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CAS NO.36791-04-5
| Ribavirin Basic information |
| Product Name: | Ribavirin |
| Synonyms: | REBETOL;RIBAVIRIN;rtca;tribavirin;vilona;VIRAMID;VIRAZID;VIRAZOLE |
| CAS: | 36791-04-5 |
| MF: | C8H12N4O5 |
| MW: | 244.2 |
| EINECS: | |
| Product Categories: | Active Pharmaceutical Ingredients;Antivirals for Research and Experimental Use;Biochemistry;Chemical Reagents for Pharmacology Research;Nucleosides and their analogs;Nucleosides, Nucleotides & Related Reagents;Anti-virals;Inhibitors;Intermediates & Fine Chemicals;Non-nucleoside Reverse Transcriptase;Pharmaceuticals;API's;Antiviral;Bases & Related Reagents;Carbohydrates & Derivatives;Nucleotides |
| Mol File: | 36791-04-5.mol |
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| Ribavirin Chemical Properties |
| mp | 174-176°C |
| refractive index | -36 ° (C=1, H2O) |
| storage temp. | 2-8°C |
| Water Solubility | >=10 g/100 mL at 19 ºC |
| Merck | 8198 |
| EPA Substance Registry System | 1H-1,2,4-Triazole- 3-carboxamide, 1-.beta.-D-ribofuranosyl-(36791-04-5) |
| Safety Information |
| Hazard Codes | T,Xi |
| Risk Statements | 61-36/38 |
| Safety Statements | 53-22-45-37/39-26 |
| WGK Germany | 3 |
| RTECS | XZ4250000 |
| Hazardous Substances Data | 36791-04-5(Hazardous Substances Data) |
| MSDS Information |
| Provider | Language |
|---|---|
| 1-beta-D-Ribofuranosyl-1,2,4-triazole-3-carboxamide | English |
| SigmaAldrich | English |
| Ribavirin Usage And Synthesis |
| Antiviral drugs | Ribavirin is a novel non-selective nucleoside class broad-spectrum antiviral drug, belonging to the inosine monophosphate (IMP) dehydrogenase inhibitor. It can participate in the guanine participate in the human body metabolism, interfere with the biosynthesis of guanine, prevent the replication of the virus and has inhibitory effect on a variety of DNA and RNA viruses. Ribavirin has a stronger antiviral effect than amantadine and vidarabine, etc with definite efficacy and small drug side effects. Rare adverse reactions include conjunctivitis and hypotension with the former exhibiting as intraocular foreign body sensation, photophobia, itching, swelling and hematoma and the latter manifested as blurred vision, dizziness, and fatigue. It is used for clinical treatment of viral upper respiratory tract infection, respiratory syncytial virus-induced viral pneumonia and bronchitis, influenza, para-influenza, epidemic encephalris, mumps, chickenpox, shingles, herpes zoster, autumn diarrhea, children early-stage adenovirus pneumonia, acute Lassa fever, rubella, viral pneumonia, genital herpes, herpes simplex virus keratitis, psoriasis, etc with special efficacy. It also have certain efficacy on treating epidemic hemorrhagic fever, hepatitis B, and hepatitis A. Applying this drug in early stage of epidemic hemorrhagic fever can shorten the period, reducing the damage of kidney and vascular and symptoms of poisoning. |
| Pharmacological effects |
1, Ribavirin can be subject to phosphorylation in red blood cells to generate ribavirin monophosphate, diphosphate and triphosphate, wherein the ribavirin monophosphate is the strong inhibitor of the inosine monophosphate dehydrogenase which can inhibit cellular guanylate synthesis, decrease the tri-phosphorylation of the intracellular guanylate triphosphate, and blocking the synthesis of viral nucleic acid. 2, ribavirin triphosphate can inhibit the influenza virus RNA polymerase and interfere with viral replication. 3, ribavirin triphosphate can inhibit the synthesis of viral mRNA 5 'end and transcriptase, thereby inhibiting the DNA and RNA synthesis. It has inhibitory effect on various kinds of viruses (including DNA viruses and RNA viruses). It also has prevention and treatment effect on the influenza, adenovirus pneumonia, hepatitis, herpes, and measles and is also effective on treating the epidemic hemorrhagic fever. 4, it is mainly excreted through urine in the prototype with also a small amount of de-sugarized ribavirin metabolites with a small amount discharged from the feces. The above information is edited by the Chemicalbook of Dai Xiongfeng. |
| Chemical Properties | This product is colorless or white crystalline powder and is odorless with no taste. It is stable in room temperature. It is easily soluble in water and slightly soluble in ethanol, chloroform and ether. It has its mp being 174-176 ℃ or 160-167 ℃ (refined products include two crystals). |
| Application |
It is a kind of broad-spectrum antiviral drugs for treating influenza (influenza A and B viruses), adenovirus pneumonia, hepatitis, herpes, measles with prevention and treatment effect; it is also effective on treating the epidemic hemorrhagic fever, particularly effective treatment of patients in their early stages. Oral administration can cause diarrhea without other significant toxicity but may cause neutropenia. Large dose can inhibit the maturation of hemoglobin and red blood cells, causing reversible anemia. There have been reports regarding to the teratogenicity and embryo toxicity in animal experiments. Pregnant women should be hanged. Ribavirin is a broad-spectrum antiviral nucleoside drug used for treating influenza, adenovirus pneumonia of children, viral hepatitis, respiratory syncytial virus infection, acute keratitis, conjunctivitis, epidemic hemorrhagic fever and herpes zoster. |
| Production method |
Take nucleotide or nucleoside as the starting material First hydrolyze the guanosine and guanylate upon the action of glacial acetic acid and acetic anhydride to generate ribose-1-phosphate, which is then subject to the catalysis of double - para-nitro phenol to have reaction with triazide amide to generate condensate with aminolysis to obtain the product. Guanosine (or guanylate) [acetic anhydride, glacial acetic acid]→[hydrolysis] ribose-1-phosphate [bis- (p-nitrophenol)-phosphate]→[triazide carboxamide] condensates [aminolysis]→Ribavirin Enzymatic synthesis First hydrolyze the guanosine and guanosine acid under the action of pyrimidine nucleoside phosphorylase to form ribose-1-phosphate which then, under the action of purine nucleoside phosphorylase, has reaction with triazide amide to directly generate triazole nucleosides. Guanosine (or guanylate) [pyrimidine nucleoside phosphorylase] → ribose-1 nucleic acid [purine nucleotide cyclase] → Ribavirin. |
| Chemical Properties | Colourless Solid |
| Usage | Purine nucleoside analog; inhibits inosine monophosphate dehydrogenase (IMPDH). Used as an antiviral agent. |
| Usage | aldosterone antagonist; antifibrogenic |
| Usage | anti-infective, anti-fungal |
| General Description | White powder. Exists in two polymorphic forms. |
| Air & Water Reactions | Water soluble. |
| Reactivity Profile | Ribavirin may be sensitive to prolonged exposure to light. |
| Fire Hazard | Flash point data for Ribavirin are not available; however, Ribavirin is probably combustible. |
| Ribavirin Preparation Products And Raw materials |
| Preparation Products | 6-BENZYLAMINOPURINE |
| Raw materials | SULPHOSUCCINIC ACID ESTER-->Ribonucleic acid-->Inosine-->5'-Guanylic acid-->2-Amino-9-beta-D-ribofuranosyl-9H-purine-6-(1H)-one hydrate-->D-Ribose-->L-DIHYDROOROTIC ACID-->PHOSPHORYLASE B FROM RABBIT MUSCLE-->NUCLEOSIDE PHOSPHORYLASE BACTERIAL |