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Encyclopedia > Aciclovir
Aciclovir
Systematic (IUPAC) name
2-amino-9-(2-hydroxyethoxymethyl)-
3H-purin-6-one
Identifiers
CAS number 59277-89-3
ATC code J05AB01 D06BB03 S01AD03
PubChem 2022
DrugBank APRD00567
Chemical data
Formula C8H11N5O3 
Mol. mass 225.21 g/mol
Synonyms acycloguanosine
Physical data
Melt. point 256.5 °C (494 °F)
Pharmacokinetic data
Bioavailability 10–20% (oral)
Protein binding 9-33%
Metabolism Viral thymidine kinase
Half life 2.2–20 hours
Excretion Renal
Therapeutic considerations
Pregnancy cat.

B3 (Au), B (U.S.) Image File history File linksMetadata No higher resolution available. ... Image File history File links Aciclovir. ... 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. ... A section of the Anatomical Therapeutic Chemical Classification System. ... 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. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... This article is about the chemistry of hydrogen. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless gas Atomic mass 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) Atomic mass 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). ... Look up Synonym in Wiktionary, the free dictionary. ... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ... 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. ... Many drugs are bound to Blood plasma proteins. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... 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. ... Kidneys viewed from behind with spine removed The kidneys are bean-shaped excretory organs in vertebrates. ... 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 Constitutional monarchy (federal)  - Queen Elizabeth II  - Governor-General Michael Jeffery  - Prime Minister John Howard Independence from the UK   - Constitution 1 January 1901   - Statute of Westminster 11 December 1931... 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

unscheduled/S4 (Au), POM (UK) The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ...

Routes IV, oral, topical

Aciclovir (INN) (IPA: [eɪˈsaɪklovir]) or acyclovir (USAN, former BAN) is a guanine analogue antiviral drug primarily used for the treatment of herpes simplex virus infection. It is one of the most commonly-used antiviral drugs, and is marketed under trade names such as Zovirax and Zovir (GSK). 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 intravenous drip in a hospital Intravenous therapy or IV therapy is the administration of liquid substances directly into a vein. ... 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. ... For information on how to read IPA transcriptions of English words see here. ... There have been a number of attempts to coin an alternative to American as an adjective (a demonym) for United States nationals. ... A British Approved Name (BAN) is the official non-proprietary or generic name given to a pharmaceutical substance, as defined in the British Pharmacopoeia (BP). ... Guanine is one of the five main nucleobases found in the nucleic acids DNA and RNA; the others being adenine, cytosine, thymine, and uracil. ... Antiviral drugs are a class of medication used specifically for treating viral infections. ... This article is about the virus. ... GlaxoSmithKline plc (LSE: GSK NYSE: GSK) is a British based pharmaceutical, biologicals, and healthcare company. ...


Aciclovir was seen as the start of a new era in antiviral therapy, as it is extremely selective and low in cytotoxicity. Pharmacologist Gertrude B. Elion was awarded the 1988 Nobel Prize in Medicine partly for the development of aciclovir. Antiviral drugs are a class of medication used specifically for treating viral infections. ... Cytotoxicity is the quality of being poisonous to cells. ... Gertrude Belle Elion (January 23, 1918 – February 21, 1999) was an American biochemist and pharmacologist, and a 1988 recipient of the Nobel Prize in Physiology or Medicine. ... 1988 (MCMLXXXVIII) was a leap year starting on Friday of the Gregorian calendar. ... The Nobel Prizes (Swedish: ) are awards in physics, chemistry, literature, peace, and physiology or medicine. ...

Contents

Pharmacology

Mechanism of action

Aciclovir differs from previous nucleoside analogues in that it contains only a partial nucleoside structure – the sugar ring is replaced by an open-chain structure. It 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. Nucleoside analogues are a range of antiviral products used to prevent viral replication in infected cells. ... Nucleosides are glycosylamines made by attaching a nucleobase (often reffered to simply as bases) to a ribose ring. ... 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. ...


Therefore, aciclovir can be considered a prodrug – it is administered in an inactive (or less active form) and is metabolised into a more active species after administration. A prodrug is a pharmacological substance (drug) which is administered in an inactive (or significantly less active) form. ... Overview of the citric acid cycle The citric acid cycle, one of the central metabolic pathways in aerobic organisms. ...


Microbiology

Aciclovir 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. 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 aciclovir 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]


Pharmacokinetics

Aciclovir is poorly water soluble and has poor oral bioavailability (10–20%), hence intravenous administration is necessary if high concentrations are required. When orally administered, peak plasma concentration occurs after 1–2 hours. Aciclovir has a high distribution rate, only 30% is protein-bound in plasma. The elimination half-life of aciclovir is approximately 3 hours. It is renally excreted, partly by glomerular filtration and partly by tubular secretion. 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. ... An intravenous drip in a hospital Intravenous therapy or IV therapy is the administration of liquid substances directly into a vein. ... 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. ... Renal physiology is the study of the physiology of the kidneys. ... Renal physiology is the study of the physiology of the kidneys. ...


Clinical use

400 mg pills of acyclovir
400 mg pills of acyclovir

Image File history File linksMetadata Size of this preview: 600 × 600 pixel Image in higher resolution (707 × 707 pixel, file size: 55 KB, MIME type: image/jpeg) 400 mg pills of the antiviral drug acyclovir (aciclovir). ... Image File history File linksMetadata Size of this preview: 600 × 600 pixel Image in higher resolution (707 × 707 pixel, file size: 55 KB, MIME type: image/jpeg) 400 mg pills of the antiviral drug acyclovir (aciclovir). ...

Indications

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

It has been claimed that the evidence for the effectiveness of topically applied cream for recurrent labial outbreaks is weak.[4] Likewise oral therapy for episodes is inappropriate for most non-immunocompromised patients, whilst there is evidence for oral prophylactic role in preventing recurrences.[5] 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. ... The Herpes simplex virus infection (common names: herpes, cold sores) is a common, contagious, incurable, and in some cases sexually transmitted disease caused by a double-stranded DNA virus. ... Herpes zoster, colloquially known as shingles, is the reactivation of varicella zoster virus (one of the Herpesviridae group), leading to a crop of painful blisters over the area of a dermatome. ... Chickenpox, also spelled chicken pox, is the common name for Varicella simplex, classically one of the childhood infectious diseases caught and survived by most children. ... The herpes simplex virus (HSV) (also known as Cold Sore, Night Fever, or Fever Blister) is a virus that manifests itself in two common viral infections, each marked by painful, watery blisters in the skin or mucous membranes (such as the mouth or lips) or on the genitals. ... Blepharitis is inflammation of the eyelids. ...


Dosage forms

Aciclovir is commonly marketed as tablets (200 mg and 400 mg), topical cream (5%), intravenous injection (25 mg/mL) and ophthalmic ointment (3%). Cream preparations are used primarily for labial herpes simplex. The intravenous injection is used when high concentrations of aciclovir are required. The ophthalmic ointment preparation is only used for herpes simplex keratitis .


Adverse effects

Systemic therapy

Common adverse drug reactions (≥1% of patients) associated with systemic aciclovir therapy (oral or IV) include: nausea, vomiting, diarrhoea and/or headache. In high doses, hallucinations have been reported. Infrequent adverse effects (0.1–1% of patients) include: agitation, vertigo, confusion, dizziness, oedema, arthralgia, sore throat, constipation, abdominal pain, rash and/or weakness. Rare adverse effects (<0.1% of patients) include: coma, seizures, neutropenia, leukopenia, 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. ... A hallucination is a sensory perception experienced in the absence of an external stimulus, as distinct from an illusion, which is a misperception of an external stimulus. ... Vertigo, sometimes called a headrush, 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. ... It has been suggested that Agranulocytosis be merged into this article or section. ... Leukopenia or leukocytopenia refers to a decrease in the number of circulating white blood cells (leukocytes) in the blood. ... 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 is a gastroenterological disease, featuring inflammation of the liver. ... 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. ...


Additional common adverse effects, when aciclovir is administered IV, include encephalopathy (1% of patients) and injection site reactions. The injection formulation is alkaline (pH 11), and extravasation may cause local tissue pain and irritation.[3] Renal impairment has been reported when aciclovir is given in large, fast doses intravenously, due to the crystallisation of aciclovir in the kidneys. The common (Arrhenius) definition of a base is a chemical compound that either donates hydroxide ions or absorbs hydrogen ions when dissolved in water. ... The correct title of this article is . ... Extravasation refers to the leakage of a fluid out of its container. ...


Topical therapy

Aciclovir topical cream is commonly associated (≥1% of patients) with: dry or flaking skin and/or transient stinging/burning sensations. Infrequent adverse effects include erythema and/or itch.[3] Erythema is an abnormal redness of the skin caused by capillary congestion. ...


When applied to the eye, aciclovir is commonly associated (≥1% of patients) with transient mild stinging. Infrequently (0.1–1% of patients), ophthalmic aciclovir is associated with superficial punctate keratitis and/or allergic reactions.[3]


Toxicity

Since aciclovir can be incorporated also into the cellular DNA, it is a chromosome mutagen, therefore, its use should be avoided during pregnancy. However it has not been shown to cause any teratogenic nor carcinogenic effects. The acute toxicity (LD50) of aciclovir when given orally is greater than 1 g/kg, due to the low oral bioavailability. Single cases have been reported, where extremely high (up to 80 mg/kg) doses have been accidentally given intravenously without causing any major adverse effects. The structure of part of a DNA double helix Deoxyribonucleic acid (DNA) is a nucleic acid that contains the genetic instructions for the development and function of living organisms. ... Figure 1: A representation of a condensed eukaryotic chromosome, as seen during cell division. ... In biology, a mutagen (Latin, literally origin of change) is a physical or chemical agent that changes the genetic information (usually DNA) of an organism and thus increases the number of mutations above the natural background level. ... Teratogenesis is a medical term from the Greek, literally meaning monster making. ... The term carcinogen refers to any substance, radionuclide or radiation which is an agent directly involved in the promotion of cancer or in the facilitation of its propagation. ... An LD50 test being administered In toxicology, the LD50 or colloquially semilethal dose of a particular substance is a measure of how much constitutes a lethal dose. ...


Footnotes

  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 c d e Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006. ISBN 0-9757919-2-3
  4. ^ Graham Worrall (6 Jul 1996). "Evidence for efficacy of topical acyclovir in recurrent herpes labialis is weak". BMJ 313: 46. - Letter
  5. ^ Graham Worrall (6 Jan 1996). "Acyclovir in recurrent herpes labialis". BMJ 312: 6.  - Editorial

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. ...

Further reading

  • Harvey Stewart C. in Remington’s Pharmaceutical Sciences 18th edition: (ed. Gennard, Alfonso R.) Mack Publishing Company, 1990. ISBN 0-912734-04-3.
  • Huovinen P., Valtonen V. in Kliininen Farmakologia (ed. Neuvonen et al.). Kandidaattikustannus Oy, 1994. ISBN 951-8951-09-8.
  • Périgaud C., Gosselin G., Imbach J. -L.: Nucleoside analogues as chemotherapeutic agents: a review. Nucleosides and nucleotides 1992; 11(2-4)
  • Rang H.P., Dale M.M., Ritter J.M.: Pharmacology, 3rd edition. Pearson Professional Ltd, 1995. 2003 (5th) edition ISBN 0-443-07145-4; 2001 (4th) edition ISBN 0-443-06574-8; 1990 edition ISBN 0-443-03407-9.

External links

  • Links to external chemical sources


Antivirals (primarily J05A, also S01AD and D06BB) edit
Anti-herpesvirus agents   Aciclovir, Cidofovir, Docosanol, Famciclovir, Fomivirsen, Foscarnet, Ganciclovir, Idoxuridine, Penciclovir, Trifluridine, Tromantadine, Valaciclovir, Valganciclovir, Vidarabine
Anti-influenza agents Amantadine, Oseltamivir, Peramivir, Rimantadine, Zanamivir, Arbidol
 
Antiretroviral drugs   NRTIs Abacavir, Didanosine, Emtricitabine, Lamivudine, Stavudine, Zalcitabine, Zidovudine
NtRTIs   Tenofovir
NNRTIs   Efavirenz, Delavirdine, Nevirapine
PIs Amprenavir, Atazanavir, Darunavir, Fosamprenavir, Indinavir, Lopinavir, Nelfinavir, Ritonavir, Saquinavir, Tipranavir
Fusion inhibitors Enfuvirtide
 
Other antiviral agents Adefovir, Fomivirsen, Imiquimod, Inosine, Interferon, Podophyllotoxin, Ribavirin, Viramidine

  Results from FactBites:
 
Aciclovir - Wikipedia, the free encyclopedia (889 words)
Aciclovir (INN) (IPA: [eɪˈsaɪklovir]) or acyclovir (USAN, former BAN) is a guanine analogue antiviral drug primarily used for the treatment of herpes simplex virus infection.
Aciclovir was seen as the start of a new era in antiviral therapy, as it is extremely selective and low in cytotoxicity.
Infrequently (0.1–1% of patients), ophthalmic aciclovir is associated with superficial punctate keratitis and/or allergic reactions.
Valaciclovir - Wikipedia, the free encyclopedia (403 words)
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.
Aciclovir, the active metabolite of valaciclovir, is active against most species in the herpesvirus family.
  More results at FactBites »

 
 

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