289665-64-1

Usage

Type of drug

Antiretroviral

Purpose

Treating HIV/AIDS

Mechanism of action

Inhibits the activity of the reverse transcriptase enzyme, preventing HIV replication and spread

Classification

Nucleoside reverse transcriptase inhibitor (NRTI)

Group

Part of the larger group of antiretroviral drugs used in the treatment of HIV/AIDS

Current use

Less common due to potential toxicities and the development of newer, more effective antiretroviral drugs

Chemical structure

Complex, featuring a synthetic nucleoside analog

Development

Originally synthesized as a potential antiviral agent, later found to be effective against HIV

Administration

Oral

Side effects

Potential toxicities, including kidney and liver problems

Monitoring

Requires regular blood tests to monitor kidney and liver function during treatment

Resistance

HIV can develop resistance to ddI, limiting its effectiveness over time

Combination therapy

Often used in combination with other antiretroviral drugs to increase treatment effectiveness and reduce the risk of resistance development.

Upstream product

• 65-71-4 thymin 
• 289665-51-6 6-O-benzoyl-5-deoxy-1,4:2,3-dianhydro-D-allitol 
• 2946-01-2 (3aR,5R,6S,6aR)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate 
• 75646-85-4 3-p-toluenesulphonate of 1,2-O-isopropylidene-5,6-O-methoxymethylidene-α-D-glucofuranose 
• 289665-46-9 6-benzoyl-1,2-O-isopropylidene-3-O-tosyl-5-deoxy-α-D-glucofuranose 
• 289665-47-0 Benzoic acid 2-[(2R,3R,4S)-4-hydroxy-3-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-yl]-ethyl ester 
• 43138-33-6 5β-vinyl-4β-tosyl-2α,3α-O-isopropylidene tetrahydrofuran 
• 62102-11-8 5-deoxy-1,2-O-isopropylidene-3-O-p-tolylsulfonyl-α-D-xylo-hexofuranose 

Downstream Products

• 458541-41-8 1',4'-anhydro-2',5'-dideoxy-6'-O-(4,4'-dimethoxytriphenylmethyl)-2'-(thymin-1-yl)-D-altritol 

Relevant academic research and scientific papers

Novel isonucleoside analogues: synthesis of 2'-deoxy-2'-nucleobase-5'-deoxy-1',4'-anhydro-D-altritol

A new class of isonucleoside analogues with branched-sugar 2'-deoxy-2'-nucleobase-5'-deoxy-1',4'-anhydro-D-altritol (21, 23a-c) has been synthesized from D-glucose in 11 steps. The construction of branched-chain sugars has been carried out by hydroboration-oxidation of a double bond in the corresponding hexose. The key intermediate 12 was synthesized from the branched-chain sugar 11 by the reductive cleavage reaction in the presence of TMSOTf and triethylsilane. A strong solvent effect was observed in the intramolecular nucleophilic substitution of 12. The protic solvent is favorable to form the bicyclic compound 18 by double S(N)2 substitution. The opening reaction of epoxide 17 by nucleobases was achieved regioselectively to give the desired isonucleosides in reasonable yield. Copyright (C) 2000 Elsevier Science Ltd.