ChemicalBook
Chinese Japanese Germany Korea

Albendazole

Pharmacology and mechanism of action Indications Side effects Contraindications and precautions Preparations Product description Solubility Pharmacodynamics Usage and dosage Chemical Properties Uses Production method References
Albendazole
Albendazole structure
CAS No.
54965-21-8
Chemical Name:
Albendazole
Synonyms
ALBEN;ZEBEN;Monil;ZENTAL;ZENTEL;Atasol;Bruzol;ALBENZA;Bilutac;S-oxide
CBNumber:
CB0241320
Molecular Formula:
C12H15N3O2S
Formula Weight:
265.33
MOL File:
54965-21-8.mol

Albendazole Properties

Melting point:
208-210 °C
Density 
1.2561 (rough estimate)
refractive index 
1.6740 (estimate)
storage temp. 
0-6°C
solubility 
Practically insoluble in water, freely soluble in anhydrous formic acid, very slightly soluble in methylene chloride, practically insoluble in ethanol (96 per cent).
form 
neat
Merck 
14,210
InChIKey
HXHWSAZORRCQMX-UHFFFAOYSA-N
CAS DataBase Reference
54965-21-8(CAS DataBase Reference)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS07,GHS08
Signal word  Warning
Hazard statements  H302-H361-H373-H312+H332-H360
Precautionary statements  P201-P202-P261-P271-P302+P352+P312+P362+P364-P304+P340+P312-P308+P313-P405-P501-P301+P312a-P501a-P281-P260-P280
Hazard Codes  T,Xn
Risk Statements  61-36/37/38-48/22-63-33
Safety Statements  53-45-37/39-26-36/37-24/25
WGK Germany  2
RTECS  FD1100000
HS Code  29332990

Albendazole price More Price(13)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich A4673 Albendazole analytical standard, ≥98% 54965-21-8 10g $64.4 2018-11-20 Buy
Sigma-Aldrich 1012553 Albendazole United States Pharmacopeia (USP) Reference Standard 54965-21-8 200mg $352.8 2018-11-20 Buy
TCI Chemical A1943 Albendazole >98.0%(N) 54965-21-8 5g $30 2018-11-22 Buy
TCI Chemical A1943 Albendazole >98.0%(N) 54965-21-8 25g $88 2018-11-22 Buy
Alfa Aesar H25925 Albendazole, 98+% 54965-21-8 10g $59.2 2018-11-13 Buy

Albendazole Chemical Properties,Uses,Production

Pharmacology and mechanism of action

Albendazole is a benzimidazole carbamate derivative which is structurally related to mebendazole. It was originally introduced as a veterinary drug in 1975 and later as a human anthelminthic drug. It has a wide spectrum of activity against intestinal nematodes (hook worm, Ascaris lumbricoides, Enterobius vermicularis, Strongyloides stercoralis, Trichuris trichiura and Capillaria philippinensis), systemic nematodes (Trichinella spiralis and cutaneous larva migrans) and cestodes (Echinococcus granulosis, E. multilocularis and neurocysticercosis) [1]. Albendazole is active against both larval and adult stages of intestinal nematodes and ovicidal against Ascaris lumbricoides and Trichuris trichiura [1]. Its main metabolite, albendazole sulphoxide, may largely be responsible for the pharmacological effects of the drug.
The mechanism of action of albendazole is similar to that of other benzimidazoles (see mebendazole).
 

Indications

Single or mixed infections caused by Ascaris lumbricoides, Enterobius vermicularis, Ancylostoma duodenale, Trichuris trichiura. Albendazole may be effective against cutaneous larva migrans and Strongyloides stercoralis, but controlled studies are needed to confirm its advantage over thiabendazole. Limited data indicate that albendazole is useful in neurocysticercosis [2,3]. Albendazole seems to be the drug of choice for the treatment of inoperable hydatid cases, but its long term benefit needs further assessment.
 

Side effects

After a single dose treatment of albendazole 400 mg, minor and transient side effects such as epigastric pain and diarrhoea were seen. Less than 6% of treated patients experience these effects [4]. During the treatment of hydatid disease, where higher doses are used for longer time periods, side effects were more common and severe. In two randomized double-blind multicentre phase I and II studies [5,6] involving 139 patients given high doses of the drug, about 20% of the patients showed side effects. These included elevation of serum transaminases (6 patients), leucopenia (3 patients), gastrointestinal symptoms (8 patients), severe headache (4 patients), loss of hair (3 patients), urticaria and itching (2 patients), fever and fatigue (1 patient), and thrombocytopenia (1 patient).

Contraindications and precautions

There are no known contraindications to the drug during single dose treatment of intestinal nematodes. During treatment against hydatid disease, liver transaminases, leukocyte and platelet counts must be monitored regularly.
 

Preparations

• Zentel® (SmithKline Beecham). Tablets 400 mg. Suspension 2%.
• Eskazole® (SmithKline Beecham). Tablets 400 mg.
 

Product description

Albendazole is studied and developed by the company SmithKline Beecham (GSK's predecessor). It is a kind of broad spectrum thiabendazole class anthelmintics which can be applied by both human and animal. It can inhibit the parasite growth and reproduction by inhibiting the intestinal and absorbing the intracellular protein, resulting in the failure of parasite in sugar uptake which is indispensable for their survival, thus causing the endogenous glycogen depletion of insects and further inhibiting fumarate reductase system, preventing the generation of adenosine triphosphate, causing that the parasites are not be able to further survive and reproduce, and ultimately die due to energy depletion. Albendazole has capability of completely killing the eggs of whipworm and hookworm as well as partially killing Ascaris’ eggs; it can also get rid of various kinds of nematodes parasitizing inside animal bodies, and has effects on either getting rid of or directly killing tapeworms and cysticerci. It is thus useful in the treatment of hydatid and the nervous system (cysticercosis) caused by infection of pork worm, and also in the treatment of hookworm, roundworm, pinworm, nematode trichinella, tapeworm, whipworm and stercoralis nematode.
The above information is edited by the chemicalbook of Dai Xiongfeng.

Solubility

It is slightly soluble in acetone or chloroform, but insoluble in water; it is also slightly soluble in hot diluted hydrochloric acid, and soluble in methanol, ethanol, and acetic acid.

Pharmacodynamics

Albendazole is a kind of benzimidazole derivatives. It is rapidly metabolized in vivo into the sulfoxide, sulfone and 2-polyamine sulfone alcohol. It can selectively and irreversibly suppress the glucose uptake of intestinal nematodes, thus resulting in endogenous glycogen depletion of the worm; at the same time, it also inhibit the activity of fumarate reductase, and thus preventing the generation of adenosine triphosphate, finally causing death of the parasites.
Similar as mebendazole, through causing the denaturation of cytoplasmic microtubules of intestinal parasites and binding to the tubulin, it causes clogging of intracellular transport, causing the accumulation of Golgi endocrine particles; cytoplasm is further gradually dissolved, causing the final death of the parasites.
This product can completely kill hookworm eggs, pinworm eggs, spin wool eggs, tapeworm eggs and cysticercosis whip eggs and partially kill Ascaris’ eggs.

Usage and dosage

Roundworm disease and pinworm disease: take 400mg daily per time.
Hookworm disease, whipworm disease, stercoralis disease: take 400mg each time, 2 times a day, continue for 3 days.
Trichinella spirallis disease, take 600mg or 800mg daily in 2 times; a course of treatment is one week.
Neurocysticercosis take daily 18mg/kg in 2 times of oral administration; 10 days is a course of treatment; you can also extend the course to one month according to the specific disease situation.
Hydatid disease: take 20mg/kg daily in 2 times of oral administration with the course being 1 month; it usually needs multiple times of treatment.

Chemical Properties

It is white to light yellow crystalline powder and is odorless. Its melting point is 207-211°C (decomposition). It is slightly soluble in organic solvents but insoluble in water. Rats by oral administration: LD50: 2.4g/kg; sheep by oral administration: LD50:100mg/kg.

Uses

1. It can be used as anthelmintic which is effective in treating both animal gastrointestinal nematodes as well as liver trematode. It can also be supplemented into the feed.
2. It is a kind of efficient broad-spectrum anthelmintic. It is of both broad anti-worm spectrum and highest potency as a kind of benzimidazole derivative drug. It is appropriate for getting rid of roundworm, pinworm, hookworm, and whipworm and for treatment of various types of cysticercosis; it can also be used for getting rid of worm in animal.
3. It can be used to control cabbage downy mildew, rice blast, tobacco powdery mildew, and anthracnose, etc.
4. It is a broad-spectrum anthelmintic. It can be used to get rid of roundworm, pinworm, tapeworm, and whipworm.
5. The product is a high-efficient, broad-spectrum anthelmintic drugs; it has significant efficacy in treating fasciola, tapeworm, and lung & gastrointestinal nematodes. It is one the most potent drugs in benzimidazole derivatives and is listed as the primary choice of drugs in prevention and treatment of livestock and poultry parasitic disease. The product is effective in treating cattle, goat fasciola adults and larvae as well as fasciola gigantic with the worm reduction rate being as high as 90-100%. In recent years, it was found that the product has a strong effect on treating cysticercus bovis. After the treatment, cysticercus number was significantly reduced and the lesions also disappeared. In addition, the product can also be used for preventing parasitic infections, and thus having a good efficacy in promoting the growth of sheep as well as increasing the wool production output.
6. It is a kind of high-efficient and broad-spectrum anthelmintic. It can block the parasites’ absorption on various kinds of nutrition and glucose, resulting in parasite glycogen depletion, and finally causing the failure of the survival and reproduction of the parasite. It can be used to treat single or mixed infection caused by roundworm, pinworm, whipworm, and hookworm.

Production method

1. Take 2-acetamido-4-chloro-nitrobenzene as the starting material, have it react with propyl mercaptan to obtain 2-amino-4-propylthio nitrobenzene which was further converted to 2-amino-4-propylthio aniline undergoing the palladium-charcoal reduction. It is further cyclized with cyanamide methyl formate to obtain albendazole.
2. o-nitroaniline was taken as the starting material; it was first reacted with the sodium thiocyanate to obtain 2-nitro-4-thiocyano aniline and further reacted with bromopropane to generate 2-nitro-4-propylthio aniline which is reduced into 2-amino-propylthio aniline by sodium sulfide; without separation, directly have it be cyclized with cyanamide methyl formate to generate albendazole with the yield being 60%.
3. Take carbendazim as the raw material; have it reacted with sodium sulfocyanide to obtain cyano-benzimidazol-2-carbamate with the yield being 90%; further have reduction reaction, and have it subjected directly to condensation reaction with bromopropane without separation with the yield being 94%. Alternatively, we can also have carbendazim reacted with cyanuric acid to generate 5-sulfonyl chloride-benzimidazol-2-methyl carbamate with a yield of 93%, followed by reduction into 2-mercapto-2-benzimidazole-2-methyl carbamate by iron powder (or zinc powder), and further reaction with bromine propane to obtain the finished product.
4. Sodium sulfide was dissolved in 95% ethanol; add 2-nitro-4-thiocyanate aniline at 50 °C. Stir at 60 °C and cool to 40 °C, pour into bromopropane at once; perform the reaction at 40 °C first and then change to 60 °C for further reaction; add sodium sulfide and have reaction at 80 °C. Distill off the ethanol under reduced pressure, and further add water; Cool and extract with chloroform; the extract was further washed with water; dry; add S-methyl-N, N-bis (methoxycarbonyl) isothiourea and acetic acid for reflux. Distill off the chloroform, add methanol, cool, filtrate, wash with methanol and dry to obtain the crude albendazole product.
5. Under the stirring and ice-cooling, add carbendazim slowly into chlorosulfonic acid carbendazim while keeping the internal temperature at 15~20 °C. After the completion of addition, stir at 40 °C. At below 0 °C, slowly add drop wise of the reaction mixture into the 95% ethanol. The precipitate was collected by filtration and washed with a small amount of ethanol, and dried to obtain the chloro-sulfonated product with a yield of 90.8%. The chloro-sulfonated product was further added into the aqueous solution containing methanoic acid, water and 40% hydrobromic acid together with aluminum metal powder. Stir at 35~40°C first, and then have reaction at 60~65 °C. After cooling and filtration, the filtrate was adjusted with 40% sodium hydroxide to pH value of 3. The precipitate was collected by filtration, washed, and dried to obtain mercapto compound in a yield of 82.5%. The mercapto compound is further added to an aqueous solution of sodium hydroxide, and bleached by activated carbon. Add tetrabutylammonium bromide, and then the methanol solution of bromopropane for reaction at 35~40 °C; cool, filter the precipitate, wash to neutrality and dry to obtain the white crystals of albendazole with the yield being 87.5% and m.p. being 207~209 °C.
In the presence of glacier acetic acid, carbendazim is reacted with sodium thiocyanate; after the introduction of sulfur cyano group, then further use sodium sulfide for reduction, followed by reaction with bromopropane which can also obtain the albendazole.
Albendazole can be refined using the following method: The crude albendazole product (calculated by dry product amount) was stirred together with 85% industrial methanoic cid (1: 3.5) and rose to 60 °C. The complete dissolution of the crude product was followed sequentially by adding sodium dithionate, activated carbon and EDTA. Continue stirring for warming up to 80 °C, keep the temperature, further subject to suction filtration with the filtrate being poured into deionized water while neutralizing with 18% to 20% aqueous ammonia upon stirring until to a Ph value of 6.5; apply suction filtration again and dry to obtain the white product with mp being 206~212 °C and the refinement yield being 93%~94%.

References

1. Rossignol JF, Mausonneuve H (1984). Albendazole: a new concept in the control of intestinal helminthiasis. Gastroenterol Clin Biol, 8, 569–576.
2. Cruz M, Cruz I, Horton J (1991). Albendazole versus praziquantel in the treatment of cerebral cysticercosis: Clinical evaluation. Trans R Soc Trop Med Hyg, 85, 244–247.
3. Takayanagui OM, Jardim E (1992). Therapy of neurocysticercosis. Comparison between albendazole and praziquantel. Arch Neurol, 49, 290–294.
4. Coulaud JP, Rossignol JF (1984). Albendazole: a new single dose anthelminthic. Acta Tropica (Basel), 41, 87–90.
5. Davies A, Dixon H, Pawlowski ZS (1989). Multicentre clinical trials of benzimidazole carbamates in human cystic echinococcosis (phase 2). Bull World Health Organ, 67, 503–508.
6. Davis A, Pawlski ZS, Dixon H (1986). Multicentre clinical trials of benzimidazole-carbamates in human echinococcosis. Bull WHO, 64, 383–388.

Chemical Properties

Colourless Crystalline Solid

Uses

progestogen

Uses

An anthelmintic

Indications

Albendazole appears to cause cytoplasmic microtubular degeneration, which in turn impairs vital cellular processes and leads to parasite death.There is some evidence that the drug also inhibits helminth-specific ATP generation by fumarate reductase.

brand name

Albenza (GlaxoSmithKline).

Antimicrobial activity

Albendazole is active against trichostrongyles and exhibits useful activity against tissue-dwelling larvae of Trichinella spiralis, larvae of animal hookworms (causing cutaneous larva migrans) and microfilariae of various filarial species. It also exhibits some activity against cysticercosis and hydatid stages of Echinococcus granulosus and Echinococcus multilocularis. It has been successfully used in infections with the protozoon Giardia lamblia and for microsporidiosis.

Pharmaceutical Applications

A benzimidazole carbamic acid methyl ester available for oral administration. Insoluble in water, soluble in dimethyl sulfoxide. Stable at room temperature.

Mechanism of action

Albendazole is given orally and is poorly and variably absorbed (5%) because of its poor water solubility. Oral bioavailability is increased as much as five times when the drug is given with a fatty meal instead of on an empty stomach. Concurrent treatment with corticosteroids increases plasma concentrations of albendazole. The drug is rapidly metabolized in the liver to an active sulfoxide metabolite.The half life of the metabolites is 8 to 12 hours.

Pharmacokinetics

Albendazole is better absorbed after oral absorption than other benzimidazole carbamates. It is extensively metabolized to the anthelmintically active albendazole sulfoxide, producing plasma concentrations of the metabolite of about 1.3 mg/L 2–5 h after a 400 mg oral dose. The half-life is about 8 h and the major route of excretion is via the bile. Plasma protein binding of the sulfoxide is around 70%.

Clinical Use

Methyl 5-(propylthio)-2-benzimidazolecarbamate (Eskazole,Zentel) is a broad-spectrum anthelmintic that is not currentlymarketed in North America. It is available from the manufactureron a compassionate use basis. Albendazole is widelyused throughout the world for the treatment of intestinalnematode infection. It is effective as a single-dose treatmentfor ascariasis, New and Old World hookworm infections,and trichuriasis. Multiple-dose therapy with albendazole caneradicate pinworm, threadworm, capillariasis, clonorchiasis,and hydatid disease. The effectiveness of albendazole againsttapeworms (cestodes) is generally more variable and lessimpressive.
Albendazole occurs as a white crystalline powder that isvirtually insoluble in water. The oral absorption of albendazoleis enhanced by a fatty meal. The drug undergoes rapidand extensive first-pass metabolism to the sulfoxide, whichis the active form in plasma. The elimination half-life ofthe sulfoxide ranges from 10 to 15 hours. Considerable biliaryexcretion and enterohepatic recycling of albendazolesulfoxide occurs. Albendazole is generally well toleratedin single-dose therapy for intestinal nematodes. The highdose,prolonged therapy required for clonorchiasis orechinococcal disease therapy can result in adverse effectssuch as bone marrow depression, elevation of hepatic enzymes,and alopecia.

Clinical Use

Albendazole has a broad spectrum of activity against intestinal nematodes and cestodes, as well as the liver flukes Opisthorchis sinensis, Opisthorchis viverrini, and Clonorchis sinensis. It also has been used successfully against Giardia lamblia. Albendazole is an effective treatment of hydatid cyst disease (echinococcosis), especially when accompanied with praziquantel. It also is effective in treating cerebral and spinal neurocysticercosis, particularly when given with dexamethasone.Albendazole is recommended for treatment of gnathostomiasis.

Clinical Use

Intestinal worm infections
Trichinosis (including chronic stage)
Cutaneous larva migrans
Hydatid disease (as an adjunct, or alternative, to surgery)
Neurocysticercosis
Lymphatic filariasis (alone or in combination with ivermectin)
Giardiasis
Microsporidiosis

Side effects

Various mild intestinal and other upsets usually resolve without treatment. With extended use, as for larval tapeworm infections, hepatic abnormalities or leukopenia may require discontinuation of treatment. In rare cases granulocytopenia, pancytopenia, agranulocytosis or thrombocytopenia may occur. It should not be given during pregnancy since it may cause fetal harm; women should be cautioned against becoming pregnant within a month of completing treatment.

Veterinary Drugs and Treatments

Albendazole is labeled for the following endoparasites of cattle (not lactating): Ostertagia ostertagi, Haemonchus spp., Trichostrongylus spp., Nematodius spp., Cooperia spp., Bunostomum phlebotomum, Oesphagostomum spp., Dictacaulus vivaparus (adult and 4th stage larva), Fasciola hepatica (adults), and Moniezia spp.
In sheep, albendazole is approved for treating the following endoparasites: Ostertagia circumcincta, Marshallagia marshalli, Haemonchus contortus, Trichostrongylus spp., Nematodius spp., Cooperia spp., Oesphagostomum spp., Chibertia ovina, Dictacaulus filaria, Fasciola hepatica, Fascioides magna, Moniezia expansa, and Thysanosoma actinoides.
Albendazole is also used (extra-label) in small mammals, goats and swine for endoparasite control.
In cats, albendazole has been used to treat Paragonimus kellicotti infections. In dogs and cats, albendazole has been used to treat capillariasis. In dogs, albendazole has been used to treat Filaroides infections. It has been used for treating giardia infections in small animals, but concerns about bone marrow toxicity have diminished enthusiasm for the drug’s use.

Albendazole Preparation Products And Raw materials

Raw materials

Preparation Products


Albendazole Suppliers

Global( 370)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Hubei xin bonus chemical co. LTD
86-13657291602
027-59338440 sales@guangaobio.com CHINA 23049 58
Shenzhen Sendi Biotechnology Co.Ltd.
0755-23311925 18102838259
0755-23311925 Abel@chembj.com CHINA 3194 55
Henan DaKen Chemical CO.,LTD.
+86-371-55531817
info@dakenchem.com CHINA 21701 58
Beijing Cooperate Pharmaceutical Co.,Ltd.
+86-10-60279497 +86(0)15646567669
+86-10-60279497 sales01@cooperate-pharm.com CHINA 1817 55
Shanghai Bojing Chemical Co.,Ltd.
+86-21-37122233
+86-21-37127788 Candy@bj-chem.com CHINA 493 55
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 20672 55
Mainchem Co., Ltd.
+86-0592-6210733
+86-0592-6210733 sales@mainchem.com CHINA 32447 55
Shanghai Yingrui Biopharma Co., Ltd.
+86-21-33585366 E-mail:sales03@shyrchem.com
+86-21-34979012 sales03@shyrchem.com CHINA 661 60
Hubei XinRunde Chemical Co., Ltd.
+8615102730682; +8618874586545
02783214688 bruce@xrdchem.cn CHINA 535 55
Hefei TNJ Chemical Industry Co.,Ltd.
86-0551-65418684 18949823763
86-0551-65418684 info@tnjchem.com China 1852 55

View Lastest Price from Albendazole manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2019-04-02 Albendazole Manufacturer; In stock GMP Factory
54965-21-8
US $1.00 / KG 1KG High quality manufacturer TOP 3 largest production factory in China Chemwill Asia Co.,Ltd.
2018-08-20 Albendazole
54965-21-8
US $1.00 / KG 1G 98% 100KG career henan chemical co
2019-04-24 Albendazole
54965-21-8
US $10.00 / kg 1kg 99% 5000kg/month Hebei Chisure Biotechnology Co., Ltd.

Albendazole Spectrum


54965-21-8(Albendazole)Related Search:


Copyright 2017 © ChemicalBook. All rights reserved