Meglumine
featured

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 540283

CAS#: 6284-40-8

Description: Meglumine is an amino sugar and sorbitol derivative used as a bulking agent in the formulation of pharmaceutical drugs.

Chemical Structure

img
Meglumine
CAS# 6284-40-8
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 540283
Name: Meglumine
CAS#: 6284-40-8
Chemical Formula: C7H17NO5
Exact Mass: 195.11
Molecular Weight: 195.215
Elemental Analysis: C, 43.07; H, 8.78; N, 7.18; O, 40.98

Price and Availability

Size Price Availability Quantity
25g USD 250 2 weeks
Bulk inquiry

Synonym: 1-Deoxy-1-(methylamino)-D-glucitol; Iosulamide; N-Methyl-D-glucamine; Sorbitol, 1-deoxy-1-methylamino-

IUPAC/Chemical Name: (2R,3R,4R,5S)-6-(methylamino)hexane-1,2,3,4,5-pentaol

InChi Key: MBBZMMPHUWSWHV-BDVNFPICSA-N

InChi Code: InChI=1S/C7H17NO5/c1-8-2-4(10)6(12)7(13)5(11)3-9/h4-13H,2-3H2,1H3/t4-,5+,6+,7+/m0/s1

SMILES Code: O[C@H]([C@H]([C@@H]([C@@H](CO)O)O)O)CNC

Appearance: Solid powder

Purity: >98% (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: >2 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:
Product Data
Instruction:
View handling instruction
Biological target: Meglumine (Methylglucamine) is an amino sugar derived from sorbitol.
In vitro activity: Meglumine-oleic acid (MEG-OA) was arranged as hexagonal liquid crystals at 30-70 wt% water content, probably due to its curvature and increased water solubility. Meglumine-stearic acid (MEG-SA) at 10-80 wt% water content self-assembled as a lamellar polymeric network, which can be explained by the low mobility of MEG-SA in water due to hydrophobic interactions between fatty acid chains and H-bonds between meglumine and water molecules. Reference: Colloids Surf B Biointerfaces. 2019 Dec 1;184:110523. https://pubmed.ncbi.nlm.nih.gov/31634799/
In vivo activity: Male Sprague-Dawley rats were subjected to 15 min global cerebral ischemia, and meglumine cyclic adenylate was treated through tail intravenous injection 30 min before ischemia. Pretreatment with meglumine cyclic adenylate not only significantly ameliorated neuron loss in CA1 region after global cerebral ischemia but also enhanced STAT3-Ser727 phosphorylation, increased mitochondrial STAT3, and decreased cytosolic Cyt c and active caspase-3. Reference: J Stroke Cerebrovasc Dis. 2023 Jan;32(1):106892. https://pubmed.ncbi.nlm.nih.gov/36402093/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 24.5 125.50
Water 44.5 227.95

Preparing Stock Solutions

The following data is based on the product molecular weight 195.22 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. Fernández OL, Ramírez LG, Díaz-Varela M, Tacchini-Cottier F, Saravia NG. Neutrophil Activation: Influence of Antimony Tolerant and Susceptible Clinical Strains of L. (V.) panamensis and Meglumine Antimoniate. Front Cell Infect Microbiol. 2021 Sep 22;11:710006. doi: 10.3389/fcimb.2021.710006. PMID: 34631596; PMCID: PMC8493214. 2. de Souza ALR, Fonseca M, Ferreira LMB, Kurokawa SSS, Kiill CP, Ferreira NN, Dos Santos Pyrrho A, Sarmento VHV, Silva AM, Gremião MPD, Ribeiro CA. Meglumine-based supra-amphiphile self-assembled in water as a skin drug delivery system: Influence of unfrozen bound water in the system bioadhesiveness. Colloids Surf B Biointerfaces. 2019 Dec 1;184:110523. doi: 10.1016/j.colsurfb.2019.110523. Epub 2019 Sep 23. PMID: 31634799. 3. Niu XQ, Li DD, Bao YJ, Yang Q, Liu YK, Lu F, Yan JZ, Yin XH, Li C. Neuroprotective effect of meglumine cyclic adenylate against ischemia/reperfusion injury via STAT3-Ser727 phosphorylation. J Stroke Cerebrovasc Dis. 2023 Jan;32(1):106892. doi: 10.1016/j.jstrokecerebrovasdis.2022.106892. Epub 2022 Nov 17. PMID: 36402093. 4. Cardoso JMO, Brito RCF, Mathias FAS, Reis LES, Vieira JFP, Ostolin TLVDP, Andrade HM, Ramos GS, Frézard F, Aguiar-Soares RDO, Roatt BM, Reis AB. Comparative evaluation of meglumine antimoniate encapsulated in a mixture of conventional and PEGylated liposomes and immunotherapy using an anti-canine IL-10 receptor-blocking monoclonal antibody on canine visceral leishmaniasis. Mol Immunol. 2022 Jan;141:70-78. doi: 10.1016/j.molimm.2021.11.011. Epub 2021 Nov 20. PMID: 34814056.
In vitro protocol: 1. Fernández OL, Ramírez LG, Díaz-Varela M, Tacchini-Cottier F, Saravia NG. Neutrophil Activation: Influence of Antimony Tolerant and Susceptible Clinical Strains of L. (V.) panamensis and Meglumine Antimoniate. Front Cell Infect Microbiol. 2021 Sep 22;11:710006. doi: 10.3389/fcimb.2021.710006. PMID: 34631596; PMCID: PMC8493214. 2. de Souza ALR, Fonseca M, Ferreira LMB, Kurokawa SSS, Kiill CP, Ferreira NN, Dos Santos Pyrrho A, Sarmento VHV, Silva AM, Gremião MPD, Ribeiro CA. Meglumine-based supra-amphiphile self-assembled in water as a skin drug delivery system: Influence of unfrozen bound water in the system bioadhesiveness. Colloids Surf B Biointerfaces. 2019 Dec 1;184:110523. doi: 10.1016/j.colsurfb.2019.110523. Epub 2019 Sep 23. PMID: 31634799.
In vivo protocol: 1. Niu XQ, Li DD, Bao YJ, Yang Q, Liu YK, Lu F, Yan JZ, Yin XH, Li C. Neuroprotective effect of meglumine cyclic adenylate against ischemia/reperfusion injury via STAT3-Ser727 phosphorylation. J Stroke Cerebrovasc Dis. 2023 Jan;32(1):106892. doi: 10.1016/j.jstrokecerebrovasdis.2022.106892. Epub 2022 Nov 17. PMID: 36402093. 2. Cardoso JMO, Brito RCF, Mathias FAS, Reis LES, Vieira JFP, Ostolin TLVDP, Andrade HM, Ramos GS, Frézard F, Aguiar-Soares RDO, Roatt BM, Reis AB. Comparative evaluation of meglumine antimoniate encapsulated in a mixture of conventional and PEGylated liposomes and immunotherapy using an anti-canine IL-10 receptor-blocking monoclonal antibody on canine visceral leishmaniasis. Mol Immunol. 2022 Jan;141:70-78. doi: 10.1016/j.molimm.2021.11.011. Epub 2021 Nov 20. PMID: 34814056.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Navaei A, Rasoolian M, Momeni A, Emami S, Rafienia M. Double-walled microspheres loaded with meglumine antimoniate: preparation, characterization and in vitro release study. Drug Dev Ind Pharm. 2014 Jun;40(6):701-10. doi: 10.3109/03639045.2013.777734. Epub 2013 Apr 17. PubMed PMID: 23594302.

2: Giorgi H, Ammerman J, Briffaux JP, Fretellier N, Corot C, Bourrinet P. Non-clinical safety assessment of gadoterate meglumine (Dotarem(®)) in neonatal and juvenile rats. Regul Toxicol Pharmacol. 2015 Dec;73(3):960-70. doi: 10.1016/j.yrtph.2015.09.018. Epub 2015 Sep 14. PubMed PMID: 26382613.

3: Ferreira FM, Castro RA, Batista MA, Rossi FM, Silveira-Lemos D, Frézard F, Moura SA, Rezende SA. Association of water extract of green propolis and liposomal meglumine antimoniate in the treatment of experimental visceral leishmaniasis. Parasitol Res. 2014 Feb;113(2):533-43. doi: 10.1007/s00436-013-3685-8. Epub 2013 Nov 30. PubMed PMID: 24292604.

4: Khouri Chalouhi K, Papini GDE, Bandirali M, Sconfienza LM, Di Leo G, Sardanelli F. Less is better? Intraindividual and interindividual comparison between 0.075 mmol/kg of gadobenate dimeglumine and 0.1 mmol/kg of gadoterate meglumine for cranial MRI. Eur J Radiol. 2014 Jul;83(7):1245-1249. doi: 10.1016/j.ejrad.2014.03.030. Epub 2014 Apr 13. PubMed PMID: 24816087.

5: Ferreira e Vasconcellos Ede C, Pimentel MI, Valete-Rosalino CM, Madeira Mde F, Schubach Ade O. Resolution of cutaneous leishmaniasis after acute eczema due to intralesional meglumine antimoniate. Rev Inst Med Trop Sao Paulo. 2014 Jul-Aug;56(4):361-2. PubMed PMID: 25076440; PubMed Central PMCID: PMC4131825.

6: Gutiérrez J, Vallejo B, Barbosa H, Pinzón J, Delgado G. In vitro analysis regarding the safety of components used in a film-based therapeutic system loaded with meglumine antimoniate and its activity toward Leishmania major experimental infections: a preliminary study. Immunopharmacol Immunotoxicol. 2013 Jun;35(3):321-8. doi: 10.3109/08923973.2013.768635. Epub 2013 Mar 11. PubMed PMID: 23473403.

7: Kramer JH, Arnoldi E, François CJ, Wentland AL, Nikolaou K, Wintersperger BJ, Grist TM. Dynamic and static magnetic resonance angiography of the supra-aortic vessels at 3.0 T: intraindividual comparison of gadobutrol, gadobenate dimeglumine, and gadoterate meglumine at equimolar dose. Invest Radiol. 2013 Mar;48(3):121-8. doi: 10.1097/RLI.0b013e31827752b4. PubMed PMID: 23211552; PubMed Central PMCID: PMC3818529.

8: Rubiano LC, Miranda MC, Muvdi Arenas S, Montero LM, Rodríguez-Barraquer I, Garcerant D, Prager M, Osorio L, Rojas MX, Pérez M, Nicholls RS, Gore Saravia N. Noninferiority of miltefosine versus meglumine antimoniate for cutaneous leishmaniasis in children. J Infect Dis. 2012 Feb 15;205(4):684-92. doi: 10.1093/infdis/jir816. Epub 2012 Jan 11. PubMed PMID: 22238470; PubMed Central PMCID: PMC3266136.

9: Saridomichelakis MN, Xenoulis PG, Chatzis MK, Kasabalis D, Steiner JM, Suchodolski JS, Petanides T. Thyroid function in 36 dogs with leishmaniosis due to Leishmania infantum before and during treatment with allopurinol with or without meglumine antimonate. Vet Parasitol. 2013 Oct 18;197(1-2):22-8. doi: 10.1016/j.vetpar.2013.04.038. Epub 2013 Apr 26. PubMed PMID: 23685064.

10: Córdoba S, Gandolfo Cano M, Aguado M, Huerta-Brogera M, Romero A, Martínez-Morán C, Borbujo J. Delayed allergic skin reactions due to intralesional meglumine antimoniate therapy for cutaneous leishmaniasis. Allergy. 2012 Dec;67(12):1609-11. doi: 10.1111/all.12050. Epub 2012 Oct 16. PubMed PMID: 23067046.

11: Ezzine Sebai N, Mrabet N, Khaled A, Zeglaoui F, Kharfi M, Fazaa B, Kamoun MR. [Side effects of meglumine antimoniate in cutaneous leishmaniasis: 15 cases]. Tunis Med. 2010 Jan;88(1):9-11. French. PubMed PMID: 20415206.

12: Delgado G, Sánchez Y, Plaza D, Mariño A, Granados D. An experimental approach to studying the effectiveness and safety of meglumine antimoniate formulations. Biomed Pharmacother. 2011 Dec;65(8):569-77. doi: 10.1016/j.biopha.2010.12.016. Epub 2011 Jun 23. PubMed PMID: 21733656.

13: Layegh P, Rahsepar S, Rahsepar AA. Systemic meglumine antimoniate in acute cutaneous leishmaniasis: children versus adults. Am J Trop Med Hyg. 2011 Apr;84(4):539-42. doi: 10.4269/ajtmh.2011.10-0002. PubMed PMID: 21460006; PubMed Central PMCID: PMC3062445.

14: Friedrich K, Vieira FA, Porrozzi R, Marchevsky RS, Miekeley N, Grimaldi G Jr, Paumgartten FJ. Disposition of antimony in rhesus monkeys infected with Leishmania braziliensis and treated with meglumine antimoniate. J Toxicol Environ Health A. 2012;75(2):63-75. doi: 10.1080/15287394.2012.624826. PubMed PMID: 22129235.

15: Munir A, Janjua SA, Hussain I. Clinical efficacy of intramuscular meglumine antimoniate alone and in combination with intralesional meglumine antimoniate in the treatment of old world cutaneous leishmaniasis. Acta Dermatovenerol Croat. 2008;16(2):60-4. PubMed PMID: 18541100.

16: Semelka RC, Ramalho J, Vakharia A, AlObaidy M, Burke LM, Jay M, Ramalho M. Gadolinium deposition disease: Initial description of a disease that has been around for a while. Magn Reson Imaging. 2016 Dec;34(10):1383-1390. doi: 10.1016/j.mri.2016.07.016. Epub 2016 Aug 13. PubMed PMID: 27530966.

17: Borborema SE, Schwendener RA, Osso JA Jr, de Andrade HF Jr, do Nascimento N. Uptake and antileishmanial activity of meglumine antimoniate-containing liposomes in Leishmania (Leishmania) major-infected macrophages. Int J Antimicrob Agents. 2011 Oct;38(4):341-7. doi: 10.1016/j.ijantimicag.2011.05.012. Epub 2011 Jul 23. PubMed PMID: 21783345.

18: Shamsi Meymandi S, Zandi S, Aghaie H, Heshmatkhah A. Efficacy of CO(2) laser for treatment of anthroponotic cutaneous leishmaniasis, compared with combination of cryotherapy and intralesional meglumine antimoniate. J Eur Acad Dermatol Venereol. 2011 May;25(5):587-91. doi: 10.1111/j.1468-3083.2010.03781.x. PubMed PMID: 20666876.

19: Liu L, Tamama K, Peck Palmer OM. Selenium Overload? Clin Chem. 2016 Apr;62(4):658. doi: 10.1373/clinchem.2015.247551. PubMed PMID: 27022127.

20: Kato KC, Morais-Teixeira E, Reis PG, Silva-Barcellos NM, Salaün P, Campos PP, Dias Corrêa-Junior J, Rabello A, Demicheli C, Frézard F. Hepatotoxicity of pentavalent antimonial drug: possible role of residual Sb(III) and protective effect of ascorbic acid. Antimicrob Agents Chemother. 2014;58(1):481-8. doi: 10.1128/AAC.01499-13. Epub 2013 Nov 4. PubMed PMID: 24189251; PubMed Central PMCID: PMC3910754.