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A4669

Sigma-Aldrich

Acycloguanosine

≥99% (HPLC), powder

Synonym(s):

9-[(2-Hydroxyethoxy)methyl]guanine, Acyclovir

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500 G
CN¥2,444.35

CN¥2,444.35

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500 G
CN¥2,444.35

About This Item

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

CN¥2,444.35

Available to ship onApril 23, 2025Details

Request a Bulk Order

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

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Show Differences

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This Item
D5287D7400B5002
2′-Deoxyuridine ≥98.5%

D5412

2′-Deoxyuridine

2′-Deoxyinosine ≥98%

D5287

2′-Deoxyinosine

2′-Deoxyadenosine monohydrate ≥99%

D7400

2′-Deoxyadenosine monohydrate

5-Bromo-2′-deoxyuridine ≥99% (HPLC)

B5002

5-Bromo-2′-deoxyuridine

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

assay

≥98.5%

assay

≥98%

assay

≥99%

assay

≥99% (HPLC)

form

powder

form

powder

form

powder

form

powder

solubility

water: 50 mg/mL, clear to slightly hazy, colorless to faintly yellow

solubility

1 M NH4OH: 50 mg/mL, clear, colorless

solubility

water: 25 mg/mL, clear to slightly hazy, colorless to faintly yellow

solubility

DMSO: 50 mg/mL, clear, colorless to very faintly yellow

impurities

Thymidine, free

impurities

inosine, essentially free

impurities

-

impurities

-

General description

Acycloguanosine or acyclovir is a guanosine analog.[1]

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[2]
  • in infection studies to test its effect on voltage-gated sodium channels (VGSC) using human dorsal root ganglion-derived neuronal (HD10.6) cells[3]
  • to test its effect on the interferon-stimulated gene (ISG) expression induction (Mx1 and ISG15) in human foreskin fibroblast cells[4]

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.[1] It is less effective against cytomegalovirus and Epstein-Barr virus.[5] Acycloguanosine has been used to study herpes simplex virus latency.[5] It may act against human immunodeficiency virus 1 (HIV-1) as well.[6]

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 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
  • Specification Sheet

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    Certificates of Analysis (COA)

    Lot/Batch Number
    117F0756

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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
    Haniza Hassan et al.
    Nanomaterials (Basel, Switzerland), 10(9) (2020-09-13)
    Acyclovir is an antiviral drug used for the treatment of herpes simplex virus infection. Its oral bioavailability is low; therefore, frequent and high doses are prescribed for optimum therapeutic efficacy. Moreover, the current therapeutic regimen of acyclovir is associated with
    J J O'Brien et al.
    Drugs, 37(3), 233-309 (1989-03-01)
    Acyclovir (aciclovir) is a nucleoside antiviral drug with antiviral activity in vitro against members of the herpes group of DNA viruses. As an established treatment of herpes simplex infection, intravenous, oral and to a lesser extent topical formulations of acyclovir
    Andrea Lisco et al.
    Cell host & microbe, 4(3), 260-270 (2008-09-10)
    For most viruses, there is a need for antimicrobials that target unique viral molecular properties. Acyclovir (ACV) is one such drug. It is activated into a human herpesvirus (HHV) DNA polymerase inhibitor exclusively by HHV kinases and, thus, does not
    View All Related Papers

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