Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C8H15NO6 |
Molecular Weight | 221.2078 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO
InChI
InChIKey=MBLBDJOUHNCFQT-LXGUWJNJSA-N
InChI=1S/C8H15NO6/c1-4(12)9-5(2-10)7(14)8(15)6(13)3-11/h2,5-8,11,13-15H,3H2,1H3,(H,9,12)/t5-,6+,7+,8+/m0/s1
Molecular Formula | C8H15NO6 |
Molecular Weight | 221.2078 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
N-Acetylglucosamine (N-acetyl-D-glucosamine, or GlcNAc,) is a monosaccharide and a derivative of glucose. It is part of a biopolymer in the bacterial cell wall, built from alternating units of GlcNAc and N-acetylmuramic acid (MurNAc), cross-linked with oligopeptides at the lactic acid residue of MurNAc. This layered structure is called peptidoglycan (formerly called murein). GlcNAc is the monomeric unit of the polymer chitin, which forms the outer coverings of insects and crustaceans. It is the main component of the radulas of mollusks, the beaks of cephalopods, and a major component of the cell walls of most fungi. It is lnsown, that the breakdown of glycosaminoglycans is an important consequence of inflammation at mucosal surfaces, and inhibition of metalloprotease activity may be effective in treating chronic inflammation. GlcNAc directly incorporates into glycosaminoglycans and glycoproteins, as a substrate for tissue repair mechanisms. It was shown, that GlcNAc was promising substance for treatment of chronic inflammatory bowel disease, with a mode of action which is distinct from conventional treatments. In experiments on rabbits with osteoarthritis, was found chondroprotective effects of aminomonosaccharide glucosamine, but no statistically significant difference was found between study groups. It was also investigated for the treatment of Multiple sclerosis, however, as a drug development target, GlcNAc had significant limitations. GlcNAc has poor membrane permeability, requiring high concentrations for biological effects.
Approval Year
PubMed
Title | Date | PubMed |
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Two human IgM myeloma proteins with unusual specificities for streptococcal carbohydrate-associated epitopes. | 1985 Feb |
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The cellular prion protein: a new partner of the lectin CBP70 in the nucleus of NB4 human promyelocytic leukemia cells. | 2002 |
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Significance of the sulfonylurea receptor (SUR) as the target of diflubenzuron in chitin synthesis inhibition in Drosophila melanogaster and Blattella germanica. | 2004 Aug |
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Production of N-acetyl-beta-D-glucosamine from chitin by Aeromonas sp. GJ-18 crude enzyme. | 2005 Aug |
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Chitinase family GH18: evolutionary insights from the genomic history of a diverse protein family. | 2007 Jun 26 |
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Antifungal activity of chitinases from Trichoderma aureoviride DY-59 and Rhizopus microsporus VS-9. | 2008 Jan |
Patents
Sample Use Guides
N-acetyl glucosamine (GlcNAc) (total daily dose 3-6 g) was administered orally as adjunct therapy to 12 children with severe treatment-resistant inflammatory bowel disease (10 Crohn's disease, 2 ulcerative colitis). Rectal administration induced remission in two cases, clear improvement in three and no effect in two
in rabbits: osteoarthritis: Rabbits were randomized into four groups, each consisting of eight rabbits. Two weeks after the operation, intraarticular injections were performed to the right knees once a week for 5 weeks; intraarticular glucosamine to the first group, intraarticular hyaluronate to the second group, intraarticular hyaluronate and intramuscular glucosamine to the third group, and intraarticular saline solution to the fourth group, which served as the control group. At the end of the eighth week, the rabbits were sacrificed and their right knees with proximal femur and distal tibia were harvested.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10649686
The effect of N-acetylglucosamine (NAG) on in vitro synthesis of glycosaminoglycans by human peritoneal mesothelial cells and fibroblasts was studied. In contrast to isosmotic concentrations of glucose, NAG increases the synthesis of hyaluronan by mesothelial cells and fibroblasts in a dose-dependent manner. Glucose inhibits synthesis of sulphated glycosaminoglycans by peritoneal mesothelial cells and fibroblasts, whereas NAG stimulates their production. It was demonstrated that NAG was an effective stimulator of the in vitro glycosaminoglycans synthesis by human peritoneal mesothelial cells and fibroblasts.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 17:32:01 UTC 2023
by
admin
on
Fri Dec 15 17:32:01 UTC 2023
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Record UNII |
V956696549
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
767420
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DSLD |
1095 (Number of products:142)
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73685
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C1505
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CONCEPT | Dietary Supplement | ||
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V956696549
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231-368-2
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m5764
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PRIMARY | Merck Index | ||
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506227
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7512-17-6
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1010022
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17411
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V956696549
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400525
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524344
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DTXSID3045855
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100000085222
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28009
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72-87-7
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1738118
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C83975
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1362871
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DB00141
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SUB21868
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N-ACETYLGLUCOSAMINE
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4615
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ACTIVE MOIETY |
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