Acyclovir

Base Information

• Chemical Name: Acyclovir
• CAS No.: 59277-89-3
• Molecular Formula: C8H11N5O3
• Molecular Weight: 225.207
• Hs Code.: 29335990
• Mol file: 59277-89-3.mol

Synonyms:Acyclovir

Chemical Property of Acyclovir

Chemical Property:

• Appearance/Colour: White to light yellow crystal powder
• Melting Point: 256-257 °C
• Refractive Index: 1.8000 (estimate)
• Boiling Point: 595 °C at 760 mmHg
• PKA: pKa 2.27 (Uncertain);9.25 (Uncertain)
• Flash Point: 313.6 °C
• PSA: 119.05000
• Density: 1.77 g/cm³
• LogP: -0.75060
• Storage Temp.: −20°C
• Solubility.: H2O: 0.7 mg/mL
• Water Solubility.: Soluble in 1M HCl at 50mg/ml. Soluble in water at 0.7mg/ml. Also soluble in DMSO

Purity/Quality:

99% ^*data from raw suppliers

Acyclovir ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-40-20/21/22
• Safety Statements: 22-24/25-36-26-23

MSDS Files:

SDS file from LookChem

Useful:

• Description: As it is evident from the chemical structure, acyclovir looks like a nucleoside analog of guanosine in side chain of which, instead of the traditional cyclic sugar residue a 2-hydroxyethoxymethyl acyclic side chain is present. Acyclovir possesses antiviral activity with respect to types 1 and 2 of herpes simplex, shingles virus, Epstein–Barr virus, and cytomegalovirus.
• Uses: Acyclovir (Zovirax) is a synthetic purine analog derived from guanine. It exerts its effects on the herpes simplex virus (HSV) and varicella-zoster virus by interfering with DNA synthesis through phosphorylation by viral thymidine kinase and subsequent inhibition of viral DNA polymerase, thereby inhibiting viral replication. It is effective against HSV-1 and 2, varicella-zoster virus, Epstein-Barr virus, herpesvirus simiae, and cytomegalovirus. Acyclovir may be administered intravenously, orally, or topically. Orally active acyclic nucleoside with inhibitory activity towards several herpes viruses. Antiviral; hypnotic. Inhibits cytomegalovirus replication; induces apoptosis
• Indications: Acyclovir (Zovirax) is a synthetic purine analog derived from guanine. It exerts its effects on the herpes simplex virus (HSV) and varicella-zoster virus by interfering with DNA synthesis through phosphorylation by viral thymidine kinase and subsequent inhibition of viral DNA polymerase, thereby inhibiting viral replication. It is effective against HSV-1 and 2, varicella-zoster virus, Epstein-Barr virus, herpesvirus simiae, and cytomegalovirus. Acyclovir may be administered intravenously, orally, or topically.Acyclovir (400 mg PO b.i.d. or 200 mg PO five times a day) or other antiviral antibiotics can suppress herpes-associated EM. It is of no value once the EM has started. Not all episodes of a herpes simplex recurrence are associated with EM, but in recurrent cases, a 6-month trial of suppressive therapy can be helpful.
• Therapeutic Function: Antiviral
• Clinical Use: Aciclovir Herpes simplex keratitis Chickenpox and herpes zoster Herpes simplex encephalitis and neonatal herpes Prophylaxis of HSV infections in the severely immunocompromised Valaciclovir Herpes zoster and genital HSV infections

Technology Process of Acyclovir

There total 96 articles about Acyclovir which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.5%

2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3) → acycloguanosine (59277-89-3)

Guidance literature:

With sodium hydroxide; In water; at 85 - 95 ℃; for 3h;

DOI:10.1021/jo982304y

Reference yield: 91.0%

9-<(2-acetoxyethoxy)methyl>-2-N-acetyl-6-O-(diphenylcarbamoyl)guanine (112233-78-0) → acycloguanosine (59277-89-3)

Guidance literature:

With ammonia; In methanol; water; at 60 ℃;

DOI:10.1139/v87-243

Reference yield: 80.0%

2-[(2-amino-6-oxo-3,6-dihydro-9H-purin-9-yl)methoxy]ethyl pyrrolidinophosphate ammonium salt (1400637-35-5) → acycloguanosine (59277-89-3) + acyclovir monophosphate

Guidance literature:

With potassium chloride; potassium hydroxide; In water; at 25 ℃; pH=12;

DOI:10.1016/j.bmc.2012.08.008

upstream raw materials:

2-amino-6-chloro-9-<(2-hydroxyethoxy)methyl>-9H-purine

2,6-diamino-9-{(2-hydroxyethoxy)methyl}purine

(2-benzoyloxyethyl)oxymethyl chloride

2-amino-1,9-dihydro-6H-purin-6-one

Downstream raw materials:

2-Benzyloxycarbonylamino-propionic acid 2-(2-amino-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-ethyl ester

9-<<2-(azidoacetoxy)ethoxy>methyl>guanine

3-Benzyloxycarbonylamino-propionic acid 2-(2-amino-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-ethyl ester

bis<2-(guanin-9-ylmethoxy)ethyl> 4-(methylthio)phenyl phosphate

Refernces

Syntheses, molecular structures, and antiviral activities of 1- and 2-(2′-deoxy-d-ribofuranosyl)cyclohepta[d][1,2,3]triazol-6(1H)-ones and 1-(2′-deoxy-d-ribofuranosyl)cyclohepta[b]pyrrol-8(1H)-one

10.1016/j.tet.2012.04.109

The research focuses on the synthesis, molecular structures, and antiviral activities of a novel class of 20-deoxyribonucleosides featuring tropone-fused nitrogen heterocycles as nucleobases. The purpose of this study was to develop a new class of nucleoside analogs with potential antiviral properties. The researchers synthesized these compounds through the reaction of alkali metal salts of 1H-cyclohepta[d][1,2,3]triazol-6-one and 1H-cyclohepta[b]pyrrol-8-one with 2-deoxy-3,5-di-O-(p-toluoyl)-α-D-ribofuranosyl chloride (α-chlorosugar), leading to a mixture of N1- and N2-coupled glycosylation products. The synthesized nucleosides were then deprotected to yield the desired 20-deoxyribonucleosides, which were characterized by X-ray structural analyses. The conclusions drawn from the study were that the synthesized nucleosides showed weak antiviral activities against herpes simplex virus type 1 and type 2 compared to acyclovir (ACV), and they exhibited no cytotoxicity on lung and colon cancer cell lines. The key chemicals used in the synthesis process included 1H-cyclohepta[d][1,2,3]triazol-6-one, 1H-cyclohepta[b]pyrrol-8-one, and α-chlorosugar, along with various solvents and reagents for the glycosylation and deprotection steps.