): 363–88. March 2014. doi:10.1016/j.joca.2014.01.003. PMID 24462672. 
  36. ↑ "Glucosamine Settlement". www.glucosaminesettlement.com. http://glucosaminesettlement.com/. 
  37. ↑ "21st Century Glucosamine/Chondroitin Triple Strength Class Action Lawsuit". www.topclassactions.com. 2012-09-14. http://www.topclassactions.com/lawsuit-settlements/lawsuit-news/2452-21st-century-glucosaminechondroitin-triple-strength-class-action-lawsuit. 
  38. ↑ "Wal-Mart, Rite Aid Face Suit Over Glucosamine Promises". www.law360.com. http://www.law360.com/articles/432329/wal-mart-rite-aid-face-suit-over-glucosamine-promises. 
  39. ↑ 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. 
  40. ↑ Persiani S; Roda E; Rovati LC; Locatelli M; Giacovelli G; Roda A (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. 
  41. ↑ "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. 2004. doi:10.1002/art.20609. PMID 15529373. 
  42. ↑ Herbs & natural supplements: an evidence-based guide. Marrickville, New South Wales: Elsevier Australia. 2007. ISBN 978-0-7295-3796-4. 
  43. ↑ Gupta, R. C.; Canerdy, T. D.; Lindley, J; Konemann, M; Minniear, J; Carroll, B. A.; Hendrick, C; Goad, J. T. 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. 
  44. ↑ d'Altilio, M; Peal, A; Alvey, M; Simms, C; Curtsinger, A; Gupta, R. C.; Canerdy, T. D.; Goad, J. T. 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. 
  45. ↑ 45.0 45.1 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. 
  46. ↑ 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. 
  47. ↑ 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. 
  48. ↑ Laverty, S; Sandy, J. D.; Celeste, C; Vachon, P; Marier, J. F.; Plaas, A. H. (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. 
  49. ↑ Meulyzer, M; Vachon, P; Beaudry, F; Vinardell, T; Richard, H; Beauchamp, G; Laverty, S (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. 
  50. ↑ Higler, M. H.; Brommer, H; l'Ami, J. J.; De Grauw, J. C.; Nielen, M; Van Weeren, P. R.; Laverty, S; Barneveld, A 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. 
  51. ↑ Koenig, T. J.; Dart, A. J.; McIlwraith, C. W.; Horadagoda, N; Bell, R. J.; Perkins, N; Dart, C; Krockenberger, M 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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