A4669

Acycloguanosine

≥99% (HPLC), powder

• Synonym(s): 9-[(2-Hydroxyethoxy)methyl]guanine, Acyclovir
• 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

Properties

• Quality Level: 200
• 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)

Description

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.

Safety Information

• 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