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.

[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).

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.)