Dideoxyinosine

Base Information

• Chemical Name: Dideoxyinosine
• CAS No.: 69655-05-6
• Molecular Formula: C10H12N4O3
• Molecular Weight: 236.23
• Hs Code.: 29335990
• Mol file: 69655-05-6.mol

Synonyms:2',3'-Dideoxyinosine;BMY 40900;BMY-40900;BRN 3619529;CCRIS 805;DRG-0016;Didanosina;Didanosinum;Dideoxyinosine;HSDB 6548;UNII-K3GDH6OH08;Videx;Videx EC;

Chemical Property of Dideoxyinosine

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 1.33E-14mmHg at 25°C
• Melting Point: 193-195 °C
• Refractive Index: -28 ° (C=0.34, H2O)
• Boiling Point: 586.5 °C at 760 mmHg
• PKA: 9.12(at 25℃)
• Flash Point: 308.5 °C
• Density: 1.76 g/cm³
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMSO or methanol
• Water Solubility.: 1-5 g/100 mL at 21 ºC

Purity/Quality:

99% ^*data from raw suppliers

2’,3’-Dideoxyinosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-36/37
• Safety Statements: 26-27-36/37/39-45-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Description: Didanosine is an orally active purine dideoxynucleoside analog indicated for adult and pediatric patients with advanced HIV infection who are either intolerant or significantly deteriorated on zidovudine. It appears to increase CD4 cell counts and decrease p24 antigen levels.Major adverse effects are pancreatitis, peripheral neuropathy and diarrhea.Unlike zidovudine, didanosine exhibits insignificant bone marrow suppression.
• Uses: Antiviral;Transrcriptase inverse inhibitor 2?,3?-Dideoxyinosine is a potent anti-retroviral agent. It is most effective in combination therapy for the treatment of HIV and related lymphoma.
• Indications: Didanosine (ddI, Videx) is an adenosine analogue with activity against HIV-1, HIV-2, and HTLV-I. It is approved as part of a multidrug regimen for the therapy of HIV infection and is also used as postexposure HIV prophylaxis
• Therapeutic Function: Antiviral
• Clinical Use: The most common adverse effect produced by didanosine is diarrhea.Abdominal pain, nausea, vomiting, anorexia, and dose-related peripheral neuropathy may occur. Pancreatitis occurs rarely, as do hyperuricemia, bone marrow suppression, retinal depigmentation, and optical neuritis. Resistance to didanosine appears to result from mutations different from those responsible for zidovudine resistance.
• Drug interactions: Potentially hazardous interactions with other drugsAllopurinol: concentration of didanosine increased - avoid.Antibacterials: ciprofloxacin, tetracyclines, and other antibiotics affected by indigestion remedies - do not administer within 2 hours of didanosine.Antivirals: absorption of atazanavir reduced (give at least 2 hours before or 1 hour after didanosine tablets); manufacturer of darunavir advises to take didanosine 1 hour before or 2 hours after darunavir; didanosine tablets reduce absorption of indinavir (give at least 1 hour apart); concentration possibly increased by ganciclovir, valganciclovir and tenofovir - avoid with tenofovir; give didanosine and ritonavir at least 2.5 hours apart; increased risk of side effects with ribavirin and stavudine - avoid; concentration reduced by tipranavir (give tipranavir and didanosine capsules at least 2 hours apart); give didanosine 2 hours before or 4 hours after rilpivirine.Cytotoxics: increased risk of toxicity with hydroxycarbamide - avoid. Orlistat: absorption of didanosine possibly reduced.

Technology Process of Dideoxyinosine

There total 57 articles about Dideoxyinosine 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: 96.0%

9-[(2R,5S)-5-(2,4,4-Trimethyl-5-oxo-[1,3]dioxolan-2-yloxymethyl)-tetrahydro-furan-2-yl]-1,9-dihydro-purin-6-one (389128-06-7) → Dideoxyinosine (69655-05-6)

Guidance literature:

With methylamine; In methanol; for 16h; Ambient temperature;

DOI:10.1080/00397919208021616

Reference yield: 94.0%

1-(5-O-tert-butyldimethylsilyl-2,3-dideoxy-β-D-glyceropentofuranosyl)imidazo[4,5-d]pyridazin-4(5H)-one (177779-56-5) → Dideoxyinosine (69655-05-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1016/S0968-0896(99)00184-4

Reference yield: 90.0%

2',3'-didehydro-2',3'-dideoxyinosine (42867-68-5) → Dideoxyinosine (69655-05-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; under 760.051 Torr;

DOI:10.1080/15257770701508414

upstream raw materials:

2',3'-didehydro-2',3'-dideoxyinosine

[(S)-5-(6-Amino-purin-9-yl)-tetrahydro-furan-2-yl]-methanol

9-[(2R,5S)-5-(2,4,4-Trimethyl-5-oxo-[1,3]dioxolan-2-yloxymethyl)-tetrahydro-furan-2-yl]-1,9-dihydro-purin-6-one

9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl>hypoxanthine

Downstream raw materials:

2',3'-Dideoxyuridine

2',3'-dideoxyguanosine

2,6-diaminopurine 2',3'-dideoxyriboside

2',3'-Dideoxyadenosine

Refernces

• 1、 Christoffersen,Serra,Terreni,Piskur. "Nucleoside phosphorylases from clostridium perfringens in the synthesis of 2',3'-dideoxyinosine". . p. 445 - 448. Retrieved 2010.
• 2、 Shen, Bo,Jamison, Timothy F.. "Continuous flow photochemistry for the rapid and selective synthesis of 2′-deoxy and 2′,3′-dideoxynucleosides". . p. 157 - 164. Retrieved 2013/04/10.
• 3、 Shen, Bo,Bedore, Matthew W.,Sniady, Adam,Jamison, Timothy F.. "Continuous flow photocatalysis enhanced using an aluminum mirror: Rapid and selective synthesis of 2′-deoxy and 2′,3′-dideoxynucleosides". supporting information; experimental part. p. 7444 - 7446. Retrieved 2012/10/08.