Albendazole
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Albendazole
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| Systematic (IUPAC) name | |
| Methyl [6-(propylthio)-1H-benzoimidazol-2-yl]carbamate | |
| Identifiers | |
| CAS number | |
| ATC code | P02 QP52 |
| PubChem | |
| DrugBank | |
| ChemSpider | |
| Chemical data | |
| Formula | C12H15N3O2S |
| Mol. mass | 265.333 g/mol |
| SMILES | & |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | oxidation of sulfur atom to sulfoxide, the active metabolite |
| Half life | About 8.5 hours |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
D |
| Legal status |
prescription |
| Routes | only oral route |
Albendazole, marketed as Albenza, Eskazole, and Zentel, is a member of the benzimidazole compounds used as a drug indicated for the treatment of a variety of worm infestations. Although this use is widespread in the United States, the U.S. Food and Drug Administration (FDA) has not approved albendazole for this indication. It is marketed by GlaxoSmithKline.
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[edit] Main uses
It is effective (first line of treatment) against:
- Flatworms
- Flukes/trematodes
- Tapeworm/cestodes
- Nematodes
[edit] Other uses
In Africa, albendazole (donated by GlaxoSmithKline) is being used to treat lymphatic filariasis as part of efforts to stop transmission of the disease.[2] In sub-Saharan Africa, albendazole is used in conjunction with ivermectin, and elsewhere in the world, the medicine is used in combination with diethylcarbamazine.[2]
In Brazil and another countries is used against giardiasis[3].
[edit] Mode of action
As a vermicidal, albendazole causes degenerative alterations in the tegument and 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 in the endoplasmic reticulum, the mitochondria of the germinal layer, and the subsequent release of lysosomes result in decreased production of adenosine triphosphate (ATP), which is the energy required for the survival of the helminth. Due to diminished energy production, the parasite is immobilized and eventually dies.
Albendazole also has been shown to inhibit the enzyme fumarate reductase, which is helminth-specific. This action may be considered secondary to the effect on the microtubules due to the decreased absorption of glucose. This action occurs in the presence of reduced amounts of nicotinamide-adenine dinucleotide in reduced form (NADH), which is a coenzyme involved in many cellular oxidation-reduction reactions.
Albendazole has larvicidal effects in necatoriasis and ovicidal effects in ascariasis, ancylostomiasis, and trichuriasis.
[edit] Dosage
Hydatid disease:
- Patients 60 kg or greater: 400 mg twice daily, with meals.
- Patients less than 60 kg: 15 mg/kg/day given in divided doses twice daily with meals (maximum total daily dose 800 mg).
- Treatment interval: 28-day cycle followed by a 14-day albendazole-free interval, for a total of 3 cycles.
NOTE: When administering albendazole in the pre- or post-surgical setting, optimal killing of cyst contents is achieved when 3 courses of therapy have been given.
Neurocysticerosis:
- Patients 60 kg or greater: 400 mg twice daily, with meals.
- Patients less than 60 kg: 15 mg/kg/day given in divided doses twice daily with meals (maximum total daily dose 800 mg).
- Treatment interval: 8-30 days.
Note: Patients being treated for neurocysticercosis should receive appropriate steroid and anticonvulsant therapy as required. Oral or intravenous corticosteroids should be considered to prevent cerebral hypertensive episodes during the first week of treatment.
[edit] Side effects
Albendazole may cause 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, change in amount of urine. Allergic reactions are also possible.
CBC and hepatic functions have to be obtained regulary in patients receiving Albendazole.
[edit] Drug interactions
[edit] Antiepileptics
The drugs Carbamazepine, Phenytoin and Phenobarbital lower the plasmatic concentration and the half life of albendazole.[4]
[edit] Antacids/histamine H2 antagonists
The drug cimetidine heightens serum albendazole concentrations, and increases the half life of albendazole.[5]
This might be a helpful interaction on more severe cases, because it boosts the potency of albendazole.[6]
[edit] Contraindications
Hypersensitivity to the benzimidazole class of compounds.
[edit] Pregnancy class
D (Australia) - Do not take when pregnant, and do not become pregnant for one month after taking this drug.
[edit] See also
[edit] References
- ^ Horton J (April 2003). "Albendazole for the treatment of echinococcosis". Fundam Clin Pharmacol 17 (2): 205–12. doi:. PMID 12667231. http://www3.interscience.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=0767-3981&date=2003&volume=17&issue=2&spage=205.
- ^ a b The Carter Center, "Lymphatic Filariasis Elimination Program", http://www.cartercenter.org/health/lf/index.html, retrieved on 2008-07-17
- ^ See http://www.wjgnet.com/1007-9327/10/1215.pdf
- ^ Lanchote VL, Garcia FS, Dreossi SA, Takayanagui OM (June 2002). "Pharmacokinetic interaction between albendazole sulfoxide enantiomers and antiepileptic drugs in patients with neurocysticercosis". Therapeutic Drug Monitoring 24 (3): 338–45. PMID 12021623. http://meta.wkhealth.com/pt/pt-core/template-journal/lwwgateway/media/landingpage.htm?issn=0163-4356&volume=24&issue=3&spage=338. Retrieved on 2009-06-22.
- ^ Schipper, H.G.; Koopmans, R.P.; Nagy, J.; Butter, J.J.; Kager, P.A.; Van Boxtel, C.J. (2000). "Effect of dose increase or cimetidine co-administration on albendazole bioavailability". The American journal of tropical medicine and hygiene 63 (5): 270–273. http://www.ajtmh.org/cgi/content/abstract/63/5/270. Retrieved on 2009-06-22.
- ^ Wen H, Zhang HW, Muhmut M, Zou PF, New RR, Craig PS (February 1994). "Initial observation on albendazole in combination with cimetidine for the treatment of human cystic echinococcosis". Annals of Tropical Medicine and Parasitology 88 (1): 49–52. PMID 8192515.
[edit] External links
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