2-amino-9-[(2-hydroxyethoxy)methyl]-6,9-dihydro-1H-purin-6-one

• ChemBase ID: 44444
• Molecular Formular: C8H11N5O3
• Molecular Mass: 225.20464
• Monoisotopic Mass: 225.08618924
• SMILES: c12c(ncn2COCCO)c(=O)[nH]c(n1)N
• Canonical SMILES: OCCOCn1cnc2c1nc(N)[nH]c2=O
• 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-1H-purin-6-one
• IUPAC Traditional name: acyclovir; 2-amino-9-[(2-hydroxyethoxy)methyl]-6,9-dihydro-1H-purin-6-one; zovir
• Synonyms: Acyclovir; 2-amino-9-((2-hydroxyethoxy)methyl)-1H-purin-6(9H)-one; Activir; Avirax; Cycloviran; Geavir; Herpetad; Milavir; Soothelip; Supraviran; Virasorb; Mirolex; Virovir; Zyclir; Aciclovir; Aciclovir; Acycloguanosine; Zovirax; 9-[(2-Hydroxyethoxy)-methyl]guanine;Acyclovir; ACYCLOGUANOSINE; 9-[(2-Hydroxyethoxy)methyl]guanine; Acyclovir; Acycloguanosine

Database IDs

• CAS Number: 59277-89-3
• EC Number: 261-685-1
• MDL Number: MFCD00057880
• PubChem SID: 162049207; 24278078
• PubChem CID: 2022

CALCULATED PROPERTIES

• Acid pKa: 10.159839
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.5496677
• LogD (pH = 7.4): -1.550233
• Log P: -1.5495676
• Molar Refractivity: 55.0668 cm^3
• Polarizability: 19.994585 Å^3
• Polar Surface Area: 114.76 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 1 M HCl: soluble50 mg/mL; DMSO; DMSO: soluble7 mg/mL; H2O: soluble0.7 mg/mL
• Apperance: white powder
• Melting Point: 250°C
• Absorption Wavelength: ε1mM/256 nm 11.8

Safety Information

• Storage Condition: -20°C; Room Temperature (15-30°C)
• Storage Warning: IRRITANT
• RTECS: UP0791400
• German water hazard class: 2
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... HV1S(3365), NP(4860)
• Mechanism of Action: Aciclovir triphosphate competitively inhibits viral DNA polymerase and competes with the natural deoxyguanosine triphosphate, for incorporation into viral DNA.; and finally to the triphosphate by phosphoglycerate kinase, phosphoenolpyruvate carboxykinase, and pyruvate kinase.; Guanosine analog that acts as an antimetabolite.; Once incorporated, aciclovir triphosphate inhibits DNA synthesis by acting as a chain terminator.; Viral (HSV-1, HSV-2 and VZV) thymidine kinase converts aciclovir to the aciclovir monophosphate, which is then converted to the diphosphate by cellular guanylate kinase,

Product Information

• Purity: >98%; ≥99% (HPLC)
• Salt Data: Free Base
• Application(s): Antiviral agent.; Used especially against herpes.

DETAILS

MP Biomedicals - 02154713

(9-[(2-Hydroxyethoxy)- methyl]guanine;Acyclovir) This product inhibits the replication of cytomegalovirus by a mechanism that is independent of its phosphorylation by viral or cellular thymidine kinase. It can be used to induce apoptosis in cells tra

Selleck Chemicals - S1807

Research Area: Infection
Biological Activity:
Acyclovir is a synthetic nucleoside analogue active against herpesviruses. It is a guanosine analogue antiviral drug. Aciclovir differs from previous nucleoside analogues in that it contains only a partial nucleoside structure: the sugar ring is replaced by an open-chain structure. It is selectively converted into acyclo-guanosine monophosphate (acyclo-GMP) by viral thymidine kinase, which is far more effective (3000 times) in phosphorylation than cellular thymidine kinase. [1]

Sigma Aldrich - A4669

Application
Acycloguanosine has been used to study herpes simplex virus latency and reactivation, as well as HIV retrovirus reproduction. Acycloguanosine inhibits replication of cytomegalovirus by a mechanism that is independent of its phosphorylation by viral or cellular thymidine kinase.
Biochem/physiol Actions
Antiviral agent. Phosphorylation by herpes simplex virus thymidine kinase (HSV-TK) leads to the formation of acycloguanosine triphosphate that competitively inhibits the viral DNA polymerase.
Antiviral agent. Phosphorylation by herpes simplex virus thymidine kinase (HSV-TK) leads to the formation of acycloguanosine triphosphate that competitively inhibits the viral DNA polymerase. Acycloguanosine can be used to induce apoptosis in cells transfected with HSV-TK. Inhibits replication of cytomegalovirus by a mechanism that is independent of its phosphorylation by viral or cellular thymidine kinase.

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