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A4669

Sigma-Aldrich

Acycloguanosine

≥99% (HPLC), powder

Synonyme(s) :

9-[(2-Hydroxyethoxy)methyl]guanine, Acyclovir

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About This Item

Formule empirique (notation de Hill):
C8H11N5O3
Numéro CAS:
59277-89-3
Poids moléculaire :
225.20
Numéro CE :
261-685-1
Numéro MDL:
MFCD00057880
Code UNSPSC :
12352200
ID de substance PubChem :
24278078
Nomenclature NACRES :
NA.77

Niveau de qualité

200

Pureté

≥99% (HPLC)

Forme

powder

Couleur

white

Solubilité

H2O: 0.7 mg/mL
1 M HCl: 50 mg/mL
DMSO: 7 mg/mL

ε (coefficient d'extinction)

11.8 at 256 nm at 1 mM

Spectre d'activité de l'antibiotique

viruses

Mode d’action

DNA synthesis | interferes

Auteur

GlaxoSmithKline

Chaîne SMILES 

NC1=Nc2c(ncn2COCCO)C(=O)N1

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)

Clé InChI

MKUXAQIIEYXACX-UHFFFAOYSA-N

Informations sur le gène

human ... HV1S(3365) , NP(4860)

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Description générale

Acycloguanosine or acyclovir is a guanosine analog.

Application

Acycloguanosine has been used as an inhibitor of herpes simplex virus type I:
  • to serve as a positive control to compare the antiviral activities of mushroom extracts in cytotoxic assays using Vero cells
  • in infection studies to test its effect on voltage-gated sodium channels (VGSC) using human dorsal root ganglion-derived neuronal (HD10.6) cells
  • to test its effect on the interferon-stimulated gene (ISG) expression induction (Mx1 and ISG15) in human foreskin fibroblast cells

Actions biochimiques/physiologiques

Acycloguanosine is an antiviral agent and is converted to acycloguanosine triphosphate by herpes simplex virus thymidine kinase (HSV-TK). It competitively inhibits the viral DNA polymerase. It is less effective against cytomegalovirus and Epstein-Barr virus. Acycloguanosine has been used to study herpes simplex virus latency. It may act against human immunodeficiency virus 1 (HIV-1) as well.

Caractéristiques et avantages

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by GlaxoSmithKline. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Faith O Osinaga et al.
Pharmaceuticals (Basel, Switzerland), 16(8) (2023-08-26)
We reported that gamma-hydroxybutyrate (GHB) is released upon Herpes Simplex Virus Type-1 (HSV-1) acute infection. However, the cellular biochemical processes involved in the production of GHB in infected cells are unclear. This study aims to shed light on the biochemical
Haniza Hassan et al.
Nanomaterials (Basel, Switzerland), 10(9) (2020-09-13)
Acyclovir is an antiviral drug used for the treatment of herpes simplex virus infection. Its oral bioavailability is low; therefore, frequent and high doses are prescribed for optimum therapeutic efficacy. Moreover, the current therapeutic regimen of acyclovir is associated with
Antiviral nanodelivery systems: current trends in acyclovir administration
Haniza H, et al.
Journal of Nanomaterials (2016)
Andrea Lisco et al.
Cell host & microbe, 4(3), 260-270 (2008-09-10)
For most viruses, there is a need for antimicrobials that target unique viral molecular properties. Acyclovir (ACV) is one such drug. It is activated into a human herpesvirus (HHV) DNA polymerase inhibitor exclusively by HHV kinases and, thus, does not
J J O'Brien et al.
Drugs, 37(3), 233-309 (1989-03-01)
Acyclovir (aciclovir) is a nucleoside antiviral drug with antiviral activity in vitro against members of the herpes group of DNA viruses. As an established treatment of herpes simplex infection, intravenous, oral and to a lesser extent topical formulations of acyclovir
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