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
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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Immunochemical studies on bacterial blood group substances. VIII. The structure of oligosaccharides from blood group H-active polysaccharide of Escherichia coli 2B-V. | 1976 Apr |
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Two human IgM myeloma proteins with unusual specificities for streptococcal carbohydrate-associated epitopes. | 1985 Feb |
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Characterization of surface associated antigens of axenic Giardia lamblia trophozoites & their recognition by human sera. | 1991 Jan |
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Protection of pig kidney (PK15) cells from the cytotoxic effect of anti-pig antibodies by alpha-galactosyl oligosaccharides. | 1994 Mar 27 |
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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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Partial characterisation of carbohydrate-rich Echinococcus granulosus coproantigens. | 2003 Nov |
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Chemo-enzymatic synthesis of a tetra- and octasaccharide fragment of the capsular polysaccharide of Streptococcus pneumoniae type 14. | 2003 Nov 14 |
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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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N-acetyl-beta-D-hexosaminidase from Trichomonas vaginalis: substrate specificity and activity of inhibitors. | 2005 Jun |
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Optimization of an enzymatic method for the determination of lysosomal N-acetyl-beta-D-hexosaminidase and beta-glucuronidase in synovial fluid. | 2006 |
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Overlapping humoral autoimmunity links rheumatic fever and the antiphospholipid syndrome. | 2006 Jul |
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Antibody-mediated neuronal cell signaling in behavior and movement disorders. | 2006 Oct |
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cDNA cloning and 1.75 A crystal structure determination of PPL2, an endochitinase and N-acetylglucosamine-binding hemagglutinin from Parkia platycephala seeds. | 2006 Sep |
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Carbohydrate-appended curdlans as a new family of glycoclusters with binding properties both for a polynucleotide and lectins. | 2007 Aug 7 |
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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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Chitin induces accumulation in tissue of innate immune cells associated with allergy. | 2007 May 3 |
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Normal human serum contains high levels of anti-Gal alpha 1-4GlcNAc antibodies. | 2007 Nov |
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Metamorphic changes in localization of sugars in skin of the leopard frog, Rana pipiens. | 2008 Aug |
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Antifungal activity of chitinases from Trichoderma aureoviride DY-59 and Rhizopus microsporus VS-9. | 2008 Jan |
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Conformational preferences of the aglycon moiety in models and analogs of GlcNAc-Asn linkage: crystal structures and ab initio quantum chemical calculations of N-(beta-D-glycopyranosyl)haloacetamides. | 2008 Jul 2 |
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Structural elucidation of the capsular polysaccharide isolated from Kaistella flava. | 2008 Sep 22 |
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Changes in motility of the rhizobacterium Azospirillum brasilense in the presence of plant lectins. | 2009 |
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Concise and efficient synthesis of 2-acetamido-2-deoxy-beta-D-hexopyranosides of diverse aminosugars from 2-acetamido-2-deoxy-beta-D-glucose. | 2009 Jan 16 |
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5a-Carba-glycopyranoside primers: potential building blocks for biocombinatorial synthesis of glycosphingolipid analogues. | 2009 Oct 12 |
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Conformational properties of the disaccharide building units of hyaluronan. | 2009 Sep 8 |
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Fluorometric detection and estimation of fungal biomass on cultural heritage materials. | 2010 Feb |
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.
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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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506227
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7512-17-6
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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