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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

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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Antiviral nanodelivery systems: current trends in acyclovir administration
Haniza H, et al.
Journal of Nanomaterials (2016)
L Z Rubsam et al.
Cancer research, 58(17), 3873-3882 (1998-09-10)
Enzyme-prodrug therapy using ganciclovir and herpes simplex virus-thymidine kinase (HSV-TK) has demonstrated excellent antitumor activity in many different types of malignant cells. Previously, we noted that ganciclovir was substantially more cytotoxic than other HSV-TK substrates. Therefore, we embarked on a
Adalbert Krawczyk et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(17), 6760-6765 (2013-04-10)
Despite the availability of antiviral chemotherapy, herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) infections remain a severe global health problem. Of particular concern is the growing incidence of drug resistance in immunocompromised patients, which stresses the urgency
Daniel S Owers et al.
The Cochrane database of systematic reviews, 2(2), CD005133-CD005133 (2013-03-02)
Cytomegalovirus (CMV) is a significant cause of morbidity and mortality in solid organ transplant recipients. Pre-emptive treatment of patients with CMV viraemia using antiviral agents has been suggested as an alternative to routine prophylaxis to prevent CMV disease. This is
Sonia Burrel et al.
Journal of clinical virology : the official publication of the Pan American Society for Clinical Virology, 58(1), 321-324 (2013-06-05)
Herpes simplex virus type 1 (HSV-1) is a leading cause of corneal blindness. Acyclovir (ACV) constitutes the standard treatment of HSV infections including herpetic keratitis (HK). HSV resistance to ACV is mainly described in immunocompromised patients. We describe two cases
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