Albendazole

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Albendazole
File:Albendazole2DACS.svg
250px
Systematic (IUPAC) name
Methyl [5-(propylthio)-1H-benzoimidazol-2-yl]carbamate
Clinical data
Trade names Albenza
AHFS/Drugs.com monograph
MedlinePlus a610019
Pregnancy
category
  • AU: D
  • US: C (Risk not ruled out)
Legal status
Routes of
administration		 Oral
Pharmacokinetic data
Bioavailability <5%[1]
Protein binding 70%[1]
Metabolism Hepatic[1]
Biological half-life 8-12 hours[1]
Excretion Urine, faeces[1]
Identifiers
CAS Number 54965-21-8 YesY
ATC code P02CA03 (WHO) QP52AC11 (WHO)
PubChem CID: 2082
DrugBank DB00518 YesY
ChemSpider 1998 YesY
UNII F4216019LN YesY
KEGG D00134 YesY
ChEBI CHEBI:16664 YesY
ChEMBL CHEMBL1483 YesY
NIAID ChemDB 007895
Chemical data
Formula C12H15N3O2S
Molecular mass 265.333 g/mol
  • O=C(OC)Nc2nc1ccc(SCCC)cc1n2
  • InChI=1S/C12H15N3O2S/c1-3-6-18-8-4-5-9-10(7-8)14-11(13-9)15-12(16)17-2/h4-5,7H,3,6H2,1-2H3,(H2,13,14,15,16) YesY
  • Key:HXHWSAZORRCQMX-UHFFFAOYSA-N YesY
Physical data
Melting point 208 to 210 °C (406 to 410 °F)
  (verify)

Albendazole, marketed as Albenza among others, is medication used for the treatment of a variety of parasitic worm infestations. It is useful for giardiasis, trichuriasis, filariasis, neurocysticercosis, hydatid disease, pinworm disease, and ascariasis, among others. It is taken by mouth.[2]

Common side effects include nausea, abdominal pains, and headaches. Potentially serious side effects include bone marrow suppression which usually improves on stopping the medication. Liver inflammation has been reported and those with prior liver problems are at greater risk.[2] It is pregnancy category C in the United States and category D in Australia, meaning it may cause harm if taken by a pregnant women.[2][3] Albendazole is a broad-spectrum antihelminthic agent of the benzimidazole type.[2]

Albendazole came into use in 1971.[4] It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system.[5] In many areas of the world the wholesale cost is between 0.01 and 0.06 USD per dose.[6] In the United States, however, it is very expensive as of 2014 at about 50 USD per dose.[2][7]

Medical uses

It is effective first-line of treatment against:

Other uses

File:US Navy 090308-N-0506A-393 Empty bottles of the de-worming medication albendazole are discarded in a box during a Combined Joint Task Force-Horn of Africa medical civil action project.jpg
Discarded bottles of albendazole distributed in Africa

In Africa, albendazole is being used to treat lymphatic filariasis as part of efforts to stop transmission of the disease.[11] In sub-Saharan Africa, albendazole is used in conjunction with ivermectin, and elsewhere in the world, the medicine is used in combination with diethylcarbamazine.[11]

As an antiprotozoal agent, it may be used against giardiasis[2] and microsporidiosis.[12]

Contraindications

Hypersensitivity to the benzimidazole class of compounds contraindicates its use.

Pregnancy class

In Australia, albendazole is assigned class D. Pharmacokinetic studies have shown trace amounts of albendazole appears in semen. Given its potential for teratogenicity, the manufacturers advise the male sexual partner should use adequate protections. It should not be taken when pregnant, and within one month after taking this drug.

Side effects

Albendazole may cause abdominal pain, dizziness, headache, fever, nausea, vomiting, or temporary hair loss.

In rare cases, it may cause persistent sore throat, severe headache, seizures, vision problems, yellowing eyes or skin, dark urine, stomach pain, easy bruising, mental/mood changes, very stiff neck, or changes in amount of urine. Elevation of liver enzymes during treatment is a common side effect, but in rare cases, acute liver failure has been reported. Allergic reactions are also possible.

Rarely, albendazole has been reported to cause marrow suppression, agranulocytosis, or aplastic anemia, which may be permanent.[13] The risk of developing this side effect seems to be increased in patients with liver disease, including echinococcal cysts. Because of this dangerous side effect, it is important to regularly monitor complete blood counts.

Drug interactions

Antiepileptics

The drugs carbamazepine, phenytoin, and phenobarbital lower the plasmatic concentration and the half life of albendazole.[14]

Antacids

The drug cimetidine heightens serum albendazole concentrations, and increases the half life of albendazole.[15] This might be a helpful interaction on more severe cases, because it boosts the potency of albendazole.[16]

Mechanism of action

As a vermicidal, albendazole causes degenerative alterations in the intestinal cells of the worm by binding to the colchicine-sensitive site of tubulin, thus inhibiting its polymerization or assembly into microtubules. The loss of the cytoplasmic microtubules leads to impaired uptake of glucose by the larval and adult stages of the susceptible parasites, and depletes their glycogen stores. Degenerative changes occur in the endoplasmic reticulum, the mitochondria of the germinal layer, and the subsequent release of lysosome.

Metabolism

Albendazole gets oxidized into albendazole sulfoxide (also known as ricobendazole and albendazole oxide (INN), an anthelmintic too[17][18]) with the help of a liver enzyme called albendazole monooxygenase.

Society and culture

Brand names

Brand names include: Albenza,[19] Alworm, Andazol, Eskazole, Noworm, Zentel, Alben-G, ABZ etc.

Cost

In many areas of the world it costs between 0.01 and 0.06 USD per dose.[6] In the United States, however, it is very expensive as of 2014 at about 50 USD per dose.[2][7]

In Raleigh, NC, USA the brand name prescription cost was around $800 USD and $540 USD generic. The pharmaceutical company Amedra raised the price after purchasing the rights to the drug, drawing criticism from patients' rights advocates and US Democratic Party politicians.[20]

In 2013, GlaxoSmithKline donated 763 million albendazole tablets for the treatment and prevention of parasitic infections in developing countries, bringing the total to over 4 billion tablets donated since 1998.[21]

Other animals

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Albendazole has been used as an anthelminthic and for control of flukes in a variety of animal species, including cattle, sheep, goats, swine, camels, dogs, cats, elephants, poultry, and others. In many countries, it is very commonly used for ruminant livestock. It is marketed for this purpose by Zoetis (formerly Pfizer Animal Health) in numerous countries (including the United States and Canada) as Valbazen in oral suspension and paste formulations; by Interchemie in the Netherlands and elsewhere as Albenol-100; by Channelle Animal Health Ltd. in the United Kingdom as Albex; and by Ravensdown in New Zealand (as Albendazole). Although most formulations are administered orally, Ricomax (ricobendazole, or albendazole sulfoxide) is administered by subcutaneous injection.

Labeled usage (with regard to host species, dosage, withdrawal intervals, reproductive or lactational status, etc.) varies among nations. The US label for Valbazen oral suspension provides examples of some considerations in albendazole use in animals: it specifies dosage of 10 mg of albendazole per kg live mass for cattle and goats, and 7.5 mg per kg live mass for sheep. With an albendazole concentration of 113.6 mg/ml in the suspension, these dosages are equivalent to 4 ml and 3 ml of suspension, respectively, per 100 pounds of body weight. Minimum intervals between administration and slaughter for food are 27 days (cattle) and 7 days (sheep and goats). This anthelminthic is not approved for use in female dairy cattle of breeding age or lactating does. The US label indicates albendazole is not to be administered to female cattle during the first 45 days of pregnancy, or for 45 days after removal of bulls; or to ewes or does in the first 30 days of pregnancy, or for 30 days after removal of rams or bucks.

The limitations in early pregnancy are due to a limited period during which teratogenic effects may occur. Summarized research data relating to the durations of these preslaughter and early pregnancy periods when albendazole should not be administered are found in US FDA NADA 110-048 (cattle) and 140-934 (sheep). Some data and inferences regarding goats are found in US FDA Supplemental NADA 110-048 (approved January 24, 2008).

Maximum residue limits (MRLs) for albendazole in food, adopted by the FAO/WHO Codex Alimentarius in 1993, are 5000, 5000, 100, and 100 micrograms per kilogram of body weight (μg/kg) for kidney, liver, fat, and muscle, respectively, and 100 μg/L for milk. For analysis purposes, MRLs of various nations may pertain to concentration of a marker substance which has been correlated with concentrations of the administered substance and its metabolized products. For example, in Canada, the marker substance specified by Health Canada is albendazole-2-aminosulfone, for which the MRL in liver of cattle is 200 μg/kg.

See also

References

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  7. ↑ 7.0 7.1 Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ 8.0 8.1 Lua error in package.lua at line 80: module 'strict' not found.
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  10. ↑ 10.0 10.1 10.2 10.3 10.4 10.5 10.6 Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ 11.0 11.1 Lua error in package.lua at line 80: module 'strict' not found.
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  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  14. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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  18. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  19. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  20. ↑ http://www.slate.com/articles/health_and_science/medical_examiner/2015/09/generic_drug_price_gouging_how_shkreli_and_other_monopolists_cornered_the.html
  21. ↑ Lua error in package.lua at line 80: module 'strict' not found.

External links

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