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A4669

Sigma-Aldrich

Acycloguanosine

≥99% (HPLC), powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C8H11N5O3
CAS Number:
59277-89-3
Molecular Weight:
225.20
EC Number:
261-685-1
MDL number:
MFCD00057880
UNSPSC Code:
12352200
PubChem Substance ID:
24278078
NACRES:
NA.77

Assay

≥99% (HPLC)

form

powder

color

white

solubility

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

ε (extinction coefficient)

11.8 at 256 nm at 1 mM

antibiotic activity spectrum

viruses

Mode of action

DNA synthesis | interferes

originator

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)

InChI key

MKUXAQIIEYXACX-UHFFFAOYSA-N

Gene Information

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

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General description

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

Biochem/physiol Actions

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.

Features and Benefits

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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