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:
Assay:
≥99% (HPLC)
Form:
powder
Product Name
Acycloguanosine, ≥99% (HPLC), powder
Quality Segment
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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