Glucosamine

Structural formula
α anomer
General
Non-proprietary name	Glucosamine
other names	2-amino-2-deoxy- D -glucose chitosamine (3 R , 4 R , 5 S , 6 R ) -3-Amino-6- (hydroxymethyl) oxane-2,4,5-triol GlcN (biochemical abbreviation)
Molecular formula	C 6 H 13 NO 5 C 6 H 13 NO 5 HCl (glucosamine hydrochloride )
External identifiers / databases
CAS number 3416-24-8 28905-11-5 (α-shape) 28905-10-4 (β-form) 66-84-2 (D - (+) - glucosamine hydrochloride) EC number 222-311-2 ECHA InfoCard 100.020.284 PubChem 439213 ChemSpider 388352 DrugBank DB01296 Wikidata Q327506
Drug information
ATC code	M01 AX05
Drug class	Anti-rheumatic drug
properties
Molar mass	179.17 g · mol -1
Melting point	88 ° C (α-form) 110 ° C (decomposition) (β-form)
solubility	very soluble in water, somewhat soluble in boiling methanol, hardly soluble in cold methanol or ethanol, practically insoluble in ether or chloroform (β-form)
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Glucosamine is a naturally occurring amino sugar . In the human body it is part of the connective tissue , cartilage and synovial fluid .

Biological importance

Glucosamine occurs naturally in the human body. As a derivative of dextrose ( D - glucose ), it differs from this only in the substitution of an amino group for the hydroxyl group on the second carbon . Glucosamine is a component of connective tissue, cartilage and synovial fluid.

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

use

"Cartilage protection"

There are various dietary supplements on the market that contain glucosamine. Their administration is based on the idea that the supplied glucosamine is "built into" the cartilage. Orally, glucosamine is usually used in doses of 700 to 1250 mg per day. Often glucosamine is combined with chondroitin . Chondroitin is largely converted into glucosamine and glucuronic acid in the digestive process .

In the opinions published to date on several health claims for glucosamine as a food ingredient submitted to the European Food Safety Authority (EFSA), the authority found that insufficient scientific evidence of effectiveness in the healthy general population had been presented. With misleading information, foods (food supplements are among the foods) may not be marketed according to European legal provisions ( Health Claims Regulation ).

arthrosis

Glucosamine is used orally to relieve the symptoms of mild to moderate osteoarthritis ("joint wear and tear") of the knee , such as joint swelling, joint stiffness after rest and pain.

Various studies found a cartilage-protecting effect, but no pain-relieving effect could be proven:

• In 2006, the US National Institutes of Health (NIH) initiated a multicenter, placebo-controlled , six-month blind study on the effectiveness of chondroitin and glucosamine in osteoarthritis of the knee. It found no statistically significant effect on osteoarthritis symptoms in patients with milder pain. Joint swelling was reduced. Treatment effects were found in a subgroup of patients with moderate to severe pain, but the informative value was not conclusive due to the small number of patients in this subgroup.
• A double-blind, randomized, placebo-controlled study from 2006 on 1,585 patients suggests a possible effectiveness in combination with chondroitin sulfate for moderate and severe knee pain.
• The result of meta-studies (2007 and 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 from 2013, carried out by the University of Sydney with 605 test subjects (age 45–75 years, knee joint osteoarthritis ) was able to observe a statistically significant weakening of the receding joint space . For 2 years, 2 × 750 mg glucosamine sulfate and 2 × 400 mg chondroitin sulfate were taken daily. A reduction in joint pain was seen in all groups [1) glucosamine sulfate 2 × 750 mg, 2) chondroitin sulfate 2 × 400 mg, 3) glucosamine sulfate 2 × 750 mg + chondroitin sulfate 2 × 400 mg, 4) placebo] - without significant differences between the groups - to be watched.

In vitro (i.e. outside of a living organism) glucosamine has an anti-inflammatory effect.

Life extension

The doctor and scientist Michael Ristow was able to show that the administration of glucosamine can extend the life expectancy of the model organism Caenorhabditis elegans , but also of pre-aged mice. At the same time and subsequently, it was shown in humans that glucosamine intake is associated with a longer life expectancy and that this supplement improves inflammation parameters in the blood.

unwanted effects

In the usual oral doses of up to 1250 mg per day, glucosamine is well tolerated. No serious side effects were found in clinical studies at this dose range . Due to a lack of data, it is not possible to evaluate the intake of glucosamine in pregnant or breastfeeding women or in children or adolescents. There is therefore cause for caution with these groups of people (BfR, 2007). People who take coumarin anticoagulants as a blood clotting inhibitor have the possibility of bleeding due to the intensifying effect of glucosamine on the drug (BfR, 2010). The European Food Safety Authority (EFSA) has again dealt with the risk of glucosamine as a food ingredient in connection with the use of coumarin and in 2012 confirmed the BfR's assessment .

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

Manufacturing, biosynthesis

Glucosamine is produced biologically from fructose-6-phosphate and glutamine .

Glucosamine is produced industrially from chitin . This requires deacetylation and hydrolytic cleavage of the polymer into the monomers . Both steps take place simultaneously in hot hydrochloric acid . If only the deacetylation were to take place, the result would be chitosan , if only the hydrolysis would take place, N- acetylglucosamine would result .

The starting material chitin is predominantly as a secondary raw material from the waste of the fishing of crustaceans ( crabs , shrimp ) obtained . In principle, the glucosamine can also be obtained from the chitin of insects (e.g. silkworms or bees ) or from mushrooms (e.g. Aspergillus niger ).

Glucosamine is mostly in the form of a salt ( hydrochloride or sulfate ). Glucosamine is the international non-proprietary name for 2-amino-2-deoxy-α / β- D -glucopyranose.

Trade names

Arthro Genial (D, A, CH), Dona (D), Flexove (A), Glucosana (D), Leka (D), Progona (D, A), Voltaflex (A), A.Vogel Glucosamin Plus (CH) , pro sana Glucosamin plus (CH), Dolex (D)

See also

• Collagen hydrolyzate

Individual evidence

1. ^ ^{A b c} The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006; P. 769, ISBN 978-0-911910-00-1 .
2. ↑ Data sheet D - (+) - Glucosamine hydrochloride from Sigma-Aldrich , accessed on April 3, 2011 ( PDF ).
3. ↑ ^{a b} DO Clegg, DJ Reda, CL Harris, MA Klein, l JR O'Del, MM Hooper, JD Bradley, CO Bingham 3rd, MH Weisman, CG Jackson, NE Lane, JJ Cush, LW Moreland, HR Schumacher Jr, CV Oddis, F Wolfe, JA Molitor, DE Yocum, TJ Schnitzer, DE Furst, AD Sawitzke, H Shi, KD Brandt, RW Moskowitz, HJ Williams: Glucosamine, chondroitin sulfate, and the two in combination for painful knee osteoarthritis . In: New Engl J Med . , 354, No. 8, 2006, pp. 795-808, doi : 10.1056 / NEJMoa052771 , PMID 16495392 .
4. ^ S. Reichenbach, R. Sterchi, M. Scherer, S. Trelle, E. Bürgi, U. Bürgi, PA Dieppe, P. Jüni: Meta-analysis: chondroitin for osteoarthritis of the knee or hip. In: Annals of Internal Medicine . Volume 146, Number 8, April 2007, pp. 580-590, PMID 17438317 .
5. ↑ S. Wandel, P. Jüni, B. Tendal, E. Nüesch, PM Villiger, NJ Welton, S. Reichenbach, S. Trelle: Effects of glucosamine, chondroitin, or placebo in patients with osteoarthritis of hip or knee: network meta -analysis. In: BMJ (Clinical research ed.). Volume 341, 2010, p. C4675, PMID 20847017 . PMC 2941572 (free full text).
6. ↑ M. Fransen, M. Agaliotis, L. Nairn, M. Votrubec, L. Bridgett, S. Su, S. Jan, L. March, J. Edmonds, R. Norton, M. Woodward, R. Day: Glucosamine and chondroitin for knee osteoarthritis: a double-blind randomized placebo-controlled clinical trial evaluating single and combination regimens. In: Annals of the rheumatic diseases. Volume 74, number 5, May 2015, pp. 851-858, doi : 10.1136 / annrheumdis-2013-203954 , PMID 24395557 .
7. ↑ Weimer, S. et al. (2013): D-Glucosamine supplementation extends life span of nematodes and of aging mice. In: Nature Comm 8, 3563e, PMID 24714520 .
8. ^ Daily Mail : Could a popular arthritis supplement be the key to a longer life? Glucosamine could extend life 'by 8 years' .
9. ↑ 20 minutes : This is how you live around eight years longer .
10. ↑ Bell, GA et al. (2012): Use of glucosamine and chondroitin in relation to mortality. In: Eur J Epidemiol 27, 593-603, PMID 22828954 .
11. ↑ Navarro, SL et al. (2015): Randomized trial of glucosamine and chondroitin supplementation on inflammation and oxidative stress biomarkers and plasma proteomics profiles in healthy humans. In: PLoS ONE 26; 10 (2): e0117534, PMID 25719429 .
12. ↑ Opinion No. 032/2007 of the Federal Institute for Risk Assessment (BfR) of June 15, 2007.
13. ↑ Opinion No. 04/2010 of the Federal Institute for Risk Assessment (BfR) of August 14, 2010 ( PDF ).
14. ↑ Suzan Fiack: Glucosamine in food supplements: also risky for patients who use coumarin anticoagulants. Federal Institute for Risk Assessment (BfR), press release from February 23, 2012 at the Informationsdienst Wissenschaft (idw-online.de), accessed on August 24, 2015.
15. ↑ Javid S. Mojarrad, Mahboob Nemati, Hadi Valizadeh, Masood Ansarin, Samira Bourbour: Preparation of Glucosamine from exoskeleton of shrimp and Predicting Production Yield by Response Surface Methodology. In: Journal of Agricultural and Food Chemistry. 55, 2007, pp. 2246-2250, doi : 10.1021 / jf062983a .
16. ↑ Heike Finger: Chitin and Chitosan - New raw materials on the way to industrial use . (PDF; 249 kB).

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !