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A4669

Acycloguanosine

Name: Acycloguanosine
Brand: SIGMA

≥99% (HPLC), powder

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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

PubChem Substance ID:

24278078

NACRES:

NA.77

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)

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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 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

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Antiviral nanodelivery systems: current trends in acyclovir administration

Haniza H, et al.

Journal of Nanomaterials (2016)

Early Events after Herpes Simplex Virus-Type 1 Entry Are Necessary for the Release of Gamma-Hydroxybutyrate upon Acute Infection.

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

In Vitro Evaluation of the Antiviral Activity of Some Mushrooms from Turkey.

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

Acyclovir-Loaded Solid Lipid Nanoparticles: Optimization, Characterization and Evaluation of Its Pharmacokinetic Profile.

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

Acyclovir. An updated review of its antiviral activity, pharmacokinetic properties and therapeutic efficacy.

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

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