Related Searches: Ribavirin

Ribavirin(CAS No. 36791-04-5)

Ribavirin C8H12N4O5 (cas 36791-04-5) Molecular Structure

36791-04-5 Structure

Identification and Related Records

【CAS Registry number】
Ribavirin (JAN/USP)
1,2,4-Triazole-3-carboxamide, 1-.beta.-D-ribofuranosyl-
1H-1,2,4-Triazole-3-carboxamide, 1-.beta.-D-ribofuranosyl-
ICN 1229
1-.beta.-D-Ribofuranosyl-1H-1,2, 4-triazole-3-carboxamide
Virazole (TN)
Ribavirin (Virazole)
Ribavirin EP5
【Molecular Formula】
C8H12N4O5 (Products with the same molecular formula)
【Molecular Weight】
【Canonical SMILES】
【Isomers smiles】
【MOL File】

Chemical and Physical Properties

Colourless Solid
2.08 g/cm3
【Melting Point】
【Boiling Point】
639.8 oC at 760 mmHg
【Refractive Index】
-36 ° (C=1, H2O)
【Flash Point】
>=10 g/100 mL at 19℃
>=10 g/100 mL at 19 oC
White crystalline powder
No data.
【Storage temp】
【Spectral properties】
Specific optical rotation: -36.5 deg at 25 deg C/D
【Computed Properties】
Molecular Weight:244.20468 [g/mol]
Molecular Formula:C8H12N4O5
H-Bond Donor:4
H-Bond Acceptor:5
Rotatable Bond Count:3
Tautomer Count:2
Exact Mass:244.08077
MonoIsotopic Mass:244.08077
Topological Polar Surface Area:144
Heavy Atom Count:17
Formal Charge:0
Isotope Atom Count:0
Defined Atom Stereocenter Count:4
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:5
Feature 3D Donor Count:4
Feature 3D Cation Count:2
Feature 3D Ring Count:2
Effective Rotor Count:4
Conformer Sampling RMSD:0.6
CID Conformer Count:60

Safety and Handling

【Hazard Codes】
Mildly toxic by ingestion. An experimental teratogen.
【Risk Statements】
【Safety Statements 】

Other safty informations of Ribavirin (36791-04-5):
Hazard Codes?:ToxicT,IrritantXi
Risk Statements?:
? R61: May cause harm to the unborn child
? R36/38 :Irritating to eyes and skin
Safety Statements?:
? S53:Avoid exposure - obtain special instruction before use
? S22:Do not breathe dust
? S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
? S37/39:Wear suitable gloves and eye/face protection
? S26 :In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3

Vials, 6 g Delivered /as an aerosol/ to an infant oxygen hood (or administered by face mask or oxygen tent if necessary). Is administered using a small particle aerosol generator (model SPAG-2) ... .
Oral: Capsules: 200 mg Rebetol (Schering); Tablets, film-coated: 200 mg Copegus (Roche).
Nasal and Oral Inhalation: For inhalation solution: 6 g Virazole (Valeant).
Successfully administered by topical, parenteral, oral, and aerosol routes.
【Exposure Standards and Regulations】
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl ribavirin, approved on the basis of safety and effectiveness by FDA under sections 505 and 507 of the Federal Food, Drug, and Cosmetic Act.
【Other Preventative Measures】
Ribavirin can precipitate on contact lenses of health-care personnel exposed to aerosolized drug, and such precipitation may be associated with conjunctivitis. Therefore, it has been suggested that contact lens wearers use eyeglasses rather than contact lenses or, alternatively, use protective goggles while potentially in contact with aerosolized ribavirin.
Because of uncertainties about potential risk, procedures to minimize environmental exposure to aerosolized ribavirin generally should be developed. Whenever possible, patients receiving ribavirin inhalation therapy should be located in rooms where potential exposure of personnel and other patients is minimized (e.g., private rooms with adequate ventilation or, preferably, the National Institute for Occupational Safety and Health [NIOSH] recommends isolation rooms that are under negative pressure and have adequate air exchange and exhaust to the outside).
In deciding the method of administration of ribavirin inhalation therapy, current data on associated exposure levels should be considered, and, whenever possible, methods associated with the lowest levels of exposure employed. Except when immediate care is necessary, the small-particle aerosol generator should be turned off (using a remote switch) temporarily, but for at least 5-10 minutes before entering the room, when attending to the patient and when handling the respiratory apparatus. In addition, the air pressure of the ribavirin treatment room should be evaluated (e.g., using tissue paper at the ajar doorway) and ideally be negative relative to the hallway prior to initiation of a treatment session. An aerosol delivery hood intended for use in administering oxygen and aerosolized ribavirin and that includes a vacuum exhaust filtration system has recently become available from the manufacturer of ribavirin (Valeant) and reportedly can substantially reduce the risk of aerosol emission into the environment during ribavirin inhalation therapy.
【Octanol/Water Partition Coefficient】
log Kow = -1.85
【Disposal Methods】
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Synthesis: Acid-catalyzed fusion of methyl 1,2,4-triazole-3-carboxylate and 1,2,3,5-tetra-O-acetyl--d-ribofuranose or 1-O-acetyl-2,3,5-tri-O-benzoyl--d-ribofuranose yields blocked methyl ester nucleosides. Ribavirin is obtained after treatment of the blocked nucleoside with methanolic NH3.

Used as an antiviral agent

【Sampling Procedures】
NIOSH Method 5027. Analyte: Ribavirin. MATRIX: Air. Sampler: Filter (1 mm, 37 mmglass fiber). Flow Rate: 1 to 4 l/min: Sample Size: 50 liters. SHIPMENT: Routine. Sample Stability: Stable in dark at room temperature.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Drugs that are chemically similar to naturally occurring metabolites, but differ enough to interfere with normal metabolic pathways. (From AMA Drug Evaluations Annual, 1994, p2033)
- Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly.
【Therapeutic Uses】
Antimetabolites; Antiviral Agents
Oral and intravenous ribavirin are used in the treatment of Lassa fever and as post-exposure prophylaxis in contacts at hgh risk. It may be similarly effective with other viral hemorrhagic fevers, including hemorrhagic fever with renal syndrome, Crimean-Congo hemorrhagic fever, and Rift Valley fever. /NOT included in US product labeling/
Ribavirin inhalation solution is used as a secondary agent in the treatment of influenza A and B in young adults when treatment is started early (eg, within 24 hours of initial symptoms) in the course of the disease. /NOT included in US product labeling/
Ribavirin inhalation solution is for the treatment of severe lower respiratory tract infections (including bronchiolitis and pneumonia) caused by respiratory syncytial virus (RSV) in hospitalized infants and young children who are at high risk for severe or complicated RSV infection; this category includes premature infants and infants with structural or physiologic cardiopulmonary disorder, bronchopulmonary dysplasia, immunodeficiency, or imminent respiratory failure. Ribavirin is indicated in the treatment of RSV infections in infants requiring mechanical ventilator assistance. /Included in US product labeling/
【Biomedical Effects and Toxicity】
Ribavirin is absorbed systemically from the respiratory tract following nasal and oral inhalation. The bioavailability of ribavirin administered via nasal and oral inhalation has not been determined but may depend on the method of drug delivery during nebulization (eg, oxygen hood, face mask, oxygen tent). At a constant flow rate, the amount of drug delivered to the respiratory tract theoretically is directly related to the concentration of nebulized drug solution and the duration of inhalation therapy. In addition, alterations in the method of aerosol delivery can affect the amount of drug reaching the respiratory tract. The fraction of an inhaled dose of ribavirin that is deposited in the respiratory tract during oral and nasal inhalation of a nebulized solution containing 190 ug/L using a small particle aerosol generator has been estimated to average about 70%, but the actual amount deposited depends on several factors including respiratory rate and tidal volume.
Peak plasma ribavirin concentrations generally appear to occur at the end of the inhalation period when the drug is inhaled orally and nasally using a small particle aerosol generator, and increase with increasing duration of the inhalation period. Following nasal and oral inhalation (via face mask) of 0.82 mg/kg/hr for 2.5 hr daily for 3 days in a limited number of pediatric patients, peak plasma ribavirin concentrations averaged 0.19 (range: 0.11-0.388) ug/mL. Peak plasma ribavirin concentrations averaged 0.275 (range: 0.21-0.35) or 1.1 (range: 0.45-2.18) ug/mL in a limited number of patients inhaling 0.82 mg/kg per hour for 5 or 8 hr daily, respectively, for 3 days, and averaged 1.7 (range: 0.38-3.58) ug/mL in a limited number of pediatric patients inhaling 0.82 mg/kg per hour via face mask, mist tent, or respirator for 20 hr daily for 5 days. Highest plasma concentrations for a given dosage of ribavirin appear to be achieved in patients receiving the drug from the aerosol generator via an endotracheal tube. ... Peak plasma ribavirin concentrations achieved with nasal and oral inhalation of usual dosages of the drug are less than concentrations that reportedly reduce respiratory syncytial virus plaque formation by 85-98%.
Concentrations of ribavirin achieved in respiratory tract secretions in patients inhaling the drug nasally and orally are likely to be substantially greater than those achieved in plasma. In a limited number of pediatric patients who received a nasally and orally inhaled ribavirin dose of 0.82 mg/kg per hour for 8 hr daily for 3 days, peak concentrations of the drug in respiratory tract secretions (from endotracheal tube) ranged from 250-1925 ug/mL. In pediatric patients who received 0.82 mg/kg per hour via nasal and oral inhalation for 20 hr daily for 5 days, ribavirin concentrations in respiratory tract secretions (from endotracheal tube) ranged from 313-28,250 ug/mL during therapy, with peak concentrations averaging 3075 (range: 313-7050) ug/mL at the end of therapy. Concentrations of ribavirin achieved in respiratory tract secretions via nasal and oral inhalation are likely to be substantially greater than concentrations necessary to inhibit plaque formation of susceptible strains of respiratory syncytial virus in vitro; however, because respiratory syncytial virus is found within virus infected cells in the respiratory tract, the manufacturer states that intracellular respiratory tract drug concentrations may be more closely related to plasma ribavirin concentrations than to those measured in respiratory tract secretions.
Ribavirin is rapidly absorbed following oral administration, with peak plasma concentrations of the drug occurring within 1-3 hr after multiple doses. However, the absolute bioavailability of ribavirin averages only 64% following oral administration because the drug undergoes first-pass metabolism.
Following nasal and oral inhalation, highest ribavirin concentrations are found in the respiratory tract and erythrocytes. Following parenteral administration of single doses in monkeys and baboons, ribavirin and/or its metabolites are distributed in highest concentrations into skeletal muscle; blood cells, principally erythrocytes; and liver.
Studies in animals and humans have shown that ribavirin and/or its metabolites accumulate in erythrocytes. The extent of accumulation of ribavirin and/or its metabolites in erythrocytes following inhalation of the drug has not been established, but, following oral administration of a single 3 mg/kg dose, erythrocyte concentrations of the drug have been reported to peak within approximately 4 days, exceeding concurrent plasma concentrations at 4 days by about 100 fold, and then declining with a half-life of about 40 days. During the initial 1-2 hr following oral administration of a single dose of the drug, erythrocyte concentrations increase at a rate similar to plasma concentrations; thereafter, erythrocyte concentrations continue to increase for about 4 days as plasma drug concentrations decline. Approximately 3% of a single ribavirin dose is present in erythrocytes 72 hr after oral administration.
Ribavirin appears to distribute slowly into CSF. Following chronic (4-7 wks) oral administration of ribavirin in patients with acquired immunodeficiency syndrome or AlDS-related complex, CSF concentrations of the drug were approximately 70% of concurrent plasma concentrations. It is not known whether ribavirin crosses the placenta or distributes into milk in humans. The drug appears to be only minimally bound to plasma proteins.
Elimination of /ribavirin/ from the respiratory tract may result from distribution across respiratory membranes, clearance by macrophages in the respiratory tract, and/or upward ciliary activity.
Ribavirin is excreted principally in urine. In healthy adults with normal renal function, approximately 53% of a single oral dose is excreted in urine within 72-80 hr, with about 33% excreted within the first 24 hr. Approximately 37, 30, and 30% of the fraction excreted in urine appears as unchanged drug, 1,2,4-triazole-3-carboxamide, and 1,2,4-triazole-3-carboxylic acid, respectively, within 1.5-2 hr, and approximately 17, 50, and 22%, respectively, within 24 hr. About 15% of a single oral dose is excreted in feces within 72 hr. Little, if any, ribavirin appears to be eliminated in expired CO2.
There is extensive accumulation of ribavirin following multiple (twice daily) doses of the drug, such that peak plasma ribavirin concentrations at steady state are fourfold higher than those following a single dose. Following oral administration of single or multiple 600-mg doses of ribavirin (as capsules), mean peak plasma concentrations in adults average 0.782 or 3.7 ug/mL, respectively. In patients weighing more than 75 kg, ribavirin 1.2 g daily (as tablets) given with food for 12 weeks resulted in peak plasma ribavirin concentrations of 2.7 ug/mL. In children 5-16 years of age, mean peak plasma concentrations average 2.7-3.2 mcg/mL following ribavirin dosages of 12-15 mg/kg twice daily (as capsules).

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