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리바비린 구조식 이미지
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포뮬러 무게:
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리바비린 속성

D25 -36.5° (c = 1 in water); D20 -38° (c = 1 in water)
끓는 점
387.12°C (rough estimate)
1.4287 (rough estimate)
-36 ° (C=1, H2O)
저장 조건
Freely soluble in water, slightly soluble in ethanol (96 per cent), slightly soluble or very slightly soluble in methylene chloride. It shows polymorphism (5.9).
물리적 상태
White solid
산도 계수 (pKa)
>=10 g/100 mL at 19 ºC
CAS 데이터베이스
Ribavirin (36791-04-5)
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 T,Xi
위험 카페고리 넘버 61-36/38
안전지침서 53-22-45-37/39-26
WGK 독일 3
RTECS 번호 XZ4250000
HS 번호 29349990
유해 물질 데이터 36791-04-5(Hazardous Substances Data)
독성 LD50 i.p. in mice: 1.3 g/kg; orally in rats: 5.3 g/kg (Witkowski, 1972)
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H360 태아 또는 생식능력에 손상을 일으킬 수 있음 생식독성 물질 구분 1A, 1B 위험
P201 사용 전 취급 설명서를 확보하시오.
P202 모든 안전 조치 문구를 읽고 이해하기 전에는 취급하지 마시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P308+P313 노출 또는 접촉이 우려되면 의학적인 조치· 조언를 구하시오.
P405 밀봉하여 저장하시오.
P501 ...에 내용물 / 용기를 폐기 하시오.

리바비린 MSDS


리바비린 C화학적 특성, 용도, 생산

화학적 성질

Colourless Solid


Purine nucleoside analog; inhibits inosine monophosphate dehydrogenase (IMPDH). Used as an antiviral agent.


aldosterone antagonist; antifibrogenic


anti-infective, anti-fungal


A broad spectrum antiviral nucleoside and inhibitor of inosine monophosphate dehydrogenase.


Ribavirin is a guanosine analog with antiviral properties against DNA and RNA viruses, including respiratory syncytial virus, hepatitis C, and influenza. It acts as a prodrug that can be activated by either mono- or tri-phosphorylation by cellular kinases. These phosphorylated derivatives of ribavirin have diverse effects on both cellular and viral enzymes, resulting in suppression of viral replication.


ChEBI: A 1-ribosyltriazole that is the 1-ribofuranosyl derivative of 1,2,4-triazole-3-carboxamide. An inhibitor of HCV polymerase.


Ribavirin is a synthetic guanosine analogue that possesses broad antiviral inhibitory activity against many viruses, including influenza A and B, parainfluenza,RSV, HCV, HIV-1, and various herpesviruses, arenaviruses, and paramyxoviruses. Its exact mechanism of action has not been fully elucidated; however, it appears to inhibit the synthesis of viral mRNA through an effect on nucleotide pools. Following absorption, host cell enzymes convert ribavirin to its monophosphate, diphosphate, and triphosphate forms. Ribavirin monophosphate inhibits the guanosine triphosphate (GTP) synthesis pathway and subsequently inhibits many GTP-dependent processes. Ribavirin triphosphate inhibits the 5 capping of viral mRNA with GTP and specifically inhibits influenza virus RNA polymerase. Ribavirin may also act by increasing the mutation rate of RNA viruses, leading to the production of nonviable progeny virions. Ribavirin resistance has not been documented in clinical isolates.


Copegus (Roche); Rebetol (Schering); Virazole (Valeant).


Development of resistant virus strains has not been demonstrated.

일반 설명

White powder. Exists in two polymorphic forms.

일반 설명

Ribavirin is 1-β-D-ribofuranosyl-1,2,4-thiazole-3-carboxamide.The compound is a purine nucleoside analog with amodified base and a D-ribose sugar moiety.
Ribavirin inhibits the replication of a very wide variety ofRNA and DNA viruses,68 including orthomyxoviruses,paramyxoviruses, arenaviruses, bunyaviruses, herpesviruses,adenoviruses, poxvirus, vaccinia, influenza virus(types A and B), parainfluenza virus, and rhinovirus. In spiteof the broad spectrum of activity of ribavirin, the drug hasbeen approved for only one therapeutic indication—thetreatment of severe lower respiratory infections caused byRSV in carefully selected hospitalized infants and youngchildren.

공기와 물의 반응

Water soluble.

반응 프로필

Ribavirin may be sensitive to prolonged exposure to light.


Mildly toxic by ingestion. An experimental teratogen.


Flash point data for Ribavirin are not available; however, Ribavirin is probably combustible.

Pharmaceutical Applications

A synthetic nucleoside. It is neither a classic pyrimidine nor a purine, but stereochemical studies indicate that it is a guanosine analog. It is usually formulated for administration by inhalation, but oral and intravenous preparations are also used.

Mechanism of action

Ribavirin, a guanosine analogue, has broad-spectrum antiviral activity against both DNA and RNA viruses. It is phosphorylated by adenosine kinase to the triphosphate, resulting in the inhibition of viral specific RNA polymerase, disrupting messenger RNA and nucleic acid synthesis.


Oral and intravenous ribavirin are associated with additional adverse effects.When given via these routes, ribavirin can produce hemolytic anemia that is reversible following dosage reduction or cessation of therapy. When given in combination with interferon- , ribavirin increases the incidence of many of its side effects, such as fatigue, nausea, insomnia, depression, and anemia, and may cause fatal or nonfatal pancreatitis. Ribavirin is mutagenic, teratogenic, and embryotoxic in animals at doses below the therapeutic level in humans. It is contraindicated in pregnant women and in the male partners of pregnant women. Women of childbearing potential and male partners of these women must use two effective forms of contraception during ribavirin treatment and for 6 months post therapy. Pregnant women should not directly care for patients receiving ribavirin.


Oral absorption: 36–46%
Cmax 3 mg/kg oral: 4.1–8.2 μmol/L after 1–1.5 h
600 mg intravenous: 43.6 μmol/L end infusion
Plasma half-life: c. 24 h
Volume of distribution: 647 L
Plasma protein binding: <10%
It is rapidly absorbed after oral administration. Mean peak concentrations after 1 week of oral doses of 200, 400 and 800 mg every 8 h were 5.0, 11.1 and 20.9 μmol/L, respectively. Trough levels 9–12 h after the end of 2 weeks’ therapy were 5.1, 13.2 and 18.4 μmol/L, respectively, indicating continued accumulation of the drug. Drug was still detectable 4 weeks later. Mean peak plasma concentrations after intravenous doses of 600, 1200 and 2400 mg were 43.6, 72.3 and 160.8 μmol/L, respectively; at 8 h the mean plasma concentrations were 2.1, 5.6 and 10.2 μmol/L. Aerosolized doses (6 g in 300 mL distilled water) are generally administered at a rate of 12–15 mL/h using a Collison jet nebulizer, the estimated dosage being 1.8 mg/kg per h for infants and 0.9 mg/kg per h for adults. When administered by small particle aerosol for 2.5–8 h, plasma concentrations ranged from 0.44 to 8.7 μmol/L.
Metabolism and excretion
It is rapidly degraded by deribosylation or amide hydrolysis, and together with its metabolites is slowly eliminated by the kidney. About 50% of the drug or its metabolites appear in the urine within 72 h and 15% is excreted in the stools. The remainder seems to be retained in body tissues, principally in red blood cells, which concentrate the drug or metabolites to a peak at 4 days, with a half-life of around 40 days. After intravenous administration 19.4% of the dose was eliminated during the first 24 h (compared with 7.3% after an oral dose), the difference reflecting the bioavailability.

Clinical Use

RSV infections in infants (by nebulizer) in emergency situations (i.e. transplant recipients)
Lassa fever
Hepatitis C (in combination with interferon-α)
Use in RSV pneumonia in infants is no longer routine. It reduces mortality from Hantaan virus, the agent responsible for hemorrhagic fever with renal syndrome.

Clinical Use

Ribavirin aerosol (Virazole) is indicated in the treatment of high-risk infants and young children with severe bronchiolitis or pneumonia due to RSV infection. Treatment is most effective if begun within 3 days of the onset of symptoms.
Although ribavirin monotherapy is ineffective against HCV, oral ribavirin in combination with interferon-α (Rebatron) is approved for this indication and is effective in patients resistant to interferon therapy alone. Intravenous ribavirin may be useful in the therapy of Hantaan virus infection, Crimean or Congo virus hemorrhagic fever, Lassa fever, and severe adenovirus infection.


Most adverse effects associated with aerosol ribavirin are local. Pulmonary function may decline if aerosol ribavirin is used in adults with chronic obstructive lung disease or asthma. Deterioration of pulmonary and cardiovascular function has also been seen in severely ill infants given this preparation. Rash, conjunctivitis, and rare cases of anemia have been reported. Health care workers exposed to aerosol ribavirin during its administration have reported adverse effects including headache, conjunctivitis, rash, and rarely, bronchospasm.


It is generally well tolerated, though adverse reactions appear to be related to dose and duration of therapy. Minor adverse reactions include metallic taste, dry mouth sensation and increased thirst, flatulence, fatigue and CNS complaints, including headache, irritability and insomnia. Daily doses of 1 g may cause unconjugated bilirubin levels to double and the reticulocyte count to increase. Hemoglobin concentrations may decrease with treatment or higher dosages; with doses of 3.9–12.6 g per day, a drop in hemoglobin was noted by days 7–13 of treatment, which was generally ‘rapidly’ reversible on withdrawal of the drug, but in some instances necessitated blood transfusion.
Aerosol administration of about 2 g in 36 or 39 h during 3 days is well tolerated, does not affect results of pulmonary function tests, and seems non-toxic.
It is both teratogenic and embryotoxic in laboratory animals, so precautions must be observed in women of childbearing age.

Chemical Synthesis

Ribavirin, 1-β-D-ribofuranosyl-1H-1,2,4-triazol-3-carboxamide (36.1.28), is synthesized by reacting methyl ester of 1,2,4-triazol-3-carboxylic acid with O-1,2,3, 5-tetraacetyl-β-D-ribofuranose to make methyl ester of 1-O-2,3,5-tetraacetyl-β-D-ribofuranosyl-1,2,4-triazol-3-carboxylic acid (36.1.27), which is treated with an ammonia solution of methanol to simultaneously dezacylate the carbohydrate part and amidation of the carboxyl part of the product to give ribavirin.

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