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Encyclopedia > Didanosine

ddI
2'-3'-dideoxyinosine
Molecular Weight 236.23
Empiric Formula C10H12N4O3
ATC code J05AF02
Metabolism Renal elimination
Pregnancy category C (USA)
B2 (Aus)

Didanosine (2'-3'-dideoxyinosine, ddI) is sold under the trade names Videx® and Videx EC®. It is a reverse transcriptase inhibitor, effective against HIV and usually used in combination with other antiviral drug therapy as part of highly active antiretroviral therapy (HAART). Image File history File links Didanosine. ... The molecular mass (abbreviated MM) of a substance, called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother. ... Motto: none (formerly Advance Australia) Anthem: Advance Australia Fair Capital Canberra Largest city Sydney Official language(s) English (de facto)1 Government  â€¢ Queen  â€¢ Governor-General  â€¢ Prime Minister Const. ... This article needs to be cleaned up to conform to a higher standard of quality. ... Human immunodeficiency virus, commonly known by the initialism HIV, formerly known as HTLV-III and lymphadenopathy-associated virus, is a retrovirus that primarily infects vital components of the human immune system such as CD4+ T cells, macrophages and dendritic cells. ... Antiviral drugs are a class of medication used specifically for treating viral infections. ...

Contents


History

Didanosine was developed by Samuel Broder, Hiroaki Mitsuya, and Robert Yarchoan in the National Cancer Institute (NCI). Since the NCI cannot market a product, the National Institutes of Health (NIH) awarded a ten-year exclusive licensed to Bristol-Myers Squibb Co. (BMS) to market and sell ddI as Videx® tablets. Samuel Broder is an oncologist and medical researcher. ... Hiroaki Mitsuya (1950 - ) is a Japanese virologist famous for his discovery of the anti-HIV drug AZT. Mitsuya obtained his M.D. and Ph. ... Robert Yarchoan (born 1950) is a medical researcher who played an important role in the development of the first effective drugs for AIDS. Dr. Yarchoan attended Amherst College and subsequently received his M.D. from the University of Pennsylvania. ... The National Cancer Institute (NCI) is the United States federal governments principal agency for cancer research and training, and the first institute of the present-day National Institutes of Health. ... The National Institutes of Health (NIH) is the primary agency of the United States government responsible for medical research. ... Bristol-Myers Squibb NYSE: BMY, colloquially referred to as BMS, is a pharmaceutical corporation, formed by a 1989 merger between pharmaceutical companies Bristol-Myers Company and Squibb Corporation. ...


Didanosine became the second drug approved for the treatment of HIV infection in many other countries, including in the United States by the Food and Drug Administration (FDA) on Oct 9, 1991. Its FDA approval helped bring down the price of zidovudine (AZT), the initial anti-HIV drug. The Food and Drug Administration (FDA) of the United States is the government agency responsible for regulating food (human and animal), dietary supplements, drugs (human and animal), cosmetics, medical devices (human and animal), biologics, and blood products in the United States. ... October 9 is the 282nd day of the year in the Gregorian calendar (283rd in Leap years). ... 1991 (MCMXCI) was a common year starting on Tuesday of the Gregorian calendar. ... Zidovudine (INN) or azidothymidine (AZT) (also called ZDV) is an antiretroviral drug, the first one approved for treatment of HIV. It is also sold under the names Retrovir® and Retrovis®, and as an ingredient in Combivir® and Trizivir®. It is an analog of thymidine. ...


Didanosine has weak acid stability and is easily damaged by stomach acid. Therefore, the original formula approved by the FDA used chewable tablets that included an antacid buffering compound to neutralize stomach acid. The chewable tablets were not only large and fragile, they also were foul-tasting and the buffering compound would cause diarrhea. Although the FDA had not approved the original formulation for once-a-day dosing it was possible for some people to take it that way. The examples and perspective in this article or section may not represent a worldwide view. ...


At the end of its ten-year license, BMS re-formulated Videx® as Videx EC® and patented that, which reformulation the FDA approved in 2000. The new formulation is a smaller capsule containing coated microspheres instead of using a buffering compound. It is approved by the FDA for once-a-day dosing. Also at the end of that ten-year period, the NIH licensed didanosine to Barr Laboratories under a non-exclusive license, and didanosine became the first generic anti-HIV drug marketed in the United States.


One of the patents for ddI will expire in the United States on 2006-08-29, but other patents extend beyond that time. 2006 (MMVI) is a common year starting on Sunday of the Gregorian calendar. ... August 29 is the 241st day of the year in the Gregorian Calendar (242nd in leap years), with 124 days remaining. ...


Mechanism of action

Didanosine (ddI) is a nucleoside analogue of adenosine. It differs from other nucleoside analogues, because it does not have any of the regular bases, instead it has hypoxanthine attached to the sugar ring. Within the cell, ddI is, by cellular enzymes, phosphorylated to active metabolite of dideoxyadenosine triphosphate, ddATP. Like other anti-HIV nucleside analogs, it acts as a chain terminator by incorporation and inhibits viral reverse transcriptase by competing with natural dATP. Nucleosides are glycosylamines made by attaching a nucleobase to a ribose ring. ... An analog is in chemistry a chemical closely related to another usually sharing the same nucleus. ... The chemical structure of adenosine Adenosine is a nucleoside comprised of adenine attached to a ribose (ribofuranose) moiety via a β-N9-glycosidic bond. ... Hypoxanthine is a naturally occurring purine derivative, and one of the products of the action of xanthine oxidase on xanthine, though more normally in purine degradation, hypoxanthine is oxidized by xanthine oxidase to form xanthine. ... Adenosine 5-triphosphate (ATP) is a multifunctional nucleotide primarily known in biochemistry as the molecular currency of intracellular energy transfer. ...


Oral absorption of ddI is fairly low (40%) but rapid. The half-life in plasma is only 30 minutes, but in intracellular environment more than 12 hours. An enteric-coated formulation is now marketed as well. The kidneys actively secrete didanosine, the amount being 20 % of the oral dose.


Adverse affects

The side effects of didanosine are mainly headache and nausea, but also peripheral neuropathy, insomnia, pancreatitis and alterations of liver functions have been reported. Drug resistance to didanosine does develop, though slower than to Zidovudine (AZT). Neuropathy is a disease of the peripheral nervous system. ... It has been suggested that Primary insomnia be merged into this article or section. ... Pancreatitis is inflammation of the pancreas. ... Zidovudine (INN) or azidothymidine (AZT) (also called ZDV) is an antiretroviral drug, the first one approved for treatment of HIV. It is also sold under the names Retrovir® and Retrovis®, and as an ingredient in Combivir® and Trizivir®. It is an analog of thymidine. ...


References

* Yarchoan R, Mitsuya H, Broder S. AIDS therapies. Sci Am 1988;259(4):110-9


* Männistö P.T., Tuominen R.K. in Farmakologia ja Toksikologia, 5th edition: (ed. Koulu, Tuomisto, Paasonen) Medicina, 1996


* Rang H.P., Dale M.M., Ritter J.M.: Pharmacology, 3rd edition. Pearson Professional Ltd, 1995


* Watson et. al.: Molecular Biology of the Gene 4th edition. The Benjamin/Cummings Publishing Company, 1987


* Mitsuya H, Yarchoan R, Broder S. Molecular targets for AIDS therapy. Science 1990;249(4976):1533-44


* Yarchoan R, Mitsuya H, Thomas RV, et al. In vivo activity against HIV and favorable toxicity profile of 2',3'-dideoxyinosine. Science 1989;245(4916):412-5


* NIH Oral History of Samuel Broder describing development of AIDS drugs


* NIH Oral History of Robert Yarchoan describing development of AIDS drugs

Antivirals (ATC J05A) edit
Anti-herpesvirus agents   Aciclovir · Cidofovir · Docosanol · Famciclovir · Foscarnet · Fomivirsen · Ganciclovir · Idoxuridine · Penciclovir · Trifluridine · Tromantadine · Valaciclovir · Valganciclovir · Vidarabine
Anti-influenza agents Amantadine · Oseltamivir · Peramivir · Rimantadine · Zanamivir
 
Antiretroviral drugs   NRTIs Zidovudine · Didanosine · Stavudine · Zalcitabine · Lamivudine · Abacavir · Tenofovir
NNRTIs   Nevirapine · Efavirenz · Delavirdine
PIs Saquinavir · Indinavir · Atazanavir · Ritonavir · Nelfinavir · Amprenavir · Lopinavir · Tipranavir
 
Other antiviral agents Fomivirsen · Enfuvirtide · Imiquimod · Interferon · Ribavirin · Viramidine

  Results from FactBites:
 
Didanosine - Wikipedia, the free encyclopedia (610 words)
Didanosine was developed by Samuel Broder, Hiroaki Mitsuya, and Robert Yarchoan in the National Cancer Institute (NCI).
Didanosine became the second drug approved for the treatment of HIV infection in many other countries, including in the United States by the Food and Drug Administration (FDA) on Oct 9, 1991.
The side effects of didanosine are mainly headache and nausea, but also peripheral neuropathy, insomnia, pancreatitis and alterations of liver functions have been reported.
Didanosine (Videx, dideoxyinosine, ddI) (1509 words)
A comparison of didanosine with zidovudine monotherapy in adults with advanced HIV disease(1) found that zidovudine was superior in previously untreated subjects, while didanosine was superior (in terms of mortality or progression to AIDS) in subjects with 8-16 weeks of prior zidovudine therapy.
Didanosine and zalcitabine should not be used in combination because of their overlapping potential side effects of pancreatitis and peripheral neuropathy, as well as their similar resistance profiles, and the lack of demonstrated efficacy of this combination.
Coadministration of tenofovir with didanosine increases serum levels of didanosine; dose reduction of didanosine is recommended.(4) Didanosine tablets or powder should not be taken at the same time as indinavir or delavirdine because the buffer present in the tablets interferes with the absorption of these drugs.
  More results at FactBites »

 
 

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