Glucosamine

• 2-amino- 2-deoxy- D- glucosechitosamin
• (3R, 4R, 5S, 6R )-3- amino-6- (hydroxymethyl) oxan -2 ,4,5 -triol

• C6H13NO5
• C6H13NO5 · HCl ( glucosamine hydrochloride · )

• 3416-24-8
• 28905-11-5 ( α - form)
• 28905-10-4 ( β - form)
• 66-84-2 ( D-( )- glucosamine · hydrochloride)

M01AX05

Anti-inflammatory drug

• 88 ° C ( α - form)
• 110 ° C (decomposition) ( β - form)

Highly soluble in water, slightly soluble in boiling methanol, hardly soluble in cold methanol, or ethanol, practically insoluble in ether and chloroform ( β - form)

Template: Infobox chemical / molecular formula search available

Glucosamine is the generally accepted common name for 2-Amino-2-desoxy-α/β-D-glucopyranose. It is a derivative of D-glucose, from which it differs only by the substitution of the hydroxy group at the second carbon with an amino group.

• 4.1 Security
• 4.2 allergy

Pharmacology

D- Glucosamine is taken as a remedy for osteoarthritis of the knee orally. It is usually present as hydrochloride or sulfate.

Use

Glucosamine is an amino sugar that occurs naturally in the human body. It is a component of connective tissue, cartilage and synovial fluid. There are numerous Glucosaminpräparate offered on the market as a dietary supplement. The dietary supplement is based on the idea that the supplied glucosamine is " built into" the cartilage. In vitro (ie, outside of a living organism) glucosamine has an anti-inflammatory effect. Glucosamine is normally used orally in doses of 700-1250 mg per day. Frequently glucosamine combined with chondroitin. But chondroitin is taken orally not bioavailable, but is mostly converted into glucosamine and glucuronic acid in the digestive process.

Protect cartilage, osteoarthritis

Glucosaminpräparate are offered with the effect promise to protect joints and maintain mobility. Further, they are used as food supplements recommended for degenerative diseases ( arthrosis ), to improve the symptoms of osteoarthritis, joint pain, impaired joint function or, for example, the joint structure or as a building block for cartilage and joints.

Effectiveness

Several studies found a chondroprotective effect, an analgesic effect could not be proved.

• 2006 was initiated by the National Institutes of Health ( NIH ) of the United States, a multicenter, placebo-controlled, six -month -blind study on the efficacy of chondroitin and glucosamine in osteoarthritis of the knee. She presented no statistically significant effect on the symptoms of osteoarthritis in patients with minor aches and pains permanently. Joint swelling were reduced. Treatment effects were observed in a subgroup of patients with moderate to severe pain, but the significance was not valid due to the small number of patients in this subgroup.
• A double-blind, randomized, placebo- controlled trial of 2006 patients 1,585 sets in combination with chondroitin sulfate suggest a possible effectiveness at medium and severe knee pain.

• The result of recent meta-studies ( 2007 & 2010) was that chondroitin, glucosamine, and their combination have no clinically relevant effects on perceived joint pain or on joint wear.

• A double-blind, randomized, placebo-controlled study of 2013 conducted by the University of Sydney with 605 subjects ( age 45-75 years, osteoarthritis of the knee ) was able to observe a statistically significant attenuation of the decrease in joint space. It has been used here for 2 years daily 2 x 750 mg glucosamine sulfate and 2 x 400 mg chondroitin sulfate. A decrease in the joint was in all groups [1 ) 2 x 750 mg glucosamine, 2) 2 x 400 mg chondroitin sulfate, 3) 2 x 750 mg Glucosamine Chondroitin Sulfate 2 x 400 mg, 4) placebo ] - with no significant difference between the groups - are observed.

Production, biosynthesis

Biologically produced glucosamine from fructose -6-phosphate and glutamine.

Industrial Glucosamine is produced from Chitin. This deacetylation is required as well as hydrolytic cleavage of the polymer to the monomers. Both steps proceed simultaneously in hot hydrochloric acid. If only the deacetylation, chitosan resulted, would only be the hydrolysis resulted N -acetylglucosamine.

The starting material chitin is mainly produced as secondary raw materials from the waste of the fisheries of crustaceans ( crabs, shrimps). In principle, the glucosamine (eg Aspergillus niger) also obtained from the chitin of insects (eg silkworms and bees ) or fungi.

Biological Significance

→ Main article: N- acetylglucosamine

The acetylated on the nitrogen D- glucosamine, N- acetylglucosamine, playing in bacteria, archaea and eukaryotes, including humans, a special role.

Security

In the usual oral doses up to 1250 mg per day of glucosamine is well tolerated. No serious adverse effects were observed in this dose range in clinical trials. Because of missing data, the health assessment of the supply of glucosamine in pregnant women or lactating women and in children or adolescents is not possible. In these groups, therefore, there is cause for caution ( BfR, 2007). People taking coumarin anticoagulants anticoagulant, is from the reinforcing effects of glucosamine on the drug for the possibility of bleeding occurring (BfR, 2010). The European Food Safety Authority (EFSA ) has once again employed as a food ingredient in connection with the use of coumarin with the risk of glucosamine and confirms the assessment of the BfR recently.

Allergy

Glucosamine, which is made from crustaceans and shellfish, can cause allergic reactions or other intolerance.