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Encyclopedia > Viramidine

Viramidine chemical structure
Viramidine Image File history File links Viramidine. ...

1-[(2R,3R,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboximidamide (also commonly 1-(β-D-Ribofuranosyl)-1,2,4-triazole-3-carboximide)
IUPAC name
CAS number
119567-79-2
ATC code
J05AB04
PubChem
451448
DrugBank
none
Chemical formula C8H13N5O4
Molecular weight 243.220 (279.681 for HCl salt)
Bioavailability
Metabolism Metabolized to 5'phosphates, de-riboside, and deriboside carboxylic acid
Elimination half-life 12 days - Multiple Dose; 120-170 hours - Single Dose
Excretion 10% fecal, remainder in urine (30% unchanged, remainder metabolites)
Pregnancy category US: X; AU: X
Legal status In Phase III drug trials.
Routes of administration oral capsule

Viramidine (ICN 3142) is an anti-viral drug in Phase III human trials, but not yet approved for pharmaceutical use. It is a prodrug of ribavirin, active against a number of DNA and RNA viruses. Viramidine has better liver-targetting than ribavirin, and has a shorter life in the body due to less penetration and storage in red blood cells. It is expected eventually to be the drug of choice for viral hepatitis syndromes in which ribavirin is active. These include hepatitis C and perhaps also hepatitis B and yellow fever. IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules . ... DrugBank is a database available at the University of Alberta that provides information about thousands of products. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The molecular mass of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of medication that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Santorio Santorio (1561-1636) in his steelyard balance, from Ars de statica medecina, first published 1614 Metabolism (from μεταβολισμος (metabolismos)) is the biochemical modification of chemical compounds in living organisms and cells. ... The elimination half-life of a drug (or any xenobiotic agent) refers to the timecourse necessary for the quantity of the xenobiotic agent in the body (or plasma concentration) to be reduced to half of its original level through various elimination processes. ... Excretion is the biological process by which an organism chemically separates waste products from its body. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother. ... The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... Ribavirin (Copegus®; Rebetol®; Ribasphere®; Vilona®,Virazole®, also generics from Sandoz, Teva, Warrick) is an anti-viral drug which is active against a number of DNA and RNA viruses. ... The general structure of a section of DNA Deoxyribonucleic acid (DNA) is a nucleic acid —usually in the form of a double helix— that contains the genetic instructions specifying the biological development of all cellular forms of life, and most viruses. ... Ribonucleic acid (RNA) is a nucleic acid polymer consisting of covalently bound nucleotides. ... The human immunodeficiency virus (HIV) A bacteriophage virus A virus is a submicroscopic obligate parasitic particle that infects cells in biological organisms. ... Human red blood cells Red blood cells are the most common type of blood cell and are the vertebrate bodys principal means of delivering oxygen to body tissues via the blood. ... Hepatitis C is a blood-borne viral disease which can cause liver inflamation, fibrosis, cirrhosis and liver cancer. ... Originally known as serum hepatitis, hepatitis B has only been recognized as such since World War II, and has caused current epidemics in parts of Asia and Africa. ...


Viramidine is as active against influenza as ribavirin in animal models, with slightly less toxicity, so it may also eventually replace ribavirin as an anti-influenza agent. PMID 16087250


Viramidine is being developed by Valeant Pharmaceuticals International, formerly Ribapharm, the company which first reported synthesis and testing of the drug in 1973. Valeant Pharmaceuticals International is a pharmaceutical company with activities spanning the drug discovery pipeline from target identification through clinical trials and commercialization. ...


Note on formulas: The carboxamidine group of this molecule is somewhat basic, and therefore this drug is also known and administered as the hydrochloride salt (with a corresponding .HCl chemical formula and different ChemID / PubChem number). At physiologic pH, the positive charge on the molecule from partial protonation of the carboximide group contributes to the relative slowness with which the drug crosses cell membranes (such as in red blood cells) until it has been metabolized into ribavirin. In the liver, however, the transformation from carboxamidine to carboxamide happens on first-pass metabolism and contributes to the higher levels of ribavirin found in liver cells and bile when viramidine is administered. Ribavirin (Copegus®; Rebetol®; Ribasphere®; Vilona®,Virazole®, also generics from Sandoz, Teva, Warrick) is an anti-viral drug which is active against a number of DNA and RNA viruses. ...


References

1. Witkowski, J. T., Robins, R. K., Khare, G. P. et al. (1973). Synthesis and antiviral activity of 1,2,4-triazole-3-thiocarboxamide and 1,2,4-triazole-3-carboxamidine ribonucleosides. Journal of Medicinal Chemistry 16, 935–7. PMID 4355593


2. Barnard, D. (2002). Viramidine (Ribapharm). Current Opinion in Investigational Drugs 3, 1585–9. PMID 12476957


External links

  • http://www.jac.oxfordjournals.org/cgi/reprint/dki405v1


Antivirals (ATC J05A) edit
Anti-herpesvirus agents   Aciclovir · Cidofovir · Docosanol · Famciclovir · Foscarnet · Fomivirsen · Ganciclovir · Idoxuridine · Penciclovir · Trifluridine · Tromantadine · Valaciclovir · Valganciclovir · Vidarabine
Anti-influenza agents Amantadine · Oseltamivir · Peramivir · Rimantadine · Zanamivir
 
Antiretroviral drugs   NRTIs Zidovudine · Didanosine · Stavudine · Zalcitabine · Lamivudine · Abacavir · Tenofovir
NNRTIs   Nevirapine · Efavirenz · Delavirdine
PIs Saquinavir · Indinavir · Atazanavir · Ritonavir · Nelfinavir · Amprenavir · Lopinavir · Tipranavir
 
Other antiviral agents Fomivirsen · Enfuvirtide · Imiquimod · Interferon · Ribavirin · Viramidine
Wikipedia does not yet have an article with this exact name. ... A section of the Anatomical Therapeutic Chemical Classification System. ... Genera Subfamily Alphaherpesvirinae    Simplexvirus    Varicellovirus    Mardivirus    Iltovirus Subfamily Betaherpesvirinae    Cytomegalovirus    Muromegalovirus    Roseolovirus Subfamily Gammaherpesvirinae    Lymphocryptovirus    Rhadinovirus Unassigned    Ictalurivirus The Herpesviridae is a family of DNA viruses that cause diseases in humans and animals. ... Aciclovir (INN) or acyclovir (USAN), marketed as Zovirax®, is one of the main antiviral drugs. ... Chemical structure of cidofovir Cidofovir is an injectable antiviral medication for the treatment of cytomegalovirus (CMV) retinitis in patients with AIDS. It suppresses CMV replication by selective inhibition of viral DNA synthesis. ... Docosanol 10% cream is a topical treatment for recurrent herpes simplex labialis episodes (episodes of cold sores or fever blisters). ... Famciclovir is an antiviral medicine that stops the varicella zoster virus that causes shingles. ... Ganciclovir sodium (Cytovene®) is an antiviral medication used to treat cytomegalovirus (CMV) infections. ... Tromantadine Tromantadine is an antiviral medicine used to treat herpes simplex virus. ... Valaciclovir (INN) or valacyclovir (USAN) is an antiviral drug used in the management of herpes simplex. ... Valganciclovir hydrochloride (Valcyte®) is an antiviral medication used to treat cytomegalovirus infections. ... Chemical structure of vidarabine Vidarabine is an anti-viral drug which is active against herpes simplex and varicella zoster viruses. ... Influenza, commonly known as the flu or the grippe, is a contagious disease of the upper airways and the lungs, caused by an RNA virus of the orthomyxoviridae family. ... Amantadine, 1-aminoadamantane, is an antiviral drug that was approved by the FDA in 1976 for the treatment of influenza type A in adults. ... Oseltamivir (pronounced ah sell TAH mih veer) is an antiviral drug used in the treatment and prophylaxis of both Influenzavirus A and Influenzavirus B. Like zanamivir, oseltamivir is a neuraminidase inhibitor, acting as a transition-state analogue inhibitor of influenza neuraminidase and thereby preventing new viruses from emerging from infected... Please expand this article. ... Rimantadine (systematic name 1-(1-aminoethyl)adamantane) is an orally administered medicine used to treat, and in rare cases prevent, Influenzavirus A infection. ... Zanamivir is a neuraminidase inhibitor used in the treatment of and prophylaxis of both influenza A and influenza B. Zanamivir was the first neuraminidase inhibitor commercially developed. ... Antiretroviral drugs are medications for the treatment of infection by retroviruses, primarily HIV. Different classes of antiretroviral drugs act at different stages of the HIV life cycle. ... Reverse transcriptase inhibitors (RTIs) are a class of antiretroviral drug used to treat HIV infection. ... Zidovudine (INN) or azidothymidine (AZT) is an antiretroviral drug, the first one approved for treatment of HIV. It is also sold under the names Retrovir® and Retrovis®, and as an ingredient in Combivir® and Trizivir®. It is an analog of thymidine. ... Didanosine (2-3-dideoxyinosine, ddI, Videx®) differs from other nucleoside analogues, because it does not have any of the regular bases, instead it has hypoxanthine attached to the sugar ring. ... Stavudine (2-3-didehydro-2-3-dideoxythymidine, d4T, brand name Zerit®) is a thymidine analogue active against HIV. It is phosphorylated by cellular kinases into active triphosphate. ... Zalcitabine (2-3-dideoxycytidine, ddC), is a derivative of the naturally existing deoxycytidine, made by replacing the hydroxyl group in position 3 with a hydrogen. ... Lamivudine (2,3-dideoxy-3-thiacytidine, 3TC) is a potent reverse transcriptase inhibitor. ... Abacavir (ABC) is extremely potent reverse transcriptase inhibitor, meant for the treatment of AIDS. ABC is capable of crossing the blood-brain barrier. ... Tenofovir disoproxil fumarate belongs to a class of antiretroviral drugs known as nucleotide analogue reverse transcriptase inhibitors (NtRTIs), which block reverse transcriptase, an enzyme crucial to viral production in HIV-infected people. ... Reverse transcriptase inhibitors (RTIs) are a class of antiretroviral drug used to treat HIV infection. ... Nevirapine, with trade name of Viramune®, is a controversial non-nucleoside reverse transcriptase inhibitors (NNRTIs) meant to treat HIV and AIDS. History Nevirapine was the first NNRTI (tenth antiretroviral) approved by the Food and Drug Administration (FDA). ... This article needs to be cleaned up to conform to a higher standard of quality. ... Protease inhibitors are a class of medication used to treat or prevent viral infections. ... Saquinavir (Fortovase®, Roche) is a protease inhibitor, used as a component of HIV therapy. ... Categories: Possible copyright violations ... Categories: Stub ... Ritonavir is a drug from the protease inhibitor class used to treat AIDS. It is manufactured as Norvir® by Abbott Laboratories. ... Nelfinavir (Viracept®) is an antiretroviral drug used in the treatment of the human immunodeficiency virus (HIV). ... Tipranavir is a new protease inhibitor (PI) that was approved by the FDA in June 2005. ... Enfuvirtide is a novel antiretroviral drug used in combination therapy for the treatment of HIV-1 infection. ... Imiquimod (Aldaraâ„¢) is a prescription medication used to treat certain diseases of the skin, including skin cancer (malignant melanoma and actinic keratosis) as well as genital warts. ... Interferons (IFNs) are natural proteins produced by the cells of the immune systems of most animals in response to challenges by foreign agents such as viruses, bacteria, parasites and tumor cells. ... Ribavirin (Copegus®; Rebetol®; Ribasphere®; Vilona®,Virazole®, also generics from Sandoz, Teva, Warrick) is an anti-viral drug which is active against a number of DNA and RNA viruses. ...

 
 

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