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
Quality Level
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)
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
11 - Combustible Solids
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2
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Antiviral nanodelivery systems: current trends in acyclovir administration
Haniza H, et al.
Journal of Nanomaterials (2016)
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
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