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
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
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 |
DescriptionSources: https://www.drugbank.ca/drugs/DB01296Curator'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
Sources: https://www.drugbank.ca/drugs/DB01296
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1743121 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23571415 |
|||
Target ID: CHEMBL1697668 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23571415 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26684635
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1518840
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
Edited
Sat Dec 16 01:27:21 GMT 2023
by
admin
on
Sat Dec 16 01:27:21 GMT 2023
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Record UNII |
58L064K8RR
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Record Status |
Validated (UNII)
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Record Version |
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441477
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m5764
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14257-69-3
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28905-10-4
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SUPERSEDED |
Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |