Glucosamine sulfate
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MedKoo CAT#: 573274

CAS#: 29031-19-4 (sulfate)

Description: Glucosamine sulfate is a natural sugar found in and around the fluid and cartilage that cushion joints.


Chemical Structure

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Glucosamine sulfate
CAS# 29031-19-4 (sulfate)

Theoretical Analysis

MedKoo Cat#: 573274
Name: Glucosamine sulfate
CAS#: 29031-19-4 (sulfate)
Chemical Formula: C6H15NO9S
Exact Mass: 0.00
Molecular Weight: 277.244
Elemental Analysis: C, 25.99; H, 5.45; N, 5.05; O, 51.94; S, 11.56

Price and Availability

Size Price Availability Quantity
1g USD 250 2 Weeks
2g USD 350 2 Weeks
5g USD 550 2 Weeks
10g USD 750 2 Weeks
25g USD 1250 2 Weeks
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Related CAS #: 29031-19-4 (sulfate)   3416-24-8 (free base)   66-84-2 (HCl)  

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

Appearance: Solid powder

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

More Info:

Product Data:
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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 4.0 14.43
Water 90.0 324.62

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.

Recalculate based on batch purity %
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.

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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.