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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
Structure of N-ACETYLGLUCOSAMINE

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

HIDE SMILES / InChI

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

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
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 Mon Mar 31 18:47:43 GMT 2025
Edited
by admin
on Mon Mar 31 18:47:43 GMT 2025
Record UNII
V956696549
Record Status Validated (UNII)
Record Version
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Name Type Language
ACETYL GLUCOSAMINE
INCI  
INCI  
Preferred Name English
N-ACETYLGLUCOSAMINE
DSC   MI   USP-RS   WHO-DD  
Systematic Name English
N-ACETYLGLUCOSAMINE [DSC]
Common Name English
N-ACETYLGLUCOSAMINE [MI]
Common Name English
2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSE
Systematic Name English
N-Acetylglucosamine [WHO-DD]
Common Name English
NSC-400525
Code English
GREENNAG
Brand Name English
N-ACETYL GLUCOSAMINE
Systematic Name English
ACETYLGLUCOSAMINE
Systematic Name English
ACETYL-GLUCOSAMINE
Systematic Name English
GLUCOPYRANOSE, 2-ACETAMIDO-2-DEOXY-
Systematic Name English
N-ACETYL-D-GLUCOSAMINE
Systematic Name English
GLCNAC
Common Name English
NSC-524344
Code English
N-ACETYLGLUCOSAMINE [USP-RS]
Common Name English
N-((2R,3R,4S,5R)-3,4,5,6-TETRAHYDROXY-1-OXOHEXAN-2-YL)ACETAMIDE
Systematic Name English
D-GLUCOSE, 2-(ACETYLAMINO)-2-DEOXY-
Systematic Name English
N-ACETYL GLUCOSAMINE D-
Common Name English
D-GLUCOPYRANOSE, 2-(ACETYLAMINO)-2-DEOXY-
Systematic Name English
MARINE SWEET
Brand Name English
D-GLUCOSE, 2-ACETAMIDO-2-DEOXY-
Systematic Name English
NAG
Common Name English
N-((3R,4R,5S,6R)-2,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)TETRAHYDRO-2H-PYRAN-3-YL)ACETAMIDE
Systematic Name English
BIO-NAG
Brand Name English
GLUCOSAMINE SULFATE POTASSIUM CHLORIDE IMPURITY A [ EP IMPURITY]
Common Name English
GLUCOPYRANOSE, 2-ACETAMIDO-2-DEOXY-, D-
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
CHEBI
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
NCI_THESAURUS
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
DAILYMED
V956696549
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PRIMARY
ECHA (EC/EINECS)
231-368-2
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PRIMARY
MERCK INDEX
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
CHEBI
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
CAS
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
RS_ITEM_NUM
1010022
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PRIMARY
CHEBI
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
FDA UNII
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
NSC
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
NSC
524344
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PRIMARY
EPA CompTox
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
SMS_ID
100000085222
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PRIMARY
CHEBI
28009
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PRIMARY
CAS
72-87-7
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ALTERNATIVE
PUBCHEM
1738118
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PRIMARY
NCI_THESAURUS
C83975
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PRIMARY
RXCUI
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
DRUG BANK
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
EVMPD
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
WIKIPEDIA
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
DRUG CENTRAL
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