Synonym
D-Glucosamine sulphate, Gevolox, Glucosamine sulfate, Glucosamine sulphate
IUPAC/Chemical Name
2-Amino-2-deoxy-D-glucose sulfate (salt)
InChi Key
FGNPLIQZJCYWLE-BTVCFUMJSA-N
InChi Code
1S/C6H13NO5.H2O4S/c7-3(1-8)5(11)6(12)4(10)2-9;1-5(2,3)4/h1,3-6,9-12H,2,7H2;(H2,1,2,3,4)/t3-,4+,5+,6+;/m0./s1
SMILES Code
S(=O)(O)(=O)O.C([C@H](N)[C@@H](O)[C@@H]([C@@H](CO)O)O)=O
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Glucosamine sulfate (D-Glucosamine sulfate) is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylated proteins and lipids, is used as a dietary supplement.
In vitro activity:
The effects of glucosamine on osteoblasts was examined. The potential underlying mechanisms were explored. The results showed
that glucosamine had a biphasic effect on the viability of hFOB1.19 osteoblasts. At low concentrations (<0.6 mM), glucosamine
induced hFOB1.19 cell proliferation, whereas at high concentrations (>0.8 mM) it induced apoptosis. The autophagy inhibitor 3-
methyladenine (3-MA) was used to verify that glucosamine modulated hFOB1.19 cell viability via autophagy. The induction of
apoptosis by high concentrations of glucosamine was significantly exacerbated by 3-MA, whereas the promotion of cell proliferation
by low concentrations of glucosamine was significantly suppressed by 3-MA. Autophagy was examined by western blot detection of
autophagy-related proteins including LC3, Beclin-1, and SQSTM1/p62 and by immunofluorescence analysis of autophagosomes.
Glucosamine activated autophagy in a time- and concentration-dependent manner. Investigation of the underlying mechanism showed
that glucosamine inhibited the phosphorylation of m-TOR in a concentration-dependent manner within 48 h. These results
demonstrated that glucosamine promoted hFOB1.19 cell proliferation and increased autophagy by inhibiting the m-TOR pathway,
suggesting its potential as a therapeutic agent for osteoporosis.
Reference: Biomed Pharmacother. 2018 Mar;99:271-277. https://linkinghub.elsevier.com/retrieve/pii/S0753-3322(17)36142-5
In vivo activity:
The aim of the current study was to investigate the effects of glucosamine (GlcN) on septic lethality and sepsis-induced inflammation
using animal models of mice and zebrafish. GlcN pretreatment improved survival in the cecal ligation and puncture (CLP)-induced
sepsis mouse model and attenuated lipopolysaccharide (LPS)-induced septic lung injury and systemic inflammation. GlcN suppressed
LPS-induced M1-specific but not M2-specific gene expression. Furthermore, increased expressions of inflammatory genes in visceral
tissue of LPS-injected zebrafish were suppressed by GlcN. GlcN suppressed LPS-induced activation of mitogen-activated protein
kinase (MAPK) and NF-κB in lung tissue. LPS triggered a reduction in O-GlcNAc levels in nucleocytoplasmic proteins of lung, liver,
and spleen after 1 day, which returned to normal levels at day 3. GlcN inhibited LPS-induced O-GlcNAc down-regulation in mouse
lung and visceral tissue of zebrafish. Furthermore, the O-GlcNAcase (OGA) level was increased by LPS, which were suppressed by
GlcN in mouse and zebrafish. OGA inhibitors suppressed LPS-induced expression of inflammatory genes in RAW264.7 cells and the
visceral tissue of zebrafish. Stable knockdown of Oga via short hairpin RNA led to increased inducible nitric oxide synthase (iNOS)
expression in response to LPS with or without GlcN in RAW264.7 cells. Overall, our results demonstrate a protective effect of GlcN
on sepsis potentially through modulation of O-GlcNAcylation of nucleocytoplasmic proteins.
Reference: J Biol Chem. 2019 Jan 11;294(2):608-622. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/30455348/
|
Solvent |
mg/mL |
mM |
Solubility |
DMSO |
4.0 |
14.43 |
Water |
90.0 |
324.62 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
277.24
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Lv C, Wang L, Zhu X, Lin W, Chen X, Huang Z, Huang L, Yang S. Glucosamine promotes osteoblast proliferation by modulating
autophagy via the mammalian target of rapamycin pathway. Biomed Pharmacother. 2018 Mar;99:271-277. doi:
10.1016/j.biopha.2018.01.066. PMID: 29334671.
2. Lei X, Ma N, Liang Y, Liu J, Zhang P, Han Y, Chen W, Du L, Qu B. Glucosamine protects against radiation-induced lung injury
via inhibition of epithelial-mesenchymal transition. J Cell Mol Med. 2020 Sep;24(18):11018-11023. doi: 10.1111/jcmm.15662. Epub
2020 Jul 22. PMID: 32700471; PMCID: PMC7521322.
3. Hwang JS, Kim KH, Park J, Kim SM, Cho H, Lee Y, Han IO. Glucosamine improves survival in a mouse model of sepsis and
attenuates sepsis-induced lung injury and inflammation. J Biol Chem. 2019 Jan 11;294(2):608-622. doi: 10.1074/jbc.RA118.004638.
Epub 2018 Nov 19. PMID: 30455348; PMCID: PMC6333887.
In vitro protocol:
1. Lv C, Wang L, Zhu X, Lin W, Chen X, Huang Z, Huang L, Yang S. Glucosamine promotes osteoblast proliferation by modulating
autophagy via the mammalian target of rapamycin pathway. Biomed Pharmacother. 2018 Mar;99:271-277. doi:
10.1016/j.biopha.2018.01.066. PMID: 29334671.
2. Lei X, Ma N, Liang Y, Liu J, Zhang P, Han Y, Chen W, Du L, Qu B. Glucosamine protects against radiation-induced lung injury
via inhibition of epithelial-mesenchymal transition. J Cell Mol Med. 2020 Sep;24(18):11018-11023. doi: 10.1111/jcmm.15662. Epub
2020 Jul 22. PMID: 32700471; PMCID: PMC7521322.
In vivo protocol:
1. Hwang JS, Kim KH, Park J, Kim SM, Cho H, Lee Y, Han IO. Glucosamine improves survival in a mouse model of sepsis and
attenuates sepsis-induced lung injury and inflammation. J Biol Chem. 2019 Jan 11;294(2):608-622. doi: 10.1074/jbc.RA118.004638.
Epub 2018 Nov 19. PMID: 30455348; PMCID: PMC6333887.
2. Lei X, Ma N, Liang Y, Liu J, Zhang P, Han Y, Chen W, Du L, Qu B. Glucosamine protects against radiation-induced lung injury
via inhibition of epithelial-mesenchymal transition. J Cell Mol Med. 2020 Sep;24(18):11018-11023. doi: 10.1111/jcmm.15662. Epub
2020 Jul 22. PMID: 32700471; PMCID: PMC7521322.
1: Becherirat S, Lanhers MC, Socha M, Yemloul M, Astier A, Loboda C, Aniceto N, Gibaud S. The antitumor effects of an arsthinol-cyclodextrin complex in a heterotopic mouse model of glioma. Eur J Pharm Biopharm. 2013 Nov;85(3 Pt A):560-8. doi: 10.1016/j.ejpb.2013.06.021. Epub 2013 Jul 4. PubMed PMID: 23831266. 2: Ajana I, Astier A, Gibaud S. Arsthinol nanosuspensions: pharmacokinetics and anti-leukaemic activity on NB4 promyelocytic leukaemia cells. J Pharm Pharmacol. 2009 Oct;61(10):1295-301. doi: 10.1211/jpp/61.10.0004. PubMed PMID: 19814860. 1: Gommans YMM, Runhaar J, Jacobs ML, Bierma-Zeinstra SMA. The Effect of Prolonged Glucosamine Usage on HbA1c Levels and New-Onset Diabetes Mellitus in Overweight and Obese Middle-Aged Women. Am J Med. 2017 Jun;130(6):731-737.e6. doi: 10.1016/j.amjmed.2016.11.038. Epub 2016 Dec 21. PubMed PMID: 28011309.
2: Pohlig F, Ulrich J, Lenze U, Mühlhofer HM, Harrasser N, Suren C, Schauwecker J, Mayer-Kuckuk P, von Eisenhart-Rothe R. Glucosamine sulfate suppresses the expression of matrix metalloproteinase-3 in osteosarcoma cells in vitro. BMC Complement Altern Med. 2016 Aug 25;16(1):313. doi: 10.1186/s12906-016-1315-6. PubMed PMID: 27562075; PubMed Central PMCID: PMC5000453.
3: Bruyère O, Altman RD, Reginster JY. Efficacy and safety of glucosamine sulfate in the management of osteoarthritis: Evidence from real-life setting trials and surveys. Semin Arthritis Rheum. 2016 Feb;45(4 Suppl):S12-7. doi: 10.1016/j.semarthrit.2015.11.011. Epub 2015 Dec 2. Review. PubMed PMID: 26806187.
4: Notarnicola A, Maccagnano G, Moretti L, Pesce V, Tafuri S, Fiore A, Moretti B. Methylsulfonylmethane and boswellic acids versus glucosamine sulfate in the treatment of knee arthritis: Randomized trial. Int J Immunopathol Pharmacol. 2016 Mar;29(1):140-6. doi: 10.1177/0394632015622215. Epub 2015 Dec 18. PubMed PMID: 26684635; PubMed Central PMCID: PMC5806735.