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Aciclovir information


Aciclovir
Clinical data
Pronunciation/ˈsklvɪər/
Trade namesZovirax, others[1]
Other namesAcycloguanosine, acyclovir (BAN UK), acyclovir (USAN US)
AHFS/Drugs.com
  • Acyclovir Monograph
  • Acyclovir topical Monograph
MedlinePlusa681045
License data
  • US DailyMed: Acyclovir
Pregnancy
category
  • AU: B3
Routes of
administration
Intravenous, by mouth, topical, eye ointment
ATC code
  • J05AB01 (WHO) D06BB03 (WHO), S01AD03 (WHO), D06BB53 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only[2]
  • UK: POM (Prescription only)
  • US: ℞-only
Pharmacokinetic data
Bioavailability15–20% (by mouth)[3]
Protein binding9–33%[3]
MetabolismLiver
Elimination half-life2–4 hours
ExcretionKidney (62–90% as unchanged drug)
Identifiers
IUPAC name
  • 2-amino-1,9-dihydro-9-((2-hydroxyethoxy)methyl)-3H-purin-6-one
CAS Number
  • 59277-89-3 checkY
PubChem CID
  • 2022
PubChem SID
  • 46506002
IUPHAR/BPS
  • 4829
DrugBank
  • DB00787 checkY
ChemSpider
  • 1945 checkY
UNII
  • X4HES1O11F
KEGG
  • D00222 checkY
  • C06810 ☒N
ChEBI
  • CHEBI:2453 checkY
ChEMBL
  • ChEMBL184 checkY
PDB ligand
  • AC2 (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID1022556 Edit this at Wikidata
ECHA InfoCard100.056.059 Edit this at Wikidata
Chemical and physical data
FormulaC8H11N5O3
Molar mass225.208 g·mol−1
3D model (JSmol)
  • Interactive image
Melting point256.5 °C (493.7 °F)
SMILES
  • O=C2/N=C(\Nc1n(cnc12)COCCO)N
InChI
  • InChI=1S/C8H11N5O3/c9-8-11-6-5(7(15)12-8)10-3-13(6)4-16-2-1-14/h3,14H,1-2,4H2,(H3,9,11,12,15) checkY
  • Key:MKUXAQIIEYXACX-UHFFFAOYSA-N checkY
  (verify)

Aciclovir, also known as acyclovir,[4] is an antiviral medication.[5] It is primarily used for the treatment of herpes simplex virus infections, chickenpox, and shingles.[6] Other uses include prevention of cytomegalovirus infections following transplant and severe complications of Epstein–Barr virus infection.[6][7] It can be taken by mouth, applied as a cream, or injected.[6]

Common side effects include nausea and diarrhea.[6] Potentially serious side effects include kidney problems and low platelets.[6] Greater care is recommended in those with poor liver or kidney function.[6] It is generally considered safe for use in pregnancy with no harm having been observed.[6][8] It appears to be safe during breastfeeding.[9][10] Aciclovir is a nucleoside analogue that mimics guanosine.[6] It works by decreasing the production of the virus's DNA.[6]

Aciclovir was patented in 1974 by Burroughs Wellcome, and approved for medical use in 1981.[11] It is on the World Health Organization's List of Essential Medicines.[12][13] It is available as a generic medication and is marketed under many brand names worldwide.[1] In 2021, it was the 169th most commonly prescribed medication in the United States, with more than 3 million prescriptions.[14][15]

  1. ^ a b "Aciclovir". Drugs.com. Archived from the original on 23 September 2015. Retrieved 6 September 2015.
  2. ^ "Skin health". Health Canada. 9 May 2018. Retrieved 13 April 2024.
  3. ^ a b "Zovirax (acyclovir) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. Archived from the original on 19 February 2014. Retrieved 5 February 2014.
  4. ^ Kevin ES. "The Aciclovir" (in German). Kevin. Retrieved 25 May 2017.
  5. ^ de Clercq E, Field HJ (5 October 2005). "Antiviral prodrugs – the development of successful prodrug strategies for antiviral chemotherapy". British Journal of Pharmacology. Vol. 147, no. 1. Wiley-Blackwell (published January 2006). pp. 1–11. doi:10.1038/sj.bjp.0706446. PMC 1615839. PMID 16284630.
  6. ^ a b c d e f g h i "Acyclovir". The American Society of Health-System Pharmacists. Archived from the original on 2015-01-05. Retrieved Jan 1, 2015.
  7. ^ Rafailidis PI, Mavros MN, Kapaskelis A, Falagas ME (November 2010). "Antiviral treatment for severe EBV infections in apparently immunocompetent patients". Journal of Clinical Virology. 49 (3): 151–157. doi:10.1016/j.jcv.2010.07.008. PMID 20739216.
  8. ^ "Prescribing medicines in pregnancy database". Australian Government. 3 March 2014. Archived from the original on 8 April 2014. Retrieved 22 April 2014.
  9. ^ Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 59. ISBN 9781284057560.
  10. ^ "Acyclovir use while Breastfeeding". Mar 10, 2015. Archived from the original on 5 March 2016. Retrieved 8 March 2016. Even with the highest maternal dosages, the dosage of acyclovir in milk is only about 1% of a typical infant dosage and would not be expected to cause any adverse effects in breastfed infants
  11. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 504. ISBN 9783527607495.
  12. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  13. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  14. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  15. ^ "Acyclovir - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

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Aciclovir

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appears to be safe. It is a prodrug, which works after being converted to aciclovir in a person's body. Valaciclovir was patented in 1987 and came into medical...

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help with the symptoms. Treatments with antiviral medication such as aciclovir or valaciclovir can lessen the severity of symptomatic episodes. Worldwide...

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Chickenpox

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those at increased risk of complications, antiviral medication such as aciclovir is recommended. Chickenpox occurs in all parts of the world. In 2013,...

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Shingles

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occurs, its severity. If shingles develops, antiviral medications such as aciclovir can reduce the severity and duration of disease if started within 72 hours...

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Viral meningitis

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For herpes the treatment of choice is aciclovir. If encephalitis is suspected, empiric treatment with IV aciclovir is often warranted. Surgical management...

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Brivudine

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daily, in contrast to aciclovir, valaciclovir and other antivirals. A study has found that it is more effective than aciclovir, but this has been disputed...

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WHO Model List of Essential Medicines

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Itraconazole Nystatin Voriconazole Complementary: Micafunginα Potassium iodideα Aciclovir Abacavir Lamivudine Tenofovir disoproxil fumarate Zidovudine Efavirenz...

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International nonproprietary name

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cholesterol-lowering agents (e.g. simvastatin) -vir for antivirals (e.g. aciclovir or ritonavir) -navir for antiretroviral protease inhibitors (e.g. darunavir)...

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other nucleoside analogues, such as the more widely used aciclovir. A difference between aciclovir and penciclovir is that the active triphosphate form of...

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Drug nomenclature

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stems what drug class the drug belongs to. For example, one can tell that aciclovir is an antiviral drug because its name ends in the -vir suffix. The earliest...

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used its power to mandate a warning on fluoroquinolones, ceftriaxone, aciclovir, and pioglitazone. Health Canada terms its version of boxed warnings "serious...

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Prodrug

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Examples Type I Intracellular Type IA Therapeutic target tissues/cells Aciclovir, fluorouracil, cyclophosphamide, diethylstilbestrol diphosphate, L-DOPA...

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Conjunctivitis

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by herpes simplex viruses, can be serious and requires treatment with aciclovir. Acute hemorrhagic conjunctivitis is a highly contagious disease caused...

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Virus

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nucleoside analogues are aciclovir for Herpes simplex virus infections and lamivudine for HIV and hepatitis B virus infections. Aciclovir is one of the oldest...

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Lymphocytic pleocytosis

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Intravenous aciclovir, can be used to prevent viral replication, and in the event of persistent lymphocytic pleocytosis, higher doses of aciclovir can also...

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Cidofovir

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cytomegalovirus retinitis. Cidofovir has also shown efficacy in the treatment of aciclovir-resistant HSV infections. Cidofovir has also been investigated as a treatment...

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South East England

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manufactured by Wellcome in 1987 in Kent; they also introduced Zovirax (aciclovir), and the naturally occurring digoxin, a cardiac glycoside. After a plane...

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Neonatal meningitis

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Chemical structure of aciclovir...

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Uveitis

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of herpetic uveitis, anti-viral medications, such as valaciclovir or aciclovir, may be administered to treat the causative viral infection. Uveitis affects...

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Tizanidine

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(amiodarone, mexiletine, propafenone, verapamil), cimetidine, famotidine, aciclovir, ticlopidine and oral contraceptives) is contraindicated. Concomitant...

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cyclophosphamide, amphotericin B Tubular obstruction: sulphonamides, methotrexate, aciclovir, diethylene glycol, triamterene. Main article : Acute interstitial nephritis...

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Simple Explanation

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there, and Foreman suggests melioidosis. They start her on an IV drip and aciclovir, which works, until she starts gasping. Thirteen suggests polyserositis...

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Nucleoside analogue

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zalcitabine (ddC)(HIV) guanosine and deoxyguanosine analogues: abacavir (HIV) aciclovir entecavir (hepatitis B) thymidine and deoxythymidine analogues: stavudine...

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Herpes simplex keratitis

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results from inability of the corneal epithelium to heal. But on the viral aciclovir eye ointment q.i.d can be used together a systemic antiviral drug t.d...

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Angular cheilitis

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in the same way as a cold sore, with topical antiviral drugs such as aciclovir. 22% of cases of angular cheilitis are due to irritants. Saliva contains...

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Eczema herpeticum

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[citation needed] It can be treated with systemic antiviral drugs, such as aciclovir or valganciclovir. Foscarnet may also be used for immunocompromised host...

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ATC code D06

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