Mizoribine
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MedKoo CAT#: 406375

CAS#: 50924-49-7

Description: Mizoribine (INN, trade name Bredinin) is an immunosuppressive drug. The compound was first observed in Tokyo, Japan, in 1971. It is a natural product, first isolated from the mould Eupenicillium brefeldianum. Mizoribine (MZB) is an imidazole nucleoside that has been used in renal transplantation, and in steroid-resistant nephrotic syndrome, IgA nephropathy, lupus, as well as for adults with rheumatoid arthritis, lupus nephritis and other rheumatic diseases.

Chemical Structure

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Mizoribine
CAS# 50924-49-7
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 406375
Name: Mizoribine
CAS#: 50924-49-7
Chemical Formula: C9H13N3O6
Exact Mass: 259.08
Molecular Weight: 259.220
Elemental Analysis: C, 41.70; H, 5.05; N, 16.21; O, 37.03

Price and Availability

Size Price Availability Quantity
50mg USD 90 Ready to ship
100mg USD 150 Ready to ship
200mg USD 250 Ready to ship
500mg USD 550 Ready to ship
1g USD 950 Ready to ship
2g USD 1650 Ready to ship
5g USD 3650 Ready to ship
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Synonym: Mizoribine; Bredinin; HE 69; He69; He-69; NSC289637; NSC-289637; NSC 289637.

IUPAC/Chemical Name: 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-hydroxy-1H-imidazole-4-carboxamide

InChi Key: HZQDCMWJEBCWBR-UUOKFMHZSA-N

InChi Code: InChI=1S/C9H13N3O6/c10-7(16)4-8(17)12(2-11-4)9-6(15)5(14)3(1-13)18-9/h2-3,5-6,9,13-15,17H,1H2,(H2,10,16)/t3-,5-,6-,9-/m1/s1

SMILES Code: O=C(C1=C(O)N([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C=N1)N

Appearance: white 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, not in water

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:  MZB exerts its activity through selective inhibition of inosine monophosphate synthetase and guanosine monophosphate synthetase, resulting in the complete inhibition of guanine nucleotide synthesis without incorporation into nucleotides. It arrests DNA synthesis in the S phase of cellular division. Thus, MZB has less toxicity than azathioprine, another immunosuppressant used for some of the same diseases. (http://en.wikipedia.org/wiki/Mizoribine) (Last updated: 8/06/2015)    

Biological target: Mizoribine (NSC 289637) inhibits HCV RNA replication with IC50 of approximately 100 μM.
In vitro activity: The ECIS data (Fig. 2) showed that the capacitance of the 3 cell types was significantly higher in the groups treated with 1 or 10µg/ml doses of MZR (Mizoribine) compared with the group treated with 0.1µg/ml of MZR and the positive control group (p＜0.05). For the NRK cells, the group treated with 10µg/ml of MZR exhibited higher capacitance compared with the group treated with 1µg/ml of MZR (p＜0.05). However, the ECIS data for the UB and rKS56 cells treated with 10µg/ml of MZR were not significantly different from the corresponding data for the groups of each cell type treated with 1µg/ml of MZR. These results suggested that MZR suppressed cell proliferation and that the proliferation-suppressive capacity of MZR is dose-dependent. Reference: Acta Med Okayama. 2014;68(1):7-15. https://pubmed.ncbi.nlm.nih.gov/24553483/
In vivo activity: The present study demonstrated that immunosuppressant therapy with mizoribine alleviates renal inflammation and cell death accompanied by caspase-1 activation in aldosterone-salt-treated rats. Mizoribine also shows beneficial effects on hypertension, urinary protein excretion, and renal fibrosis. Therefore, mizoribine may be a therapeutic option for salt-sensitive hypertension and renal fibrosis. Reference: PLoS One. 2014; 9(4): e93513. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3973594/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 43.0 165.88
Water 51.0 196.74

Preparing Stock Solutions

The following data is based on the product molecular weight 259.22 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. Horimoto N, Kitamura S, Tsuji K, Makino H. Mizoribine inhibits the proliferation of renal stem/progenitor cells by G1/S arrest during renal regeneration. Acta Med Okayama. 2014;68(1):7-15. doi: 10.18926/AMO/52138. PMID: 24553483. 2. Picard-Jean F, Bougie I, Shuto S, Bisaillon M. The immunosuppressive agent mizoribine monophosphate is an inhibitor of the human RNA capping enzyme. PLoS One. 2013;8(1):e54621. doi: 10.1371/journal.pone.0054621. Epub 2013 Jan 17. PMID: 23349942; PMCID: PMC3547949. 3. Li SF, Gong MJ, Sun YF, Shao JJ, Zhang YG, Chang HY. In Vitro and in Vivo Antiviral Activity of Mizoribine Against Foot-And-Mouth Disease Virus. Molecules. 2019 May 3;24(9):1723. doi: 10.3390/molecules24091723. PMID: 31058822; PMCID: PMC6539406. 4. Doi T, Doi S, Nakashima A, Ueno T, Yokoyama Y, Kohno N, Masaki T. Mizoribine ameliorates renal injury and hypertension along with the attenuation of renal caspase-1 expression in aldosterone-salt-treated rats. PLoS One. 2014 Apr 2;9(4):e93513. doi: 10.1371/journal.pone.0093513. PMID: 24695748; PMCID: PMC3973594.
In vitro protocol: 1. Horimoto N, Kitamura S, Tsuji K, Makino H. Mizoribine inhibits the proliferation of renal stem/progenitor cells by G1/S arrest during renal regeneration. Acta Med Okayama. 2014;68(1):7-15. doi: 10.18926/AMO/52138. PMID: 24553483. 2. Picard-Jean F, Bougie I, Shuto S, Bisaillon M. The immunosuppressive agent mizoribine monophosphate is an inhibitor of the human RNA capping enzyme. PLoS One. 2013;8(1):e54621. doi: 10.1371/journal.pone.0054621. Epub 2013 Jan 17. PMID: 23349942; PMCID: PMC3547949.
In vivo protocol: 1. Li SF, Gong MJ, Sun YF, Shao JJ, Zhang YG, Chang HY. In Vitro and in Vivo Antiviral Activity of Mizoribine Against Foot-And-Mouth Disease Virus. Molecules. 2019 May 3;24(9):1723. doi: 10.3390/molecules24091723. PMID: 31058822; PMCID: PMC6539406. 2. Doi T, Doi S, Nakashima A, Ueno T, Yokoyama Y, Kohno N, Masaki T. Mizoribine ameliorates renal injury and hypertension along with the attenuation of renal caspase-1 expression in aldosterone-salt-treated rats. PLoS One. 2014 Apr 2;9(4):e93513. doi: 10.1371/journal.pone.0093513. PMID: 24695748; PMCID: PMC3973594.

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1: Zhang X, Fu S, Han S, Zheng X, Wang L. The argument for the use of mizoribine in renal transplantation: a meta-analysis and systemic review. Transpl Immunol. 2013 Mar;28(2-3):106-11. doi: 10.1016/j.trim.2012.12.003. Epub 2013 Jan 9. Review. PubMed PMID: 23313278.

2: Sawada T. [Treatment of rheumatic diseases: current status and future prospective. Topics: II. Immunosuppressant/antirheumatic drugs; 5. Leflunomide and mizoribine]. Nihon Naika Gakkai Zasshi. 2011 Oct 10;100(10):2929-35. Review. Japanese. PubMed PMID: 22175133.

3: Kawasaki Y. Mizoribine: a new approach in the treatment of renal disease. Clin Dev Immunol. 2009;2009:681482. doi: 10.1155/2009/681482. Epub 2009 Dec 13. Review. PubMed PMID: 20052390; PubMed Central PMCID: PMC2801010.

4: Kondo H, Iizuka N. [Mizoribine]. Nihon Rinsho. 2005 May;63 Suppl 5:708-12. Review. Japanese. PubMed PMID: 15954433.

5: Tanaka H, Abe T, Nishimura S, Sakai H, Kimura H, Oki M, Nojima M, Taga M, Matsumoto S, Takahashi H, Imai K. [A case of rheumatoid arthritis/Sjogren's syndrome with acute renal failure due to hyperuricemia associated with mizoribine therapy]. Nihon Rinsho Meneki Gakkai Kaishi. 2004 Jun;27(3):171-6. Review. Japanese. PubMed PMID: 15291254.

6: Tsuzuki K. Role of mizoribine in renal transplantation. Pediatr Int. 2002 Apr;44(2):224-31. Review. PubMed PMID: 11896891.

7: Honda M. Nephrotic syndrome and mizoribine in children. Pediatr Int. 2002 Apr;44(2):210-6. Review. PubMed PMID: 11896889.

8: Takei S. Mizoribine in the treatment of rheumatoid arthritis and juvenile idiopathic arthritis. Pediatr Int. 2002 Apr;44(2):205-9. Review. PubMed PMID: 11896888.

9: Yokota S. Mizoribine: mode of action and effects in clinical use. Pediatr Int. 2002 Apr;44(2):196-8. Review. PubMed PMID: 11896886.

10: Ishikawa H. Mizoribine and mycophenolate mofetil. Curr Med Chem. 1999 Jul;6(7):575-97. Review. PubMed PMID: 10390602.