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Encyclopedia > Ganciclovir
Ganciclovir
Systematic (IUPAC) name
2-amino-9-(1,3-dihydroxypropan-2-yloxymethyl)-
3H-purin-6-one
Identifiers
CAS number 82410-32-0
ATC code J05AB06 S01AD09
PubChem 3454
DrugBank APRD00263
Chemical data
Formula C9H13N5O4 
Mol. mass 255.23 g/mol
Pharmacokinetic data
Bioavailability 5% (oral)
Metabolism Thymidine kinase
Half life 2.5–5 hours
Excretion Renal
Therapeutic considerations
Pregnancy cat.

D (Au), C (U.S.) Image File history File links Size of this preview: 405 × 599 pixelsFull resolution (500 × 740 pixel, file size: 9 KB, MIME type: image/png) Structure of ganciclovir. ... 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. ... 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 or section does not cite any 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 Mr) 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. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... Thymidine kinase TK, is an enzyme, a phosphotransferase (a kinase): 2-deoxythymidine kinase, ATP-thymidine 5-phosphotransferase, {{{EC 2. ... 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 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 IV, oral, intravitreal

Ganciclovir (INN) (IPA: [gænˈsaɪkləvir]) is an antiviral medication used to treat or prevent cytomegalovirus (CMV) infections, and there are many errors and omissions in this article. Get your information on ganciclovir somewhere else. It was synthesized by Julian Verheyden and John Martin at Syntex Research. Ganciclovir sodium is marketed under the trade names Cytovene and Cymevene (Roche). Ganciclovir for ocular use is marketed under the trade name Vitrasert (Bausch & Lomb). A prodrug form with improved oral bioavailability (valganciclovir) has also been developed. 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. ... Articles with similar titles include the NATO phonetic alphabet, which has also informally been called the “International Phonetic Alphabet”. For information on how to read IPA transcriptions of English words, see IPA chart for English. ... Antiviral drugs are a class of medication used specifically for treating viral infections. ... Species see text Cytomegalovirus (CMV) (from the Greek cyto-, cell, and -mega-, large) is a viral genus of the Herpesviruses group: in humans it is commonly known as human herpesvirus 5 (HHV-5). ... Hoffmann-La Roche, Ltd. ... Bausch and Lomb (German pronunciation BOWsh and LAWM) is an American company based in Rochester, New York, specialized in medical optics like contact lenses and surgical instruments. ... 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. ... Valganciclovir hydrochloride (Valcyte®) is an antiviral medication used to treat cytomegalovirus infections. ...

Contents

Mechanism of action

Ganciclovir is a synthetic analogue of 2'-deoxy-guanosine. It is first phosphorylated to a deoxyguanosine triphosphate (dGTP) analog. This competitively inhibits the incorporation of dGTP by viral DNA polymerase, resulting in the termination of elongation of viral DNA. The chemical structure of Guanosine Guanosine is a nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a β-N9-glycosidic bond. ... A phosphorylated serine residue Phosphorylation is the addition of a phosphate (PO4) group to a protein or a small molecule or the introduction of a phosphate group into an organic molecule. ... Guanosine triphosphate (GTP) is also known as guanosine-5-triphosphate. ... 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. ... The structure of part of a DNA double helix Deoxyribonucleic acid, or DNA, is a nucleic acid molecule that contains the genetic instructions used in the development and functioning of all known living organisms. ...


Clinical use

Indications

Ganciclovir is indicated for:[1]

It is also used for acute CMV colitis in HIV/AIDS and CMV pneumonitis in immunosuppressed patients. CMV (Cytomegalovirus) is a DNA virus in the family Herpesviridae. ... Immunosuppression is the medical suppression of the immune system. ... Pneumonia is an inflammation of the lung. ... Bone marrow transplantation or hematopoietic stem cell transplantation (HSCT) is a medical procedure in the field of hematology and oncology that involves transplantation of hematopoietic stem cells (HSC). ... An organ transplant is the moving of a whole or partial organ from one body to another (or from a donor site on the patients own body), for the purpose of replacing the recipients damaged or failing organ with a working one from the donor site. ...


Adverse effects

Ganciclovir is commonly associated with a range of serious haematological adverse effects. Common adverse drug reactions (≥1% of patients) include: granulocytopenia, neutropenia, anaemia, thrombocytopenia, fever, nausea, vomiting, dyspepsia, diarrhoea, abdominal pain, flatulence, anorexia, raised liver enzymes, headache, confusion, hallucination, seizures, pain and phlebitis at injection site (due to high pH), sweating, rash, itch, increased serum creatinine and blood urea concentrations.[1] Hematology is the branch of medicine that is concerned with blood and its disorders. ... An adverse drug reaction (abbreviated ADR) is a term to describe the unwanted, negative consequences sometimes associated with the use of medications. ... This page is a candidate to be moved to Wiktionary. ... 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). ... This article discusses the medical condition. ... Thrombocytopenia (or -paenia, or thrombopenia in short) is the presence of relatively few platelets in blood. ... Phlebitis is an inflammation of a vein, usually in the legs. ... This article needs additional references or sources for verification. ... Urea is an organic compound of carbon, nitrogen, oxygen and hydrogen, with the formula CON2H4 or (NH2)2CO. Urea is also known as carbamide, especially in the recommended International Nonproprietary Names (rINN) in use in Europe. ...


Toxicity

Ganciclovir is considered a potential human carcinogen, teratogen, and mutagen. It is also considered likely to cause inhibition of spermatogenesis. Thus, it is used judiciously and handled as a cytotoxic drug in the clinical setting.[1][2] The hazard symbol for carcinogenic chemicals in the Globally Harmonized System. ... Teratogenesis is a medical term from the Greek, literally meaning monster making. ... 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. ... This article or section is in need of attention from an expert on the subject. ... Chemotherapy (pronounced keem-o-therapy) is the use of certain drugs to treat disease, as distinct from other forms of treatment, such as surgery. ...


Pharmacokinetics

Absorption of the oral form is very limited - about 5% fasting, about 8% with food. It achieves a concentration in the central nervous system of about 50% of the plasma level. About 90% of plasma ganciclovir is eliminated unchanged in the urine, with a half-life of 2-6 hrs, depending on renal function (elimination takes over 24 hours in end-stage renal disease). A diagram showing the CNS: 1. ... Blood plasma is the liquid component of blood, in which the blood cells are suspended. ... This article or section is in need of attention from an expert on the subject. ... Half-Life For a quantity subject to exponential decay, the half-life is the time required for the quantity to fall to half of its initial value. ... In medicine (nephrology) renal function is an indication of the state of the kidney and its role in physiology. ...


Administration

Acute infections are treated in two phases:

  • induction phase, 5 mg per kilogram intravenously every 12 hours for 14-21 days, the intravenous dose given as a 1 hour infusion
  • maintenance phase, 5 mg per kg intravenously every day

Stable disease is treated with 1000 mg orally three times daily. Similar dosing is used to prevent disease in high-risk patients, such as those infected with human immunodeficiency virus (HIV) or those with organ transplants.


Ganciclovir is also available in slow-release formulations for insertion into the vitreous humour of the eye, as treatment for CMV retinitis (associated with HIV infection). Vitreous humour is the clear aqueous solution that fills the space between the lens and the retina of the vertebrate eyeball. ... A human eye Eyes are organs of vision that detect light. ... CMV (Cytomegalovirus) is a DNA virus in the family Herpesviridae. ...


References

  1. ^ a b c Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006. ISBN 0-9757919-2-3
  2. ^ Roche Products Pty Ltd. Cymevene (Australian Approved Product Information). Dee Why (NSW): Roche; 2005.

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

  • Noble S, Faulds D. Ganciclovir. An update of its use in the prevention of cytomegalovirus infection and disease in transplant recipients. Drugs. 1998;56(1):115-46
  • Spector SA. Oral ganciclovir. Adv Exp Med Biol. 1999;458:121-7
  • Couchoud C. Cytomegalovirus prophylaxis with antiviral agents for solid organ transplantation. Cochrane Database Syst Rev. 2000;(2):CD001320.

  Results from FactBites:
 
BioMed Central | Full text | Dexamethasone inhibits the HSV-tk/ ganciclovir bystander effect in malignant glioma cells (4996 words)
The effects of dexamethasone on cell proliferation and sensitivity to ganciclovir were assessed with a thymidine incorporation assay and a MTT test.
Ganciclovir monophosphate is subsequently bis and tri-phosphorylated by cellular kinases and is then incorporated in the DNA of replicating cells, blocking the cell cycle and inducing apoptosis [1,4,5].
The reasons why ganciclovir failed to enhance the toxicity of sFAS-L on U87-TK cells remain unknown and are beyond the scope of the present work, as is the thorough assessment of the effects of dexamethasone on HSV-TK/GCV-induced apoptosis.
Definition of ganciclovir - NCI Dictionary of Cancer Terms (70 words)
Definition of ganciclovir - NCI Dictionary of Cancer Terms
An antiviral agent used to prevent or treat cytomegalovirus infections that may occur when the body's immune system is suppressed.
In gene therapy, ganciclovir is used with an altered herpes simplex virus-1 gene to kill advanced melanoma cells and brain tumor cells.
  More results at FactBites »

 
 

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