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59277-89-3-Aciclovir Aciclovir

Aciclovir

For research use only, not for therapeutic use.

  • CAT Number: A001066
  • CAS Number: 59277-89-3
  • Molecular Formula: C8H11N5O3
  • Molecular Weight: 225.2
  • Purity: ≥95%
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Acyclovir (CAS 59277-89-3) is an antiviral agent with activity against herpes simplex virus types 1 and 2 (HSV-1 and HSV-2) and varicella zoster virus. Acyclovir is converted by a herpesvirus enzyme into acyclovir triphosphate that inhibits the synthesis of deoxyribonucleic acid (DNA) molecules in the virally infected cells, thereby inhibiting viral replication. It induces apoptosis in cells transfected with HSV-TK (suicidal gene therapy).


Catalog Number A001066
CAS Number 59277-89-3
Synonyms

Aciclovir; Acycloguanosine; 59277-89-3; Zovirax; Vipral

Molecular Formula C8H11N5O3
Purity ≥95%
Target DNA Synthesis
Solubility >11.4mg/mL in DMSO
Storage -20°C
Overview of Clinical Research

<span style="font-family:arial,helvetica,sans-serif;"><span style="color:#000000;"><span style="font-size:12px;">Acyclovir is a&nbsp;<span style="font-variant-ligatures: normal; orphans: 2; widows: 2;">DNA-directed DNA polymerase inhibitor. The p</span><span style="font-variant-ligatures: normal; orphans: 2; widows: 2;">reclinical development is ongoing in Israel.</span></span></span></span>

IUPAC Name 2-amino-9-(2-hydroxyethoxymethyl)-1H-purin-6-one
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)
InChIKey MKUXAQIIEYXACX-UHFFFAOYSA-N
SMILES C1=NC2=C(N1COCCO)NC(=NC2=O)N
Reference

1: Bogdanova-Mihaylova P, Burke D, O/&#39;Dwyer JP, Bradley D, Williams JA, Cronin SJ, Smyth S, Murphy RP, Murphy SM, Wall C, McCabe DJH. Aciclovir-induced acute kidney injury in patients with /&#39;suspected viral encephalitis/&#39; encountered on a liaison neurology service. Ir J Med Sci. 2018 Jan 6. doi: 10.1007/s11845-017-1728-3. [Epub ahead of print] PubMed PMID: 29307101.<br />
2: Arenberger P, Arenbergerova M, Hlad&iacute;kov&aacute; M, Holcova S, Ottillinger B. Comparative Study with a Lip Balm Containing 0.5% Propolis Special Extract GH 2002 versus 5% Aciclovir Cream in Patients with Herpes Labialis in the Papular/Erythematous Stage: A Single-blind, Randomized, Two-arm Study. Curr Ther Res Clin Exp. 2017 Oct 14;88:1-7. doi: 10.1016/j.curtheres.2017.10.004. eCollection 2018. PubMed PMID: 29276548; PubMed Central PMCID: PMC5737953.<br />
3: Chen Y, Kalia YN. Short-duration ocular iontophoresis of ionizable aciclovir prodrugs: A new approach to treat herpes simplex infections in the anterior and posterior segments of the eye. Int J Pharm. 2017 Dec 2;536(1):292-300. doi: 10.1016/j.ijpharm.2017.11.069. [Epub ahead of print] PubMed PMID: 29198810.<br />
4: Houston DMJ, Bugert JJ, Denyer SP, Heard CM. Correction: Potentiated virucidal activity of pomegranate rind extract (PRE) and punicalagin against Herpes simplex virus (HSV) when co-administered with zinc (II) ions, and antiviral activity of PRE against HSV and aciclovir-resistant HSV. PLoS One. 2017 Nov 20;12(11):e0188609. doi: 10.1371/journal.pone.0188609. eCollection 2017. PubMed PMID: 29155888; PubMed Central PMCID: PMC5695767.<br />
5: Bauer D, Keller J, Alt M, Schubert A, Aufderhorst UW, Palapys V, Kasper M, Heilingloh CS, Dittmer U, Laffer B, Eis-H&uuml;binger AM, Verjans GM, Heiligenhaus A, Roggendorf M, Krawczyk A. Antibody-based immunotherapy of aciclovir resistant ocular herpes simplex virus infections. Virology. 2017 Dec;512:194-200. doi: 10.1016/j.virol.2017.09.021. Epub 2017 Oct 3. PubMed PMID: 28985573.<br />
6: Semprini A, Singer J, Shortt N, Braithwaite I, Beasley R; Pharmacy Research Network. Protocol for a randomised controlled trial of 90% kanuka honey versus 5% aciclovir for the treatment of herpes simplex labialis in the community setting. BMJ Open. 2017 Aug 3;7(8):e017766. doi: 10.1136/bmjopen-2017-017766. PubMed PMID: 28775197; PubMed Central PMCID: PMC5724166.<br />
7: Houston DMJ, Bugert JJ, Denyer SP, Heard CM. Potentiated virucidal activity of pomegranate rind extract (PRE) and punicalagin against Herpes simplex virus (HSV) when co-administered with zinc (II) ions, and antiviral activity of PRE against HSV and aciclovir-resistant HSV. PLoS One. 2017 Jun 30;12(6):e0179291. doi: 10.1371/journal.pone.0179291. eCollection 2017. Erratum in: PLoS One. 2017 Nov 20;12 (11):e0188609. PubMed PMID: 28665969; PubMed Central PMCID: PMC5493292.<br />
8: Djekic L, Jankovic J, Čalija B, Primorac M. Development of semisolid self-microemulsifying drug delivery systems (SMEDDSs) filled in hard capsules for oral delivery of aciclovir. Int J Pharm. 2017 Aug 7;528(1-2):372-380. doi: 10.1016/j.ijpharm.2017.06.028. Epub 2017 Jun 12. PubMed PMID: 28619449.<br />
9: Gallacher PJ, Phelan PJ. Effective Clearance of Aciclovir Using Hemodiafiltration in a Patient With Neurotoxicity. Artif Organs. 2017 May;41(5):496-497. doi: 10.1111/aor.12774. PubMed PMID: 28543384.<br />
10: Brunnemann AK, Liermann K, Deinhardt-Emmer S, Maschkowitz G, Pohlmann A, Sodeik B, Fickenscher H, Sauerbrei A, Krumbholz A. Recombinant herpes simplex virus type 1 strains with targeted mutations relevant for aciclovir susceptibility. Sci Rep. 2016 Jul 18;6:29903. doi: 10.1038/srep29903. PubMed PMID: 27426251; PubMed Central PMCID: PMC4947914.

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