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A4669

Sigma-Aldrich

Acycloguanosin

≥99% (HPLC), powder

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C8H11N5O3
CAS-Nummer:
59277-89-3
Molekulargewicht:
225.20
EG-Nummer:
261-685-1
MDL-Nummer:
MFCD00057880
UNSPSC-Code:
12352200
PubChem Substanz-ID:
24278078
NACRES:
NA.77

Qualitätsniveau

200

Assay

≥99% (HPLC)

Form

powder

Farbe

white

Löslichkeit

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

ε (Extinktionskoeffizient)

11.8 at 256 nm at 1 mM

Wirkungsspektrum von Antibiotika

viruses

Wirkungsweise

DNA synthesis | interferes

Ersteller

GlaxoSmithKline

SMILES String

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)

InChIKey

MKUXAQIIEYXACX-UHFFFAOYSA-N

Angaben zum Gen

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

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Allgemeine Beschreibung

Acycloguanosine or acyclovir is a guanosine analog.

Anwendung

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

Biochem./physiol. Wirkung

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.

Leistungsmerkmale und Vorteile

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.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 2

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Analysenzertifikate (COA)

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Antiviral nanodelivery systems: current trends in acyclovir administration
Haniza H, et al.
Journal of Nanomaterials (2016)
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
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
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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