A4669
Acycloguanosine
≥99% (HPLC), DNA polymerase inhibitor, powder
Synonym(s):
9-[(2-Hydroxyethoxy)methyl]guanine, Acyclovir
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About This Item
Empirical Formula (Hill Notation):
C8H11N5O3
CAS Number:
Molecular Weight:
225.20
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
EC Number:
261-685-1
MDL number:
Product Name
Acycloguanosine, ≥99% (HPLC), powder
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
SMILES string
NC1=Nc2c(ncn2COCCO)C(=O)N1
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
Quality Level
Gene Information
human ... HV1S(3365), NP(4860)
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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.
General description
Acycloguanosine or acyclovir is a guanosine analog.
Storage Class
11 - Combustible Solids
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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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