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リバビリン

リバビリン 化学構造式
36791-04-5
CAS番号.
36791-04-5
化学名:
リバビリン
别名:
リバビリン;1-[3-(アミノカルボニル)-1H-1,2,4-トリアゾール-1-イル]-1-デオキシ-β-D-リボフラノース;ビラミド;コペガス;リバミジル;ビラゾール;1-β-D-リボフラノシル-1H-1,2,4-トリアゾール-3-カルボアミド;ビロナ;リバミド;1-(β-D-リボフラノシル)-3-カルバモイル-1H-1,2,4-トリアゾール;1-(β-D-リボフラノシル)-1H-1,2,4-トリアゾール-3-カルボアミド;レベトール;リバビリン標準品;1-(β-D-リボフラノシル)-1,2,4-トリアゾール-3-カルボキサミド;リバビリン (JP17)
英語化学名:
Ribavirin
英語别名:
RTC;rtca;vilona;VIRAZID;VIRAMID;REBETOL;virazol;Copegus;Ravanex;varazid
CBNumber:
CB0689324
化学式:
C8H12N4O5
分子量:
244.21
MOL File:
36791-04-5.mol

リバビリン 物理性質

融点 :
174-176°C
比旋光度 :
D25 -36.5° (c = 1 in water); D20 -38° (c = 1 in water)
沸点 :
387.12°C (rough estimate)
比重(密度) :
1.4287 (rough estimate)
屈折率 :
-36 ° (C=1, H2O)
貯蔵温度 :
2-8°C
溶解性:
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).
外見 :
White solid
酸解離定数(Pka):
12.95±0.70(Predicted)
水溶解度 :
>=10 g/100 mL at 19 ºC
Merck :
14,8198
InChIKey:
IWUCXVSUMQZMFG-AFCXAGJDSA-N
CAS データベース:
36791-04-5
EPAの化学物質情報:
Ribavirin (36791-04-5)
安全性情報
  • リスクと安全性に関する声明
  • 危険有害性情報のコード(GHS)
主な危険性  T,Xi
Rフレーズ  61-36/38
Sフレーズ  53-22-45-37/39-26
WGK Germany  3
RTECS 番号 XZ4250000
HSコード  29349990
有毒物質データの 36791-04-5(Hazardous Substances Data)
毒性 LD50 i.p. in mice: 1.3 g/kg; orally in rats: 5.3 g/kg (Witkowski, 1972)
化審法 (9)-1515
絵表示(GHS)
注意喚起語 Danger
危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード
H360 生殖能または胎児への悪影響のおそれ 生殖毒性 1A, 1B 危険
注意書き
P201 使用前に取扱説明書を入手すること。
P202 全ての安全注意を読み理解するまで取り扱わないこ と。
P280 保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。
P308+P313 暴露または暴露の懸念がある場合:医師の診断/手当てを 受けること。
P405 施錠して保管すること。
P501 内容物/容器を...に廃棄すること。

リバビリン 価格 もっと(36)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01COBOT-0885 リバビリン
Ribavirin
36791-04-5 5g ¥3600 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01COBOT-0885 リバビリン
Ribavirin
36791-04-5 25g ¥7200 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01TRCR414475
Ribavirin
36791-04-5 10mg ¥13800 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01TRCR414475
Ribavirin
36791-04-5 50mg ¥15000 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01MAS075767
Ribavirin
36791-04-5 25g ¥18000 2021-03-23 購入

リバビリン 化学特性,用途語,生産方法

外観

白色~ほとんど白色粉末~結晶

用途

ウィルス RNA ポリメラーゼ を阻害し、ウィルスの増殖阻害作用を示しま す。

用途

リバビリン(Ribavirin)は、抗ウイルス薬の一つで、主にC型肝炎やウイルス性出血熱等の治療で施行されている。

効能

抗ウイルス薬

商品名

コペガス (中外製薬); レベトール (MSD)

化学的特性

Colourless Solid

使用

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

使用

aldosterone antagonist; antifibrogenic

使用

anti-infective, anti-fungal

使用

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

使用

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.

定義

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

適応症

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.

brand name

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

獲得抵抗性

Development of resistant virus strains has not been demonstrated.

一般的な説明

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.

一般的な説明

White powder. Exists in two polymorphic forms.

空気と水の反応

Water soluble.

反応プロフィール

Ribavirin may be sensitive to prolonged exposure to light.

危険性

Mildly toxic by ingestion. An experimental teratogen.

火災危険

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

応用例(製薬)

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.

作用機序

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.

薬理学

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.

薬物動態学

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%
Absorption
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.

臨床応用

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.

臨床応用

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.

副作用

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.

副作用

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.

リバビリン 上流と下流の製品情報

原材料

準備製品


リバビリン 生産企業

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36791-04-5(リバビリン)キーワード:


  • 36791-04-5
  • REBETOL
  • RIBAVIRIN
  • rtca
  • tribavirin
  • vilona
  • VIRAMID
  • VIRAZID
  • VIRAZOLE
  • 1-BETA-D-RIBOFURANOSYL-1,2,4-TRIAZOLE-3-CAROXAMIDE
  • 1-BETA-D-RIBOFURANOSYL-1H-1,2,4-TRIAZOLE-3-CARBOXAMIDE
  • 1-BETA-D-RIBOFURANOSYL-1,2,4-TRIAZOLE-3-CARBOXAMIDE
  • biopolymers
  • LEVOVIRIN
  • ICN-1229
  • RibavirinGmp/Edmf
  • RibavirinGmp/EdmfUsp29
  • 1-b-D-Ribofuranosyl-1H-1,2,4-triazole-3-carboxamide
  • 1H-1,2,4-Triazole-3-carboxamide, 1-.beta.-D-ribofuranosyl-
  • RIBAVARIN
  • 1-((2R,3R,4S,5R)-3,4-DIHYDROXY-5-HYDROXYMETHYL-TETRAHYDRO-FURAN-2-YL)-1H-[1,2,4]TRIAZOLE-3-CARBOXYLIC ACID AMIDE
  • 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)-1H-1,2,4-triazole-3-carboxaMide
  • USP, EP, BP
  • ICN-1229 ,RTCA
  • 1-(3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-[1,2,4]triazole-3-carboxylic acid amide
  • 1h-1,2,4-triazole-3-carboxamide, 1--d-ribofuranosyl-
  • Ribavirin (Copegus)
  • Ribavirin solution,100ppm
  • Ribavirin, >=98%
  • 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-1,2,4-triazole-3-carboxamide
  • Ribovirin
  • リバビリン
  • 1-[3-(アミノカルボニル)-1H-1,2,4-トリアゾール-1-イル]-1-デオキシ-β-D-リボフラノース
  • ビラミド
  • コペガス
  • リバミジル
  • ビラゾール
  • 1-β-D-リボフラノシル-1H-1,2,4-トリアゾール-3-カルボアミド
  • ビロナ
  • リバミド
  • 1-(β-D-リボフラノシル)-3-カルバモイル-1H-1,2,4-トリアゾール
  • 1-(β-D-リボフラノシル)-1H-1,2,4-トリアゾール-3-カルボアミド
  • レベトール
  • リバビリン標準品
  • 1-(β-D-リボフラノシル)-1,2,4-トリアゾール-3-カルボキサミド
  • リバビリン (JP17)
  • 生化学
  • 試験研究用抗ウィルス剤
  • 試験研究用抗菌剤
  • 薬理研究用試薬
  • ヌクレオシド,ヌクレオチド&関連試薬
  • ヌクレオシドと類似体
  • 抗ウイルス薬
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