用户名： 密   码：
注册 | 忘记密码？
药品详细

Ribavirin(利巴韦林)

化学结构式图
中文名
利巴韦林
英文名
Ribavirin
分子式
C8H12N4O5
化学名
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-1,2,4-triazole-3-carboxamide
分子量
Average: 244.2047
Monoisotopic: 244.080769514
CAS号
36791-04-5
ATC分类
J05A Direct acting antivirals
药物类型
small molecule
阶段
approved
商品名
Copegus;Rebetol;Rebetron;Rebretron;Ribamide;Ribamidil;Ribamidyl;Ribasphere;RIBAV;Ribavirin Capsules;Ribavirin-TP;RTC;RTCA;RTP;Tribavirin;Varazid;Vilona;Viramid;Virazid;Virazole;Virazole 5'-triphosphate;
同义名
RBV;Ribavirin Triphosphate;Ribavirina [INN-Spanish];Ribavirine [INN-French];Ribavirinum [INN-Latin];
基本介绍

A nucleoside antimetabolite antiviral agent that blocks nucleic acid synthesis and is used against both RNA and DNA viruses. [PubChem]

生产厂家
  • Aurobindo pharma ltd
  • Hoffmann la roche inc
  • Sandoz inc
  • Schering corp
  • Schering plough research institute
  • Teva pharmaceuticals usa inc
  • Three rivers pharmaceuticals llc
  • Valeant pharmaceuticals international
  • Zydus pharmaceuticals usa inc
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. Sidwell RW, Bailey KW, Wong MH, Barnard DL, Smee DF: In vitro and in vivo influenza virus-inhibitory effects of viramidine. Antiviral Res. 2005 Oct;68(1):10-7. Pubmed
  2. Sidwell RW, Huffman JH, Khare GP, Allen LB, Witkowski JT, Robins RK: Broad-spectrum antiviral activity of Virazole: 1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamide. Science. 1972 Aug 25;177(50):705-6. Pubmed
  3. Alvarez D, Dieterich DT, Brau N, Moorehead L, Ball L, Sulkowski MS: Zidovudine use but not weight-based ribavirin dosing impacts anaemia during HCV treatment in HIV-infected persons. J Viral Hepat. 2006 Oct;13(10):683-9. Pubmed
  4. Bani-Sadr F, Carrat F, Pol S, Hor R, Rosenthal E, Goujard C, Morand P, Lunel-Fabiani F, Salmon-Ceron D, Piroth L, Pialoux G, Bentata M, Cacoub P, Perronne C: Risk factors for symptomatic mitochondrial toxicity in HIV/hepatitis C virus-coinfected patients during interferon plus ribavirin-based therapy. J Acquir Immune Defic Syndr. 2005 Sep 1;40(1):47-52. Pubmed
剂型
规格
化合物类型
Type small molecule
Classes
  • Carbohydrates
Substructures
  • Glycerol and Derivatives
  • Hydroxy Compounds
  • Amino Ketones
  • Triazoles
  • Ethers
  • Carbamates and Derivatives
  • Alcohols and Polyols
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Furans
  • Imines
  • Carboxylic Acids and Derivatives
  • Cyanamides
  • Carbohydrates
适应症
ANTIVIRALS 抗病毒;
药理
Indication For the treatment of chronic hepatitis C and for respiratory syncytial virus (RSV).
Pharmacodynamics Ribavirin is an anti-viral drug active against a number of DNA and RNA viruses. It is a member of the nucleoside antimetabolite drugs that interfere with duplication of the viral genetic material. The drug inhibits the activity of the enzyme RNA dependent RNA polymerase, due to it's resemblence to building blocks of the RNA molecules. The oral form is used in the treatment of hepatitis C, in combination with interferon drugs. The aerosol form is used to treat respiratory syncytial virus-related diseases in children. The primary serious adverse effect of ribavirin is hemolytic anemia, which may worsen preexisting cardiac disease.
Mechanism of action Ribavirin is readily phosphorylated intracellularly by adenosine kinase to ribavirin mono-, di-, and triphosphate metabolites. Ribavirin triphosphate (RTP) is a potent competitive inhibitor of inosine monophosphate (IMP) dehydrogenase, viral RNA polymerase and messenger RNA (mRNA) guanylyltransferase (viral) and can be incorporated into RNA in RNA viral species.. Guanylyltranserase inhibition stops the capping of mRNA. These diverse effects result in a marked reduction of intracellular guanosine triphosphate (GTP) pools and inhibition of viral RNA and protein synthesis. Ribavirin is also incorporated into the viral genome causing lethal mutagenesis and a subsequent decrease in specific viral infectivity.
Absorption Rapidly and extensively absorbed following oral administration. However, due to first-pass metabolism, the absolute bioavailability averages 64%.
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Hepatic. Results of in vitro studies using both human and rat liver microsome preparations indicated little or no cytochrome P450 enzyme-mediated metabolism of ribavirin, with minimal potential for P450 enzyme-based drug interactions. Ribavirin has two pathways of metabolism: (1) a reversible phosphorylation pathway in nucleated cells; and (2) a degradative pathway involving deribosylation and amide hydrolysis to yield a triazole carboxylic acid metabolite.
Route of elimination Not Available
Half life 9.5 hours
Clearance
  • Apparent cl=26 L/h [A single oral dose]
Toxicity Side effects include "flu-like" symptoms, such as headache, fatigue, myalgia, and fever. The LD50 in mice is 2 g/kg orally and is associated with hypoactivity and gastrointestinal symptoms (estimated human equivalent dose of 0.17 g/kg, based on body surface area conversion).
Affected organisms
  • Hepatitis C virus, RSV and other RNA/DNA viruses
Pathways Not Available
理化性质
Properties
State solid
Experimental Properties
Property Value Source
melting point 174-176 °C Not Available
water solubility 142 mg/mL (max, at 25 °C) Not Available
logP -1.85 BIOBYTE (1995)
Predicted Properties
Property Value Source
water solubility 3.32e+01 g/l ALOGPS
logP -1.9 ALOGPS
logP -2.8 ChemAxon
logS -0.87 ALOGPS
pKa (strongest acidic) 11.88 ChemAxon
pKa (strongest basic) -1.2 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 7 ChemAxon
hydrogen donor count 4 ChemAxon
polar surface area 143.72 ChemAxon
rotatable bond count 3 ChemAxon
refractivity 64.57 ChemAxon
polarizability 22.18 ChemAxon
药物相互作用
Drug Interaction
Abacavir Ribavirin may increase the hepatotoxicity of reverse transcriptase inhibitors (nucleoside) such as Abacavir. Lactic acidosis may occur. Consider modifying therapy.
Zalcitabine Ribavirin may increase the hepatotoxicity of zalcitabine. May cause lactic acidosis. MOnitor for lactic acidosis during concomitant therapy.
Zidovudine Increased risk or severity of anemia. Consider alternate therapy or monitor more closely for anemia.
食物相互作用
Not Available

返回 | 收藏