Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C9H13N3O6 |
| Molecular Weight | 259.216 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(=O)C1=C(O)N(C=N1)[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O
InChI
InChIKey=HZQDCMWJEBCWBR-UUOKFMHZSA-N
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
| Molecular Formula | C9H13N3O6 |
| Molecular Weight | 259.216 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
http://www.ncbi.nlm.nih.gov/pubmed/20052390
Curator's Comment: description was created based on several sources, including
http://www.ncbi.nlm.nih.gov/pubmed/20052390
Mizoribine (MZB) is an imidazole nucleoside and an immunosuppressive agent. Eupenicillium brefeldianum, an ascomycetes harvested from the soil of Hachijo Island, Tokyo, Japan, in 1971, produces mizoribine (MZB). MZB is a nucleoside of the imidazole class, and was found to have weak antimicrobial activity against Candida albicans, but it proved ineffective against experimental candidiasis. MZB has been approved in Japan for the treatment of lupus nephritis (1990), rheumatoid arthritis (1992), and primary nephritic syndrome (1995), and in these diseases, it has often been used in combination with corticosteroids and/or anti-inflammatory drugs. Mizoribine also has been used in renal transplantation, and in steroid-resistant nephrotic syndrome. After phosphorylation, misoribine-5’-monophosphate (MZB-P) inhibits guanosine monophosphate (GMP) synthesis by antagonistic blocking of inosine monophasphate dehydrogenase (IMPDH) and GMP-synthetase in the pathway from inosine [ 5’-] monophasphate (IMP) to GMP in the purine synthesis system. MZB-P appears to almost completely inhibits guanine nucleotide synthesis Suppressive effect of MZB on cell growth is attributable to MZB-P and not to MZB itself. Thus, MZB has less toxicity than azathioprine, another immunosuppressant used for some of the same diseases.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2002 |
4.0 nM [Ki] | ||
Target ID: CHEMBL1822 |
8.0 nM [Ki] | ||
Target ID: CHEMBL5721 |
10.0 µM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | MIZORIBINE Approved UseUnknown Launch Date1989 |
|||
| Primary | MIZORIBINE Approved UseUnknown Launch Date1991 |
|||
| Primary | Mizoribine Approved UseUnknown Launch Date1994 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.7 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17096684/ |
3 mg/kg single, oral dose: 3 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
MIZORIBINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
5.5 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17096684/ |
6 mg/kg single, oral dose: 6 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
MIZORIBINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
6.6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17096684/ |
9 mg/kg single, oral dose: 9 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
MIZORIBINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
9.6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17096684/ |
12 mg/kg single, oral dose: 12 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
MIZORIBINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
4.7 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17096684/ |
6 mg/kg 1 times / day multiple, oral dose: 6 mg/kg route of administration: Oral experiment type: MULTIPLE co-administered: |
MIZORIBINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
4.6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17096684/ |
6 mg/kg 2 times / day multiple, oral dose: 6 mg/kg route of administration: Oral experiment type: MULTIPLE co-administered: |
MIZORIBINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2.3 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18661478/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
MIZORIBINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
18.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17096684/ |
3 mg/kg single, oral dose: 3 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
MIZORIBINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
38.3 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17096684/ |
6 mg/kg single, oral dose: 6 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
MIZORIBINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
46.4 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17096684/ |
9 mg/kg single, oral dose: 9 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
MIZORIBINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
61.9 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17096684/ |
12 mg/kg single, oral dose: 12 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
MIZORIBINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
35.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17096684/ |
6 mg/kg 1 times / day multiple, oral dose: 6 mg/kg route of administration: Oral experiment type: MULTIPLE co-administered: |
MIZORIBINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
31.2 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17096684/ |
6 mg/kg 2 times / day multiple, oral dose: 6 mg/kg route of administration: Oral experiment type: MULTIPLE co-administered: |
MIZORIBINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
13.2 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18661478/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
MIZORIBINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17096684/ |
3 mg/kg single, oral dose: 3 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
MIZORIBINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17096684/ |
6 mg/kg single, oral dose: 6 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
MIZORIBINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17096684/ |
9 mg/kg single, oral dose: 9 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
MIZORIBINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17096684/ |
12 mg/kg single, oral dose: 12 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
MIZORIBINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17096684/ |
6 mg/kg 1 times / day multiple, oral dose: 6 mg/kg route of administration: Oral experiment type: MULTIPLE co-administered: |
MIZORIBINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
3.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17096684/ |
6 mg/kg 2 times / day multiple, oral dose: 6 mg/kg route of administration: Oral experiment type: MULTIPLE co-administered: |
MIZORIBINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
3.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18661478/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
MIZORIBINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
12 mg/kg single, oral Highest studied dose Dose: 12 mg/kg Route: oral Route: single Dose: 12 mg/kg Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Sources: |
|
6 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 6 mg/kg, 2 times / day Route: oral Route: multiple Dose: 6 mg/kg, 2 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Sources: |
Other AEs: Uric acid increased... Other AEs: Uric acid increased Sources: |
300 mg 2 times / day multiple, oral Recommended Dose: 300 mg, 2 times / day Route: oral Route: multiple Dose: 300 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
Disc. AE: Renal failure, Hyperuricemia... AEs leading to discontinuation/dose reduction: Renal failure Sources: Hyperuricemia |
50 mg 3 times / day multiple, oral Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Pruritus, Joint pain... AEs leading to discontinuation/dose reduction: Pruritus (1.7%) Sources: Joint pain (1.7%) Alteration of consciousness (1.7%) Liver disease (1.7%) Nausea (1.7%) Vomiting (1.7%) Diarrhea (1.7%) Abdominal pain (1.7%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Uric acid increased | 6 mg/kg 2 times / day multiple, oral Highest studied dose Dose: 6 mg/kg, 2 times / day Route: oral Route: multiple Dose: 6 mg/kg, 2 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Sources: |
|
| Hyperuricemia | Disc. AE | 300 mg 2 times / day multiple, oral Recommended Dose: 300 mg, 2 times / day Route: oral Route: multiple Dose: 300 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
| Renal failure | Disc. AE | 300 mg 2 times / day multiple, oral Recommended Dose: 300 mg, 2 times / day Route: oral Route: multiple Dose: 300 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
| Abdominal pain | 1.7% Disc. AE |
50 mg 3 times / day multiple, oral Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Alteration of consciousness | 1.7% Disc. AE |
50 mg 3 times / day multiple, oral Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Diarrhea | 1.7% Disc. AE |
50 mg 3 times / day multiple, oral Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Joint pain | 1.7% Disc. AE |
50 mg 3 times / day multiple, oral Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Liver disease | 1.7% Disc. AE |
50 mg 3 times / day multiple, oral Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Nausea | 1.7% Disc. AE |
50 mg 3 times / day multiple, oral Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Pruritus | 1.7% Disc. AE |
50 mg 3 times / day multiple, oral Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Vomiting | 1.7% Disc. AE |
50 mg 3 times / day multiple, oral Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Novel anticytomegalovirus activity of immunosuppressant mizoribine and its synergism with ganciclovir. | 2010-06 |
|
| The immunosuppressive drug mizoribine directly prevents podocyte injury in puromycin aminonucleoside nephrosis. | 2010 |
|
| Inhibitory effect of mizoribine and ribavirin on the replication of severe acute respiratory syndrome (SARS)-associated coronavirus. | 2005-06 |
|
| Mizoribine inhibits hepatitis C virus RNA replication: effect of combination with interferon-alpha. | 2005-05-13 |
|
| Inhibition of bovine viral diarrhea virus (BVDV) by mizoribine: synergistic effect of combination with interferon-alpha. | 2004-12 |
|
| Inhibitors of the IMPDH enzyme as potential anti-bovine viral diarrhoea virus agents. | 2002-11 |
|
| Inosine-5'-monophosphate dehydrogenase is required for mitogenic competence of transformed pancreatic beta cells. | 2001-01 |
|
| Mizoribine in steroid-dependent nephrotic syndrome of childhood. | 1997-10 |
|
| Mizoribine reduces urinary protein excretion in rats given puromycin aminonucleoside. | 1996 |
|
| [Comparison of the effects of various immunosuppressive drugs on subrenal capsule assay (SRC assay)]. | 1990-07 |
|
| [Suppressive effect of mizoribine on progression of bovine serum albumin nephritis in mice]. | 1987-04 |
Sample Use Guides
Oral administration, daily dose of 150mg (50mg/tablet)
Route of Administration:
Oral
The immunosuppressive drug Mizoribine (MIZ) was found to increase the antiviral activity of Acyclovir (ACV) against herpesvirus infections, raising interesting perspectives on new combined therapeutic strategies. In this study the anti-CpHV-1 activity in vitro of ACV alone or in combination with MIZ was characterized. When applied alone at non-toxic concentrations, ACV had a slight effect on CpHV-1 replication while in combination with MIZ a dose-dependent inhibition of the virus yield was observed with an IC50 of ACV of 28.5 µM.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:07:02 GMT 2025
by
admin
on
Mon Mar 31 18:07:02 GMT 2025
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| Record UNII |
4JR41A10VP
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| Record Status |
Validated (UNII)
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| Record Version |
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-
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| Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
780820
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NCI_THESAURUS |
C574
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admin on Mon Mar 31 18:07:03 GMT 2025 , Edited by admin on Mon Mar 31 18:07:03 GMT 2025
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100000080884
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SUB09019MIG
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5120
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289637
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m7578
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DB12617
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CHEMBL245019
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50924-49-7
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DTXSID8045777
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C010052
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4JR41A10VP
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Mizoribine
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3363
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C66172
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104762
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