Chondroitin Sulfate

Title: Chondroitin Sulfate
CAS Registry Number: 9007-28-7
Additional Names: Chondroitinsulfuric acid
Trademarks: Chonsurid; Structum (SKB)
Literature References: Mol wt estimated at 50,000 depending on source and method of prepn: Schubert, Fed. Proc. 17, 1099 (1958). High viscosity mucopolysaccharides (glycosaminoglycans) with N-acetylchondrosine as a repeating unit and with one sulfate group per disaccharide unit. These biological polymers act as the flexible connecting matrix between the tough protein filaments in cartilage to form a polymeric system similar to reinforced rubber. Chondroitin 4-sulfate and chondroitin 6-sulfate are the most abundant mucopolysaccharides in the body and occur both in skeletal and soft connective tissue. Isoln: Bray et al., Biochem. J. 38, 142 (1944); Patat, Elias, Z. Physiol. Chem. 316, 1 (1959); Kasavina et al., SU 157466 (1962); Wheat, Davidson, Biochem. Prep. 10, 52 (1963); Haneno, JP 64 7650 (1964 to Yasushi Hano). Structure: Davidson, Meyer, J. Am. Chem. Soc. 77, 4796 (1955). Absorption spectrum of A: Orr, Biochim. Biophys. Acta 14, 173 (1954); of B + C: Mathews, Nature 181, 421 (1958). Clinical trials in atherosclerosis: K. Nakazawa, K. Murata, J. Int. Med. Res. 6, 217 (1978); eidem, Z. Alternsforsch. 34, 153 (1979). Reviews: K. Meyer, "Chondroitin Sulfates" in Polysaccharides in Biology, Trans. 4th Conf. 1958, G. F. Springer, Ed. (Josiah Macy Jr. Foundn., New York, 1959) p 11; Muir, Am. J. Med. 47, 673-690 (1969); Rodén, Pure Appl. Chem. 35, 181-193 (1973). Review of clinical use in osteoarthritis: T. E. McAlindon et al., J. Am. Med. Assoc. 283, 1469-1475 (2000). See also Chondrosine.
Derivative Type: Chondroitin 4-sulfate
CAS Registry Number: 24967-93-9
Additional Names: Chondroitin sulfate A; CSA
Trademarks: Atheroitin
Properties: [a]D -28 to -32°.
Optical Rotation: [a]D -28 to -32°
Derivative Type: Chondroitin 4-sulfate disodium salt
CAS Registry Number: 39455-18-0
Trademarks: Condrosulf (IBSA); Lacrypos (Alcon)
Derivative Type: Chondroitin 6-sulfate
CAS Registry Number: 25322-46-7
Additional Names: Chondroitin sulfate C
Properties: [a]D -12 to -18°.
Optical Rotation: [a]D -12 to -18°
Derivative Type: Dermatan sulfate
CAS Registry Number: 24967-94-0
Additional Names: Chondroitin sulfate B; b-heparin
Literature References: Present in soft connective tissue and abundant in skin, arterial walls and heart valves. Differs from chondroitin sulfate A by containing iduronic acid in place of glucuronic acid, its epimer, at carbon atom 5. Pharmacodynamics: A. M. Traini et al., J. Int. Med. Res. 22, 323 (1994). Clinical evaluation in deep vein thrombosis: B. P. Imbimbo et al., Thromb. Haemostasis 71, 553 (1994).
Properties: [a]D -60 to -70°.
Optical Rotation: [a]D -60 to -70°
Therap-Cat: Chondroprotectant; in treatment of osteoarthritis.
Chondrosine Chonemorphine Chorionic Gonadotropin Chorismic Acid Chromafenozide