Glucosamine

Last updated
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] 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]

Contents

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 in the United States. [4] [5] [6]

Dietary supplement

Oral glucosamine is a dietary supplement and is not a prescription drug in the United States. [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]

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

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

Related Research Articles

<span class="mw-page-title-main">Cartilage</span> Resilient and smooth elastic tissue present in animals

Cartilage is a resilient and smooth type of connective tissue. It is a semi-transparent and non-porous type of tissue. It is usually covered by a tough and fibrous membrane called perichondrium. In tetrapods, it covers and protects the ends of long bones at the joints as articular cartilage, and is a structural component of many body parts including the rib cage, the neck and the bronchial tubes, and the intervertebral discs. In other taxa, such as chondrichthyans and cyclostomes, it constitutes a much greater proportion of the skeleton. It is not as hard and rigid as bone, but it is much stiffer and much less flexible than muscle. The matrix of cartilage is made up of glycosaminoglycans, proteoglycans, collagen fibers and, sometimes, elastin. It usually grows quicker than bone.

<span class="mw-page-title-main">Chondroitin sulfate</span> Sulfated glycosaminoglycan (GAG) compound

Chondroitin sulfate is a sulfated glycosaminoglycan (GAG) composed of a chain of alternating sugars. It is usually found attached to proteins as part of a proteoglycan. A chondroitin chain can have over 100 individual sugars, each of which can be sulfated in variable positions and quantities. Chondroitin sulfate is an important structural component of cartilage, and provides much of its resistance to compression. Along with glucosamine, chondroitin sulfate has become a widely used dietary supplement for treatment of osteoarthritis, although large clinical trials failed to demonstrate any symptomatic benefit of chondroitin.

<span class="mw-page-title-main">Osteoarthritis</span> Form of arthritis caused by degeneration of joints

Osteoarthritis (OA) is a type of degenerative joint disease that results from breakdown of joint cartilage and underlying bone. It is believed to be the fourth leading cause of disability in the world, affecting 1 in 7 adults in the United States alone. The most common symptoms are joint pain and stiffness. Usually the symptoms progress slowly over years. Other symptoms may include joint swelling, decreased range of motion, and, when the back is affected, weakness or numbness of the arms and legs. The most commonly involved joints are the two near the ends of the fingers and the joint at the base of the thumbs, the knee and hip joints, and the joints of the neck and lower back. The symptoms can interfere with work and normal daily activities. Unlike some other types of arthritis, only the joints, not internal organs, are affected.

<span class="mw-page-title-main">Synovial joint</span> Articulation which admits free motion in the joint; the most common type of articulation

A synovial joint, also known as diarthrosis, joins bones or cartilage with a fibrous joint capsule that is continuous with the periosteum of the joined bones, constitutes the outer boundary of a synovial cavity, and surrounds the bones' articulating surfaces. This joint unites long bones and permits free bone movement and greater mobility. The synovial cavity/joint is filled with synovial fluid. The joint capsule is made up of an outer layer of fibrous membrane, which keeps the bones together structurally, and an inner layer, the synovial membrane, which seals in the synovial fluid.

<span class="mw-page-title-main">Methylsulfonylmethane</span> Chemical compound

Dimethyl sulfone (DMSO2) is an organosulfur compound with the formula (CH3)2SO2. It is also known by several other names including methyl sulfone and (especially in alternative medicine) methylsulfonylmethane (MSM). This colorless solid features the sulfonyl functional group and is the simplest of the sulfones. It is relatively inert chemically and is able to resist decomposition at elevated temperatures. It occurs naturally in some primitive plants, is present in small amounts in many foods and beverages, and is marketed (under the MSM name) as a dietary supplement. It is sometimes used as a cutting agent for illicitly manufactured methamphetamine. It is also commonly found in the atmosphere above marine areas, where it is used as a carbon source by the airborne bacteria Afipia. Oxidation of dimethyl sulfoxide produces the sulfone, both under laboratory conditions and metabolically.

A chondroitin is a chondrin derivative.

<span class="mw-page-title-main">Synovial fluid</span> Fluid found in the cavities of synovial joints

Synovial fluid, also called synovia,[help 1] is a viscous, non-Newtonian fluid found in the cavities of synovial joints. With its egg white–like consistency, the principal role of synovial fluid is to reduce friction between the articular cartilage of synovial joints during movement. Synovial fluid is a small component of the transcellular fluid component of extracellular fluid.

<span class="mw-page-title-main">Hyaline cartilage</span> Type of cartilage in animals

Hyaline cartilage is the glass-like (hyaline) and translucent cartilage found on many joint surfaces. It is also most commonly found in the ribs, nose, larynx, and trachea. Hyaline cartilage is pearl-gray in color, with a firm consistency and has a considerable amount of collagen. It contains no nerves or blood vessels, and its structure is relatively simple.

<span class="mw-page-title-main">Pentosan polysulfate</span> Chemical compound

Pentosan polysulfate, sold under the brand name Elmiron among others, is a medication used for the treatment of interstitial cystitis. It was approved for medical use in the United States in 1996.

<span class="mw-page-title-main">Calcium pyrophosphate dihydrate crystal deposition disease</span> Medical condition

Calcium pyrophosphate dihydrate (CPPD) crystal deposition disease, also known as pseudogout and pyrophosphate arthropathy, is a rheumatologic disease which is thought to be secondary to abnormal accumulation of calcium pyrophosphate dihydrate crystals within joint soft tissues. The knee joint is most commonly affected. The disease is metabolic in origin and its treatment remains symptomatic.

<span class="mw-page-title-main">Aggrecan</span>

Aggrecan (ACAN), also known as cartilage-specific proteoglycan core protein (CSPCP) or chondroitin sulfate proteoglycan 1, is a protein that in humans is encoded by the ACAN gene. This gene is a member of the lectican (chondroitin sulfate proteoglycan) family. The encoded protein is an integral part of the extracellular matrix in cartilagenous tissue and it withstands compression in cartilage.

<span class="mw-page-title-main">Proteoglycan 4</span> Proteoglycan; lubricant; gene

Proteoglycan 4 or lubricin is a proteoglycan that in humans is encoded by the PRG4 gene. It acts as a joint/boundary lubricant.

A significant amount of research has been performed on glycosaminoglycans, especially glucosamine and chondroitin, for the treatment of arthritis. These compounds are commonly marketed as nutritional supplements and numerous 'soft therapeutic claims' are made about their health benefits - especially in aging populations. Since glucosamine is a precursor for glycosaminoglycans, and glycosaminoglycans are major components of cartilage, ingesting glucosamine might nourish joints, and thereby alleviate arthritis symptoms. Authoritative opinions on the actual therapeutic value of these compounds have been very mixed.

<span class="mw-page-title-main">Eggshell membrane</span>

Eggshell membrane or shell membrane is the clear film lining eggshells, visible when one peels a boiled bird egg. Chicken eggshell membranes are used as a dietary supplement.

The treatment of equine lameness is a complex subject. Lameness in horses has a variety of causes, and treatment must be tailored to the type and degree of injury, as well as the financial capabilities of the owner. Treatment may be applied locally, systemically, or intralesionally, and the strategy for treatment may change as healing progresses. The end goal is to reduce the pain and inflammation associated with injury, to encourage the injured tissue to heal with normal structure and function, and to ultimately return the horse to the highest level of performance possible following recovery.

<span class="mw-page-title-main">Polysulfated glycosaminoglycan</span> Injectable drug

Polysulfated glycosaminoglycan (PSGAG), sold under the brand name Adequan, is an injectable drug for dogs and horses that is used to alleviate the limpness, pain, and lowered range of motion caused by arthritis. It is made of repeat disaccharide units (comprising hexosamine and hexuronic acid), and is similar to glycosaminoglycans already present in the cartilage; PSGAG thus easily integrates itself there. In vitro studies have shown it to inhibit the enzymes that degrade cartilage and bone, as well as suppress inflammation and stimulate the synthesis of replacement cartilage. While it can cause an increased risk of bleeding, it is relatively safe and has a high LD50. PSGAG is one of the most widely prescribed joint treatments for horses.

<span class="mw-page-title-main">Senior dog diet</span>

Senior dog food diets are pet foods that are catered toward the senior or mature pet population. The senior dog population consists of dogs that are over the age of seven for most dog breeds, though in general large and giant breed dogs tend to reach this life stage earlier when compared to smaller breed dogs. Senior dog foods contain nutrients and characteristics that are used to improve the health of the aging dog. Aging in dogs causes many changes to occur physiologically that will require a change in nutrient composition of their diet.

<span class="mw-page-title-main">Post-traumatic arthritis</span> Medical condition

Post-traumatic arthritis (PTAr) is a form of osteoarthritis following an injury to a joint.

A disease-modifying osteoarthritis drug (DMOAD) is a disease-modifying drug that would inhibit or even reverse the progression of osteoarthritis. Since the main hallmark of osteoarthritis is cartilage loss, a typical DMOAD would prevent the loss of cartilage and potentially regenerate it. Other DMOADs may attempt to help repair adjacent tissues by reducing inflammation. A successful DMOAD would be expected to show an improvement in patient pain and function with an improvement of the health of the joint tissues.

Alicia L. Bertone is an American academic, administrator, researcher, and veterinary surgeon. She is a professor and a provost in the Office of Academic Affairs at the Ohio State University. Bertone has worked as the Vice-Provost of Graduate Studies, Associate Vice Provost of Data and Analysis, the ENGIE-Axium Endowed Dean of the Graduate School, and the Trueman Family Endowed Chair at the Ohio State University. Bertone is a Professor of Veterinary Clinical Sciences, and, as the Trueman Endowed Chair, established and directed the Comparative Orthopedic Research Laboratory at the University.

References

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  30. 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 (FDA). Archived from the original on 15 November 2017. Retrieved 14 May 2014. 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).
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  41. ↑ 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.
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  43. ↑ Gupta, R. C.; Canerdy, T. D.; Lindley, J; Konemann, M; Minniear, J; Carroll, B. A.; Hendrick, C; Goad, J. T.; Rohde, K; Doss, R; Bagchi, M; Bagchi, D (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.; Bagchi, M; Bagchi, D (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.
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  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. S2CID   39668131.
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  50. ↑ Higler, M. H.; Brommer, H; l'Ami, J. J.; De Grauw, J. C.; Nielen, M; Van Weeren, P. R.; Laverty, S; Barneveld, A; Back, W (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; Jeffcott, L. B.; Little, C. B. (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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