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Encyclopedia > Zalcitabine

ddC
2'-3'-dideoxycytidine
Molecular Weight 211.22
Empiric Formula C9H13N3O3
ATC code J05AF03
Metabolism Renal elimination (ca.80%)
Pregnancy category C (USA)
D (Aus)

Zalcitabine (2'-3'-dideoxycytidine, ddC), is a derivative of the naturally existing deoxycytidine, made by replacing the hydroxyl group in position 3' with a hydrogen. It was the third drug approved in the United States for the treatment of human immunodeficiency virus (HIV) infection and AIDS. Zalcitabine was developed in the National Cancer Institute by Samuel Broder, Hiroaki Mitsuya, and Robert Yarchoan, and then licensed by the US Government to Hoffman LaRoche Co. It is phosphorylated in the T cell and other HIV target cells into its active triphosphate form, ddCTP. This active metabolite works as a substrate for HIV reverse transcriptase, and also by incorporation into the viral DNA, hence terminating the chain elongation due to the missing hydroxyl group. Since zalcitabine is a reverse transcriptase inhibitor it possess activity only against retroviruses. It is used for the treatment of HIV infection only in combination with zidovudine. Image File history File links Zalcitabine. ... See also Avogadros number Atomic mass unit Dalton (unit) External links Learning by Simulations Calculation of Molecular Formulas from Molecular Masses Categories: Chemistry stubs | Mass | Chemical properties ... 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. ... ... Cytidine is a molecule (known as a nucleoside) that is formed when cytosine is attached to a ribose ring (also known as a ribofuranose) via a β-N1-glycosidic bond. ... Hydroxide is a functional group consisting of oxygen and hydrogen: -O−H It has a charge of 1-. The term hydroxyl group is used when the functional group -OH is counted as a substituent of an organic compound. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... Human immunodeficiency virus, commonly known by the acronym HIV, is a retrovirus that primarily infects vital components of the human immune system such as CD4+ T cells, macrophages and dendritic cells. ... T cells are a subset of lymphocytes that play a large role in the immune response. ... In biochemistry, reverse transcriptase (EC 2. ... In biochemistry, reverse transcriptase (EC 2. ... Genera Alpharetrovirus Betaretrovirus Gammaretrovirus Deltaretrovirus Epsilonretrovirus Lentivirus Spumavirus A Retrovirus is a virus which has a genome consisting of two plus sense RNA molecules, which may or may not be identical. ... Human immunodeficiency virus, commonly known by the acronym HIV, is a retrovirus that primarily infects vital components of the human immune system such as CD4+ T cells, macrophages and dendritic cells. ... Zidovudine (INN) or azidothymidine (abbreviated to AZT) is an antiretroviral drug, the first antiviral treatment to be approved for use against HIV. It is also sold under the names Retrovir and Retrovis, and as an ingredient in Combivir and Trizivir. ...


Zalcitabine has a very high oral absorption rate, of over 80 %. The most common side effect in the beginning of the treatment is nausea and headache. The more serious side effects are peripheral neuropathy, oesophagitis and pancreatitis. Neuropathy is a disease of the peripheral nervous system. ... Pancreatitis describes the condition of inflammation of the pancreas that causes mild to severe pain in the abdomen. ...


Due to its relatively weak potency, inconvenient dosing, and serious side effects, zalcitabine is no longer commonly used to treat HIV.


References

  • Yarchoan R, Mitsuya H, Broder S. AIDS therapies. Scientific American 1988;259(4):110-9.
  • Harvey Stewart C. in Remington's Pharmaceutical Sciences 18th edition: (ed. Gennard, Alfonso R.) Mack Publishing Company, 1990
  • Rang H.P., Dale M.M., Ritter J.M.: Pharmacology, 3rd edition. Pearson Professional Ltd, 1995.
  • Mitsuya H, Broder S. Inhibition of the in vitro infectivity and cytopathic effect of human T-lymphotropic virus type III/lymphadenopathy virus-associated virus (HTLV-III/LAV) by 2',3'-dideoxynucleosides. Proc Natl Acad Sci USA 1986;83:1911-5.
  • Yarchoan R, Perno CF, Thomas RV, et al. Phase I studies of 2',3'-dideoxycytidine in severe human immunodeficiency virus infection as a single agent and alternating with zidovudine (AZT). Lancet 1988;1:76-81.
  • Mitsuya H, Yarchoan R, Broder S. Molecular targets for AIDS therapy. Science 1990;249:1533-44.
  • NIH Bio and Oral History of Samuel Broder describing the development of anti-HIV drugs: http://aidshistory.nih.gov/transcripts/bios/Samuel_Broder.html
  • NIH Bio and Oral History of Robert Yarchoan describing the development of anti-HIV drugs: http://aidshistory.nih.gov/transcripts/bios/Robert_Yarchoan.html


Antivirals (ATC J05A)edit

Antiherpesvirus agents: {Acyclovir} {Cidofovir} {Docosanol} {Famciclovir} {Foscarnet} {Fomivirsen} {Ganciclovir} {Idoxuridine} {Penciclovir} {Trifluridine} {Valaciclovir} {Valganciclovir} {Vidarabine} Wikipedia does not yet have an article with this exact name. ... A section of the Anatomical Therapeutic Chemical Classification System. ... Aciclovir (INN) or aciclovir (USAN), marketed as Zovirax®, is one of the main antiviral drugs. ... Chemical structure of cidofovir Cidofovir is an injectable antiviral medication for the treatment of cytomegalovirus (CMV) retinitis in patients with AIDS. It suppresses CMV replication by selective inhibition of viral DNA synthesis. ... Docosanol 10% cream is a topical treatment for recurrent herpes simplex labialis episodes (episodes of cold sores or fever blisters). ... Ganciclovir sodium (Cytovene®) is an antiviral medication used to treat cytomegalovirus (CMV) infections. ... Valaciclovir (INN) or valacyclovir (USAN) is an antiviral drug used in the management of herpes simplex. ... Valganciclovir hydrochloride (Valcyte®) is an antiviral medication used to treat cytomegalovirus infections. ... Chemical structure of vidarabine Vidarabine is an anti-viral drug which is active against herpes simplex and varicella zoster viruses. ...


Antiinfluenza agents: {Amantadine} {Oseltamivir} {peramivir} {Rimantadine} {Zanamivir} Amantadine, 1-aminoadamantane, is an antiviral drug that was approved by the FDA in 1976 for the treatment of influenza type A in adults. ... Oseltamivir is an antiviral drug, a neuraminidase inhibitor used in the treatment and prophylaxis of both influenza A and influenza B. Oseltamivir was the first orally active neuraminidase inhibitor commercially developed. ... Please expand this article. ... Rimantadine is an orally administered medicine used to treat, and in rare cases prevent, type A influenza. ... Zanamivir is a neuraminidase inhibitor used in the treatment of and prophylaxis of both influenza A and influenza B. Zanamivir was the first neuraminidase inhibitor commercially developed. ...


Antiretroviral drugs
NRTIs: {Zidovudine} {Didanosine} {Stavudine} {Zalcitabine} {Lamivudine} {Abacavir} {Tenofovir}
NNRTIs: {Nevirapinelol} {Efavirenz} {Delavirdine}
PIs: {Saquinavir} {Indinavir} {Atazanavir} {Ritonavir} {Nelfinavir} {Amprenavir} {Lopinavir} {Tipranavir} Antiretroviral drugs are medications for the treatment of infection by the retrovirus HIV. Different antiretroviral drugs act at various stages of the HIV life cycle. ... Zidovudine (INN) or azidothymidine (abbreviated to AZT) is an antiretroviral drug, the first antiviral treatment to be approved for use against HIV. It is also sold under the names Retrovir and Retrovis, and as an ingredient in Combivir and Trizivir. ... Didanosine (2-3-dideoxyinosine, ddI, Videx®) differs from other nucleoside analogues, because it does not have any of the regular bases, instead it has hypoxanthine attached to the sugar ring. ... Stavudine (2-3-didehydro-2-3-dideoxythymidine, d4T, brand name Zerit®) is a thymidine analogue active against HIV. It is phosphorylated by cellular kinases into active triphosphate. ... Lamivudine (2,3-dideoxy-3-thiacytidine, 3TC) is a potent reverse transcriptase inhibitor. ... Abacavir (ABC) is extremely potent reverse transcriptase inhibitor, meant for the treatment of AIDS. ABC is capable of crossing the blood-brain barrier. ... Tenofovir disoproxil fumarate belongs to a class of antiretroviral drugs known as nucleotide analogue reverse transcriptase inhibitors (NtRTIs), which block reverse transcriptase, an enzyme crucial to viral production in HIV-infected people. ... This article needs to be cleaned up to conform to a higher standard of quality. ... Saquinavir (Fortovase®, Roche) is a protease inhibitor, used as a component of HIV therapy. ... Categories: Stub ... Ritonavir is a drug from the protease inhibitor class used to treat AIDS. It is manufactured as Norvir® by Abbott Laboratories. ... Nelfinavir (Viracept®) is an antitretroviral drug used in the treatment of the human immunodeficiency virus (HIV). ... Tipranavir is a new protease inhibitor (PI) that was approved by the FDA in June 2005. ...


Other antiviral agents: {Fomivirsen} {Fuzeon} {Imiquimod} {Interferon} {Ribavirin} (Viramidine) Enfuvirtide is a novel antiretroviral drug used in combination therapy for the treatment of HIV-1 infection. ... Imiquimod is a medication used to treat certain diseases of the skin, including skin cancer and genital warts. ... Interferons (IFNs) are natural proteins produced by the cells of the immune systems of most animals in response to challenges by foreign agents such as viruses, bacteria, parasites and tumor cells. ... Ribavirin (Copegus®; Rebetol®; Ribasphere®; Vilona®,Virazole®, also generics from Sandoz, Teva, Warrick) is an anti-viral drug which is active against a number of DNA and RNA viruses. ... Viramidine is an anti-viral drug in Phase III human trials, but not yet approved for pharmaceutical use. ...


  Results from FactBites:
 
Zalcitabine (Hivid, dideoxycytidine, ddC) (792 words)
A clinical study (1) found zalcitabine to be inferior to zidovudine as monotherapy for advanced HIV disease (CD4 count ≤200 cells/µL) in previously untreated patients, with significantly increased mortality observed in the group receiving zalcitabine.
Zalcitabine and didanosine should not be used in combination because of their overlapping potential side effects of peripheral neuropathy and pancreatitis, their similar resistance profiles, and the lack of demonstrated efficacy of this combination.
Zalcitabine and stavudine should not be used together because of the overlapping side effect of peripheral neuropathy.
  More results at FactBites »

 
 

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