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A4669

Sigma-Aldrich

Acycloguanosine

≥99% (HPLC), powder

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C8H11N5O3
Número de CAS:
59277-89-3
Peso molecular:
225.20
Número CE:
261-685-1
Número MDL:
MFCD00057880
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
24278078
NACRES:
NA.77

Nivel de calidad

200

Ensayo

≥99% (HPLC)

Formulario

powder

color

white

solubilidad

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

ε (coeficiente de extinción)

11.8 at 256 nm at 1 mM

espectro de actividad antibiótica

viruses

Modo de acción

DNA synthesis | interferes

emisor

GlaxoSmithKline

cadena 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)

Clave InChI

MKUXAQIIEYXACX-UHFFFAOYSA-N

Información sobre el gen

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

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Descripción general

Acycloguanosine or acyclovir is a guanosine analog.

Aplicación

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

Acciones bioquímicas o fisiológicas

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.

Características y beneficios

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.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 2

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
117F0756

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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
Hasan Hüseyin Doğan et al.
International journal of medicinal mushrooms, 20(3), 201-212 (2018-05-03)
Despite considerable recent work to reveal different features of mushrooms species, the few studies of antiviral activities are inadequate and therefore further studies are required. Morchella conica, M. esculenta, Terfezia boudieri, Pleurotus ostreatus, Tricholoma anatolicum, Fomes fomentarius, Laetiporus sulphureus, Phellinus
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
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