Ribavirin

Modify Date: 2024-01-02 19:36:12

Ribavirin Structure
Ribavirin structure
 Common Name Ribavirin
CAS Number 36791-04-5 Molecular Weight 244.205
Density 2.1±0.1 g/cm3 Boiling Point 639.8±65.0 °C at 760 mmHg
Molecular Formula C8H12N4O5 Melting Point 174-176°C
MSDS Chinese USA Flash Point 340.7±34.3 °C
Symbol GHS08
GHS08		 Signal Word Danger

 Use of Ribavirin


Ribavirin is an antiviral agent against a broad spectrum of viruses including HCV, HIVl, and RSV.

 Names

Name ribavirin
Synonym More Synonyms

 Ribavirin Biological Activity

Description Ribavirin is an antiviral agent against a broad spectrum of viruses including HCV, HIVl, and RSV.
Related Catalog
In Vitro Ribavirin (5, 10 and 20 μM) does not produce any significant effect on neither cell viability nor nitrites level in non-stimulated microglia. Treatmentof LPS-stimulated microglia with 5, 10 and 20 μM Ribavirin induces reduction of NO2 levels for 43% (p<0.05), 53% (p<0.05) and 59% (p<0.05), respectively. Ribavirin (10 mM) insignificantly decreases the cell surface area in non-stimulated culture, but significantly reduces cell surface area (by 32%, p<0.05) in LPS-stimulated microglia[3]. Ribavirin is active against DENV, with an EC50 of 3 μM in A549 cells, and combination of CM-10-18 with ribavirin demonstrates a clear enhancement in the reduction of virus replication[4].
In Vivo ALT, AST activities and bilirubin levels are significantly loared by administration of JAT in combination with interferon and ribavirin (p<0.01). JAT, interferon or ribavirin alone with CCl4, livers appear to exhibit some liver protection against CCl4 as evident by the presence of normal hepatic cords, absence of necrosis and lesser fatty infiltration. Groups treated with JAT, Peg-interferon and ribavirin separately or in combination shows reduction in the expression of TGF- β and Bax. In the group treated by triple combination of interferon, ribavirin, and JAT, the expression level of p53 is markedly reduced[1]. Ribavirin capsules (400 mg of ribavirin)-treated Wistar rats show a significant decrease in activin-A and significant increase in follistatin at the serum and liver levels. Ribavirin has strong antiviral activity only when ribavirin is combined with either IFN-α or Peg-IFN-α[2]. Ribavirin (40 mg/kg, p.o.) significantly improves the antiviral efficacy of CM-10-18 in mice. Ribavirin inhibits DENV virus infection in cultured cells, but it is ineffective in reducing viremia in monotherapy[4].
Cell Assay The effect of Ribavirin on microglial cell viability is evaluated by the sulforhodamine B (SRB) chemosensitivity assay. Briefly, LPS-stimulated microglial cells are incubated for 48 h in the presence or absence of Ribavirin. Afterward, the cells are fixed in 10% (w/v) trichloroacetic acid for 1 h at 4°C, rinsed in tap water and stained with 0.4% (w/v) SRB in 1% acetic acid (100 μL/well) for 30 min at room temperature (RT). The cells are then rinsed three times in 1% acetic acid to remove the unbound stain. The protein bound stain is extracted with 200 μL 10 mM Tris base (pH 10.5) per well. The optical density is read at 540 nm, with correction at 670 nm. The results are presented as percentage of the control (non-stimulated/untreated microglial cells), that is arbitrarily set to 100%.
Animal Admin The in vivo efficacy experiments are largely performed, using a dengue viremia model in AG129 mouse (defective of both type I and type II interferon receptors). Each experiment contains 6 mice (7 to 8 week-old) per dosing group. The mice are challenged with DENV (serotype 2, TSV01 strain), at 5×106 pfu/mouse via i.p. injection. Imino sugars are dosed twice daily at 12 hr intervals, and ribavirin is dosed once daily, for 3 consecutive days post-infection. Blood samples are drawn 3 days post-infection for determination of plasma virus titer by plaque assay.
References

[1]. Abdel-Hamid NM, et al. Synergistic Effects of Jerusalem Artichoke in Combination with Pegylated Interferon Alfa-2a and Ribavirin Against Hepatic Fibrosis in Rats. Asian Pac J Cancer Prev. 2016;17(4):1979-85.

[2]. Refaat B, et al. The effects of pegylated interferon-α and ribavirin on liver and serum concentrations of activin-A and follistatin in normal Wistar rat: a preliminary report. BMC Res Notes. 2015 Jun 26;8:265

[3]. Savic D, et al. Ribavirin shows immunomodulatory effects on activated microglia. Immunopharmacol Immunotoxicol. 2014 Dec;36(6):433-41

[4]. Chang J, et al. Combination of α-glucosidase inhibitor and ribavirin for the treatment of dengue virus infection in vitro and in vivo. Antiviral Res. 2011 Jan;89(1):26-34

 Chemical & Physical Properties

Density 2.1±0.1 g/cm3
Boiling Point 639.8±65.0 °C at 760 mmHg
Melting Point 174-176°C
Molecular Formula C8H12N4O5
Molecular Weight 244.205
Flash Point 340.7±34.3 °C
Exact Mass 244.080765
PSA 143.72000
LogP -2.26
Vapour Pressure 0.0±2.0 mmHg at 25°C
Index of Refraction 1.823
Storage condition 2-8°C
Water Solubility >=10 G/100 ML AT 19 ºC

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
XZ4250000
CHEMICAL NAME :
1,2,4-Triazole-3-carboxamide, 1-beta-D-ribofuranosyl-
CAS REGISTRY NUMBER :
36791-04-5
LAST UPDATED :
199612
DATA ITEMS CITED :
32
MOLECULAR FORMULA :
C8-H12-N4-O5
MOLECULAR WEIGHT :
244.24
WISWESSER LINE NOTATION :
T5OTJ B1Q CQ DQ E- AT5NN DNJ CVZ

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 :
2700 mg/kg
TOXIC EFFECTS :
Tumorigenic - active as anti-cancer agent
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
4 gm/kg
TOXIC EFFECTS :
Tumorigenic - active as anti-cancer agent
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1300 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
1500 mg/kg
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea Kidney, Ureter, Bladder - other changes Blood - hemorrhage
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
1 gm/kg/10D-I
TOXIC EFFECTS :
Blood - normocytic anemia Blood - changes in bone marrow (not otherwise specified) Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
220 mg/kg/10D-I
TOXIC EFFECTS :
Blood - changes in platelet count Nutritional and Gross Metabolic - changes in calcium
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
220 mg/kg/10D-I
TOXIC EFFECTS :
Blood - changes in platelet count Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
440 mg/kg/10D-I
TOXIC EFFECTS :
Blood - changes in bone marrow (not otherwise specified) Blood - changes in platelet count
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
25 mg/kg
SEX/DURATION :
female 9 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
37500 ug/kg
SEX/DURATION :
female 9 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - eye/ear
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
3150 mg/kg
SEX/DURATION :
male 90 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
9 gm/kg
SEX/DURATION :
male 60 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
25 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
3750 ug/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - eye/ear
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
2500 ug/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
2500 ug/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Specific Developmental Abnormalities - eye/ear
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
5 mg/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
2500 ug/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
5 mg/kg
SEX/DURATION :
female 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
5 mg/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
5 mg/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
TYPE OF TEST :
Micronucleus test
TYPE OF TEST :
Cytogenetic analysis
TYPE OF TEST :
Cytogenetic analysis

MUTATION DATA

TYPE OF TEST :
Mutation test systems - not otherwise specified
TEST SYSTEM :
Rodent - rabbit Kidney
DOSE/DURATION :
4900 ug/L
REFERENCE :
BCPCA6 Biochemical Pharmacology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1- 1958- Volume(issue)/page/year: 38,1771,1989 *** REVIEWS *** TOXICOLOGY REVIEW JACTDZ Journal of the American College of Toxicology. (Mary Ann Liebert, Inc., 1651 Third Ave., New York, NY 10128) V.1-12, 1982-1993. Discontinued. Volume(issue)/page/year: 9(5),551,1990

 Safety Information

Symbol GHS08
GHS08
Signal Word Danger
Hazard Statements H360
Precautionary Statements P201-P280-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 Xi
Risk Phrases R61
Safety Phrases 53-22-45-37/39-26
RIDADR UN 3152 9/PG 2
WGK Germany 3
RTECS XZ4250000
Packaging Group II
Hazard Class 9
HS Code 2933290090

 Synthetic Route

 Customs

HS Code 2933290090
Summary 2933290090. other compounds containing an unfused imidazole ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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 Synonyms

1-(b-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxamide
RTC
1-β-D-ribofuranosyl-1,2,4-triazole-3-carboxamide
1H-1,2,4-triazole-3-carboxamide, 1-b-D-ribofuranosyl-
Ribavirin
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H-1,2,4-triazole-3-carboxamide
UNII-49717AWG6K
MFCD00058564
rtca
Rebetol
Ravanex
1-(β-D-Ribofuranosyl)-1H-1,2,4-triazole-3-carboxamide
Virazide
Virazole
VIRAZID
Copegus
varazid
1H-1,2,4-Triazole-3-carboxamide, 1-β-D-ribofuranosyl-
1-β-D-ribofuranosyl-1H-1,2,4-triazole-3-carboxamide
tribavirin
1-(β-D-Ribofuranosyl)-1,2,4-triazole-3-carboxamide
1,2,4-Triazole-3-carboxamide, 1-β-D-ribofuranosyl-
virazol
Viramid
1-b-D-Ribofuranosyl-1H-1,2,4-triazole-3-carboxamide
vilona
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131615-57-1
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