Albendazole

Base Information

• Chemical Name: Albendazole
• CAS No.: 54965-21-8
• Molecular Formula: C12H15N3O2S
• Molecular Weight: 265.336
• Hs Code.: PRICE
• European Community (EC) Number: 259-414-7
• NSC Number: 758644,220008
• UNII: F4216019LN
• DSSTox Substance ID: DTXSID0022563
• Nikkaji Number: J11.391C
• Wikipedia: Albendazole
• Wikidata: Q411629
• NCI Thesaurus Code: C47384
• RXCUI: 430
• Pharos Ligand ID: NBW2M85L4PZW
• Metabolomics Workbench ID: 42859
• ChEMBL ID: CHEMBL1483
• Mol file: 54965-21-8.mol

Synonyms:Albendazole;Albendazole Monohydrochloride;Albendoral;Albenza;Andazol;Bendapar;Bilutac;Digezanol;Disthelm;Endoplus;Eskazole;Gascop;Lurdex;Mediamix V Disthelm;Metiazol;Monohydrochloride, Albendazole;SK and F 62979;SK and F-62979;SK and F62979;SKF 62979;SKF-62979;SKF62979;Valbazen;Zentel

Chemical Property of Albendazole

Chemical Property:

• Appearance/Colour: Colourless crystalline solid
• Melting Point: 208-210 °C
• Refractive Index: 1.634
• PKA: 10.72±0.10(Predicted)
• PSA: 92.31000
• Density: 1.3 g/cm³
• LogP: 3.31630
• 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).
• Water Solubility.: 0.75mg/L(209 oC)
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 265.08849790
• Heavy Atom Count: 18
• Complexity: 291

Purity/Quality:

95% up, ^*data from raw suppliers

Albendazole ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T,Xn
• Statements: 61-36/37/38-48/22-63-33
• Safety Statements: 53-45-37/39-26-36/37-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Anthelmintic Agents
• Canonical SMILES: CCCSC1=CC2=C(C=C1)N=C(N2)NC(=O)OC
• Recent ClinicalTrials: Safety of a Single Dose of Moxidectin Compared With Ivermectin in Individuals Living in Onchocerciasis Endemic Areas and in Individuals Living in Onchocerciasis Endemic Areas With High Levels of Lymphatic Filariasis Co-endemicity Receiving Concomitant Albendazole
• Recent EU Clinical Trials: Efficacy of AlbenDazole to inDuce mUcosal healing in Patients with Crohn's disease on anti-TNF monotherapy
• Recent NIPH Clinical Trials: Clinical study about in vitro - in vivo correlation in supersaturation of poorly soluble basic drug
• description: Albendazole (ALBENZA) is an orally administered broad-spectrum anthelmintic. Albendazole chewable tablet is included in the World Health Organization (WHO) list of essential medicines as an intestinal anthelminthic and antifilarial medicine. Albendazole tablet was developed by SmithKline Animal Health Laboratories and approved by U.S. Food and Drug Administration (FDA) in 1996.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.
• 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. 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.
• Uses: Albendazole is a drug used to treat infections caused by parasites. It can be given to treat a rare brain infection (neurocysticercosis) or it can be given to treat a parasitic infection that causes important diarrhea (microsporidiosis). Albendazole is a derivative of benzimidazole, is a drug with a broad antihelmintic spectrum. It exhibits an antihelmintic effect against sensitive cestodes and nematodes by blocking the process of glucose uptake by the parasites, which is expressed in the depletion of glycogen reserves and subsequent reduction in the level of adenosintriphophate. As a result, the parasite stops moving and dies. It is used upon infection of Acaris lumbricoides, Ancylostoma duodenale, Necator americanus, Enterobius vermicularis, and Trichuris trichiura. Synonyms of this drug are SKF 62979 and others.
• Therapeutic Function: Anthelmintic
• 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. It is widely used 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. It also is effective in treating cerebral and spinal neurocysticercosis, particularly when given with dexamethasone.Albendazole is recommended for treatment of gnathostomiasis.

Technology Process of Albendazole

There total 34 articles about Albendazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

6-(propylthio)-1H-benzo[d]imidazol-2-amine + methyl chloroformate (79-22-1) → Albendazole (54965-21-8)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 120 ℃; for 0.216667h; Sealed tube; Microwave irradiation;

DOI:10.1055/s-0037-1610843

Reference yield: 74.0%

ricobendazole (54029-12-8,122063-20-1,122063-21-2) → Albendazole (54965-21-8)

Guidance literature:

With aluminum (III) chloride; tetrabutyl-ammonium chloride; aluminium; In 1,2-dichloro-ethane; at 20 ℃; for 6h; Electrolysis; Inert atmosphere; Green chemistry;

DOI:10.1039/d1gc00591j

Reference yield: 65.1%

4-(propylthio)-1,2-phenylenediamine (66608-52-4) + O-methyl-N-(methoxycarbonyl)-isourea (40943-37-1) → Albendazole (54965-21-8)

Guidance literature:

With ethylenediaminetetraacetic acid; acetic acid; In methanol; at 110 ℃; for 5h; Inert atmosphere; Reflux;

upstream raw materials:

1,3-Dicarbomethoxy-S-methylisothiourea

4-(propylthio)-1,2-phenylenediamine

1,3-dihydro-5-n-propylthio-2H-benzimidazole-2-spirocyclohexane

CYANAMID

Downstream raw materials:

albendazole sulfone

5-(propylthio)-1H-benzimidazol-2-ylamine

Refernces

• 1、 Kong, Zhenshuo,Pan, Chao,Li, Ming,Wen, Lirong,Guo, Weisi. "Scalable electrochemical reduction of sulfoxides to sulfides". supporting information. p. 2773 - 2777. Retrieved 2021/04/21.
• 2、 Acosta-Guzmán, Paola,Mahecha-Mahecha, Camilo,Gamba-Sánchez, Diego. "Electrophilic Chlorine from Chlorosulfonium Salts: A Highly Chemoselective Reduction of Sulfoxides". supporting information. p. 10348 - 10354. Retrieved 2020/07/13.