Glucosamine

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 2-Amino-2-deoxy-glucose
	Systematic IUPAC name (3R,4R,5S)-3-Amino-6-(hydroxymethyl)oxane-2,4,5-triol
	Other names Chitosamine
Identifiers
CAS Number	3416-24-8 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1723616
ChEBI	CHEBI:5417 ;
ChEMBL	ChEMBL493287 ;
ChemSpider	388352 ;
DrugBank	DB01296 ;
ECHA InfoCard	100.020.284
EC Number	222-311-2;
Gmelin Reference	720725
KEGG	D04334 ;
MeSH	Glucosamine
PubChem CID	439213;
UNII	N08U5BOQ1K ;
CompTox Dashboard (EPA)	DTXSID4023098 ;
	InChI 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 Key: MSWZFWKMSRAUBD-SPZCMYQFSA-N ;
	SMILES N[C@H]1C(O)OC(CO)[C@@H](O)[C@@H]1O;
Properties
Chemical formula	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
ATC code	M01AX05 (WHO)
Legal status	EU: Authorized;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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 in the United States.^[4]^[5]^[6]

^ "List of nationally authorised medicinal products" (PDF). European Medicines Agency. 1 December 2022.
^ Cite error: The named reference carb was invoked but never defined (see the help page).
^ "Glucosamine". Drugs.com. 31 July 2019. Retrieved 14 September 2019.
^ "Glucosamine sulfate". MedlinePlus, US National Library of Medicine. 17 June 2019. Retrieved 14 September 2019.
^ "Glucosamine Hydrochloride". MedlinePlus. 8 January 2020. Archived from the original on 28 January 2020. Retrieved 27 January 2020.
^ Robert H. Shmerling (17 October 2016). "The latest on glucosamine/chondroitin supplements". Harvard Health Publishing, Harvard University Medical School. Retrieved 14 September 2019.

[1] "List of nationally authorised medicinal products" (PDF). European Medicines Agency. 1 December 2022.

[carb-2] Cite error: The named reference carb was invoked but never defined (see the help page).

[drugs-names-3] "Glucosamine". Drugs.com. 31 July 2019. Retrieved 14 September 2019.

[mlp-4] "Glucosamine sulfate". MedlinePlus, US National Library of Medicine. 17 June 2019. Retrieved 14 September 2019.

[Glucosamine_hydrochloride-5] "Glucosamine Hydrochloride". MedlinePlus. 8 January 2020. Archived from the original on 28 January 2020. Retrieved 27 January 2020.

[harvard-6] Robert H. Shmerling (17 October 2016). "The latest on glucosamine/chondroitin supplements". Harvard Health Publishing, Harvard University Medical School. Retrieved 14 September 2019.

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Glucosamine

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