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Didanosine

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Drug Approvals

INNs in other languages (French, Latin, and Spanish): Synonyms: BMY-40900; DDI; Didanocin; Didanosiini; Didanosin; Didanosina; Didanosinum; Didanozinas; Dideoxyinosine; NSC-612049; ddI; ddIno BAN: Didanosine USAN: Didanosine INN: Didanosine [rINN (en)] INN: Didanosina [rINN (es)] INN: Didanosine [rINN (fr)] INN: Didanosinum [rINN (la)] INN: Диданозин [rINN (ru)] Chemical name: 2´,3´-Dideoxyinosine Molecular formula: C10H12N4O3 =236.2 CAS: 69655-05-6 ATC code: J05AF02 Read code: y04GM

Pharmacopoeias

In Europe, International, and US.

European Pharmacopoeia, 6th ed. (Didanosine).

A white or almost white, crystalline powder. Sparingly soluble in water; slightly soluble in alcohol and in methyl alcohol; freely soluble in dimethyl sulfoxide.

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The United States Pharmacopeia 31, 2008 (Didanosine).

A white to off-white crystalline powder. Practically insoluble or insoluble in acetone and in methyl alcohol; very soluble in dimethyl sulfoxide. Store at a temperature of 20° to 25°, excursions permitted between 15° and 30°.

Adverse Effects

The most common serious adverse effects of didanosine are peripheral neuropathy and potentially fatal pancreatitis. Other commonly reported adverse effects include abdominal pain, diarrhoea, fatigue, headache, nausea, rash, and vomiting. Abnormal liver function tests may occur and hepatitis or fatal hepatic failure has been reported rarely; fatalities were reported most often in patients taking didanosine with stavudine and hydroxycarbamide. Retinal and optic-nerve changes have been reported in children, particularly in those taking higher than recommended doses; retinal depigmentation has been reported in adult patients. Other adverse effects include alopecia, anaemia, asthenia, dry mouth, fever, flatulence, parotid gland enlargement, leucopenia, hypersensitivity reactions including anaphylaxis, hyperuricaemia, and thrombocytopenia. Lactic acidosis and severe hepatomegaly with steatosis, sometimes fatal, and generally occurring after some months of treatment has been reported. Immune reconstitution syndrome (an inflammatory immune response resulting in clinical deterioration) has been reported during the initial phase of treatment with combination antiretroviral therapy, including didanosine, in HIV-infected patients with severe immune deficiency. Accumulation or redistribution of body fat (lipodystrophy) including central obesity, dorsocervical fat enlargement (buffalo hump), peripheral wasting, facial wasting, breast enlargement, and cushingoid appearance have been seen in patients receiving antiretroviral therapy, including didanosine. Metabolic abnormalities such as hypertriglyceridaemia, hyper-cholesterolaemia, insulin resistance, hyperglycaemia, and hyperlactataemia have also been reported. NRTIs have also been associated with mitochondrial dysfunction such as abnormal behaviour, anaemia, convulsions, hyperlipasaemia, hypertonia, and neutropenia. Elevated creatine phosphokinase, myalgia, myositis, and rarely rhabdomyolysis have been reported, particularly when nucleoside analogues have been given with HIV-protease inhibitors. For further information on adverse effects associated with NRTIs see Zidovudine.

Effects on the blood

In general, haematological abnormalities are less common in patients taking didanosine than in those taking zidovudine. However, there have been reports of thrombocytopenia associated with didanosine.

Effects on the eyes

Retinal lesions with atrophy of the retinal pigment epithelium at the periphery of the retina were reported in 4 children receiving didanosine doses of 270 to 540 mg/m daily.

Effects on the heart

For the possible risk of myocardial infarction in patients taking didanosine, see Effects on the Heart under Adverse Effects of Zidovudine.

Effects on the liver

Fatal fulminant hepatic failure was reported in a patient receiving didanosine. A further 14 cases had been noted by the manufacturer, and elevated liver enzymes have been recorded during clinical studies.

Effects on mental state

Recurrent mania associated with didanosine treatment has been reported in a patient.

Effects on metabolism

Hyperuricaemia has been reported to be a common adverse effect during clinical studies of didanosine. Hypokalaemia occurred during didanosine therapy in 3 patients, 2 of whom had diarrhoea. There has also been a report of hypertriglyceridaemia occurring on 2 occasions in a patient given didanosine; it was suggested that this hyperhpidaemic effect might be a possible aetiological factor in the development of pancreatitis.

Effects on the mouth

Xerostomia (dry mouth) may be a troublesome effect in patients receiving didanosine.

Effects on the nervous system

Peripheral neuropathy is a well recognised adverse effect of didanosine and has been the subj ect of a review.

Effects on the pancreas

Pancreatitis is recognised as being the most serious adverse effect of didanosine and can be fatal. It appears to be dose-related, occurring in up to 13% of patients receiving 750 mg of didanosine daily. Pancreatitis can resolve if didanosine is withdrawn and cautious reintroduction of didanosine has been possible in some patients. Raised amylase concentrations and glucose intolerance have been reported in patients who subsequently developed pancreatitis.

Effects on the skin

Didanosine has been implicated in a case of Stevens-Johnson syndrome and of cutaneous vasculitis.

Precautions

Didanosine should be used with extreme caution in patients with a history of pancreatitis and those with increased triglyceride concentrations should be observed carefully for signs of pancreatitis and treatment with didanosine interrupted in all patients with signs and symptoms of possible pancreatitis, until it has been excluded. Use with other drags likely to cause pancreatitis or peripheral neuropathy (see Interactions, below) should preferably be avoided; treatment with didanosine should be suspended if possible when use of such drags is essential. It may be necessary to interrupt didanosine treatment in patients who develop peripheral neuropathy; on recovery from peripheral neuropathy a reduced dose may be tolerated. Treatment should also be interrupted if uric acid concentrations are elevated. Patients co-infected with chronic hepatitis B or C and treated with combination antiretroviral therapy are at increased risk for severe and potentially fatal hepatic adverse events. Didanosine should be given with caution to patients with hepatomegaly or other risk factors for liver disease and patients with renal or hepatic impairment; dosage reduction may be necessary. Regular checks of liver function are recommended. If liver enzymes increase to 5 times the upper limit of normal during treatment then didanosine should be stopped. Treatment with didanosine may be associated with lactic acidosis and should also be stopped if there is a rapid increase in aminotransferase concentrations, progressive hepatomegaly, steatosis, or metabolic or lactic acidosis of unknown aetiology. Children should be monitored for retinal lesions and didanosine withdrawn if they occur. Monitoring should also be considered in adults.

Interactions

Use of didanosine with other drags known to cause pancreatitis (for example intravenous pentamidine) or with drags that may cause peripheral neuropathy (for example metronidazole, isoniazid, and vincristine) should be avoided. If co-administration is unavoidable, patients should be monitored carefully for these adverse effects. An increase in the area under the plasma concentration-time curve for didanosine has been reported when allopurinol or other xanthine oxidase inhibitors are given concurrently. Plasma concentrations of didanosine may be reduced by methadone and increased by ganciclovir. Didanosine formulations (chewable or dispersible preparation) contain an antacid and other drags that could be affected by an increased gastric pH (for example HIV-protease inhibitors, ketoconazole, fluoroquinolone antibacterials, and dapsone) should be given at least 2 hours before didanosine. Didanosine preparations containing magnesium or aluminium antacids should not be given with tetracyclines. Use of didanosine with tenofovir results in increased plasma concentrations of didanosine and consequently an increased risk of didanosine-related adverse effects such as peripheral neuropathy, pancreatitis, and lactic acidosis. Fatalities have been reported. There have also been reports of virological failure and emergence of resistance at an early stage of treatment when didanosine and tenofovir were given with lamivudine as part of a once daily triple nucleoside regimen. UK licensed product information for both didanosine and tenofovir does not recommend co-administration of these drags either at standard or reduced doses of didanosine. A 250 mg daily dose of didanosine had been evaluated, but resulted in virological failure and the emergence of resistance. US product information for didanosine, however, recommends that co-administration may be undertaken with caution in patients with normal renal function. For patients weighing greater than 60 kg the dose of didanosine should be reduced to 250 mg daily, while for those weighing less than 60 kg a dose of 200 mg daily is recommended. US product information for tenofovir advises against using didanosine with tenofovir in patients under 60 kg due to a lack of data. Ribavirin has been shown in vitro to increase the intra-cellular triphosphate levels of didanosine and to potentially increase the risk of adverse effects related to didanosine. UK product information for didanosine recommends that co-administration be undertaken with caution, while the US information does not recommend use of the two drags together. See also below for interactions with antivirals.

Antidiabetics

Fatal lactic acidosis has been reported in a patient given metformin with didanosine, stavudine, and tenofovir.

Antivirals

Plasma concentrations of didanosine are roughly doubled when given ganciclovir Valganciclovir, the prodrug of ganciclovir, inhibits purine nucleoside phosphorylase and increases didanosine concentrations. Significant CD4+ T lymphocyte count decline and symptoms of didanosine toxicity, despite complete viral suppression, occurred in an HIV-positive patient given an antiretroviral regimen containing didanosine plus valganciclovir for the treatment of CMV enteritis. Complete CD4+ count recovery and resolution of symptoms occurred when didanosine was replaced with abacavir. Changes in the pharmacokinetics of didanosine and zidovudine have occurred when these drugs are given together, but results of studies have not been consistent, and the effects have generally been of limited clinical significance. For further details, see under Interactions in Zidovudine. Tenofovir has been reported to significantly increase plasma concentrations of didanosine, and may increase the risk of pancreatitis associated with didanosine. There has also been a report of acute renal failure and fatal lactic acidosis when tenofovir was added to a regimen containing didanosine. Use of didanosine with delavirdine resulted in reductions in the area under the concentration-time curve for both drugs in a single-dose study Licensed product information for delavirdine recommends that these two drugs should be given at least 1 hour apart. Absorption of some HIV-protease inhibitors may be reduced by the buffers in some didanosine formulations and doses should be at least 2 hours apart.

Antiviral Action

Didanosine is converted intracellularly to its active form dideoxyadenosine triphosphate. This triphosphate halts the DNA synthesis of retrovirases, including HIV, through competitive inhibition of reverse transcriptase and incorporation into viral DNA. Didanosine-resistant strains of HIV emerge during didanosine therapy. Cross-resistance to other nucleoside reverse transcriptase inhibitors has been recognised.

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Resistance

Evidence for the development of didanosine-resistant HIV was reported in 36 of 64 patients with advanced HIV infection within 24 weeks of switching from zidovudine to didanosine monofherapy. Patients with the didanosine resistance mutation for HIV reverse transcriptase showed a greater decline in CD4+ T cell count and increase in viral burden than those without. Multiple-drug resistant mutations have been found in patients taking long-term combination antiretroviral therapy containing didanosine.

Pharmacokinetics

Didanosine is rapidly hydrolysed in the acid medium of the stomach and is therefore given orally with pH buffers or antacids. Bioavailability is reported to range from 20 to 40% depending on the formulation used; the bioavailability is substantially reduced if taken with or after food. Maximum plasma concentrations are achieved about 1 hour after oral dosage. Binding to plasma proteins is reported to be less than 5%. Didanosine has been reported not to cross the blood brain barrier. Didanosine is metabolised intracellularly to the active antiviral metabolite dideoxyadenosine triphosphate. The plasma elimination half-life is reported to be about 1.5 hours. Renal clearance is by glomeralar filtration and active tubular secretion; about 20% of an oral dose is recovered in the urine. Didanosine is partially cleared by haemodialysis but not by peritoneal dialysis. Pregnancy Fetal blood concentrations of 14 and 19% of the maternal serum-didanosine concentrations have been reported. There is evidence of extensive metabolism in the placenta.

Uses and Administration

Didanosine is a nucleoside reverse transcriptase inhibitor structurally related to inosine with antiviral activity against HIV-1. It is used in the treatment of HIV infection and AIDS. Viral resistance emerges rapidly when didanosine is used alone, and it is therefore used with other antiretrovirals. Didanosine is given orally, usually as buffered chewable/dispersible tablets or enteric-coated capsules. Doses should be taken at least 30 minutes before, or 2 hours after, a meal. The total daily dose may be given as either a single dose or as two divided doses, the choice being dependent upon both the formulation and the strength used. For adults weighing more than 60 kg the recommended dose is 400 mg daily and for those under 60 kg, 250 mg daily is given. For details of doses in children, see below. Doses of didanosine may need to be amended when given with some other antiretrovirals. For further details see under Interactions, above. Dosage reduction may be necessary in patients with renal (see below) or hepatic impairment, although no specific dose reductions are recommended in patients with hepatic impairment and close monitoring is required.

Administration in children

For the treatment of HIV infection in children, didanosine is given daily with other antiretroviral drugs in doses based on body-surface. Doses are taken on an empty stomach. In the USA an oral solution is available for paediatric use:

  • in children aged between 2 weeks and 8 months the recommended dose is 100 mg/m twice daily
  • in children over 8 months of age the recommended dose is 120 mg/m twice daily

In the UK chewable or dispersible tablets or enteric-coated capsules are available for use:

  • the chewable or dispersible tablets may be given orally to children older than 3 months of age, as either a single dose or as two divided doses, in a dose of 240 mg/m daily or 180 mg/m daily if given with zidovudine
  • enteric-coated capsules may be given orally to children older than 6 years of age in a dose of 240 mg/m daily or 180 mg/m daily if given with zidovudine

Administration in renal impairment

Dosage of didanosine should be reduced in patients with renal impairment. The following doses are recommended based on the patient's creatinine clearance (CC):

Adults greater than 60 kg:

  • CC more than 60 mL/minute: usual adult doses
  • CC 30 to 59 mL/minute: 200 mg daily as a single dose or in two equally divided doses
  • CC 10 to 29 mL/minute: 150 mg once daily
  • CC less than 10 mL/minute: 100 mg once daily

Adults less than 60 kg:

  • CC more than 60 mL/minute: usual adult doses
  • CC 30 to 59 mL/minute: 150 mg daily as a single dose or in two equally divided doses
  • CC 10 to 29 mL/minute: 100 mg once daily
  • CC less than 10 mL/minute: 75 mg once daily

Preparations

The United States Pharmacopeia 31, 2008:

Didanosine for Oral Solution; Didanosine Tablets for Oral Suspension.

Proprietary Preparations

Argentina: Aso DDI; Bandotan; Dibistic; Megavir ; Ronvir ; Videx; Australia: Videx; Austria: Videx; Belgium: Videx; Brazil: Didanox; Videx; Canada: Videx; Chile: Videx; Czech Republic: Videx; Denmark: Videx; Finland: Videx; France: Videx; Germany: Videx; Greece: Videx; Hong Kong: Videx; Hungary: Videx; India: Dinex; Ireland: Videx; Israel: Videxf; Italy: Videx; Malaysia: Videx; Mexico: Apodasil; Didasten; Videx; Norway: Videx; New Zealand: Videx; Poland: Videx; Portugal: Videx; Russia: Videx; South Africa: Videx; Singapore; Videx; Spain: Videx; Sweden: Videx; Switzerland: Videx; Thailand: Videx; Turkey: Videx; UK: Videx; USA: Videx; Venezuela: Videx

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