出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2013/09/14 23:41:16」(JST)
Systematic (IUPAC) name | |
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Methyl [5-(propylthio)-1H-benzoimidazol-2-yl]carbamate | |
Clinical data | |
Trade names | Albenza |
AHFS/Drugs.com | monograph |
MedlinePlus | a610019 |
Pregnancy cat. | D |
Legal status | prescription |
Routes | only oral route |
Pharmacokinetic data | |
Metabolism | oxidation of sulfur atom to sulfoxide, the active metabolite |
Half-life | About 8.5 h |
Identifiers | |
CAS number | 54965-21-8 Y |
ATC code | P02CA03 QP52AC11 |
PubChem | CID 2082 |
DrugBank | DB00518 |
ChemSpider | 1998 Y |
UNII | F4216019LN Y |
KEGG | D00134 Y |
ChEBI | CHEBI:16664 Y |
ChEMBL | CHEMBL1483 Y |
NIAID ChemDB | 007895 |
Chemical data | |
Formula | C12H15N3O2S |
Mol. mass | 265.333 g/mol |
SMILES
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InChI
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Y (what is this?) (verify) |
Albendazole, marketed as Albenza (United States), Eskazole, Zentel, Andazol and Alworm, is a benzimidazole drug used for the treatment of a variety of parasitic 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 Amedra Pharmaceuticals. Albendazole was first discovered at the SmithKline Animal Health Laboratories in 1972. It is a broad spectrum anthelmintic, effective against roundworms, tapeworms, and flukes of domestic animals and humans.[1]
Albendazole is a WHO Essential Medicine.
It is effective first line of treatment against:
In Africa, albendazole is being used to treat lymphatic filariasis as part of efforts to stop transmission of the disease.[3] In sub-Saharan Africa, albendazole is used in conjunction with ivermectin, and elsewhere in the world, the medicine is used in combination with diethylcarbamazine.[3]
In Brazil and other countries it is used against giardiasis.[4]
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 trichinosis.
Albendazole is only given orally (PO).
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.
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.
Single dose of 400 mg. For Filariasis, note that Albendazole has no effect on the adult worms (Lymphatic filariasis and onchocerciasis Mark J Taylor, Achim Hoerauf, Moses Bockarie, 2010, Lancet). Filariasis, albendazole and/or disintegrating filariae can affect the lymphatic system.
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, change in amount of urine. Elevation of liver enzymes during treatment is a common side effect, but in rare cases there have also been reports of acute liver failure. Allergic reactions are also possible.
Rarely Albendazole has been reported to cause marrow suppression, agranulocytosis or aplastic anemia which may be permanent.[5] 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.
The drugs carbamazepine, phenytoin and phenobarbital lower the plasmatic concentration and the half life of albendazole.[6]
The drug cimetidine heightens serum albendazole concentrations, and increases the half life of albendazole.[7]
This might be a helpful interaction on more severe cases, because it boosts the potency of albendazole.[8]
Hypersensitivity to the benzimidazole class of compounds.
D (Australia) - Do not take when pregnant, and do not become pregnant for one month after taking this drug. Pharmacokinetic studies have shown that trace amounts of albendazole appears in semen. Given this potential for teratogenicity, the manufacturers advise that the male sexual partner should also use adequate protection.
Albendazole has been used as an anthelmintic 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. For use in livestock, albendazole is marketed 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; by Ravensdown in New Zealand as Albendazole; etc. 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 livemass for cattle and goats; 7.5 mg per kg livemass 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 anthelmintic is not approved for use in female dairy cattle of breeding age or lactating does . The US label indicates that 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 relating to early pregnancy are due to a limited period during which teratogenic effects may occur. Summarized research data relating to the durations of these pre-slaughter 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).
MRLs (Maximum Residue Limits) for albendazole in food, adopted by the FAO/WHO Codex Alimentarius in 1993, are 5000, 5000, 100 and 100 micrograms/kg for kidney, liver, fat and muscle, respectively, and 100 micrograms/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 micrograms per kg.
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リンク元 | 「蠕虫」「駆虫薬」「包虫症」「アルベンダゾール」 |
蠕虫類 | 病原体名 | 病名 | 感染経路 | 寄生部位 | 症状 | 診断 | 治療 | |
線虫類 | Ancylostoma duodenale | ズビニ鉤虫 | 鈎虫症/十二指腸虫症 | F型幼虫経口感染、経皮 | 空腸上部 | 皮膚炎、若菜病、貧血 | 飽和食塩水浮遊法、遠心沈降法 | pyrantel pamoate、鉄剤 |
Necator americanus | アメリカ鉤虫 | |||||||
Strongyloides stercoralis | 糞線虫 | 糞線虫症 | F型幼虫経皮感染 | 小腸上部 | Loffler症候群 | 糞便塗沫、普通寒天平板培養による R型、F型幼虫の検出 |
thiabendazole, ivermectin | |
Enterobius vermicularis | 蟯虫 | 蟯虫症 | 虫卵経口感染 | 盲腸~大腸 | 夜間の掻痒、不眠、情緒不安定 | 肛囲検査法「柿の種」 | pyrantel pamoate | |
Ascaris lumbricoides | 回虫 | 回虫症 | 虫卵経口感染 | 小腸孵化→門脈→ 肺発育→食道嚥下→小腸 |
Loffler症候群。急性腹痛 | 糞便虫の虫卵の証明 | pyrantel pamoate | |
Toxocara canis | イヌ回虫 | 幼虫移行症 | 生後1-2ヶ月の感染犬の 糞から経口感染 |
なし | 幼虫移行症→失明 | 免疫診断 | 治療法無し? | |
Wuchereria bancrofti | バンクロフト糸状虫 | フィラリア症/糸状虫症 | アカイエカ | リンパ系 | 急性期:リンパ肝炎、リンパ腺炎を伴う熱発作(filarial fever) 慢性期:乳糜尿、リンパ管瘤、陰嚢水腫、象皮病 |
急性期:夜間のmicrofilariaの検出 慢性期:特有の症状を考慮 |
diethylcarbamazine & ivermectin | |
Brugia malayi | マレー糸状虫 | |||||||
Dirofilaria immitis | イヌ糸状虫 | アカイエカ | なし | 幼虫移行症→肺血管閉塞→胸部X線画像銭形陰影 | ||||
Gnathostoma spinigerum | 有棘顎口虫 | 顎口虫症 | ドジョウ、雷魚、ヘビの生食 | 消化管壁貫通→皮下移動による腫瘤や線状皮膚炎 | 移動性腫瘤、皮膚爬行疹 雷魚やドジョウの生殖の問診 免疫血清診断 |
なし | ||
Gnathostoma hispidum | 剛棘顎口虫 | |||||||
Gnathostoma doloresi | ドロレス顎口虫 | |||||||
Gnathostoma nipponicum | 日本顎口虫 | |||||||
Anisakis simplex, larva | アニキサス幼虫 | アニサキス症 (1)胃アニサキス症、 (2)腸アニサキス症、 (3)異所性アニサキス症 |
経口感染 終宿主:クジラ、イルカ。 中間宿主:オキアミ。 待機宿主:サバ、ニシン、アジ、タラなど |
胃や腸 | (1)急激な上腹部痛"胃けいれん" (2)腹痛、急性虫垂炎、イレウス様。劇症型と緩和型がある (3)腹腔内の炎症性肉芽腫 |
胃内視鏡検査 | 内視鏡による虫体摘出 | |
Pseudoterranova decipiens | ||||||||
Trichinella spiralis | 旋毛虫 | 旋毛虫症 | 経口感染 豚肉、クマ肉の生食 |
(1)成虫侵襲期:下痢、腹痛 (2)幼虫筋肉移行期:顔面浮腫、心筋障害など (3)幼虫被嚢期:全身浮腫、衰弱 |
急性期:ステロイド 殺虫:mebendazole | |||
鞭虫症 | 盲腸 | 慢性下痢、腹痛、異食症、貧血 | セロファン重層塗沫法、 ホルマリンエーテル法 |
mebendazole | ||||
Spirurin nematode larva | 旋尾線虫 | 旋尾線虫幼虫 | ホタルイカの生食 | なし | 皮膚爬行疹、イレウス様症状 | 予防:-30℃24時間。 生食には-30℃4日間以上 |
摘出 | |
吸虫類 | Shistosoma japonicum | 日本住血吸虫 | 日本住血吸虫症 | 糞便虫の虫卵→ミラシジウム→ ミヤイリガイ体内でセルカリア→ 人畜の皮膚より浸入→循環系→ 門脈に寄生 |
門脈 | (1)潜伏期:侵入部の掻痒性皮膚炎。肺移行期:咳、発熱 (2)急性期:虫卵の門脈系寄生、産卵。住血吸虫性赤痢。 (3)慢性期:虫卵の肝、脳などの塞栓。肝硬変。脾腫、腹水 |
糞便虫の虫卵の検出。 直腸粘膜層掻爬法、 肝穿刺による組織内虫卵の検出。 補助診断として免疫血清学的検査。 |
praziquantel |
Paragonimus westermani | ウェステルマン肺吸虫 | 肺吸虫症/肺ジストマ症 | 経口感染 淡水産のカニ、イノシシ肉の生食 |
肺 | 痰、咳、胸痛、時に喀血 | 痰や便の虫卵検査、 胸部写真、 断層写真で明らかな虫嚢。 免疫学血清検査 |
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Paragonimus miyazakii | 宮崎肺吸虫 | 肺 | 気胸、胸水貯留、膿胸、好酸球増加 | praziquantel | ||||
Clonorchis sinensis | 肝吸虫 | 肝吸虫症/肝ジストマ症 | 経口感染 虫卵→(マメタニシ:セルカリア)→ セルカリア→(魚:メタセルカリア)→ 摂取→(ヒト:成虫)→虫卵 |
胆管 | 胆汁流出障害による肝障害→肝硬変 | 糞便、胆汁(十二指腸ゾンデ法)。 肝吸虫卵の検出。CT像。エコー検査。 |
praziquantel | |
横川吸虫症 | 淡水魚(アユ、フナ、ウグイ、シラウオ)の生食 | 小腸粘膜 | 下痢、腹痛 | 糞便虫の虫卵 | praziquantel | |||
条虫類 | Taeniarhynchus saginatus | 無鉤条虫 | 腸管条虫症 | 経口感染。中間宿主:ウシ | 小腸 | 無症状。下痢。 広節裂頭条虫感染では悪性貧血。 |
糞便虫の虫卵と体節により診断 | praziquantel。 有鉤条虫の場合はガストログラフィン。 有鉤条虫の駆虫の際、 虫体を破壊しない →虫体の融解による嚢虫症 |
Taenia solium | 有鉤条虫 | 経口感染。中間宿主:ブタ | ||||||
Diphyllobothrium latum | 広節裂頭条虫 | 経口感染。中間宿主:サケ、マス | ||||||
日本海裂頭条虫 | 経口感染。中間宿主:サケ | |||||||
腸管外条虫症 | ||||||||
有鉤嚢虫症 | 有鉤条虫の虫卵の経口摂取 | 皮下、筋肉内 脳、脊髄、眼球 |
皮下、筋肉内:小指頭大の無症状腫瘤 脳、脊髄、眼球:Jacksonてんかん。痙性麻痺など |
皮下の虫嚢 | 外科的摘出。 成虫寄生がなければ、praziquantel, albendazole + ステロイド | |||
Echinococcus granulosus | 単包虫 | 包虫症/ エキノコックス症 (単包虫症) |
終宿主:イヌ、キツネなど。 中間宿主:ヒト、ブタ、野ネズミなど。 終宿主の糞便虫の虫卵を中間宿主が接種して発症 |
肝、肺、まれに脳、腎、筋肉 | 肝寄生:肝部疼痛、満腹、時に黄疸、下肢浮腫 肺寄生:胸部圧迫感、胸痛、咳、血痰、時に喀血 |
肝や肺の嚢胞形成から疑う。 早期に診断に皮内反応→ CT、エコー→ 生検。免疫血清学的診断法 |
外科的切除。 albendazoleの長期投与 | |
Echinococcus multilocularis | 多包虫 | 包虫症/ エキノコックス症 (多包虫症) |
antiplatyhelmintic agents | Antitrematodals (schistosomicides) |
binds tubulin | benzimidazole (Triclabendazole#) |
acetylcholinesterase inhibitor | phosphonic acid (metrifonate) | ||
Other/unknown | quinoline (praziquantel#, oxamniquine#) · phenol (bithionol) · thiazole ([[niridazole]) · arylsulfonate (stibophen) | ||
anticestodals (taeniacides) |
binds tubulin | benzimidazole (albendazole#) | |
Other/unknown | salicylanilide (niclosamide)# · aminoacridine (quinacrine) · butyrophenone (desaspidin) · chlorophenol (dichlorophen) | ||
antinematodal agents (macrofilaricides) |
binds tubulin | benzimidazole (mebendazole#, thiabendazole, albendazole#, fenbendazole, ciclobendazole, flubendazole) | |
chloride channel | macrolide (ivermectin#) | ||
NMDA | tetrahydropyrimidine (pyrantel#, pyrantel pamoate, oxantel) | ||
Other/unknown | piperazine (piperazine · diethylcarbamazine#) · thiazole (levamisole#) · quinolinium (pyrvinium) · benzylammonium (bephenium) · naphthalenesulfonate (suramin#) · tribendimidine |
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