Related Searches: Albendazole, albendazole sulfoxide

Albendazole(CAS No. 54965-21-8)

Albendazole C12H15N3O2S (cas 54965-21-8) Molecular Structure

54965-21-8 Structure

Identification and Related Records

【Name】
Albendazole
【Iupac name】
methyl N-(6-propylsulfanyl-1H-benzimidazol-2-yl)carbamate
【CAS Registry number】
54965-21-8
【Synonyms】
Albendazole Bolus/tablet
O-Methyl N-(5-(propylthio)-2-benzimidazolyl)carbamate
Albendazole (CP/USP)
Albenza (TN)
Eskazole
Vermitan
(5-(Propylthio)-1H-benzimidazol-2-yl)carbamic acid methyl ester
Carbamic acid,[5-(propylthio)-1Hbenzimidazol- 2-yl]-,methyl ester
Methyl 5-(propylthio)-2-benzimidazolecarbamate
SKF-62979
Albendazole [USAN:BAN:INN:JAN]
Albendazol [INN-Spanish]
Bilutac
Carbamic acid, [5- (propylthio)-1H-benzimidazol-2-yl]-, methyl ester
Albenza
methyl N-(5-propylsulfanyl-3H-benzoimidazol-2-yl)carbamate
Zental
Albendazole (JAN/USP)
((Propylthio)-5 1H-benzimidazolyl-2) carbamate de methyle [French]
Proftril
[5-(Propythio)-1H-benzimidazol-2-yl]carbamic acid methyl ester
SKF 62979
Prestwick_675
SKandF 62979
Zentel
Albendazole cp2005
【EINECS(EC#)】
259-414-7
【Molecular Formula】
C12H15N3O2S (Products with the same molecular formula)
【Molecular Weight】
265.33
【Inchi】
InChI=1/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)
【Canonical SMILES】
CCCSC1=CC2=C(C=C1)N=C(N2)NC(=O)OC
【MOL File】
54965-21-8.mol

Chemical and Physical Properties

【Appearance】
Colourless crystalline solid
【Density】
1.3 g/cm3
【Melting Point】
208-210℃
【Refractive Index】
1.634
【Solubilities】
Insoluble
【Color/Form】
Colorless crystals
【Stability】
Stable under normal shipping and handling conditions.
【Storage temp】
0-6°C
【Computed Properties】
Molecular Weight:265.3314 [g/mol]
Molecular Formula:C12H15N3O2S
XLogP3:2.9
H-Bond Donor:2
H-Bond Acceptor:3
Rotatable Bond Count:5
Tautomer Count:5
Exact Mass:265.088497
MonoIsotopic Mass:265.088497
Topological Polar Surface Area:92.3
Heavy Atom Count:18
Formal Charge:0
Complexity:291
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:1
Feature 3D Donor Count:2
Feature 3D Hydrophobe Count:1
Feature 3D Ring Count:2
Effective Rotor Count:6
Conformer Sampling RMSD:0.8
CID Conformer Count:26

Safety and Handling

【Hazard Codes】
T:Toxic
【Risk Statements】
R36/37/38;R61
【Safety Statements 】
S26;S37/39;S45;S53
【Safety】
Hazard Codes: ToxicT
Risk Statements: 61-36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
R61:May cause harm to the unborn child.
Safety Statements: 53-45-37/39-26
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S53:Avoid exposure - obtain special instructions before use.
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany 2
RTECS FD1100000
【Formulations/Preparations】
Oral: Tablets, film-coated: 200 mg Albenza, Tiltab ( with povidone), (GlaxoSmithKline).
Trade names: Eskadole, Valbazen.
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl albendazole, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
Oral dosage form new animal drugs. Albendazole suspension. Conditions of use in cattle: Indications for use: Indications for use. For removal and control of the following internal parasites of cattle: Adult liver flukes (Fasciola hepatica); heads and segments of tapeworms (Moniezia benedeni, M. expansa); adult and 4th stage larvae of stomach worms (brown stomach worms including 4th stage inhibited larvae (Ostertagia ostertagi), barberpole worm (Haemonchus contortus, H. placei), small stomach worm (Trichostrongylus axei)); adult and 4th stage larvae of intestinal worms (thread-necked intestinal worm (Nematodirus spathiger, N. helvetianus), small intestinal worm (Cooperia punctata and C. oncophora)); adult stages of intestinal worms (hookworm (Bunostomum phlebotomum), bankrupt worm (Trichostrongylus colubriformis), nodular worm (Oesophagostomum radiatum)); adult and 4th stage larvae of lungworms (Dictyocaulus viviparus). Conditions of use in sheep: For removal and control of the following internal parasites of sheep: Adult liver flukes (Fasciola hepatica, Fascioloides magna); heads and segments of common tapeworms (Moniezia expansa) and fringed tapeworm (Thysanosoma actinioides); adult and fourth stage larvae of stomach worms (brown stomach worm (Ostertagia circumcinta and Marshallagia marshalli), barberpole worm (Haemonchus contortus), small stomach worm (Trichostrongylus axei)); adult and fourth stage larvae of intestinal worms (thread-necked intestinal worm (Nematodirus spathiger and N. filicollis), Cooper's worm (Cooperia oncophora), bankrupt worm (Trichostrongylus colubriformis), nodular worm (Oesophagostomum columbianum), and large-mouth bowel worm (Chabertia ovina)); adult and larval stages of lungworms (Dictyocaulus filaria).
Oral dosage form new animal drugs. Albendazole paste. Conditions of use in cattle: For removal and control of the following internal parasites of cattle: adult liver flukes (Fasciola hepatica); heads and segments of tapeworms (Moniezia benedeni, M. expansa); adult and 4th stage larvae of stomach worms (brown stomach worms including 4th stage inhibited larvae (Ostertagia ostertagi); barberpole worm (Haemonchus contortus, H. placei); small stomach worm (Trichostrongylus axei)); adult and 4th stages larvae of intestinal worms (thread-necked intestinal worm (Nematodirus spathiger, N. helvetianus); small intestinal worm (Cooperia punctata and C. oncophora)); adult stages of intestinal worms (hookworm (Bunostomum phlebotmum); bankrupt worm (Trichostrongylus colubriformis), nodular worm (Oesophagostomum radiatum)); adult and 4th stage larvae of lungworms (Dictyocaulus viviparus).
Tolerances - (1) Cattle. A tolerance is established for albendazole 2-aminosulfone (marker residue) in liver (target tissue) of 0.2 part per million and in muscle of 0.05 part per million. (2) Sheep. A tolerance is established for albendazole 2-aminosulfone (marker residue) in liver (target tissue) of 0.25 part per million and in muscle of 0.05 part per million.
The Generic Animal Drug and Patent Restoration act requires that each sponsor of an approved animal drug must submit to the FDA certain information regarding patents held for the animal drug or its method of use. The Act requires that this information, as well as a list of all animal drug products approved for safety and effectiveness, be made available to the public. Albendazole is included on this list.
【Specification】
Albendazole , its cas register number is 54965-21-8. It also can be called Methyl 5-propylthio-2-benzimidazolecarbamate . It may cause dizziness, headache, fever, nausea, vomiting, or temporary hair loss. It is colourless crystalline solid.
【Octanol/Water Partition Coefficient】
log Kow = 1.27
【Disposal Methods】

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing
/Synthesis:/ 4-chloro-2-nitroaniline is first acetylated with acetic anhydride to give 1-acetamido-4-chloro-2-nitrobenzene. Treatment of this intermediate compound with potassium thiocyanate furnishes the key intermediate 1-acetamido-2-nitro-4-thiocyanatobenzene. Conversion of the thiocyanato group into the required n-propylthio analogue, with a simultaneous conversion of the acetamido group to the free amine, is effected by treating the last intermediate with 1-bromopropane in the presence of a base. Further reduction of the nitro group provides the diamine, which is subsequently ring closed to albendazole.
【Usage】
An anthelmintic

Biomedical Effects and Toxicity

【Pharmacological Action】
- Agents destructive to parasitic worms. They are used therapeutically in the treatment of HELMINTHIASIS in man and animal.
- Agents used to treat tapeworm infestations in man or animals.
- Substances that are destructive to protozoans.
- Agents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES.
【Therapeutic Uses】
Mesh Headings: anthelmintics, anticestodalagents, antiprotozoal agents
Albendazole is a benzimidazole carbamate, used for the treatment of gastrointestinal infestations with roundworms, lungworms and tapeworms and adult flukes of Fasciola hepatica.
Certain microsporidial species that cause intestinal infections in people with AIDS respond partially (Enterocytozoon bieneusi) or completely (Encephalitozoon intestintalis and related Encephalitozoon species) to albendazole; albendazole's sulfoxide metabolite appears to be especially effective against these parasites in vitro.
MEDICATION: Used against nematode infections: Ascaris, Necator, Ancylostoma, Trichuris, Enterobius, and systemic nematodes such as Trichinella spiralis, Gnathostoma spinigerum, and larval Angiostrongylus cantonensis. In addition it is used against the larval stages of the cestodes Echinococcus granulosus and E. multilocularis and for treatment of neurocysticercosis caused by Taenia solium.
MEDICATION (VET): Anthelmintic. Used to treat endoparasites (Ostertagia ostertagi, Haemonchus spp., Trichostrongylus spp., Netatodius spp., Copperia spp., Bunostomum phlebotomum, Oesphagostomum spp., Dictacaulus spp., Fasciola hepatica (adults) and Moniezia spp.) in cattle.
Albendazole is used in the treatment of tissue infections caused by the larval forms of certain cestodes (tapeworms) including neurocysticercosis caused by Cysticercus cellulosae, the larval form of Taenia solium (pork tapeworm). Albendazole also is used for the treatment of hydatid disease caused by the larval form of Echinococcus granulosus (dog tapeworm). Other anthelmintics (usually praziquantel or nitazoxanide) are used for the treatment of intestinal infections caused by adult forms of cestodes.
THERAP CAT: Anthelmintic (Cestodes)
THERAP CAT (VET): Anthelmintic
Mebendazole and albendazole are active against both larval and adult stages of nematodes and are ovicidal for Ascaris and Trichuris. Immobilization and death of susceptible gastrointestinal parasites occur slowly, and their clearance from the gastrointestinal tract may not be complete until a few days after treatment. Albendazole is superior to mebendazole in curing hookworm infections in children and against strongyloidiasis, cystic hydatid disease caused by Echinococcus granulosus, and neurocysticercosis caused by larval forms of Taenia solium. The benzimidazoles probably are active against the intestinal stages of Trichinella spiralis in human beings but probably do no affect the larval stages in tissues While benzimidazoles have antifungal activity, their clinical use against human mycoses is limited. /Benzimidazoles/
Albendazole is highly effective against the migrating forms of dog and cat hookworms that cause cutaneous larval migrans.
Toward controlling lymphatic filariasis, albendazole itself has delayed microfilaricidal activity but only slight macrofilaricidal activity against Wuchereria bancrofti. But a single dose of albendazole given alone with a single dose of either diethylcarbamazine or ivermectin markedly decreases the microfilaremia in W. bancrofti infection for well over a year. By annual dosing for 4 to 6 yr, the strategy is to maintain the microfilaremia at such low levels that transmission cannot occur. The period of therapy is estimated to correspond to the duration of fecundity of adult worms. Albendazole is given with diethylcarbamazine to treat lymphatic filariasis in most parts of the world. However, to avoid serious reactions to dying microfilariae, the albendazole/ivermectin combination should be used in locations where filariasis coexists with either onchocerciasis or loiasis.
Regimens in which albendazole with either ivermectin or diethylcarbamazine are given as single annual doses show great promise for controlling lymphatic filariasis occurring either alone or together with other filarial infections. Such combined therapy has the additional benefit of reducing intestinal roundworm infections in school-aged children.
Albendazole has become the drug of choice for treating cysticercosis and cystic hydatid disease, but is not effective against Fasciola hepatica. Certain microsporidial species that cause intestinal infections in people with AIDS respond partially (Enterocytozoon bieneusi) or completely (Encephalitozoon intestintalis and related Encephalitozoon species) to albendazole; albendazole's sulfoxide metabolite appears to be especially effective against these parasites in vitro. Albendazole also has some efficacy against anaerobic protozoa such as Trichomonas vaginalis and Giardia lamblia.
For treatment of enterobiasis, ascariasis, trichuriasis, and hookworm infections, albendazole is taken as a single oral dose and cure rates for light to moderate Ascaris infections are typically over 97%, although heavy infections may require therapy for 2 to 3 days. Albendazole is the drug of choice for treating people with cystic hydatid disease due to Echinococcus granulosus. While the drug provides only a modest cure rate when used alone, it produces superior results when used before and after either surgery to remove cysts or aspiration/injection of cysts with protoscolicidal agents. While still the best drug available, albendazole appears to be just marginally effective against alveolar echinococcosis caused by E. multilocularis. Albendazole also is the preferred treatment of neurocysticercosis caused by larval forms of Taenia solium. Glucocorticoids usually are given for several days prior to the start of albendazole therapy to reduce the incidence of side effects resulting from inflammatory reactions to dead and dying cysticerci. Such pretreatment also increases plasma levels of albendazole sulfoxide.
Albendazole at 10 to 12 mg/kg/day has been given continuously for 3 to 6 mo without producing serious or irreversible toxicity. Albendazole produces few side effects when used for short-term therapy of gastrointestinal helminthiasis, even in patients with heavy worm burdens.
To estimate the effectiveness of delivering an anthelmintic through a community child health program on the weight gain of preschool children in Uganda a cluster randomized controlled trial in Eastern Uganda was performed. PARTICIPANTS: 48 parishes participating in a new program for child health: 24 offered children an additional service of anthelmintic treatment. The outcome is based on measurements from 27,995 children. INTERVENTION: Treatment of children aged between 1 and 7 years with 400 mg albendazole added to standard services offered during child health days over a three year period. The main outcome measure was weight gain and the provision of periodic anthelmintic treatment as a part of child health services in Uganda resulted in an increase in weight gain of about 10% (166 g per child per year, 95% confidence interval 16 to 316) above expected weight gain when treatments were given twice a year, and an increase of 5% when the treatment was given annually. The authors concluded that Deworming of preschool children in Uganda as part of regularly scheduled health services seems practical and associated with increased weight gain. [Alderman H et al; BMJ 333 (7559): 122 (2006)]
【Biomedical Effects and Toxicity】
Albendazole is variably and erractically absorbed after oral admin; absorption is enhanced by the presence of fatty foods and possibly by bile salts as well. After a 400-mg oral dose, albendazole cannot be detected in plasma, because the drug is rapidly metabolized in the liver and possibly in the intestine as well, to albendazole sulfoxide, which has potent anthelmintic activity. Both the (+) and (-) enantiomers of albendazole sulfoxide are formed, but in human beings the (+) enantiomer reaches much higher peak concn in plasma and is cleared much more slowly than the (-) form. Total sulfoxide attains peak plasma concn of about 300 ng/mL, but with wide interindividual variation. Albendazole sulfoxide is about 70% bound to plasma proteins. It is well distributed into various tissues, including hydatid cysts, where it reaches a concn of about one-fifth that in plasma. Both sulfoxide derivatives are oxidized further to the nonchiral sulfone metabolite of albendazole, which is pharmacologically inactive; this reaction favors the (-) sulfoxide and probably becomes rate limiting in determining the clearance. Albendazole metabolites are excreted mainly in the urine.
Oral bioavailability of albendazole appears to be increased when the drug is administered with a fatty meal; when the drug is administered with meals containing about 40 g of fat, plasma concentrations of albendazole sulfoxide are up to 5 times higher than those observed when the drug is administered to fasting patients
Sheep bearing permanent ruminal and abomasal cannulae were given a single oral dose of 10 mg/kg bw albendazole as a 2.5% formulation. Albendazole was absorbed unchanged from the rumen. Once in the body it was rapidly degraded, and sulfone metabolites were detected in plasma, the former achieving the greater level. All 3 compounds were present in the abomasum. Presumably albendazole was passed through the stomachs while the metabolites were secreted or diffused into this organ. Non-detectable levels of all 3 compounds were reached in plasma and rumen at 96 hr and in abomasum at 120 hr.
The parent compound was virtually undetectable in the plasma of Sprague Dawley males and females given a single gavage dose of 10.6 mg/kg bw albendazole in an aqueous suspension. Rapid metabolism let to the appearance of the sulfoxide and subsequently the sulfone derivatives in plasma. Both metabolites decreased to very low levels at 18 hr. Daily dosing at 10.6 mg/kg bw in males for a period of 10 days resulted in lower plasma levels of sulfoxide and higher levels of the sulfone. Albendazole induces certain hepatic drug-metabolising enzymes, which may be responsible for enhancing the degradation of sulfoxide to sulfone following repeated administration.
Male Charles River CD mice were given a single gavage dose of (14)C-ring labelled albendazole. The dose of 13.2 mg/kg bw was suspended in 1% carboxymethylcellulose. Over a 72 hr period, 20.5% of the administered radioactivity was recovered in the urine. Using TLC and autoradiography it was revealed that the sulfoxide and metabolites accounted for 81% of the label. Low levels of parent drug, the sulfone, and metabolites were also detected.
Steers were given a single oral dose of 7.5 mg/kg bw of an albendazole formulation. Albendazole could not be detected in plasma.
Fenbendazole (FBZ), oxfendazole (fenbendazole sulfoxide, FBZSO), and albendazole (ABZ) were administered orally to donkeys at 10 mg/kg body weight. Blood and fecal samples were collected from 1 to 120 hr post-treatment. The plasma and fecal samples were analyzed by high performance liquid chromatography (HPLC). The parent molecule and its sulfoxide and sulfone (FBZSO(2)) metabolites did not reach detectable concentrations in any plasma samples following FBZ administration. ABZ was also not detected in any plasma samples, but its sulfoxide and sulfone metabolites were detected, demonstrating that ABZ was completely metabolized by first-pass mechanisms in donkeys. Maximum plasma concentrations (C(max)) of FBZSO (0.49 mug/mL) and FBZSO(2) (0.60 ug/mL) were detected at (t(max)) 5.67 and 8.00 hr, respectively, following administration of FBZSO. The area under the curve (AUC) of the sulfone metabolite (10.33 ugh/mL) was significantly higher than that of the parent drug FBZSO (5.17ug/mL). C(max) of albendazole sulfoxide (ABZSO) (0.08 g/mL) and albendazole sulfone (ABZSO(2)) (0.04 ug/mL) were obtained at 5.71 and 8.00 hr, respectively, following ABZ administration. The AUC of the sulfoxide metabolite (0.84 ug/mL) of ABZ was significantly higher than that of the sulfone metabolite (0.50 ug/mL). The highest dry-fecal concentrations of parent molecules were detected at 32, 34 and 30 hr for FBZSO, FBZ and ABZ, respectively. The sulfide metabolite was significantly higher than the parent molecule after FBZSO administration. The parent molecule was predominant in the fecal samples following FBZ administration. After ABZ administration, the parent molecule was significantly metabolized, probably by gastrointestinal microflora, to its sulfoxide metabolite (ABZSO) that showed a similar excretion profile to the parent molecule in the fecal samples. The AUC of the parent FBZ was significantly higher than that of FBZSO and ABZ in faeces. It is concluded that the plasma concentration of FBZSO was significantly higher than that of FBZ and ABZ. Although ABZ is not licensed for use in Equidae, its metabolites presented a greater plasma kinetic profile than FBZ which is licensed for use in horses. A higher metabolic capacity, first-pass effects and lower absorption of benzimidazoles in donkeys decrease bioavailability and efficacy compared to ruminants. [Gokbulut C et al; Vet J 172 (1): 166-72 (2006)] PubMed Abstract
In ruminants, oral doses of albendazole are readily absorbed from the gut (cattle absorb about 50% of oral doses of albendazole). Mice and rats absorb about 20 to 30% of oral doses of albendazole.
Experience from use of albendazole in human medicine shows that oral doses of albendazole are not well absorbed from the human gut: about 1% is absorbed. Thus oral exposure to albendazole would be expected to be less toxic to humans than to laboratory animals or farm animals.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
A base-catalyzed second-order hydrolysis rate constant of 2.6X10-4 L/mole-sec(SRC) was estimated using a structure estimation method(1); this corresponds to half-lives of 840 and 84 years at pH values of 7 and 8, respectively(1). Measured half-lives for the direct photolysis of albendazole in sunlit water at pH 5,7, and 9 are 10, 16, and 6 minutes, respectively, under summer conditions and 50, 80, and 20 minutes, respectively, under winter conditions(2,3).

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