Bredinin
Basic information
- CAS
50924-49-7- Standard SMILES
NC(=O)c1ncn(C2OC(CO)C(O)C2O)c1O- InChIKey
HZQDCMWJEBCWBR-UHFFFAOYSA-N- Molecular formula
- C9H13N3O6
- Average molar mass
- 259.22 g/mol
- Monoisotopic mass
- 259.08043514
Names & identifiers
- Preferred name
- Bredinin
- IUPAC
- 1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxyimidazole-4-carboxamide
- English name
- Mizoribine
- Molecular formula
- C9H13N3O6
- Molecular weight
- 259.22
Names & synonyms
1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxyimidazole-4-carboxamide1-(3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)-5-hydroxyimidazole-4-carboxamideRefChem:917534BredininNSC289637NSC 289637;HE 69SCHEMBL7119orb3218421H-Imidazole-4-carboxamide, 5-hydroxy-1-.beta.-D-ribofuranosyl-CHEMBL165000HMS3372M17HMS3869H13
Show more names
bredinineHE 69MizorbineMIZORIBINEMizoribinab-BredininNSC 289637Brn 4151713Mizoribine RS
s1384AKOS0158959341-[3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-hydroxy-imidazole-4-carboxamideLS-13657NCI60_002375N'-(beta-D-Ribofuranosyl)-5-hydroxy-imida-zole-4-carboxamide
Database identifiers
- CAS
50924-49-7- PubChem CID
- 4213
- ChEMBL
CHEMBL165000
Properties
Computed structural properties
- XLogP
- -1.9
- Topological polar surface area
- 151 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 3
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 329
Physicochemical properties
- Melting point
- 2000 C · >2000C
- alpha
- 27 · D27 -35° (c = 0.8 in H2O)
- Boiling point
- 402.47 °C · 402.47°C (rough estimate)
- Density
- 1.4155 · 1.4155 (rough estimate)
- refractive index
- 1.51 · 1.5100 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- DMSO (Slightly), Water (Slightly)
- form
- Solid
- pka
- 6.75 · 6.75(at 25℃)
- color
- White to Off-White
- λmax
- 280 nm · 280nm(lit.)
- Merck
- 14 · 14,6222
- InChI
- InChI=1/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-/s3
- InChIKey
- HZQDCMWJEBCWBR-UUOKFMHZSA-N
- SMILES
- C1N([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(O)=C(C(N)=O)N=1 |&1:2,4,7,9,r|
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- rtecs
- NI3980000
- hs_code
- 29349990
- Toxicity
- LD50 in mice (g/kg): >1.5 i.v., >2.4 i.p. (Mizuno, 1975)
- risk_code
- 46-60-61-36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- T
- safety_code
- 53-22-26-36/37/39-45
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335-H360
- Hazard Classifications
- Eye Irrit. 2Repr. 1BSkin Irrit. 2STOT SE 3
- Precautionary statements
- P201-P302+P352-P305+P351+P338-P308+P313
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.
Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms.
Agents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585)
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging.
Substances that inhibit the growth or reproduction of BACTERIA.
Applications
DescriptionMizoribine is an orally active immunosuppressant isolated from Eupenicillium brefeldianum. It is reported to inhibit both cell-mediated and antibody mediated immune responses. Mizoribine is approved for use in the prevention of rejection of kidney transplants.
DescriptionMizoribine is an imidazole nucleoside with immunosuppressive properties. It inhibits T cell proliferation in response to various mitogenic stimuli by 10-100% when used at concentrations ranging from 1 to 50 μg/mL. Mizoribine inhibits proliferation of stimulated T cells (IC50 = 5 μg/ml), which can be reversed by guanosine. It also inhibits guanine nucleotide formation in T cells, reducing GTP pools by 40-60% when used at a concentration of 5 μg/ml. Mizoribine inhibits replication of hepatitis C virus (HCV) RNA in vitro (IC50 = 100 μM). It suppresses glomerulosclerosis, urinary albumin excretion, interstitial fibrotic lesions, and macrophage infiltration into glomeruli and the interstitium in a rat model of type 2 diabetes when used at doses of 5 or 10 mg/kg. Mizoribine also reduces MCP-1, osteopontin (OPN), and TGF-β1 mRNA expression in the kidney in the same model. Formulations containing mizoribine have been used for the prevention of rejection after renal transplantation as well as in the treatment of lupus nephritis, rheumatoid arthritis, and primary nephritic syndrome.
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