4458. Glucosamine

Nomenclature

CAS number: 3416-24-8
2-Amino-2-deoxy-d-glucose; chitosamine.
C6H13NO5; mol wt 179.17.
C 40.22%, H 7.31%, N 7.82%, O 44.65%.

Description and references

Found in chitin, in mucoproteins, and in mucopolysaccharides. Isoln from chitin: Ledderhose, Z. Physiol. Chem. 2, 213 (1878); Hackman, Aust. J. Biol. Sci. 7, 168 (1954). Synthesis: Fischer, Leuchs, Ber. 35, 3787 (1902); 36, 24 (1903). Separation of α- and β-forms: Westphal, Holzmann, ibid. 75B, 1274 (1942). Structure: Haworth et al., J. Chem. Soc. 1939, 271; Cutler, Peat, ibid. 782; Cox, Jeffrey, Nature 143, 894 (1939). Pharmacokinetics in dog and man: I. Setnikar et al., Arzneim.-Forsch. 36, 729 (1986). HPTLC/densitometry determn in herbal supplement: V. Esters et al., J. Chromatogr. A 1112, 156 (2006). HPLC determn in plasma and bioequivalence: L. Zhang et al., J. Chromatogr. B 842, 8 (2006). Antioxidant activity and immunostimulating properties: Y. Yan et al., Int. Immunopharmacol. 7, 29 (2007). Clinical trials in arthrosis: Y. Vajarudal, Clin. Ther. 3, 336 (1981); M. J. Tapadinhas et al., Pharmatherapeutica 3, 157 (1982). Review: Foster, Stacey, “The Chemistry of the 2-Amino Sugars” in C. S. Hudson et al., Advan. Carbohyd. Chem. vol. 7 (Academic Press, New York, 1952) pp 247-288. Review of pharmacology, toxicology and clinical efficacy: J. W. Anderson et al., Food Chem. Toxicol. 43, 187-201 (2005).

Chemical structure

Derivative

α-Form.

Nomenclature

CAS number: 28905-11-5

Properties

Crystals, mp 88°. [α]D20 +100° changing to +47.5° after 30 min (water).

Derivative

β-Form.

Nomenclature

CAS number: 28905-10-4

Properties

Needles from methanol, dec 110°. [α]D20 +28° changing to +47.5° after 30 min (water). Very sol in water, sol in about 38 parts boiling methanol; sparingly sol in cold methanol or ethanol. Practically insol in ether, chloroform.

Derivative

N-Acetylglucosamine.

Nomenclature

CAS number: 7512-17-6
C8H15NO6; mol wt 221.21.
C 43.44%, H 6.83%, N 6.33%, O 43.40%.

Properties

Needles from methanol + ether, mp 205°. [α]D18 +64° changing to +40.9° (in water).

Derivative

Sulfate salt.

Nomenclature

CAS number: 29031-19-4
Dona (Rottapharm); Faximin (Novartis).
C6H13NO5.xH2SO4.

Use

Pharmaceutic aid.

Therapeutic Category

Antiarthritic.

Therapeutic Category (Veterinary)

Antiarthritic.

Keywords

Antiarthritic/Antirheumatic