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 |
|---|---|---|
| Molecular mimicry between streptococcal pyrogenic exotoxin B and endothelial cells. | 2010-10 |
|
| Glycosaminoglycans and glycoconjugates in the adult anuran integument (Lithobates catesbeianus). | 2010-08 |
|
| Synthesis and cytotoxic activity of the N-acetylglucosamine-bearing triterpenoid saponins. | 2010-03-30 |
|
| Fluorometric detection and estimation of fungal biomass on cultural heritage materials. | 2010-02 |
|
| 5a-Carba-glycopyranoside primers: potential building blocks for biocombinatorial synthesis of glycosphingolipid analogues. | 2009-10-12 |
|
| Conformational properties of the disaccharide building units of hyaluronan. | 2009-09-08 |
|
| Concise and efficient synthesis of 2-acetamido-2-deoxy-beta-D-hexopyranosides of diverse aminosugars from 2-acetamido-2-deoxy-beta-D-glucose. | 2009-01-16 |
|
| Changes in motility of the rhizobacterium Azospirillum brasilense in the presence of plant lectins. | 2009 |
|
| Structural elucidation of the capsular polysaccharide isolated from Kaistella flava. | 2008-09-22 |
|
| Metamorphic changes in localization of sugars in skin of the leopard frog, Rana pipiens. | 2008-08 |
|
| 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. | 2008-07-02 |
|
| Antifungal activity of chitinases from Trichoderma aureoviride DY-59 and Rhizopus microsporus VS-9. | 2008-01 |
|
| Normal human serum contains high levels of anti-Gal alpha 1-4GlcNAc antibodies. | 2007-11 |
|
| Carbohydrate-appended curdlans as a new family of glycoclusters with binding properties both for a polynucleotide and lectins. | 2007-08-07 |
|
| Chitinase family GH18: evolutionary insights from the genomic history of a diverse protein family. | 2007-06-26 |
|
| Chitin induces accumulation in tissue of innate immune cells associated with allergy. | 2007-05-03 |
|
| Antibody-mediated neuronal cell signaling in behavior and movement disorders. | 2006-10 |
|
| cDNA cloning and 1.75 A crystal structure determination of PPL2, an endochitinase and N-acetylglucosamine-binding hemagglutinin from Parkia platycephala seeds. | 2006-09 |
|
| Overlapping humoral autoimmunity links rheumatic fever and the antiphospholipid syndrome. | 2006-07 |
|
| Characterisation of a secreted N-acetyl-beta-hexosaminidase from Trichinella spiralis. | 2006-01 |
|
| Optimization of an enzymatic method for the determination of lysosomal N-acetyl-beta-D-hexosaminidase and beta-glucuronidase in synovial fluid. | 2006 |
|
| Molecular cloning and functional characterization of mouse chitotriosidase. | 2005-08-29 |
|
| Late type of daughter cell wall synthesis in one of the Chlorellaceae, Parachlorella kessleri (Chlorophyta, Trebouxiophyceae). | 2005-08 |
|
| Production of N-acetyl-beta-D-glucosamine from chitin by Aeromonas sp. GJ-18 crude enzyme. | 2005-08 |
|
| N-acetyl-beta-D-hexosaminidase from Trichomonas vaginalis: substrate specificity and activity of inhibitors. | 2005-06 |
|
| Synthesis and antibody-binding studies of a series of parasite fuco-oligosaccharides. | 2005-05-16 |
|
| Significance of the sulfonylurea receptor (SUR) as the target of diflubenzuron in chitin synthesis inhibition in Drosophila melanogaster and Blattella germanica. | 2004-08 |
|
| Glycoconjugate localization in larval and adult skin of the bullfrog, Rana catesbeiana: a lectin histochemical study. | 2004-08 |
|
| Inhibition of the activating signals in NK92 cells by recombinant GST-sHLA-G1a chain. | 2004-04 |
|
| Ultracytochemical demonstration of glycoproteins in the canine knee synovium. | 2003-12 |
|
| Chemo-enzymatic synthesis of a tetra- and octasaccharide fragment of the capsular polysaccharide of Streptococcus pneumoniae type 14. | 2003-11-14 |
|
| Partial characterisation of carbohydrate-rich Echinococcus granulosus coproantigens. | 2003-11 |
|
| Mimicry and autoantibody-mediated neuronal cell signaling in Sydenham chorea. | 2003-07 |
|
| Ultrastructural and cytochemical study of cell wall modification by lactoferrin, lactoferricin and penicillin G against Staphylococcus aureus. | 2003 |
|
| Analysis of urinary N-acetyl-beta-D-glucosaminidase using 2,4-dinitrophenyl-1-thio N-acetyl-beta-D-glucosaminide as the substrate. | 2003 |
|
| Synthesis of an ether-linked alkyl 5a-carba-beta-D-glucoside, a 5a-carba-beta-D-galactoside, a 2-acetamido-2-deoxy-5a-carba-beta-D-glucoside, and an alkyl 5a'-carba-beta-lactoside. | 2002-11-19 |
|
| The cellular prion protein: a new partner of the lectin CBP70 in the nucleus of NB4 human promyelocytic leukemia cells. | 2002 |
|
| Protection of pig kidney (PK15) cells from the cytotoxic effect of anti-pig antibodies by alpha-galactosyl oligosaccharides. | 1994-03-27 |
|
| Identification of alpha-galactosyl and other carbohydrate epitopes that are bound by human anti-pig antibodies: relevance to discordant xenografting in man. | 1993 |
|
| Characterization of surface associated antigens of axenic Giardia lamblia trophozoites & their recognition by human sera. | 1991-01 |
|
| Two human IgM myeloma proteins with unusual specificities for streptococcal carbohydrate-associated epitopes. | 1985-02 |
|
| Immunochemical studies on bacterial blood group substances. VIII. The structure of oligosaccharides from blood group H-active polysaccharide of Escherichia coli 2B-V. | 1976-04 |
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
Mon Mar 31 18:47:43 GMT 2025
by
admin
on
Mon Mar 31 18:47:43 GMT 2025
|
| Record UNII |
V956696549
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Preferred Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Brand Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Brand Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
FDA ORPHAN DRUG |
767420
Created by
admin on Mon Mar 31 18:47:43 GMT 2025 , Edited by admin on Mon Mar 31 18:47:43 GMT 2025
|
||
|
DSLD |
1095 (Number of products:142)
Created by
admin on Mon Mar 31 18:47:43 GMT 2025 , Edited by admin on Mon Mar 31 18:47:43 GMT 2025
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
73685
Created by
admin on Mon Mar 31 18:47:43 GMT 2025 , Edited by admin on Mon Mar 31 18:47:43 GMT 2025
|
PRIMARY | |||
|
C1505
Created by
admin on Mon Mar 31 18:47:43 GMT 2025 , Edited by admin on Mon Mar 31 18:47:43 GMT 2025
|
CONCEPT | Dietary Supplement | ||
|
V956696549
Created by
admin on Mon Mar 31 18:47:43 GMT 2025 , Edited by admin on Mon Mar 31 18:47:43 GMT 2025
|
PRIMARY | |||
|
231-368-2
Created by
admin on Mon Mar 31 18:47:43 GMT 2025 , Edited by admin on Mon Mar 31 18:47:43 GMT 2025
|
PRIMARY | |||
|
m5764
Created by
admin on Mon Mar 31 18:47:43 GMT 2025 , Edited by admin on Mon Mar 31 18:47:43 GMT 2025
|
PRIMARY | Merck Index | ||
|
506227
Created by
admin on Mon Mar 31 18:47:43 GMT 2025 , Edited by admin on Mon Mar 31 18:47:43 GMT 2025
|
PRIMARY | |||
|
7512-17-6
Created by
admin on Mon Mar 31 18:47:43 GMT 2025 , Edited by admin on Mon Mar 31 18:47:43 GMT 2025
|
PRIMARY | |||
|
1010022
Created by
admin on Mon Mar 31 18:47:43 GMT 2025 , Edited by admin on Mon Mar 31 18:47:43 GMT 2025
|
PRIMARY | |||
|
17411
Created by
admin on Mon Mar 31 18:47:43 GMT 2025 , Edited by admin on Mon Mar 31 18:47:43 GMT 2025
|
PRIMARY | |||
|
V956696549
Created by
admin on Mon Mar 31 18:47:43 GMT 2025 , Edited by admin on Mon Mar 31 18:47:43 GMT 2025
|
PRIMARY | |||
|
400525
Created by
admin on Mon Mar 31 18:47:43 GMT 2025 , Edited by admin on Mon Mar 31 18:47:43 GMT 2025
|
PRIMARY | |||
|
524344
Created by
admin on Mon Mar 31 18:47:43 GMT 2025 , Edited by admin on Mon Mar 31 18:47:43 GMT 2025
|
PRIMARY | |||
|
DTXSID3045855
Created by
admin on Mon Mar 31 18:47:43 GMT 2025 , Edited by admin on Mon Mar 31 18:47:43 GMT 2025
|
PRIMARY | |||
|
100000085222
Created by
admin on Mon Mar 31 18:47:43 GMT 2025 , Edited by admin on Mon Mar 31 18:47:43 GMT 2025
|
PRIMARY | |||
|
28009
Created by
admin on Mon Mar 31 18:47:43 GMT 2025 , Edited by admin on Mon Mar 31 18:47:43 GMT 2025
|
PRIMARY | |||
|
72-87-7
Created by
admin on Mon Mar 31 18:47:43 GMT 2025 , Edited by admin on Mon Mar 31 18:47:43 GMT 2025
|
ALTERNATIVE | |||
|
1738118
Created by
admin on Mon Mar 31 18:47:43 GMT 2025 , Edited by admin on Mon Mar 31 18:47:43 GMT 2025
|
PRIMARY | |||
|
C83975
Created by
admin on Mon Mar 31 18:47:43 GMT 2025 , Edited by admin on Mon Mar 31 18:47:43 GMT 2025
|
PRIMARY | |||
|
1362871
Created by
admin on Mon Mar 31 18:47:43 GMT 2025 , Edited by admin on Mon Mar 31 18:47:43 GMT 2025
|
PRIMARY | RxNorm | ||
|
DB00141
Created by
admin on Mon Mar 31 18:47:43 GMT 2025 , Edited by admin on Mon Mar 31 18:47:43 GMT 2025
|
PRIMARY | |||
|
SUB21868
Created by
admin on Mon Mar 31 18:47:43 GMT 2025 , Edited by admin on Mon Mar 31 18:47:43 GMT 2025
|
PRIMARY | |||
|
N-ACETYLGLUCOSAMINE
Created by
admin on Mon Mar 31 18:47:43 GMT 2025 , Edited by admin on Mon Mar 31 18:47:43 GMT 2025
|
PRIMARY | |||
|
4615
Created by
admin on Mon Mar 31 18:47:43 GMT 2025 , Edited by admin on Mon Mar 31 18:47:43 GMT 2025
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
PARENT -> IMPURITY |
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |
|