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Acyclovir Synthesis

This document discusses the classification and synthesis of various antiviral agents. Antivirals are classified based on the infection they treat and their mechanism of action. Acyclovir is described as a purine nucleoside analogue used to treat herpes viruses. Its synthesis involves reacting 2-amino-1H-purin-6(9H)-one with 2-(chloromethoxy)ethyl benzoate followed by hydrolysis and salt formation. Acyclovir has low bioavailability and is metabolized to an inactive form. Related drugs valacyclovir and famciclovir are prodrugs that are metabolized to the active form acyclovir.

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77 views2 pages

Acyclovir Synthesis

This document discusses the classification and synthesis of various antiviral agents. Antivirals are classified based on the infection they treat and their mechanism of action. Acyclovir is described as a purine nucleoside analogue used to treat herpes viruses. Its synthesis involves reacting 2-amino-1H-purin-6(9H)-one with 2-(chloromethoxy)ethyl benzoate followed by hydrolysis and salt formation. Acyclovir has low bioavailability and is metabolized to an inactive form. Related drugs valacyclovir and famciclovir are prodrugs that are metabolized to the active form acyclovir.

Uploaded by

saquib khan
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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372 Chemotherapy

NH2 HN

N N N

N O H2N N N
HO HO
O

S
Lamivudine Abacavir

Classification According to the Treatment Protocol


According to the treatment protocol antiviral agents are classified as follows:
I. Treatment of respiratory virus infection
Adamantane derivatives: Amantadine, Rimantadine
II. Treatment of herpes and cytomegalo viruses infection.
a. Purine nucleotides: Acyclovir, Ganciclovir, Vidarabine.
b. Pyrimidine nucleosides: Trifluouridine, Idoxuridine.
c. Phosphorus derivatives: Foscarnet sodium.
III. Treatment of HIV infections
a. RT inhibition.
1. Purine derivatives: Didanosine.
2. Pyrimidine derivative: Zidovudine, Stavudine.
3. Non-nucleosides: Nevirapine, Delaviridine, Efavirenz.
b. Protease inhibition: Saquinavir, Indinavir, Ritonavir, Nelfinavir, Amprenavir, Lopinavir.
c. Integration inhibition: Zintevir.

SYNTHESIS AND DRUG PROFILE


I. Nucleotide analogues
a. Purine nucleosides and nucleotides
i. Acyclovir (Ocuvir, Zovirax, Cyclovir)
O

N
HN

H2N N
N
CH2OCH2CH2OH

2-Amino-9-((2-hydroxyethoxy)methyl)-1H-purin-6(9H)-one
Antiviral Agents 373

Synthesis
O O
(i) [(CH3)3Si]2N2
N N
HN (C2H5)3N HN

(ii) C6H5COOCH2CH2OCH2Cl
H2N N H 2N N N
N 2-(chloromethoxy)
H ethyl benzoate CH2OCH2CH2OCOC6H5
2-Amino-1H-purin-6(9H)-one –HCl

NaOH
–C6H5COONa

N
HN

H2N N N

CH2OCH2CH2OH
Acyclovir

Metabolism: The bioavailability of acyclovir is 15%–30 % and it is metabolized to 9-carboxy-methoxyme-


thyl guanine, which is inactive.
Properties and uses: Acyclovir is a white crystalline powder, slightly soluble in water, soluble in dimethyl
sulphoxide and in dilute mineral acids and alkali hydroxides, and very slightly soluble in ethanol. It is a
purine nucleoside analogue, used as antiviral agent against herpes viruses.

Assay: Dissolve the sample in anhydrous acetic acid and titrate with 0.1 M perchloric acid. Determine the
end point potentiometrically. Perform a blank titration.
Dose: For herpes virus infections the administered dose for immuno-suppressed patients is up to 10 mg/kg
body weight every 8 h.
Dosage forms: Acyclovir cream B.P., Acyclovir eye ointment B.P., Acyclovir intravenous infusion B.P.,
Acyclovir oral suspension B.P., Acyclovir tablets B.P., Dispersible acyclovir tablets B.P.

Metabolism of Valacyclovir: The related analogue 6-deoxy acyclovir is a prodrug form of acyclovir that is
activated through metabolism by xanthine oxidase.
Metabolism of Cidofovir: It is metabolized by phosphorylation and it gives cidofovir diphosphate.

Metabolism of Famciclovir: It is a prodrug of penciclovir, which is formed in vivo by hydrolysis of acetyl


groups and oxidation at the 6th position by the mixed function oxidase. Penciclovir and its metabolite pen-
ciclovir triphosphate posseses antiviral activity.

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