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Encyclopedia > Valaciclovir
Valaciclovir
Systematic (IUPAC) name
2-[(2-amino-6-oxo-3,9-dihydropurin-9-yl)methoxy]
ethyl-2-amino-3-methyl-butanoate
Identifiers
CAS number 124832-27-5
ATC code J05AB11
PubChem 60773
DrugBank APRD00697
Chemical data
Formula C13H20N6O4 
Mol. mass 324.336 g/mol
Pharmacokinetic data
Bioavailability 55%
Protein binding 13–18%
Metabolism Hepatic (to aciclovir)
Half life <30 minutes (valaciclovir);
2.5-3.6 hours (aciclovir)
Excretion Renal 40–50% (aciclovir),
faecal 47% (aciclovir)
Therapeutic considerations
Pregnancy cat.

B3 (Au), B (U.S.) Image File history File links Valaciclovir. ... 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, mixtures 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. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... This article does not cite its references or sources. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... The molecular mass (abbreviated MM) of a substance, formerly also 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 unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... A drugs efficacy may be affected by the degree to which it binds to the proteins within blood plasma. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... Aciclovir (INN) (IPA: ) or acyclovir (USAN, former BAN) is a guanine analogue antiviral drug primarily used for the treatment of herpes simplex virus infection. ... It has been suggested that Effective half-life be merged into this article or section. ... Excretion is the process of eliminating waste products of metabolism and other materials that are of no use. ... 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 during pregnancy. ... Anthem Advance Australia Fair Royal anthem: God Save the Queen Capital Canberra Largest city Sydney Official languages English (de facto 1) Government Federal constitutional monarchy and parliamentary democracy  -  Queen Elizabeth II  -  Governor-General Michael Jeffery  -  Prime Minister John Howard Independence from the United Kingdom   -  Constitution 1 January 1901   -  Statute of... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from...

Legal status

S4 (Au), POM (UK), ℞-only (U.S.) The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ...

Routes Oral

Valaciclovir (INN) or valacyclovir (USAN) is an antiviral drug used in the management of herpes simplex and herpes zoster (shingles). It is a prodrug, being converted in vivo to aciclovir. It is marketed by GlaxoSmithKline under the trade name Valtrex or Zelitrex. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... An International Nonproprietary Name (INN) is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization. ... There have been a number of attempts to coin an alternative to American as an adjective (a demonym) for United States nationals. ... Antiviral drugs are a class of medication used specifically for treating viral infections. ... This article is about the disease. ... Herpes zoster, colloquially known as shingles, is the reactivation of varicella zoster virus (VZV, primary infection of which leads to chicken pox), one of the Herpesviridae group, leading to a crop of painful blisters over the area of a dermatome. ... A prodrug is a pharmacological substance (drug) which is administered in an inactive (or significantly less active) form. ... In vivo (Latin for (with)in the living). ... Aciclovir (INN) (IPA: ) or acyclovir (USAN, former BAN) is a guanine analogue antiviral drug primarily used for the treatment of herpes simplex virus infection. ... GlaxoSmithKline plc (LSE: GSK NYSE: GSK) is a British based pharmaceutical, biologicals, and healthcare company. ...

Contents

Pharmacology

Mechanism of action

Valaciclovir is a prodrug that is converted by esterases to the active drug aciclovir via hepatic first-pass metabolism. Aciclovir is selectively converted into a monophosphate form by viral thymidine kinase, which is far more effective (3000 times) in phosphorylation than cellular thymidine kinase. Subsequently, the monophosphate form is further phosphorylated into the active triphosphate form, aciclo-GTP, by cellular kinases. Aciclo-GTP is a very potent inhibitor of viral DNA polymerase; it has approximately 100 times higher affinity to viral than cellular polymerase. Its monophosphate form also incorporates into the viral DNA, resulting in chain termination. It has also been shown that the viral enzymes cannot remove aciclo-GMP from the chain, which results in inhibition of further activity of DNA polymerase. Aciclo-GTP is fairly rapidly metabolised within the cell, possibly by cellular phosphatases. An esterase is an hydrolase enzyme that splits esters into a acid and an alcohol in a chemical reaction with water called hydrolysis. ... Aciclovir (INN) (IPA: ) or acyclovir (USAN, former BAN) is a guanine analogue antiviral drug primarily used for the treatment of herpes simplex virus infection. ... The liver is an organ in vertebrates including humans. ... The first pass effect (or first pass metabolism) is a phenomenon of drug metabolism. ... Thymidine kinase TK, is an enzyme, a phosphotransferase (a kinase): 2-deoxythymidine kinase, ATP-thymidine 5-phosphotransferase, {{{EC 2. ... In biochemistry, a kinase is a type of enzyme that transfers phosphate groups from high-energy donor molecules, such as ATP, to specific target molecules (substrates); the process is termed phosphorylation. ... 3D structure of the DNA-binding helix-hairpin-helix motifs in human DNA polymerase beta A DNA polymerase is an enzyme that assists in DNA replication. ... An overview of protein synthesis. ... A phosphatase is an enzyme that hydrolyses phosphoric acid monoesters into a phosphate ion and a molecule with a free hydroxyl group. ...


Microbiology

Aciclovir, the active metabolite of valaciclovir, is active against most species in the herpesvirus family. In descending order of activity:[1] Genera Subfamily Alphaherpesvirinae    Simplexvirus    Varicellovirus    Mardivirus    Iltovirus Subfamily Betaherpesvirinae    Cytomegalovirus    Muromegalovirus    Roseolovirus Subfamily Gammaherpesvirinae    Lymphocryptovirus    Rhadinovirus Unassigned    Ictalurivirus The Herpesviridae are a family of DNA viruses that cause diseases in humans and animals. ...

Activity is predominantly active against HSV, and to a lesser extent VZV. It is only of limited efficacy against EBV and CMV. It is inactive against latent viruses in nerve ganglia. Species Herpes simplex virus 1 (HSV-1) Herpes simplex virus 2 (HSV-2) This article is about the virus. ... The varicella-zoster virus (VZV), also known as human herpes virus 3 (HHV-3), is one of the eight herpes viruses known to affect humans (and other vertebrates). ... The Epstein-Barr virus (EBV), also called Human herpesvirus 4 (HHV-4), is a virus of the herpes family (which includes Herpes simplex virus and Cytomegalovirus), and is one of the most common viruses in humans. ... species see text Cytomegalovirus (CMV), is a genus of Herpes viruses; in humans the species is known as Human herpesvirus 5 (HHV-5). ... This is a dorsal root ganglion (DRG) from a chicken embryo (around stage of day 7) after incubation overnight in NGF growth medium stained with anti-neurofilament antibody. ...


To date, resistance to valaciclovir has not been clinically significant. Mechanisms of resistance in HSV include deficient viral thymidine kinase; and mutations to viral thymidine kinase and/or DNA polymerase, altering substrate sensitivity.[2]


Clinical use

Indications

Valaciclovir is indicated for the treatment of HSV and VZV infections, including:[3]

  • Genital herpes simplex (treatment and prophylaxis)
  • Reduction of HSV transmission from people with recurrent infection to uninfected individuals
  • Herpes zoster (shingles)
  • Prevention of CMV disease following organ transplantation

This article is about the disease. ... Prophylaxis refers to any medical or public health procedure whose purpose is to prevent, rather than treat or cure, disease. ... Herpes zoster, colloquially known as shingles, is the reactivation of varicella zoster virus (VZV, primary infection of which leads to chicken pox), one of the Herpesviridae group, leading to a crop of painful blisters over the area of a dermatome. ... species see text Cytomegalovirus (CMV), is a genus of Herpes viruses; in humans the species is known as Human herpesvirus 5 (HHV-5). ... An organ transplant is the transplantation of an organ (or part of one) from one body to another, for the purpose of replacing the recipients damaged or failing organ with a working one from the donor. ...

Adverse effects

Common adverse drug reactions (≥1% of patients) associated with valaciclovir therapy are the same as for aciclovir, its active metabolite, and include: nausea, vomiting, diarrhoea and/or headache. Infrequent adverse effects (0.1–1% of patients) include: agitation, vertigo, confusion, dizziness, oedema, arthralgia, sore throat, constipation, abdominal pain, rash, weakness and/or renal impairment. Rare adverse effects (<0.1% of patients) include: coma, seizures, neutropenia, leukopenia, tremor, ataxia, encephalopathy, psychotic symptoms, crystalluria, anorexia, fatigue, hepatitis, Stevens-Johnson syndrome, toxic epidermal necrolysis and/or anaphylaxis.[3] An adverse drug reaction (abbreviated ADR) is a term to describe the unwanted, negative consequences sometimes associated with the use of medications. ... Aciclovir (INN) (IPA: ) or acyclovir (USAN, former BAN) is a guanine analogue antiviral drug primarily used for the treatment of herpes simplex virus infection. ... Vertigo, a specific type of dizziness, is a major symptom of a balance disorder. ... Edema (BE: oedema, formerly known as dropsy) is swelling of any organ or tissue due to accumulation of excess fluid. ... Arthralgia is a term used to describe pain in the joints. ... Renal failure is when the kidneys fail to function properly. ... Neutropenia (or neutropaenia, adjective neutrop(a)enic) is a hematological disorder characterized by an abnormally low number of neutrophil granulocytes (a type of white blood cell). ... Leukopenia or leukocytopenia refers to a decrease in the number of circulating white blood cells (leukocytes) in the blood. ... Ataxia (from Greek ataxiā, meaning failure to put in order) is unsteady and clumsy motion of the limbs or torso due to a failure of the gross coordination of muscle movements. ... Encephalopathy is a container term for various conditions affecting the brain. ... Crystalluria refers to crystals found in the urine when performing a urine test. ... Anorexia (deriving from the Greek α(ν)- (a(n)-, a prefix that denotes absence) + όρεξη (orexe) = appetite) is the decreased sensation of appetite. ... Hepatitis (plural hepatitides) implies injury to liver characterised by presence of inflammatory cells in the liver tissue. ... Stevens-Johnson syndrome (SJS) is a severe and life-threatening condition. ... Toxic epidermal necrolysis is a life-threatening and usually drug-induced dermatological condition that occurs more often in women than in men. ... }} In medicine, anaphylaxis is a severe and rapid multi-system allergic reaction. ...


Valaciclovir is contraindicated in immuno-suppressed patients such as those infected with HIV as it may cause thrombotic thrombocytopenic purpura and hemolytic uremic syndromes resulting in kidney failure. Aciclovir is preferred in these patients.


References

  1. ^ O'Brien JJ, Campoli-Richards DM. Acyclovir. An updated review of its antiviral activity, pharmacokinetic properties and therapeutic efficacy. Drugs 1989;37(3):233-309. PMID 2653790
  2. ^ Sweetman S, editor. Martindale: The complete drug reference. 34th ed. London: Pharmaceutical Press; 2004. ISBN 0-85369-550-4
  3. ^ a b Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006. ISBN 0-9757919-2-3

The Australian Medicines Handbook or AMH is a medical reference text commonly used in practice by health professionals (particularly general practitioners and pharmacists) in Australia. ...

External links


  Results from FactBites:
 
What oral anti-viral medications exist? (516 words)
Valaciclovir also cuts down the time during which the virus is detected on genital skin surfaces ('viral shedding').
In clinical tests, valaciclovir prevented the development of painful blisters and ulcers in one third more patients who took the drug within 24 hours of noticing the first symptoms of the outbreak, compared to those who took an ineffective placebo.
Like valaciclovir, aciclovir also shortens the time during which the herpes virus is detected on skin surfaces (known as 'viral shedding') - a time when the disease can be passed on to a sexual partner.
  More results at FactBites »

 
 

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