U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C6H13NO5
Molecular Weight 179.1711
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of .BETA.-GLUCOSAMINE, D-

SMILES

N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O

InChI

InChIKey=MSWZFWKMSRAUBD-QZABAPFNSA-N
InChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4-,5-,6-/m1/s1

HIDE SMILES / InChI

Molecular Formula C6H13NO5
Molecular Weight 179.1711
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/28306711 | https://www.ncbi.nlm.nih.gov/pubmed/26684635 | https://www.ncbi.nlm.nih.gov/pubmed/27050908 | https://www.ncbi.nlm.nih.gov/pubmed/23571415 | https://www.ncbi.nlm.nih.gov/pubmed/1518840

Glucosamine is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylated proteins and lipids. Glucosamine is part of the structure of the polysaccharides chitosan and chitin, which compose the exoskeletons of crustaceans and other arthropods, as well as the cell walls of fungi and many higher organisms. Glucosamine is one of the most abundant monosaccharides. It is produced commercially by the hydrolysis of crustacean exoskeletons or, less commonly, by fermentation of a grain such as corn or wheat. Evidence for the effectiveness of glucosamine supplements is mixed. In the United States, it is one of the most common non-vitamin, non-mineral, dietary supplements used by adults. Glucosamine is marketed to support the structure and function of joints, and the marketing is targeted to people suffering from osteoarthritis. Commonly sold forms of glucosamine are glucosamine sulfate, glucosamine hydrochloride, and N-acetylglucosamine. Of the three commonly available forms of glucosamine, only glucosamine sulfate is given a "likely effective" rating for treating osteoarthritis. Glucosamine is often sold in combination with other supplements such as chondroitin sulfate and methylsulfonylmethane. Glucosamine, along with commonly used chondroitin, is not routinely prescribed to treat people who have symptomatic osteoarthritis of the knee, as there is insufficient evidence that this treatment is helpful. As is common with heavily promoted dietary supplements, the claimed benefits of glucosamine are based principally on clinical and laboratory studies. Clinical studies are divided, with some reporting relief from arthritic pain and stiffness, while higher quality studies report no benefit above placebo. There is no evidence to date that consumption of glucosamine by sport participants will prevent or limit joint damage after injury. In a randomized placebo-controlled trial, glucosamine supplementation had no additional effect on any rehabilitation outcome when given to athletes after anterior cruciate ligament (ACL) reconstruction. Glucosamine is naturally present in the shells of shellfish, animal bones, bone marrow, and fungi. D-Glucosamine is made naturally in the form of glucosamine-6-phosphate, and is the biochemical precursor of all nitrogen-containing sugars. Specifically in humans, glucosamine-6-phosphate is synthesized from fructose 6-phosphate and glutamine by glutamine—fructose-6-phosphate transaminase as the first step of the hexosamine biosynthesis pathway. The end-product of this pathway is uridine diphosphate N-acetylglucosamine (UDP-GlcNAc), which is then used for making glycosaminoglycans, proteoglycans, and glycolipids. As the formation of glucosamine-6-phosphate is the first step for the synthesis of these products, glucosamine may be important in regulating their production; however, the way that the hexosamine biosynthesis pathway is actually regulated, and whether this could be involved in contributing to human disease remains unclear.

Originator

Sources: Berichte der Deutschen Chemischen Gesellschaft Volume 17, Pages 241-51. ISSN:0365-9496

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Structure-based identification of OATP1B1/3 inhibitors.
2013 Jun
Patents

Patents

Sample Use Guides

The patients treated with 1500 mg of glucosamine sulfate (Dona sachets 1500 mg Glucosamine sulfate, Rottapharm Ltd., Ireland) once a day.
Route of Administration: Oral
In Vitro Use Guide
Luciferase activity was measured in detergent extracts of Rat aortic smooth muscle cellsin the presence of ATP and luciferin in an LKB luminometer. Background luminescence was subtracted from all readings and was <1% of the cell-specific readings. The assay was determined to be linear in a range ±2 orders of magnitude from the range in which measurements were made. Hexose uptake was measured in confluent 35-mm dishes using 2 ILCi (74 kBq) of 2-deoxy-D-[l-3H]glucose (12 Ci/mmol; Amersham) or [6-3H]glucosamine(25 Ci/mmol; Amersham) per dish, with unlabeled sugar added to a final concentration of0.1 mM. After various times, the cells were rapidly rinsed three times in ice-cold saline and lysed in detergent for measurement of radioactivity by scintillation counting. In this assay system, the uptake of L-glucose is <1% of that observed with the D isomer
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:27:21 GMT 2023
Edited
by admin
on Sat Dec 16 01:27:21 GMT 2023
Record UNII
58L064K8RR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
.BETA.-GLUCOSAMINE, D-
Common Name English
GLUCOSAMINE .BETA.-FORM [MI]
Common Name English
GLUCOSAMINE .BETA.-FORM
MI  
Common Name English
.BETA.-GLUCOSAMINE
Common Name English
.BETA.-D-GLUCOSAMINE
Common Name English
GLUCOSAMINE, .BETA.-D
Common Name English
.BETA.-D-GLUCOPYRANOSE, 2-AMINO-2-DEOXY-
Systematic Name English
Code System Code Type Description
FDA UNII
58L064K8RR
Created by admin on Sat Dec 16 01:27:21 GMT 2023 , Edited by admin on Sat Dec 16 01:27:21 GMT 2023
PRIMARY
PUBCHEM
441477
Created by admin on Sat Dec 16 01:27:21 GMT 2023 , Edited by admin on Sat Dec 16 01:27:21 GMT 2023
PRIMARY
MERCK INDEX
m5764
Created by admin on Sat Dec 16 01:27:21 GMT 2023 , Edited by admin on Sat Dec 16 01:27:21 GMT 2023
PRIMARY Merck Index
CAS
14257-69-3
Created by admin on Sat Dec 16 01:27:21 GMT 2023 , Edited by admin on Sat Dec 16 01:27:21 GMT 2023
PRIMARY
CAS
28905-10-4
Created by admin on Sat Dec 16 01:27:21 GMT 2023 , Edited by admin on Sat Dec 16 01:27:21 GMT 2023
SUPERSEDED
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT