Acetylglucosamine is an endogenous metabolite that interacts with various proteins and enzymes involved in glycosylation and carbohydrate metabolism. It targets multiple molecules including β-4-Gal-T4, CLEC-10A, ficolin B, hexokinase, and various lectins. As a hexosamine pathway metabolite, it serves as a substrate for glycosylation reactions and modulates O-GlcNAcylation of proteins, affecting cellular signaling and gene expression.

N-Acetyl-D-Glucosamine inhibits IL-1β and TNFα production and induces nitric oxide (NO), cyclooxygenase-2 (COX-2), and IL-6 production in normal human articular chondrocytes in vitro. This immunomodulatory activity suggests potential benefits in inflammatory conditions such as osteoarthritis. The compound also serves as a substrate for hexokinase and participates in glycosaminoglycan synthesis, supporting cartilage matrix maintenance and repair.

In vivo, Acetylglucosamine is used as a dietary supplement for the treatment and prevention of osteoarthritis, by itself or in combination with chondroitin sulfate. The mechanism of action in relieving arthritic pain and in repair of cartilage remains speculative but is believed to involve stimulation of glycosaminoglycan synthesis and modulation of inflammatory pathways. It may also have benefits for irritable bowel syndrome and other inflammatory conditions.

In vitro enzyme assays for Acetylglucosamine typically involve measuring hexokinase activity using GlcNAc as a substrate. The enzyme is incubated with GlcNAc and ATP, and the production of GlcNAc-6-phosphate is measured using coupled enzyme assays or chromatographic methods. Binding assays to lectins such as CLEC-10A or ficolin B can be performed using surface plasmon resonance or ELISA-based methods to characterize carbohydrate-protein interactions.

Cellular assays for Acetylglucosamine involve culturing human articular chondrocytes or other cell types. Cells are treated with Acetylglucosamine at varying concentrations (typically 0.1-10 mM) for 24-72 hours. Cytokine production (IL-1β, TNFα, IL-6) is measured by ELISA. Nitric oxide production is measured using the Griess assay. COX-2 expression is assessed by Western blotting or qPCR. Cell viability is measured using standard assays such as MTT.

In vivo animal studies for Acetylglucosamine are typically conducted in rodent models of osteoarthritis or inflammatory bowel disease. The compound is administered orally via gavage or in the diet. Efficacy is assessed by measuring joint inflammation, cartilage degradation markers, or inflammatory cytokine levels. Dosing regimens vary, with typical doses ranging from 50-500 mg/kg/day. Studies may also assess effects on gut barrier function and intestinal inflammation.

Absorption, Distribution and Excretion
Approximately 90% of orally ingested glucosamine (in salt form) is absorbed in the small intestine. Metabolism/Metabolites A significant portion of ingested glucosamine is metabolized in the liver through first-pass metabolism.
Acetylglucosamine is well absorbed after oral administration and is distributed to various tissues, including cartilage. It is metabolized through the hexosamine pathway and incorporated into glycosaminoglycans. The compound has a molecular weight of 221.21 and a molecular formula of C8H15NO6. It is soluble in water and should be stored as a powder at -20°C for up to 3 years or at 4°C for up to 2 years.

Acetylglucosamine is generally recognized as safe (GRAS) and is well-tolerated at recommended doses. It is used as a dietary supplement and is not associated with significant toxicity. Mild gastrointestinal side effects may occur in some individuals. The compound is not approved as a drug for disease treatment but is widely available as a nutritional supplement for joint health.

[1]. O-GlcNAc cycling: how a single sugar post-translational modification is changing the way we think about signaling networks. J Cell Biochem. 2006 Jan 1;97(1):71-83.

Aldehyde-N-acetyl-D-glucosamine is the open-chain form of N-acetyl-D-glucosamine, a human metabolite.
An N-acetyl derivative of glucosamine.
N-acetylglucosamine is a metabolite found or produced in Escherichia coli (K12 strain, MG1655 strain).
D-glucose, 2-(acetamido)-2-deoxy- has been reported in Arabidopsis thaliana, humans, and other organisms with relevant data.
An N-acetyl derivative of glucosamine.
See also: polyglucosamine (monomer); adoramipalene (monomer). Adomipalene sodium (monomer)...see more...
Pharmacological Indications

For the treatment and prevention of osteoarthritis, used alone or in combination with chondroitin sulfate.
Mechanism of Action

The mechanism of action for relieving arthritis pain and repairing cartilage is not fully understood. From a biochemical perspective, glucosamine is involved in glycoprotein metabolism. Glycoproteins, also known as proteoglycans, constitute the matrix of the extracellular matrix of connective tissue cells. Proteoglycans are high-molecular-weight, polyanionic substances containing various types of heteropolysaccharide side chains covalently linked to the polypeptide backbone. These polysaccharides account for as much as 95% of the proteoglycan structure. In fact, from a chemical perspective, proteoglycans are more like polysaccharides than proteins. The polysaccharide groups in proteoglycans are called glycosaminoglycans (GAGs). GAGs include hyaluronic acid, chondroitin sulfate, dermatan sulfate, keratin sulfate, heparin, and heparan sulfate. All GAGs contain either glucosamine or galactosamine derivatives. Glucosamine derivatives are found in hyaluronic acid, keratin sulfate, and heparan sulfate. Chondroitin sulfate contains galactosamine derivatives. Glucosamine-containing glycosaminoglycans and hyaluronic acid are essential for the function of articular cartilage. GAG chains are the basic building blocks of aggregated proteoglycans in articular cartilage. Aggregated proteoglycans impart shock-absorbing properties to articular cartilage. This is achieved by providing expansion pressure to the cartilage, which is limited by the tension of collagen fibers. This balance gives articular cartilage its deformable elasticity, which is crucial for its function. In the early stages of degenerative joint disease, the biosynthesis of proteoglycans increases. However, in later stages of the disease, proteoglycan synthesis decreases, eventually leading to loss of cartilage elasticity and the appearance of most osteoarthritis symptoms. Exogenous glucosamine may play a beneficial role in the progression of osteoarthritis. It is known that, in vitro, chondrocytes synthesize more proteoglycans when glucosamine is added to the culture medium. In these in vitro studies, N-acetylglucosamine showed poorer effects. Glucosamine has also been found to have antioxidant activity and has shown benefits in animal models of experimental arthritis. The counterions of glucosamine salts (such as chloride or sulfate ions) are unlikely to affect the effects or pharmacokinetics of glucosamine. Furthermore, the sulfate in glucosamine sulfate supplements should not be confused with glucosamine sulfate present in glycosaminoglycans (GAGs) such as keratin sulfate and heparin sulfate. In supplements, sulfate is the anion of the salt. In the aforementioned glycosaminoglycans, sulfate is present in the form of an ester. In addition, chondroitin sulfate does not contain glucosamine sulfate (Source: PDRhealth).
Acetylglucosamine (GlcNAc) is an aminosugar and hexosamine pathway metabolite used as a dietary supplement for joint health and osteoarthritis. It inhibits IL-1β and TNFα production in chondrocytes and supports cartilage matrix maintenance. The compound is also known as N-Acetyl-D-glucosamine and is available as a nutritional supplement. It is not a prescription drug and is not approved for therapeutic disease treatment in many jurisdictions.

C8H15NO6

221.209

221.089

7512-17-6

D-N-Acetylgalactosamine;1811-31-0;N-Acetyl-D-glucosamine-13C;253679-94-6;N-Acetyl-D-glucosamine-13C2,15N;478529-44-1;N-Acetyl-D-glucosamine-13C,15N-1;N-Acetyl-D-glucosamine-13C6;1194446-34-8;N-Acetyl-D-glucosamine-13C-1;478518-87-5;N-Acetyl-D-glucosamine-13C-2;478518-89-7;N-Acetyl-D-glucosamine-18O;N-Acetyl-D-glucosamine-13C-3;478529-39-4;N-Acetyl-D-glucosamine-15N;478518-85-3;N-Acetyl-D-glucosamine-13C,15N;478529-40-7;N-Acetyl-D-glucosamine-13C3,15N;478529-43-0

1738118

White to off-white solid powder

1.5±0.1 g/cm3

595.4±50.0 °C at 760 mmHg

201-204ºC

313.9±30.1 °C

0.0±3.8 mmHg at 25°C

1.576

-2.48

5

6

6

15

221

4

CC(=O)N[C@@H](C=O)[C@H]([C@@H]([C@@H](CO)O)O)O

OVRNDRQMDRJTHS-FMDGEEDCSA-N

InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-,8-/m1/s1

N-Acetyl-beta-D-glucosamine

Acetylglucosamine GlcNAc Bio-NAG N-Acetylglucosamine N-Acetyl-D-glucosamineNSC 400525 NSC 524344GreenNAG Marine Sweet

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ~125 mg/mL (~565.07 mM)
H2O : ~100 mg/mL (~452.06 mM)

Solubility in Formulation 1: ≥ 3.25 mg/mL (14.69 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 32.5 mg/mL clear DMSO stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 2: ≥ 3.25 mg/mL (14.69 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 32.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 3.25 mg/mL (14.69 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 32.5 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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Solubility in Formulation 4: 50 mg/mL (226.03 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.

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 (Please use freshly prepared in vivo formulations for optimal results.)