Abacavir = Ziagen
CAS NUMBER: 188062-50-2
MOLECULAR WEIGHT: 670.74
Abacavir, sold under the brand name Ziagen, is a medication used to prevent and treat HIV/AIDS.
Similar to other nucleoside analog reverse-transcriptase inhibitors (NRTIs), abacavir is used together with other HIV medications, and is not recommended by itself.
Abacavir is taken by mouth as a tablet or solution and may be used in children over the age of three months.
Abacavir is a nucleoside reverse transcriptase inhibitor analog of guanosine.
This agent decreases HIV viral loads, retards or prevents the damage to the immune system, and reduces the risk of developing AIDS.
Abacavir is generally well tolerated.
Common side effects include vomiting, trouble sleeping, fever, and feeling tired.
More severe side effects include hypersensitivity, liver damage, and lactic acidosis.
Genetic testing can indicate whether a person is at higher risk of developing hypersensitivity.
Symptoms of hypersensitivity include rash, vomiting, and shortness of breath.
Abacavir is in the NRTI class of medications, which work by blocking reverse transcriptase, an enzyme needed for HIV virus replication.
Within the NRTI class, abacavir is a carbocyclic nucleoside.
Abacavir was patented in 1988, and approved for use in the United States in 1998.
Abacavir is on the World Health Organization's List of Essential Medicines.
Abacavir is available as a generic medication.
Commonly, abacavir is used together with other HIV medications, such as abacavir/lamivudine/zidovudine, abacavir/dolutegravir/lamivudine, and abacavir/lamivudine.
The combination abacavir/lamivudine is also an essential medicine.
Abacavir sulfate is a nucleoside analogue and reverse transcriptase inhibitor which is used in combination with other agents in the therapy of the human immunodeficiency virus (HIV) infection and the acquired immunodeficiency syndrome (AIDS).
Abacavir is a rare cause of clinically apparent drug induced liver injury.
Abacavir is a 2,6-diaminopurine that is (1S)-cyclopent-2-en-1-ylmethanol in which the pro-R hydrogen at the 4-position is substituted by a 2-amino-6-(cyclopropylamino)-9H-purin-9-yl group.
A nucleoside analogue reverse transcriptase inhibitor (NRTI) with antiretroviral activity against HIV, it is used (particularly as the sulfate) with other antiretrovirals in combination therapy of HIV infection.
Abacavir has a role as a HIV-1 reverse transcriptase inhibitor, an antiviral drug and a drug allergen.
Abacavir is a prescription medicine approved by the U.S. Food and Drug Administration (FDA) for the treatment of HIV infection in adults and children 3 months of age and older.
Abacavir is always used in combination with other HIV medicines.
For more information on the use of abacavir in people with HIV, please refer to the Guidelines for the Use of Antiretroviral Agents in Adults and Adolescents Living with HIV.
Abacavir (ABC) is a powerful nucleoside analog reverse transcriptase inhibitor (NRTI) used to treat HIV and AIDS.
Chemically, it is a synthetic carbocyclic nucleoside and is the enantiomer with 1S, 4R absolute configuration on the cyclopentene ring.
In vivo, abacavir sulfate dissociates to its free base, abacavir.
Abacavir is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1).
Abacavir is phosphorylated to active metabolites that compete for incorporation into viral DNA.
They inhibit the HIV reverse transcriptase enzyme competitively and act as a chain terminator of DNA synthesis.
The concentration of drug necessary to effect viral replication by 50 percent (EC50) ranged from 3.7 to 5.8 μM (1 μM = 0.28 mcg/mL) and 0.07 to 1.0 μM against HIV-1IIIB and HIV-1BaL, respectively, and was 0.26 ± 0.18 μM against 8 clinical isolates.
Abacavir had synergistic activity in cell culture in combination with the nucleoside reverse transcriptase inhibitor (NRTI) zidovudine, the non-nucleoside reverse transcriptase inhibitor (NNRTI) nevirapine, and the protease inhibitor (PI) amprenavir; and additive activity in combination with the NRTIs didanosine, emtricitabine, lamivudine, stavudine, tenofovir, and zalcitabine.
Abacavir is an antiviral medicine that prevents human immunodeficiency virus (HIV) from multiplying in your body.
Abacavir is used to treat HIV, the virus that can cause acquired immunodeficiency syndrome (AIDS). abacavir is for adults and children who are at least 3 months old. Abacavir is not a cure for HIV or AIDS.
Abacavir may also be used for purposes not listed in this medication guide.
Abacavir is an oral medication that is used for the treatment of infections with the human immunodeficiency virus (HIV).
Abacavir is in a class of drugs called reverse transcriptase inhibitors which also includes zalcitabine (Hivid), zidovudine (Retrovir), didanosine (Videx), lamivudine (Epivir), emtricitabine (Emtriva), and stavudine (Zerit).
During infection with HIV, the HIV virus multiplies within the body's cells.
The newly-formed viruses then are released from the cells and spread throughout the body where they infect other cells.
In this manner, the infection continually spreads to new, uninfected cells that the body is continually producing, and HIV infection is perpetuated.
When producing new viruses, the HIV virus must manufacture new DNA for each virus.
Reverse transcriptase is the enzyme that the virus uses to form this new DNA.
Specifically, abacavir is converted within the body to its active form (carbovir triphosphate).
This active form is similar to a compound (deoxyguanosine triphosphate), a chemical that is required by the HIV virus to make new DNA.
The reverse transcriptase uses carbovir triphosphate instead of deoxyguanosine triphosphate for making DNA, and it is the carbovir triphosphate that interferes with the reverse transcriptase.
Abacavir does not kill existing HIV virus, and it is not a cure for HIV. The FDA approved abacavir in December 1998.
Abacavir is a type of antiretroviral drug called a nucleoside analogue (“nuke”).
The most common side effects of abacavir can include headache, nausea, vomiting, unexpected tiredness, and loss of appetite.
Abacavir is usually taken at a dose of 600 mg daily, with or without food.
Abacavir, sold under the brand name Ziagen, is a type of antiretroviral (anti-HIV) drug called a nucleoside analogue or “nuke.”
Abacavir is used in combination with other antiretroviral drugs to treat (but not cure) HIV.
Abacavir is a guanosine nucleoside analog with potent activity against HIV. However, in the premarketing phase of drug development, multiple reports emerged of a hypersensitivity syndrome associated with abacavir, which led to significant morbidity.
Rare reports of mortality were associated with failure to recognize this clinical syndrome as drug hypersensitivity.
ZIAGEN is a prescription HIV-1 (Human Immunodeficiency Virus type 1) medicine used with other antiretroviral medicines to treat HIV-1 infection.
HIV-1 is the virus that causes Acquired Immune Deficiency Syndrome (AIDS).
Abacavir is a medication used to treat HIV.
Abacavir is marketed under the brand name Ziagen, but generic versions are also available.
Abacavir is taken in combination with other antiretroviral drugs.
The usual adult dose of abacavir is 600mg per day.
You could take two 300mg tablets once a day, or one 300mg tablet twice a day.
Abacavir is also available in combination tablets. Several companies make a pill which contains abacavir and another drug, lamivudine, in one pill.
Abacavir is also available in a combination pill with lamivudine and dolutegravir, marketed as Triumeq.
Abacavir sulfate belongs to the class of human immunodeficiency virus (HIV) medicines called nucleoside reverse transcriptase inhibitors, with antiretroviral activity against HIV.
Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Abacavir (ABC) exhibits potent in vitro antiviral activity against wild-type HIV-1 (IC50 4.0 μM, MT-4 cells).
Abacavir induces chromosomal DSBs and thereby kills ATL cells but not non-HTLV-1-infected cells.
Once abacavir is incorporated into the cells, it is phosphorylated in a unique stepwise anabolism to be converted to the triphosphated guanine analog carbovir (CBV) and then incorporated into host chromosomal DNA by replicative DNA polymerases, leading to premature termination of DNA replication, collapse of the replication fork, and DSB formation.
Abacavir induces S/G2-phase arrest and apoptosis in ED-40515(−) cells, but not in Jurkat cells.
In vivo Abacavir efficiently inhibits the growth of ATL cell xenografts in NOD/SCID mice. In adults, Abacavir is rapidly absorbed after oral administration, with peak concentrations occurring 0.63-1 hour after dosing.
The absolute bioavailability of abacavir is approximately 83%. Abacavir pharmacokinetics are linear and doseproportional over the range of 300-1200 mg/day.
The apparent volume of distribution of abacavir after intravenous administration is approximately 0.86 ± 0.15 L/kg, suggesting that abacavir is distributed to extravascular spaces.
Binding to plasma proteins is about 50% and is independent of the plasma abacavir concentration. Abacavir is extensively metabolized by the liver; less than 2% is excreted as unchanged drug in the urine.
Abacavir is primarily metabolized via two pathways, uridine diphosphate glucuronyltransferase and alcohol dehydrogenase, resulting in the inactive glucuronide metabolite and the inactive carboxylate metabolite.
The terminal elimination half-life of abacavir is approximately 1.5 hours. The antiviral effect of abacavir is due to its intracellular anabolite, carbovirtriphosphate (CBV-TP).
Abacavir is not significantly metabolized by cytochrome P450 (CYP) enzymes, nor does it inhibit these enzymes.
Abacavir (Ziagen) is a first choice HIV antiretroviral (ARV) used in combination with other HIV ARVs for the treatment of HIV.
Abacavir requires a genetic test before you start taking it because it can cause a severe allergic reaction.
Abacavir (Ziagen), is a drug used as part of antiretroviral therapy (ART).
Abacavir is manufactured by ViiV Healthcare. The FDA approved abacavir late in 1998.
Generic versions have been approved under PEPFAR.
Abacavir treats human immunodeficiency virus (HIV) infection.
Do not skip doses or run out of Abacavir as this may allow the virus to become harder to treat.
Abacavir is a prescription medication used to treat human immunodeficiency virus (HIV) infection.
Abacavir belongs to a group of drugs called nucleoside analogue reverse transcriptase inhibitors (NRTIs).
Abacavir works by preventing the virus from multiplying.
This medication comes in tablet and liquid forms and is usually taken once or twice daily.
Common side effects of abacavir include nausea, vomiting, tiredness, and headaches.
Abacavir is a type of drug called a nucleoside analog reverse transcriptase inhibitor, or nuke.
These drugs block the reverse transcriptase enzyme. This enzyme changes HIV’s genetic material (RNA) into the form of DNA.
This has to occur before HIV’s genetic code gets inserted into an infected cell’s own genetic codes.
Abacavir is a prescription medicine used to treat human immunodeficiency virus (HIV) infection.
Abacavir is always used with other anti-HIV medicines.
Abacavir is a human immunodeficiency virus (HIV) nucleoside analog reverse transcriptase inhibitor.
The drug abacavir, which functions as a reverse transcriptase inhibitor, prevents the virus from replicating itself by preventing the copying of the virus genetic material.
This agent reduces HIV viral loads, delays or prevents damage to the immune system and reduces the risk of developing AIDS.
HIV is derived from the initials of the words "human immunodeficiency virus" in English and is the virus that causes the infection known as AIDS disease among the people.
Abacavir is the active ingredient of the drug used in the treatment of HIV virus.
The chemical classification of abacavir is Nucleoside Analog.
Its molecular formula is C14H18N6O, its molecular weight is 286,339 g/mol.
Abacavir is an approved nucleoside reverse transcriptase inhibitor used to treat human immunodeficiency virus 1 (HIV-1) infection in combination with other antiretrovirals.
Adherence to antiretroviral therapy is one of the top determinants of favorable HIV treatment outcomes and is necessary to decrease the occurrence of drug resistance.
This activity reviews indications, dosing, contraindications, and adverse effects of abacavir and emphasizes the importance of an interprofessional team approach to caring for patients with HIV.
Abacavir is an antiretroviral medicine. It is used for human immunodeficiency virus (HIV) infection.
It slows the progress of HIV infection, but it is not a cure. HIV destroys cells in the body, called CD4 T cells.
These cells are a type of white blood cell and are important because they are involved in protecting your body from infection.
If left untreated, the HIV infection weakens your immune system so that your body cannot defend itself against bacteria, viruses and other germs.
Abacavir slows down the progress of HIV infection by reducing the amount of virus in your body.
Abacavir does this by stopping the virus from copying (replicating) itself.
Abacavir is the generic name for a drug used to treat individuals with the human immunodeficiency virus (HIV).
While it doesn't cure the condition, it helps manage the symptoms and the spread of the virus.
Abacavir is available as a liquid or tablet, often given with other types of medication.
The drug is extensively metabolized via stepwise phosphorylation to 5′-mono-, di-, and triphosphate.
Abacavir is well absorbed (>75%) and penetrates the CNS.
The drug can be taken without regard to meals.
The drug does not show any clinically significant drug–drug interactions.
Abacavir has been reported to produce life-threatening hypersensitivity reactions.
The major use of abacavir appears to be in combination with other nucleoside RT inhibitors.
A fixed-combination product has recently been approved by the U.S. FDA consisting of 300 mg of ABC, 150 mg of 3TC, and 300 mg of ZDV (Trizivar).
The combination has been shown to be superior to other combinations in reducing viral load as well as to show improvement in CD4 cell count.
The drug is a nucleoside reverse transcriptase inhibitor (NRTI).
While it doesn't destroy already existing virus samples, it helps prevent the virus from reproducing.
This helps slow the spread throughout the body.
The amount of virus present in the body is called the viral load, and the lower this number, the stronger the immune system and the less exposure there is typically to HIV-related illnesses.
Rarely, abacavir will be given to people who know they are at risk or have been exposed to contracting HIV. This includes giving it to women who are pregnant to help prevent transmission of HIV to the unborn baby.
Abacavir is a component of several brand-name drugs that are given to adults with the disease and those at risk.
However, Abacavir is not a foolproof drug that completely prevents the development of disease-related diseases.
Medications and ancillaries taking it can still spread the virus to other people through physical contact or sharing needles.
Abacavir is not uncommon for proper administration of abacavir to help relieve symptoms of the disease, but medical professionals will continue to prescribe and administer it because the virus is still in the system.
Taking the medication at the same time each day usually works best.
Abacavir is also not uncommon for individuals who are allergic to abacavir.
Typically, this allergy manifests itself in the form of side effects, including gastrointestinal distress; tiredness; a rash; difficulty breathing; and cold symptoms such as fever and sore throat.
If a person taking abacavir skips a few doses and then starts taking it again, it's possible that their body may develop an allergy that wasn't there for the initial treatment.
A medical professional may change the dose throughout treatment, so many will request it from someone who takes the medication through regular medical checkups.
Abacavir will be prescribed for you by a doctor who is a specialist.
Abacavir belongs to a group of antiretroviral medicines known as nucleoside reverse transcriptase inhibitors (NRTIs).
Abacavir is given alongside a number of other antiretroviral medicines, as part of a combination therapy.
Taking three or more antiretroviral medicines at the same time is more effective than taking one alone.
Some brands of abacavir contain one or more other antiretroviral medicine these combination brands help to reduce the total number of tablets you need to take each day.
Taking a combination of different medicines reduces the risk that the virus will become resistant to any individual medicine.
Abacavir is vital to take your antiretroviral medicines exactly as prescribed to maintain success and to help to prevent the virus from becoming resistant to the medicines.
These medicines are usually taken for life.
Abacavir is used along with other medications to treat human immunodeficiency virus (HIV) infection.
Abacavir is in a class of medications called nucleoside reverse transcriptase inhibitors (NRTIs).
Abacavir works by decreasing the amount of HIV in the blood.
Although abacavir does not cure HIV, it may decrease your chance of developing acquired immunodeficiency syndrome (AIDS) and HIV-related illnesses such as serious infections or cancer.
Taking these medications along with practicing safer sex and making other lifestyle changes may decrease the risk of transmitting (spreading) the HIV virus to other people.
Abacavir comes as a tablet and a solution (liquid) to take by mouth.
Abacavir is usually taken once or twice daily with or without food.
Take abacavir at around the same time(s) every day.
Follow the directions on your prescription label carefully, and ask your doctor or pharmacist to explain any part you do not understand.
Take abacavir exactly as directed. Do not take more or less of it or take it more often than prescribed by your doctor.
Abacavir helps to control HIV infection but does not cure it.
Continue to take abacavir even if you feel well.
Do not stop taking abacavir without talking to your doctor.
If you stop taking abacavir or skip doses, your condition may become more difficult to treat or you could have an allergic reaction when restarting the medication.
Do not run out of medication. When your supply of abacavir starts to run low, get more from your doctor or pharmacist.
Abacavir is also used in combination with other antiviral medications to prevent HIV infection in people who have been exposed to it.
Talk to your doctor about the possible risks of using this medication for your condition.
Abacavir is used in combination with several other antiretroviral drugs, usually including drugs from different classes, such as protease inhibitors and/or non-nukes (non-nucleoside reverse transcriptase inhibitors).
Combinations such as this are called antiretroviral therapy, or ART.
For more information on ART, see CATIE's Your Guide to HIV Treatment.
For many people with HIV, the use of ART has increased their CD4+ cell counts and decreased the amount of HIV in their blood (viral load).
These beneficial effects help to reduce the risk of developing a life-threatening infection.
Neither abacavir nor any other antiretroviral medication is a cure for HIV.
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.
These Secondary Standards are qualified as Certified Reference Materials.
These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.
Abacavir sulfate may be used as a pharmaceutical reference standard for the quantification of the analyte in pharmaceutical formulations using high-peformance liquid chromatography technique and spectrophotometric technique.
Abacavir is an FDA-approved drug used to treat HIV-1 infection in conjunction with other antiretrovirals.
Like other nucleoside reverse-transcriptase inhibitors (NRTIs), abacavir use is typically in combination with other HIV medications.
Abacavir is not recommended for use by itself.
Abacavir can be taken by mouth as a tablet or solution and it is a treatment option in patients over the age of three months.
Commonly, abacavir is dispensed together with other HIV medications such as abacavir/lamivudine/zidovudine, abacavir/dolutegravir/lamivudine, and abacavir/lamivudine.
HOW DOES ABACAVIR WORK:
When HIV infects a cell, it takes control of that cell.
HIV then forces the cell to make many more copies of the virus.
To make these copies, the cell uses proteins called enzymes.
When the activity of these enzymes is reduced the production of HIV slows.
Abacavir belongs to a class of antiretrovirals called nucleoside analogues.
Abacavir interferes with an enzyme called reverse transcriptase (RT), which is used by HIV-infected cells to make new viruses.
Since abacavir inhibits, or reduce the activity of this enzyme, this drug causes HIV-infected cells to produce fewer viruses.
Abacavir is from a class of drugs known as nucleoside reverse transcriptase inhibitors (NRTIs).
Your doctor will prescribe abacavir as part of your HIV treatment, along with antiretrovirals from another class of drugs.
Abacavir is important to take all the drugs as prescribed, every day.
Each drug class works against HIV in a different way.
The aim of HIV treatment is to reduce the level of HIV in your body (viral load).
Ideally, your viral load should become so low that it is undetectable – usually less than 50 copies of virus per ml of blood.
Taking HIV treatment and having an undetectable viral load protects your immune system and stops HIV being passed on.
MECHANISM OF ACTION:
Abacavir is a nucleoside reverse transcriptase inhibitor.
Within this class, it is specifically a carbocyclic 2'-deoxyguanosine, also known as a guanosine analog.
After oral ingestion, abacavir sulfate is rapidly absorbed and reaches peak concentrations at about 0.63 to 1 hour with an absolute bioavailability of about 83%.
Abacavir displays linear pharmacokinetics and possesses dose proportionality over the range of 300 to 1200 mg/day.
Taking abacavir with food has not had any clinically relevant effect on exposure to the drug and can be safely ingested in the presence or absence of food.
The volume of administration by parental route is about 0.86 +/- 0.15 L/kg.
Plasma protein binding is about 50% and has an independent relationship with the plasma concentration of the drug.
The liver accomplishes the majority of abacavir's metabolism.
The remaining bioavailable 2% of the compound gets excreted as an unaltered product in the urine.
Two major metabolic pathways are known as the uridine diphosphate glucuronyltransferase, and the alcohol dehydrogenase pathway processes abacavir within the liver.
Enzymatic metabolism produces an inactive glucuronide metabolite (361W94, approximately 36% of the dose recovered in the urine) and an additional inactive carboxylate metabolite (2269W93, about 30% of the dose recovered in the urine) — the other 15% of the compound ends up in the urine as minor metabolites, which comprise less than 2% of the orally ingested amount.
Elimination through stool makes up about 16% of the original dose.
CYP450 metabolism of abacavir does not play a substantial role in abacavir, and no observable drug interactions that alter clinical decision-making exist within recommended doses of methadone, zidovudine, and lamivudine.
Also, there appears to be no interaction with ethanol.
The antiviral effect of abacavir is due to its intracellular anabolite, carbovir-triphosphate, which interferes with HIV viral RNA-dependent DNA polymerase (reverse transcriptase), leading to inhibition of viral replication.
This intracellular anabolite has shown to have a long elimination half-life of greater than 20 hours, allowing for once-daily dosing.
Abacavir is administered as 300 mg twice daily or as 600 mg once daily.
Abacavir is also available as part of several co-formulated tablets.
These different co-formulations are part of nucleoside/nucleotide reverse transcriptase inhibitors (NRTIs) drug combinations.
There are no dosage adjustments recommended in patients with renal impairment, and abacavir is well-tolerated in patients that would benefit from NRTI use with renal pathology from other antiretrovirals.
The recommendation is to dose-adjust in hepatic impairment.
Mild hepatic impairment denoted as Child-Pugh class A is suggested at 200 mg twice daily as an oral solution.
Contraindications to abacavir include moderate to severe hepatic impairment, Child-Pugh class B or C, due to lack of safety evidence.
Common adverse reactions include nausea, headache, fatigue, vomiting, diarrhea, loss of appetite, and trouble sleeping.
Rare but serious side effects include hypersensitivity reaction such as rash, elevated AST and ALT, depression, anxiety, fever/chills, URI, lactic acidosis, hypertriglyceridemia, and lipodystrophy.
People with liver disease should be cautious about using abacavir because it can aggravate the condition. Signs of liver problems include nausea and vomiting, abdominal pain, dark-colored urine, yellowing of the skin, and yellowing of the whites of the eyes.
The use of nucleoside drugs such as abacavir can very rarely cause lactic acidosis.
Signs of lactic acidosis include fast or irregular heartbeat, unusual muscle pain, fatigue, difficulty breathing and stomach pain with nausea and vomiting.
Abacavir can also lead to immune reconstitution inflammatory syndrome, a change in body fat as well as an increased risk of heart attack.
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.
Abacavir is contraindicated for use in infants under three months of age.
Little is known about the effects of Abacavir overdose.
Overdose victims should be taken to a hospital emergency room for treatment.
Some myocardial degeneration has been noticed in rats and mice.
The most commonly reported adverse reactions of at least moderate intensity (incidence ≥10%) in adult HIV-1 clinical trials were nausea, headache, malaise and fatigue, nausea and vomiting, and dreams/sleep disorders.
Serious hypersensitivity reactions have been associated with abacavir which has been strongly linked to the presence of the HLA-B*57:01 allele.
This reaction manifests itself in patients within the first 6 weeks of treatment.
Patients should be tested for the presence of this allele as recommended by the U.S Food and Drug Administration (FDA).
Keep this medication in the container it came in, tightly closed, and out of reach of children.
Store it at room temperature and away from excess heat and moisture (not in the bathroom).
Store liquid medication at room temperature or in the refrigerator.
Do not freeze.
It is important to keep all medication out of sight and reach of children as many containers (such as weekly pill minders and those for eye drops, creams, patches, and inhalers) are not child-resistant and young children can open them easily.
To protect young children from poisoning, always lock safety caps and immediately place the medication in a safe location – one that is up and away and out of their sight and reach.
2-Cyclopentene-1-methanol, 4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)-, (1S,4R)-