A4669

Acycloguanosine

≥99% (HPLC), DNA polymerase inhibitor, powder

• Synonym(s): 9-[(2-Hydroxyethoxy)methyl]guanine, Acyclovir
• Empirical Formula (Hill Notation): C₈H₁₁N₅O₃
• CAS Number: 59277-89-3
• Molecular Weight: 225.20
• NACRES: NA.77
• PubChem Substance ID: 24278078
• UNSPSC Code: 12352200
• EC Number: 261-685-1
• MDL number: MFCD00057880
• Assay: ≥99% (HPLC)
• Form: powder
• Quality level: 200

Properties

• Product Name: Acycloguanosine, ≥99% (HPLC), powder
• 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[1]
• in infection studies to test its effect on voltage-gated sodium channels (VGSC) using human dorsal root ganglion-derived neuronal (HD10.6) cells[2]
• to test its effect on the interferon-stimulated gene (ISG) expression induction (Mx1 and ISG15) in human foreskin fibroblast cells[3]

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.[4] Acycloguanosine has been used to study herpes simplex virus latency.[4] It may act against human immunodeficiency virus 1 (HIV-1) as well.[5]

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: 11 - Combustible Solids
• wgk: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)
• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319
• pcodes: P264 - P280 - P302 + P352 - P305 + P351 + P338 - P332 + P313 - P337 + P313
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2