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07-SEPTEMBER-2008 03:17:44 - Abacavir Abacavir Systematic IUPAC name 1R-4-2-amino-6-cyclopropylaminopurin-9-yl- 1-cyclopent-2-enylmethanol Identifiers CAS number 136470-78-5 ATC code J05AF06 PubChem 441300 DrugBank APRD00216 Chemical data Formula C14H18N6O Mol. mass 286.333 g/mol Pharmacokinetic data Bioavailability 83% Metabolism Hepatic Half life 1.54 ± 0.63 hours Excretion Renal 1.2% abacavir, 30% 5'-carboxylic acid metabolite, 36% 5'-glucuronide metabolite, 15% unidentified minor metabolites. Fecal 16% Therapeutic considerations Pregnancy cat. B3AU CUS Legal status POMUK Routes Oral solution or tablets Abacavir ABC is a nucleoside analog reverse transcriptase inhibitor NRTI used to treat HIV and AIDS. It is available under the trade name Ziagen GlaxoSmithKline and in the combination formulations Trizivir abacavir, zidovudine and lamivudine and Kivexa/Epzicomabacavir and lamivudine . It has been well tolerated: the main side effect is hypersensitivity, which can be severe, and in rare cases, fatal. Genetic testing can indicate whether an individual will be hypersensitive; over 90% of patients can safely take abacavir. However, in a separate study, in 90% of patients, the risk of heart attack has increased.1 Two 2 Abacavir 300mg tablets Two 2 Abacavir 300mg tablets Viral strains that are resistant to zidovudine AZT or lamivudine 3TC are generally sensitive to abacavir, whereas strains that are resistant to AZT and 3TC are not as sensitive to abacavir. History Abacavir was approved by the Food and Drug Administration FDA on December 18, 1998 and is thus the fifteenth approved antiretroviral drug in the United States. Its patent will expire in the United States on 2009-12-26. Indication Abacavir tablets and oral solution, in combination with other antiretroviral agents, are indicated for the treatment of HIV-1 infection. Abacavir should always be used in combination with other antiretroviral agents. Abacavir should not be added as a single agent when antiretroviral regimens are changed due to loss of virologic response. Mechanism of action ABC is an analog of guanosine a purine. Its target is the viral reverse transcriptase enzyme. Pharmacokinetics Abacavir is given orally and has a high bioavailability 83%. It is metabolised primarily through alcohol dehydrogenase or gluconyl transferase. It is capable of crossing the blood-brain barrier. Adverse reactions Fatal hypersensitivity reactions have been associated with therapy with abacavir. Symptoms of hypersensitivity include fever, skin rash, fatigue, gastrointestinal symptoms such as nausea, vomiting, diarrhea or abdominal pain and respiratory symptoms such as pharyngitis, dyspnea, or cough. Hypersensitivity is strongly associated with HLA-B570123 for which testing is now available in most western countries. There is a strong relationship with race: the prevalence of HLA-B5701 in India is 20-50%, but is 0% in Japan; the prevalence is 5-7% in western Europe. Screening for the HLA-B5701 has been convincingly shown to reduce the incidence of abacavir hypersensitivity reactions.45 A new FDA alert concerning abacavir and abacavir containing medications was issued on July 24, 2008. FDA informed that based on data from two studies they support a recommendation for pre-therapy screening for the presence of the HLA-B5701 allele and the selection of alternative therapy in positive subjects. Genetic tests for HLA-B5701 are available and all patients should be screened for the HLA-B5701 allele before starting or restarting treatment with abacavir or abacavir containing medications. Development of clinically suspected abacavir HSR requires immediate and permanent discontinuation of abacavir therapy in all patients, including patients negative for HLA-B5701.6 Cautions and Warnings Patients with liver disease should be cautious about using abacavir because of the possibility that it can aggravate the condition. The use of nucleoside drugs such as abacavir can very rarely cause lactic acidosis. Resistance to abacavir has developed in laboratory versions of HIV which are also resistant to other HIV-specific antiretrovirals such as lamivudine, didanosine and zalcitabine. HIV strains that are resistant to protease inhibitors are not likely to be resistant to abacavir. Redistribution or accumulation of body fat may occur in people taking antiviral medications giving rise to central obesity, facial arm, leg, and/ or buttock wasting, breast enlargement, and fat accumulation at the base of the neck buffalo hump. Abacavir is contraindicated for use in infants under 3 months of age. Food Interactions None known Usual Dose Adult age 17 and over :300mg 2 times a day Child age 3 months - 16 years 3.6mg per lb. of body weight twice a day, up to a maximum of 300mg in each dose. Overdosage Little is known about the effects of Abacavir overdose. Overdose victims should be taken to a hospital emergency room for treatment. Always bring the prescription bottle or container. References Antiretroviral Therapy-Investigational NRTIs: HIV Clinical Management Vol. 3. Medscape Inc, 1998 HIV Insite Antiretroviral Drug Database; UC Regents, 1999 ^ SFGate.com ^ Mallal S, Nolan D, Witt C, et al. 2002. Association between the presence of HLA-B5701, HLA-DR7 and HLA-DQ3 and hypersensitivity to HIV-1 reverse transcriptase inhibitor abacavir. Lancet 359: 727-32. doi:10.1016/S0140-67360207873-X. ^ Hetherington S, Hughes AR, Mosteller M, et al. 2002. Genetic variations in HLA-B region and hypersensitivity reactions to abacavir. Lancet 359: 1121-2. doi:10.1016/S0140-67360208158-8. ^ Rauch A, Nolan D, Martin A, et al. 2006. Prospective genetic screening decreases the incidence of abacavir hypersensitivity reactions in the Western Australian HIV cohort study. Clin Infect Dis 43 1: 99-102. doi:10.1086/504874. ^ Zucman D, de Truchis P, Majerholc C, et al. 2007. Prospective Screening for Human Leukocyte Antigen-B5701 Avoids Abacavir Hypersensitivity Reaction in the Ethnically Mixed French HIV Population. J Acquir Immune Defic Syndr 45: 1. doi:10.1097/QAI.0b013e318046ea31. PMID 17356469. ^ http://www.fda.gov/cder/drug/InfoSheets/HCP/abacavirHCP.htm FDA abacavir alert web access July 29, 2008 External links Full Prescribing Information v d e Antivirals used against HIV HAART primarily J05 Nucleoside Nucleotide Reverse Transcriptase Inhibitors NRTI Abacavir ABC° Dexelvucitabine§ Emtricitabine° Lamivudine 3TC° Tenofovir° Didanosine Zidovudine AZT Apricitabine† Stampidine† Elvucitabine† Racivir† Amdoxovir† Stavudine‡ Zalcitabine‡ Non-Nucleoside Reverse Transcriptase Inhibitors NNRTI Ateviridine§ Capravirine§ Efavirenz° Emivirine§ Lodenosine§ Nevirapine Etravirine Rilpivirine† Loviride‡ Delavirdine‡ Quinotaline§ Protease Inhibitors PI Atazanavir° Brecanavir§ Fosamprenavir° Lopinavir° Darunavir Nelfinavir Ritonavir Saquinavir Tipranavir Amprenavir‡ Indinavir‡ Entry/fusion inhibitors Aplaviroc§ Enfuvirtide Maraviroc Vicriviroc† PRO 140† Ibalizumab† Integrase inhibitors Raltegravir Elvitegravir† Maturation inhibitors Bevirimat† Vivecon† Combined formulations Combivir Atripla Trizivir Truvada Kaletra Epzicom Other experimental agents Foscarnet Hydroxyurea Synergistic enhancers Epigallocatechin gallate Portmanteau inhibitors Globoidnan A Griffithsin Diarylpyrimidines Calanolide A Cyanovirin-N Miltefosine R-roscovitine† °DHHS preferred first-line agent. †Undergoing clinical trials, not FDA approved. ‡Formerly or rarely used agent. §Development terminated. Retrieved from http://en..org/wiki/Abacavir Categories: Nucleoside analog reverse transcriptase inhibitors | Purines Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Español Français Polski Português ไทย This page was last modified on 29 August 2008, at 06:22
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