2-amino-9-[(2-hydroxyethoxy)methyl]-6,9-dihydro-3H-purin-6-one

• ChemBase ID: 666
• Molecular Formular: C8H11N5O3
• Molecular Mass: 225.20464
• Monoisotopic Mass: 225.08618924
• SMILES: O(Cn1c2[nH]c(nc(=O)c2nc1)N)CCO
• Canonical SMILES: Nc1nc(=O)c2c([nH]1)n(COCCO)cn2
• InChI: 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)
• InChIKey: MKUXAQIIEYXACX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[(2-hydroxyethoxy)methyl]-6,9-dihydro-3H-purin-6-one
• IUPAC Traditional name: zovirax; aciclovir
• Brand Name: Alti-Acyclovir; Avirax; Vipral; Virorax; Zovir; Zovirax; Zovirax topical
• Synonyms: Wellcome-248u; Acycloguanosine; Acyclovir Sodium; AC2; Aciclovier; Acyclovir; Aciclovir Sodium; 9-Hyroxyethoxymethylguanine; Aciclovir; 2-amino-9-[(2-hydroxyethoxy)methyl]-6,9-dihydro-3H-purin-6-one; Acyclovir

Database IDs

• CAS Number: 59277-89-3
• MDL Number: MFCD00057880
• PubChem SID: 160964129; 46506002
• PubChem CID: 2022
• CHEBI ID: 2453
• ATC CODE: J05AB01; D06BB03; S01AD03
• CHEMBL: 184
• Chemspider ID: 1945
• DrugBank ID: DB00787
• KEGG ID: D00222
• Unique Ingredient Identifier: X4HES1O11F
• Wikipedia Title: Aciclovir
• Medline Plus: a681045

CALCULATED PROPERTIES

JChem

• Acid pKa: 7.9866085
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -1.0340011
• LogD (pH = 7.4): -1.1266081
• Log P: -1.0319568
• Molar Refractivity: 54.6334 cm^3
• Polarizability: 20.181852 Å^3
• Polar Surface Area: 114.76 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.95
• LOG S: -1.39
• Solubility (Water): 9.08e+00 g/l

PROPERTIES

Physical Property

• Solubility: 1.62 mg/mL at 22 oC [KRISTL,A et al. (1993)]
• Melting Point: 256.5°C (493.7°F)
• Hydrophobicity(logP): -1.56 [KRISTL,A ET AL. (1993)]; -2.605

Pharmacology Properties

• Admin Routes: Intravenous, oral, topical
• Bioavailability: 10–20% (oral)
• Excretion: Renal
• Half Life: 2.2–20 hours
• Metabolism: Viral thymidine kinase
• Protein Bound: 9–33%
• Legal Status: POM (UK); Rx-only (US); S4 (Australia)
• Pregnancy Category: B (US); B3 (Australia)
• US Licence: Acyclovir

Product Information

• Purity: 95%; 98%

DETAILS

DrugBank - DB00787

• Drug Groups: approved
• Description: A guanosine analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes. [PubChem]
• Indication: For the treatment and management of herpes zoster (shingles), genital herpes, and chickenpox
• Pharmacology: Aciclovir (INN) or acyclovir (USAN, former BAN) is a synthetic deoxyguanosine analog and it is the prototype antiviral agent that is activated by viral thymidine kinase. The selective activity of aciclovir is due to its affinity for the thymidine kinase enzyme encoded by HSV and VZV.
• Toxicity: Aciclovir may cause nephrotoxicity (crystallization of aciclovir within renal tubules, elevation of serum creatinine, transient), and neurotoxicity (coma, hallucinations, lethargy, seizures, tremors). Nephrotoxicity and neurotoxicity usually resolve after cessation of aciclovir therapy. However, there is no well-defined relationship between aciclovir concentrations in the blood and these adverse effects.
• Affected Organisms: Human Herpes Virus
• Biotransformation: Hepatic, the only major urinary metabolite that has been detected is 9-carboxymethoxymethylguanine.
• Absorption: Oral: bioavailability 10 to 20%
• Half Life: 2.5-3.3 hours
• Protein Binding: 9%-33%
• Elimination: Acyclovir is cleared renally.
• References: O'Brien JJ, Campoli-Richards DM: Acyclovir. An updated review of its antiviral activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1989 Mar;37(3):233-309. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• O'Brien JJ, Campoli-Richards DM: Acyclovir. An updated review of its antiviral activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1989 Mar;37(3):233-309. Pubmed