Mizoribine

Mizoribine
Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	none
Legal status
Legal status	℞ (Prescription only)
Identifiers
IUPAC name 5-hydroxy-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamide
Synonyms	1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxyimidazole-4-carboxamide
CAS Number	50924-49-7^Y
PubChem (CID)	104762
ChemSpider	94571
UNII	4JR41A10VP^Y
KEGG	D01392^Y
ECHA InfoCard	100.164.876
Chemical and physical data
Formula	C₉H₁₃N₃O₆
Molar mass	259.21 g/mol
3D model (Jmol)	Interactive image
SMILES C1=NC(=C(N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)N
InChI 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 Key:HZQDCMWJEBCWBR-UUOKFMHZSA-N
(verify)

Mizoribine (INN, trade name Bredinin) is an immunosuppressive drug. The compound was first observed in Tokyo, Japan, in 1971.^[1] 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. 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.

References

↑ Hiroaki Ishikawa (1999). "Mizoribine and Mycophenolate Mofetil". Current Medicinal Chemistry. Bentham Science. 6 (7): 575–597. PMID 10390602.

Immunosuppressive drugs / Immunosuppressants (L04)

Intracellular
(initiation)

Antimetabolites	purine synthesis inhibitors: Azathioprine Mycophenolic acid pyrimidine synthesis inhibitors: Leflunomide Teriflunomide antifolate: Methotrexate

Macrolides/ other IL-2 inhibitors	FKBP/Cyclophilin/Calcineurin: Tacrolimus Ciclosporin Pimecrolimus Abetimus Gusperimus

IMiDs	Lenalidomide Pomalidomide Thalidomide PDE4 inhibitor: Apremilast

Intracellular
(reception)

IL-1 receptor antagonists	Anakinra

mTOR	Sirolimus Everolimus Ridaforolimus Temsirolimus Umirolimus Zotarolimus

Extracellular

Antibodies

Monoclonal

Serum target (noncellular)	Complement component 5 (Eculizumab) TNF (Adalimumab Afelimomab Certolizumab pegol Golimumab Infliximab Nerelimomab) Interleukin 5 (Mepolizumab) Immunoglobulin E (Omalizumab) Interferon (Faralimomab) IL-6 (Elsilimomab) IL-12 and IL-23 (Lebrikizumab Ustekinumab) IL-17A (Secukinumab)

Cellular target	CD3 (Muromonab-CD3 Otelixizumab Teplizumab Visilizumab) CD4 (Clenoliximab Keliximab Zanolimumab) CD11a (Efalizumab) CD18 (Erlizumab) CD20 (Obinutuzumab Rituximab Ocrelizumab Pascolizumab) CD23 (Gomiliximab Lumiliximab) CD40 (Teneliximab Toralizumab) CD62L/L-selectin (Aselizumab) CD80 (Galiximab) CD147/Basigin (Gavilimomab) CD154 (Ruplizumab) BLyS (Belimumab Blisibimod) CTLA-4 (Ipilimumab Tremelimumab) CAT (Bertilimumab Lerdelimumab Metelimumab) Integrin (Natalizumab) Interleukin-6 receptor (Tocilizumab) LFA-1 (Odulimomab) IL-2 receptor/CD25 (Basiliximab Daclizumab Inolimomab) T-lymphocyte (Zolimomab aritox)

Unsorted	Atorolimumab Cedelizumab Fontolizumab Maslimomab Morolimumab Pexelizumab Reslizumab Rovelizumab Siplizumab Talizumab Telimomab aritox Vapaliximab Vepalimomab

Polyclonal

-cept (Fusion)

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. 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.

This article is issued from Wikipedia - version of the 4/2/2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.