Chondroitin sulfate
Identification
- Name
- Chondroitin sulfate
- Accession Number
- DB09301
- Description
Chondroitin sulfate is a glycosaminoglycan considered as a symptomatic slow-acting drug for osteoarthritis (SYSADOA).1 The SYSADOA status suggested a pain relief and increased joint mobility after a relative long regular administration, as well as a long-lasting effect after the end of the treatment. Chondroitin sulfate is composed of alternating 1,3-N-acetyl-β-d-galactosamine and 1,4-β-d-glucuronic acid units which bear 4-O- and/or 6-O-sulfations at the N-acetylgalactosamine units disposed of in specific patterns. Depending on the predominating disaccharide unit, it will present different biological activities.2 Chondroitin sulfate is sold as an OTC dietary supplement in North America and it is a prescription drug under the EMA in Europe.4
- Type
- Small Molecule
- Groups
- Approved, Investigational, Nutraceutical
- Synonyms
- Chondroitin sulfates
- Condroitín sulfato
Pharmacology
- Indication
Chondroitin sulfate, used with glucosamine, is indicated to alleviate pain and inflammation from primary osteoarthritis.7 This supplement is reported to improve joint function and slow disease progression.8 Osteoarthritis is characterized by progressive structural and metabolic changes in joint tissues, mainly cartilage degradation, subchondral bone sclerosis and inflammation of synovial membrane.4
Studies have proposed the potential use of chondroitin sulfate as a nutraceutical in dietary supplements.3
- Associated Conditions
- Associated Therapies
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
In clinical trials, chondroitin sulfate has been reported a significant pain relief. Some reports have shown no slow in joint damage. The effects of chondroitin sulfate have been very controversial.8 One of the characteristics of chondroitin is a slow onset of action with a maximal effect attained after several months.4 Chondroitin sulfate has been reported to have anti-inflammatory properties by reducing the synovitis and prevent proinflammatory cytokine up-regulation in arthritis models.4
It is also registered an anabolic effect of chondroitin sulfate in which it induces the synthesis of hyaluronate in synovial cells, it increases type II collagen and proteoglycan synthesis.4
- Mechanism of action
Chondroitin sulfate functions as a major component of the intricate extracellular matrix. It is proposed that chondroitin sulfate supply can provide new building blocks for the synthesis of new matrix components.4
The anti-inflammatory effect of chondroitin sulfate is thought to be caused by the inhibition of the synthesis of inflammatory intermediates such as the inhibition of nitric oxide synthase, COX-2, microsomal prostaglandin synthase 1 and prostaglandin E2. It is reported also an inhibitory activity in the toll-like receptor 4 which will later inhibit inflammatory cytokines, NFkB and MyD88. This activity suggests a modulation of the MAP kinase pathway. On the other hand, some reports have pointed out an induction on the PKC/PI3K/Akt pathway in neuroblastoma.4
The anabolic effect of chondroitin sulfate is suggested to be caused by the inhibition of metalloproteinases such as MMP-1, -3 and -13 as well as ADAMTS-4 and -5.4
Target Actions Organism UBrain-derived neurotrophic factor Not Available Humans UGlial cell line-derived neurotrophic factor Not Available Humans UVascular endothelial growth factor A Not Available Humans UC-C motif chemokine 2 Not Available Humans - Absorption
Chondroitin sulfate is absorbed from the gastrointestinal tract.2 The absorbed portion reaches a ratio of 10% as unchanged chondroitin sulfate and 90% as depolymerized low-molecular-weight derivatives. This absorption depends on the sulfation status. The bioavailability of chondroitin sulfate ranges from 10-20% following oral administration. Reports have shown a consistent accumulation of the compound in joint tissue. The steady-state is attained after 3-4 days and it takes around 3-6 months to obtain the maximal effect.4
After intramuscular administration of chondroitin sulfate, the peak plasma level of 3.8 mcg/ml was reached after 90 min. When given orally, the peak plasma concentration of 4.6 mcg/ml was reached after 240 min.5
- Volume of distribution
After intramuscular administration of chondroitin sulfate, the apparent volume of distribution was 0.40 ml/g. When administered orally, the apparent volume of distribution changed to 0.44ml/g.5
- Protein binding
Chondroitin sulfate protein binding reports have shown a very low percentage of protein binding of only 0.23% of the total protein.6
- Metabolism
Chondroitin sulfate is not metabolized by cytochrome P450.4 Reports have indicated the presence in plasma of mono-, oligo- and polysaccharides with a molecular weight of less of 5 kDa which are derived from the partial digestion of exogenous chondroitin sulfate.5 The reported degradation of chondroitin sulfate seems to be very complex and led by the formation of smaller digestion derivatives of the original form.9
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- Route of elimination
Chondroitin sulfate is excreted in the urine as intact polymers and as partial degradation products.2 After intramuscular administration, about 37% of the administered dose is excreted by urine during the first 24 hours as high- and low-molecular-weight derivatives.5
- Half-life
The approximate half-life of chondroitin sulfate and its derivative metabolites is 15 hours.4 After intramuscular administration of chondroitin sulfate in humans, the elimination half-life of the chondroitin sulfate was of 275 min. When administered orally, the elimination half-life was presented at 310 min.5
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
Chondroitin sulfate does not present a carcinogenic potential.7 On tolerability assays, it has been shown to present great safety and good tolerability without significant severe side effects.4
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAbacavir Abacavir may decrease the excretion rate of Chondroitin sulfate which could result in a higher serum level. Acarbose Acarbose may decrease the excretion rate of Chondroitin sulfate which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Chondroitin sulfate which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Chondroitin sulfate which could result in a higher serum level. Acenocoumarol Chondroitin sulfate may increase the anticoagulant activities of Acenocoumarol. Acetaminophen Acetaminophen may decrease the excretion rate of Chondroitin sulfate which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Chondroitin sulfate which could result in a lower serum level and potentially a reduction in efficacy. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Chondroitin sulfate which could result in a higher serum level. Aclidinium Aclidinium may decrease the excretion rate of Chondroitin sulfate which could result in a higher serum level. Acrivastine Chondroitin sulfate may decrease the excretion rate of Acrivastine which could result in a higher serum level. Additional Data Available- Extended DescriptionExtended DescriptionAvailable for Purchase
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - SeveritySeverityAvailable for Purchase
A severity rating for each drug interaction, from minor to major.
Learn more - Evidence LevelEvidence LevelAvailable for Purchase
A rating for the strength of the evidence supporting each drug interaction.
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An effect category for each drug interaction. Know how this interaction affects the subject drug.
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- Food Interactions
- No interactions found.
Products
Purchasing individual compounds or compound libraries for your research?
Learn More- Product Ingredients
Ingredient UNII CAS InChI Key Chondroitin sulfate (bovine) 6IC1M3OG5Z 9007-28-7 Not applicable Chondroitin sulfate (chicken) 7VZ9466BAB Not Available Not applicable Chondroitin sulfate (porcine) V5E8ELO4W9 Not Available Not applicable Chondroitin sulfate (shark) 2ZAJ1K50XH Not Available Not applicable Chondroitin sulfate sodium (bovine) 8QTV3DTT8W 39455-18-0 Not applicable Chondroitin sulfate sodium (chicken) 4T078B3Z6V Not Available Not applicable Chondroitin sulfate sodium (porcine) R27OH35FYQ Not Available Not applicable Chondroitin sulfate sodium (shark) Q75WVO004L Not Available Not applicable - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataTHERAFLEX Glucosamine Plus Max Capsule 500 mg/1 Oral Bayer Healthcare Llc. 2015-07-01 Not applicable US 
Additional Data Available- Application NumberApplication NumberAvailable for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct CodeAvailable for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Glucosamine Sulfate, Chondroitin Sulfate, Ibuprofen Chondroitin sulfate (bovine) (200 mg/1) + Glucosamine sulfate (250 mg/1) + Ibuprofen (100 mg/1) Capsule Oral Contract Pharmacal Corp. 2010-04-19 Not applicable US Theraflex Advance Chondroitin sulfate (bovine) (200 mg/1) + Glucosamine sulfate (250 mg/1) + Ibuprofen (100 mg/1) Tablet Oral Bayer Healthcare Llc. 2014-12-11 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Medi-flexx Rx Joint Support Formula Chondroitin sulfate (chicken) (400 mg/1) + Dimethyl sulfone (200 mg/1) + Glucosamine sulfate (500 mg/1) Tablet Oral Two Hip Consulting, Llc 2014-12-05 2016-04-11 US Remaxazon External Patch Chondroitin sulfate sodium (bovine) (3 g/100g) + Capsaicin (.0285 g/100g) + Glucosamine (5 g/100g) + Lidocaine (4 g/100g) Patch Topical Home Aide Diganostics, Inc. 2015-03-09 Not applicable US
Categories
- ATC Codes
- M01AX25 — Chondroitin sulfate
- Drug Categories
- Classification
- Not classified
Chemical Identifiers
- UNII
- Not Available
- CAS number
- 24967-93-9
- InChI Key
- Not Available
- InChI
- Not Available
- IUPAC Name
- Not Available
- SMILES
- Not Available
References
- General References
- Monfort J, Pelletier JP, Garcia-Giralt N, Martel-Pelletier J: Biochemical basis of the effect of chondroitin sulphate on osteoarthritis articular tissues. Ann Rheum Dis. 2008 Jun;67(6):735-40. Epub 2007 Jul 20. [PubMed:17644553]
- da Cunha AL, de Oliveira LG, Maia LF, de Oliveira LF, Michelacci YM, de Aguiar JA: Pharmaceutical grade chondroitin sulfate: Structural analysis and identification of contaminants in different commercial preparations. Carbohydr Polym. 2015 Dec 10;134:300-8. doi: 10.1016/j.carbpol.2015.08.006. Epub 2015 Aug 8. [PubMed:26428128]
- Volpi N: Quality of different chondroitin sulfate preparations in relation to their therapeutic activity. J Pharm Pharmacol. 2009 Oct;61(10):1271-80. doi: 10.1211/jpp/61.10.0002. [PubMed:19814858]
- Henrotin Y, Mathy M, Sanchez C, Lambert C: Chondroitin sulfate in the treatment of osteoarthritis: from in vitro studies to clinical recommendations. Ther Adv Musculoskelet Dis. 2010 Dec;2(6):335-48. doi: 10.1177/1759720X10383076. [PubMed:22870459]
- Ronca G, Conte A: Metabolic fate of partially depolymerized shark chondroitin sulfate in man. Int J Clin Pharmacol Res. 1993;13 Suppl:27-34. [PubMed:7995679]
- Saito A, Munakata H: Analysis of plasma proteins that bind to glycosaminoglycans. Biochim Biophys Acta. 2007 Feb;1770(2):241-6. doi: 10.1016/j.bbagen.2006.10.015. Epub 2006 Nov 7. [PubMed:17178194]
- Chemical selection summary [Link]
- Arthritis foundation [Link]
- Metafishnet [Link]
- External Links
- KEGG Drug
- D00080
- KEGG Compound
- C00607
- PubChem Substance
- 347910430
- 2473
- Wikipedia
- Chondroitin_sulfate
- MSDS
- Download (143 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Prevention Recurrent Cystitis 1 4 Completed Treatment Chronic Renal Failure (CRF) / Hemodialysis Treatment / Iron Deficiency Anemia (IDA) / Renal Anemia 1 4 Completed Treatment Dry Eye Syndrome (DES) 1 4 Completed Treatment Joint Diseases / Muskuloskeletal Diseases / Osteoarthritis (OA) / Psoriasis / Skin Diseases 1 4 Completed Treatment Osteoarthritis of the Knee 3 4 Unknown Status Treatment Osteoarthritis of the Knee 1 4 Unknown Status Treatment Rhizarthrosis 1 3 Completed Treatment Joint Diseases / Muskuloskeletal Diseases / Osteoarthritis (OA) / Synovitis 1 3 Completed Treatment Osteoarthritis (OA) 1 3 Completed Treatment Osteoarthritis of the Knee 5
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule Oral Tablet Oral 200 mg Tablet Oral 500 mg Capsule Oral 225 mg Capsule Oral 400 mg Tablet Oral 250 mg Granule Oral 24 g Tablet 500 mg Powder, for solution Oral 1500 mg Powder Oral 1200 mg Tablet 800 mg Powder, for solution Oral 472 mg Powder Oral 750 mg Capsule Oral 250 mg Powder, for suspension Oral 1200 mg Powder, for solution Oral 600 mg Powder, for solution Oral 10 g Tablet, coated Oral 400 mg Powder, for solution Oral 2400 mg Capsule, liquid filled Oral 400 mg Powder, for solution Oral 1200 mg Capsule Oral 105 mg Powder, for solution Oral 30 g Powder, for solution Oral 1.2 g Granule Oral 1200 mg Capsule 75 mg Tablet Oral 400 mg Capsule, coated Oral 400 mg Tablet Oral 750 mg Capsule Oral 900 mg Gel Topical 0.445 % Cream Topical 40 g Solution Ophthalmic 1 mg Capsule Oral 200 mg Tablet, effervescent Oral 750 mg Capsule Oral 375 mg Powder Oral 1500 mg Tablet, film coated 400 mg Solution Ophthalmic 1.8 mg Powder Oral 500 mg Tablet Oral Tablet 400 mg Tablet, delayed release Oral 600 mg Capsule Oral 600 mg Powder, for solution Oral 1000 mg Tablet, film coated Oral 500 mg Patch Topical Capsule Oral 500 mg Solution Ophthalmic; Topical 1 mg Capsule Oral 500 mg/1 - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 190-194ºC Lipowitz A. and Newton C. Degenerative joint disease and traumatic arthritis. water solubility Soluble 'MSDS' pKa 1.5-2 Chandran P. and Horkay F. (2012). Acta Biomater. - Predicted Properties
- Not Available
- Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Neurotrophin trkb receptor binding
- Specific Function
- During development, promotes the survival and differentiation of selected neuronal populations of the peripheral and central nervous systems. Participates in axonal growth, pathfinding and in the m...
- Gene Name
- BDNF
- Uniprot ID
- P23560
- Uniprot Name
- Brain-derived neurotrophic factor
- Molecular Weight
- 27817.72 Da
References
- Nandini CD, Mikami T, Ohta M, Itoh N, Akiyama-Nambu F, Sugahara K: Structural and functional characterization of oversulfated chondroitin sulfate/dermatan sulfate hybrid chains from the notochord of hagfish. Neuritogenic and binding activities for growth factors and neurotrophic factors. J Biol Chem. 2004 Dec 3;279(49):50799-809. Epub 2004 Sep 22. [PubMed:15385557]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Receptor binding
- Specific Function
- Neurotrophic factor that enhances survival and morphological differentiation of dopaminergic neurons and increases their high-affinity dopamine uptake.
- Gene Name
- GDNF
- Uniprot ID
- P39905
- Uniprot Name
- Glial cell line-derived neurotrophic factor
- Molecular Weight
- 23719.85 Da
References
- Nandini CD, Mikami T, Ohta M, Itoh N, Akiyama-Nambu F, Sugahara K: Structural and functional characterization of oversulfated chondroitin sulfate/dermatan sulfate hybrid chains from the notochord of hagfish. Neuritogenic and binding activities for growth factors and neurotrophic factors. J Biol Chem. 2004 Dec 3;279(49):50799-809. Epub 2004 Sep 22. [PubMed:15385557]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Vascular endothelial growth factor receptor binding
- Specific Function
- Growth factor active in angiogenesis, vasculogenesis and endothelial cell growth. Induces endothelial cell proliferation, promotes cell migration, inhibits apoptosis and induces permeabilization of...
- Gene Name
- VEGFA
- Uniprot ID
- P15692
- Uniprot Name
- Vascular endothelial growth factor A
- Molecular Weight
- 27042.205 Da
References
- Nandini CD, Mikami T, Ohta M, Itoh N, Akiyama-Nambu F, Sugahara K: Structural and functional characterization of oversulfated chondroitin sulfate/dermatan sulfate hybrid chains from the notochord of hagfish. Neuritogenic and binding activities for growth factors and neurotrophic factors. J Biol Chem. 2004 Dec 3;279(49):50799-809. Epub 2004 Sep 22. [PubMed:15385557]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- Not Available
- Gene Name
- CCL2
- Uniprot ID
- P13500
- Uniprot Name
- C-C motif chemokine 2
- Molecular Weight
- 11024.87 Da
References
- Distler JH, Jungel A, Caretto D, Schulze-Horsel U, Kowal-Bielecka O, Gay RE, Michel BA, Muller-Ladner U, Kalden JR, Gay S, Distler O: Monocyte chemoattractant protein 1 released from glycosaminoglycans mediates its profibrotic effects in systemic sclerosis via the release of interleukin-4 from T cells. Arthritis Rheum. 2006 Jan;54(1):214-25. [PubMed:16385517]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Receptor binding
- Specific Function
- Plays an important role in the degradation of dermatan and keratan sulfates.
- Gene Name
- GUSB
- Uniprot ID
- P08236
- Uniprot Name
- Beta-glucuronidase
- Molecular Weight
- 74731.46 Da
References
- Metafishnet [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Protein homodimerization activity
- Specific Function
- Responsible for the degradation of GM2 gangliosides, and a variety of other molecules containing terminal N-acetyl hexosamines, in the brain and other tissues.
- Gene Name
- HEXB
- Uniprot ID
- P07686
- Uniprot Name
- Beta-hexosaminidase subunit beta
- Molecular Weight
- 63110.745 Da
References
- Metafishnet [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Required for the lysosomal degradation of heparan sulfate and dermatan sulfate.
- Specific Function
- Iduronate-2-sulfatase activity
- Gene Name
- IDS
- Uniprot ID
- P22304
- Uniprot Name
- Iduronate 2-sulfatase
- Molecular Weight
- 61872.405 Da
References
- Metafishnet [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Removes sulfate groups from chondroitin-4-sulfate (C4S) and regulates its degradation (PubMed:19306108). Involved in the regulation of cell adhesion, cell migration and invasion in colonic epithelium (PubMed:19306108). In the central nervous system, is a regulator of neurite outgrowth and neuronal plasticity, acting through the control of sulfate glycosaminoglycans and neurocan levels (By similarity).
- Specific Function
- Arylsulfatase activity
- Gene Name
- ARSB
- Uniprot ID
- P15848
- Uniprot Name
- Arylsulfatase B
- Molecular Weight
- 59686.71 Da
References
- Metafishnet [Link]
Drug created on November 11, 2015 12:54 / Updated on June 13, 2020 10:24
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