CAS 50924-49-7|Mizoribine

Introduction：Basic information about CAS 50924-49-7|Mizoribine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Mizoribine BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Articles43
7. Synonyms

Common Name	Mizoribine
CAS Number	50924-49-7	Molecular Weight	259.216
Density	2.1±0.1 g/cm3	Boiling Point	755.9±60.0 °C at 760 mmHg
Molecular Formula	C₉H₁₃N₃O₆	Melting Point	>200ºC
MSDS	ChineseUSA	Flash Point	410.9±32.9 °C
Symbol	GHS07, GHS08	Signal Word	Danger

Names

Name	1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxyimidazole-4-carboxamide
Synonym	More Synonyms

Mizoribine BiologicalActivity

Description	Mizoribine(NSC 289637; HE 69; β-Bredinin) is an immunosuppressive agents (IC50=100 uM) that inhibit the proliferation of lymphocytes selectively, via inhibition of IMPDH.IC50 Value:Target: IMPDHin vitro: Unlike azathioprine, Mizoribine is not taken up by nucleic acids in the cell. Instead, after phosphorylation MZR-5 -monophosphate inhibits GMP synthesis by the antagonistic blocking of IMPDH (Ki = 10(-8)M) and GMP- synthetase (Ki =10(-5) M) [1]. Pretreatment of cells with MZR partially, but significantly, attenuates the expression of monocyte chemoattractant protein (MCP)-1 mRNA and protein, whereas the poly IC-induced expressions for the other functional molecules, such as CCL5, fractalkine and IL-8 were not influenced by MZR treatment [2].in vivo:MZR 150 mg was administered once a day. After 6 months, the remission rate was 72.7% (2 subjects achieved complete remission, and 9 partial remission). After 3 and 6 months, significant reductions (p < 0.01) were obtained in 24-h proteinuria (g/day) [3].
Related Catalog	Signaling Pathways >>Others >>OthersResearch Areas >>Inflammation/Immunology
References	[1]. Ishikawa H. Mizoribine and mycophenolate mofetil. Curr Med Chem. 1999 Jul;6(7):575-97. [2]. Aizawa T, et al. Mizoribine selectively attenuates monocyte chemoattractant protein-1 production in cultured human glomerular mesangial cell: A possible benefit of its use in the treatment of lupus nephritis. Nephrology (Carlton). 2014 Jan;19(1):47-52. [3]. Zhang M, et al. Study of the efficacy of mizoribine in lupus nephritis in Chinese patients. Rheumatol Int. 2013 Nov;33(11):2737-42.

Description

Mizoribine(NSC 289637; HE 69; β-Bredinin) is an immunosuppressive agents (IC50=100 uM) that inhibit the proliferation of lymphocytes selectively, via inhibition of IMPDH.IC50 Value:Target: IMPDHin vitro: Unlike azathioprine, Mizoribine is not taken up by nucleic acids in the cell. Instead, after phosphorylation MZR-5 -monophosphate inhibits GMP synthesis by the antagonistic blocking of IMPDH (Ki = 10(-8)M) and GMP- synthetase (Ki =10(-5) M) [1]. Pretreatment of cells with MZR partially, but significantly, attenuates the expression of monocyte chemoattractant protein (MCP)-1 mRNA and protein, whereas the poly IC-induced expressions for the other functional molecules, such as CCL5, fractalkine and IL-8 were not influenced by MZR treatment [2].in vivo:MZR 150 mg was administered once a day. After 6 months, the remission rate was 72.7% (2 subjects achieved complete remission, and 9 partial remission). After 3 and 6 months, significant reductions (p < 0.01) were obtained in 24-h proteinuria (g/day) [3].

Related Catalog

Signaling Pathways >>Others >>OthersResearch Areas >>Inflammation/Immunology

References

[1]. Ishikawa H. Mizoribine and mycophenolate mofetil. Curr Med Chem. 1999 Jul;6(7):575-97.

[2]. Aizawa T, et al. Mizoribine selectively attenuates monocyte chemoattractant protein-1 production in cultured human glomerular mesangial cell: A possible benefit of its use in the treatment of lupus nephritis. Nephrology (Carlton). 2014 Jan;19(1):47-52.

[3]. Zhang M, et al. Study of the efficacy of mizoribine in lupus nephritis in Chinese patients. Rheumatol Int. 2013 Nov;33(11):2737-42.

Chemical & Physical Properties

Density	2.1±0.1 g/cm3
Boiling Point	755.9±60.0 °C at 760 mmHg
Melting Point	>200ºC
Molecular Formula	C₉H₁₃N₃O₆
Molecular Weight	259.216
Flash Point	410.9±32.9 °C
Exact Mass	259.080444
PSA	151.06000
LogP	-0.17
Vapour Pressure	0.0±2.7 mmHg at 25°C
Index of Refraction	1.795
InChIKey	HZQDCMWJEBCWBR-UUOKFMHZSA-N
SMILES	NC(=O)c1ncn(C2OC(CO)C(O)C2O)c1O

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NI3980000

CHEMICAL NAME :: 1H-Imidazole-4-carboxamide, 5-hydroxy-1-beta-D-ribofuranosyl-

CAS REGISTRY NUMBER :: 50924-49-7

LAST UPDATED :: 199612

DATA ITEMS CITED :: 34

MOLECULAR FORMULA :: C9-H13-N3-O6

MOLECULAR WEIGHT :: 259.25

WISWESSER LINE NOTATION :: T5OTJ B1Q CQ DQ E- AT5N CNJ DVZ EQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2847 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3795 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >2800 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >4883 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >4883 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2800 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 150 mg/kg/30D-C

TOXIC EFFECTS :: Endocrine - changes in spleen weight Blood - normocytic anemia Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2730 mg/kg/52W-C

TOXIC EFFECTS :: Endocrine - other changes Blood - normocytic anemia Related to Chronic Data - changes in uterine weight

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 1800 mg/kg/30D-C

TOXIC EFFECTS :: Behavioral - food intake (animal) Blood - normocytic anemia Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 11 mg/kg

SEX/DURATION :: female 7-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - body wall Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 11 mg/kg

SEX/DURATION :: female 7-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 48 mg/kg

SEX/DURATION :: female 17-22 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - stillbirth Reproductive - Effects on Newborn - live birth index (measured after birth)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 80 mg/kg

SEX/DURATION :: female 17-22 day(s) after conception lactating female 4 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 5 mg/kg

SEX/DURATION :: female 11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 5 mg/kg

SEX/DURATION :: female 11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - body wall Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Specific Developmental Abnormalities - gastrointestinal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 5 mg/kg

SEX/DURATION :: female 11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - urogenital system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 5 mg/kg

SEX/DURATION :: female 9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 75 mg/kg

SEX/DURATION :: male 3 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 52 mg/kg

SEX/DURATION :: female 6-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 39 mg/kg

SEX/DURATION :: female 6-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 11 mg/kg

SEX/DURATION :: female 8-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 44 mg/kg

SEX/DURATION :: female 8-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Specific Developmental Abnormalities - other developmental abnormalities

TYPE OF TEST :: Micronucleus test

TYPE OF TEST :: Dominant lethal test

MUTATION DATA

TYPE OF TEST :: Cytogenetic analysis

TEST SYSTEM :: Rodent - hamster Fibroblast

DOSE/DURATION :: 100 umol/L

REFERENCE :: CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 35,1643,1975

Safety Information

Symbol	GHS07, GHS08
Signal Word	Danger
Hazard Statements	H315-H319-H335-H360
Precautionary Statements	P201-P261-P305 + P351 + P338-P308 + P313
Personal Protective Equipment	Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes	T: Toxic;
Risk Phrases	R46
Safety Phrases	53-22-26-36/37/39-45
RIDADR	NONH for all modes of transport
WGK Germany	3
RTECS	NI3980000

Articles43

Successful multitarget therapy using mizoribine and tacrolimus for refractory Takayasu arteritis.

Rheumatology (Oxford.) 53(8) , 1530-2, (2014)

[Treatment of rheumatic diseases: current status and future prospective. Topics: II. Immunosuppressant/antirheumatic drugs; 5. Leflunomide and mizoribine].

Nippon. Naika Gakkai Zasshi. 100(10) , 2929-35, (2011)

Spantide II, a novel tachykinin antagonist having high potency and low histamine-releasing effect.

Clin. Transplant. 10 , 116, (1996)

Two undecapeptide substance P (SP) analogues, Spantide I and Spantide II, were tested for their capacity to block the contractile effect of SP on the guinea pig isolated taenia coli and the contractil...

Synonyms

5-Hydroxy-1-(β-D-ribofuranosyl)-1H-imidazole-4-carboxamide

HE-69

Mizoribinum

Bredinin

1H-Imidazole-4-carboxamide, 5-hydroxy-1-β-D-ribofuranosyl-

Mizoribina

Mizoribine

5-Hydroxy-1-b-D-ribofuranosyl-1H-imidazole-4-carboxamide

Bredinine

4-Carbamoyl-1-(β-D-ribofuranosyl)-1H-imidazol-3-ium-5-olate

4-Carbamoyl-1-b-D-ribofuranosylimidazolium-5-olate

Mizoribine [INN:JAN]

MFCD00057221

Mizoribina [INN-Spanish]

Mizoribinum [INN-Latin]

1-(β-D-Ribofuranosyl)-5-hydroxyimidazole-4-carboxamide

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