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    Chemistry

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    Also known as: 54965-21-8, Albenza, Eskazole, Zentel, Valbazen, Proftril
    Molecular Formula
    C12H15N3O2S
    Molecular Weight
    265.33  g/mol
    InChI Key
    HXHWSAZORRCQMX-UHFFFAOYSA-N
    FDA UNII
    F4216019LN
    Albendazole
    A benzimidazole broad-spectrum anthelmintic structurally related to MEBENDAZOLE that is effective against many diseases. (From Martindale, The Extra Pharmacopoeia, 30th ed, p38)
    Albendazole is an Anthelmintic. The mechanism of action of albendazole is as a Cytochrome P450 1A Inducer.
    1 2D Structure

    Albendazole

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    methyl N-(6-propylsulfanyl-1H-benzimidazol-2-yl)carbamate
    2.1.2 InChI
    InChI=1S/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)
    2.1.3 InChI Key
    HXHWSAZORRCQMX-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCCSC1=CC2=C(C=C1)N=C(N2)NC(=O)OC
    2.2 Other Identifiers
    2.2.1 UNII
    F4216019LN
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Albendazole Monohydrochloride

    2. Albendoral

    3. Albenza

    4. Andazol

    5. Bendapar

    6. Bilutac

    7. Digezanol

    8. Disthelm

    9. Endoplus

    10. Eskazole

    11. Gascop

    12. Lurdex

    13. Mediamix V Disthelm

    14. Metiazol

    15. Monohydrochloride, Albendazole

    16. Sk And F 62979

    17. Sk And F-62979

    18. Sk And F62979

    19. Skf 62979

    20. Skf-62979

    21. Skf62979

    22. Valbazen

    23. Zentel

    2.3.2 Depositor-Supplied Synonyms

    1. 54965-21-8

    2. Albenza

    3. Eskazole

    4. Zentel

    5. Valbazen

    6. Proftril

    7. Albendazolum

    8. Andazol

    9. Sk&f 62979

    10. Methyl 5-(propylthio)-2-benzimidazolecarbamate

    11. Skf 62979

    12. Sk&f-62979

    13. 5-(propylthio)-2-carbomethoxyaminobenzimidazole

    14. Skf-62979

    15. Methyl N-[6-(propylsulfanyl)-1h-1,3-benzodiazol-2-yl]carbamate

    16. Methyl N-(6-propylsulfanyl-1h-benzimidazol-2-yl)carbamate

    17. (5-(propylthio)-1h-benzimidazol-2-yl)carbamic Acid Methyl Ester

    18. O-methyl N-(5-(propylthio)-2-benzimidazolyl)carbamate

    19. Nsc 220008

    20. Carbamic Acid, [5-(propylthio)-1h-benzimidazol-2-yl]-, Methyl Ester

    21. Carbamic Acid, (5-(propylthio)-1h-benzimidazol-2-yl)-, Methyl Ester

    22. Albendazol

    23. Bilutac

    24. Nsc-220008

    25. Chembl1483

    26. Methyl [5-(propylsulfanyl)-1h-benzimidazol-2-yl]carbamate

    27. Methyl [6-(propylsulfanyl)-1h-benzimidazol-2-yl]carbamate

    28. ((propylthio)-5 1h-benzimidazolyl-2) Carbamate De Methyle

    29. Chebi:16664

    30. Zental

    31. F4216019ln

    32. Ncgc00016876-01

    33. Cas-54965-21-8

    34. Dsstox_cid_2563

    35. Dsstox_rid_76632

    36. Dsstox_gsid_22563

    37. Albendazol [inn-spanish]

    38. Albendazolum [inn-latin]

    39. Methyl [5-(propylthio)-1h-benzimidazol-2-yl]carbamate

    40. Methyl 5-(propylthio)-1h-benzo[d]imidazol-2-ylcarbamate

    41. Methyl [5-(propylthio)benzimidazol-2-yl]carbamate

    42. Methyl N-(5-propylsulfanyl-1h-benzimidazol-2-yl)carbamate

    43. Methyl N-[5-(propylsulfanyl)-1h-1,3-benzodiazol-2-yl]carbamate

    44. Methyl (nz)-n-(5-propylsulfanyl-1,3-dihydrobenzimidazol-2-ylidene)carbamate

    45. Albenza (tn)

    46. Hsdb 7444

    47. Einecs 259-414-7

    48. Mfcd00083232

    49. Albendazole (jan/usp/inn)

    50. Zenteltrade Mark

    51. [5-(propylthio)benzimidazol-2-yl]carbamic Acid Methyl Ester

    52. Albenzatrade Mark

    53. Andazoltrade Mark

    54. Unii-f4216019ln

    55. Eskazoletrade Mark

    56. Albendazole,(s)

    57. ((propylthio)-5 1h-benzimidazolyl-2) Carbamate De Methyle [french]

    58. Prestwick_675

    59. Albendazole(albenza)

    60. Albendazole (albenza)

    61. Albendazole [usan:usp:inn:ban:jan]

    62. Spectrum_001532

    63. Cpd000036735

    64. Albendazole [mi]

    65. (5-propylsulfanyl-1h-benzoimidazol-2-yl)-carbamic Acid Methyl Ester

    66. Prestwick0_000247

    67. Prestwick1_000247

    68. Prestwick2_000247

    69. Prestwick3_000247

    70. Spectrum4_000201

    71. Spectrum5_001567

    72. Albendazole [inn]

    73. Albendazole [jan]

    74. Chemdivam_000003

    75. Chemdiv1_000190

    76. Albendazole [hsdb]

    77. Albendazole [usan]

    78. Albendazole [vandf]

    79. Albendazole [mart.]

    80. Oprea1_429292

    81. Oprea1_585016

    82. Oprea1_640007

    83. Schembl44682

    84. Albendazole [usp-rs]

    85. Albendazole [who-dd]

    86. Albendazole [who-ip]

    87. Bspbio_000034

    88. Bspbio_002548

    89. Kbiogr_000801

    90. Kbioss_002012

    91. Mls000069722

    92. Albendazolum [who-ip]

    93. Bidd:gt0615

    94. Divk1c_000704

    95. Spectrum1503903

    96. Methoxy-n-(5-propylthiobenzimidazol-2-yl)carboxamide

    97. Spbio_002253

    98. Bpbio1_000038

    99. Albendazole [green Book]

    100. Dtxsid0022563

    101. Hms502d06

    102. Hms587i14

    103. Hxhwsazorrcqmx-uhfffaoysa-

    104. Kbio1_000704

    105. Kbio2_002012

    106. Kbio2_004580

    107. Kbio2_007148

    108. Albendazole [orange Book]

    109. Ninds_000704

    110. Albendazole [ep Monograph]

    111. Hms1568b16

    112. Hms1922k04

    113. Hms2090g19

    114. Hms2093k13

    115. Hms2095b16

    116. Hms2231o03

    117. Hms3259b05

    118. Hms3369c03

    119. Hms3651c15

    120. Hms3712b16

    121. Pharmakon1600-01503903

    122. Albendazole [usp Monograph]

    123. [5-(propythio)-1h-benzimidazol-2-yl]carbamic Acid Methyl Ester

    124. Bcp12108

    125. Hy-b0223

    126. Tox21_110659

    127. Tox21_302300

    128. Ac-015

    129. Bbl005883

    130. Bdbm50241293

    131. Ccg-39620

    132. Mfcd01220143

    133. N-[6-(propylthio)-1h-benzimidazol-2-yl]carbamic Acid Methyl Ester

    134. Nsc220008

    135. Nsc758644

    136. S1640

    137. Stk387550

    138. Stl046130

    139. Zinc17146904

    140. Akos000540882

    141. Akos005431684

    142. Akos005699352

    143. Tox21_110659_1

    144. Albendazole 100 Microg/ml In Methanol

    145. Ccg-220247

    146. Db00518

    147. Ks-5159

    148. Nc00615

    149. Nsc-758644

    150. Idi1_000704

    151. Methyl [(2z)-5-(propylsulfanyl)-1,3-dihydro-2h-benzimidazol-2-ylidene]carbamate

    152. Ncgc00016876-02

    153. Ncgc00016876-03

    154. Ncgc00016876-04

    155. Ncgc00016876-05

    156. Ncgc00016876-06

    157. Ncgc00016876-07

    158. Ncgc00016876-08

    159. Ncgc00016876-09

    160. Ncgc00016876-10

    161. Ncgc00016876-12

    162. Ncgc00022896-03

    163. Ncgc00022896-04

    164. Ncgc00022896-05

    165. Ncgc00022896-06

    166. Ncgc00022896-07

    167. Ncgc00022896-08

    168. Ncgc00255250-01

    169. Albendazole, Analytical Standard, >=98%

    170. Smr000036735

    171. Albendazole 100 Microg/ml In Acetonitrile

    172. Sbi-0051849.p002

    173. Db-052669

    174. Ab00052377

    175. Ft-0621945

    176. Sw196830-3

    177. En300-49850

    178. Methyl 5-propylthio-2-benzimidazole Carbamate

    179. Vu0239747-6

    180. Bim-0051849.0001

    181. C01779

    182. D00134

    183. H10782

    184. Ab00052377-13

    185. Ab00052377-14

    186. Ab00052377_15

    187. Ab00052377_16

    188. A830429

    189. Albendazole, Antibiotic For Culture Media Use Only

    190. Q411629

    191. Sr-01000000171

    192. Sr-05000001875

    193. Methyl 5-(propylthio)-1h-benzimidazol-2-ylcarbamate

    194. Q-200603

    195. Q-200604

    196. Sr-01000000171-2

    197. Sr-05000001875-1

    198. Brd-k79131256-001-04-7

    199. Brd-k79131256-001-08-8

    200. Methyl 5-(propylthio)benzimidazol-2-ylcarbamate

    201. Methyl 6-(propylthio)-1h-benzo[d]imidazol-2-ylcarbamate

    202. Z1245635850

    203. 2-[(methoxycarbonyl)amino]-5-propylthio-1h-benzimidazole

    204. Albendazole, European Pharmacopoeia (ep) Reference Standard

    205. Methyl (6-(propylthio)-1h-benzo[d]imidazol-2-yl)carbamate

    206. Methyl 5-(propylsulfanyl)-1h-benzimidazol-2-ylcarbamate #

    207. Albendazole, United States Pharmacopeia (usp) Reference Standard

    208. Methyl N-(5-(propylthio)-1h-benzimidazol-2-yl)carbamate

    209. Albendazole, Pharmaceutical Secondary Standard; Certified Reference Material

    210. Carbamic Acid, N-[5-(propylthio)-1h-benzimidazol-2-yl]-,?methyl Ester

    2.4 Create Date
    2004-09-16
    3 Chemical and Physical Properties
    Molecular Weight 265.33 g/mol
    Molecular Formula C12H15N3O2S
    XLogP32.9
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count5
    Exact Mass265.08849790 g/mol
    Monoisotopic Mass265.08849790 g/mol
    Topological Polar Surface Area92.3 Ų
    Heavy Atom Count18
    Formal Charge0
    Complexity291
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameAlbenza
    PubMed HealthAlbendazole (By mouth)
    Drug ClassesAnthelmintic
    Drug LabelALBENZA (albendazole) is an orally administered broad-spectrum anthelmintic. Chemically, it is methyl 5-(propylthio)-2-benzimidazolecarbamate. Its molecular formula is C12H15N3O2S. Its molecular weight is 265.34. It has the following chemical structu...
    Active IngredientAlbendazole
    Dosage FormTablet
    RouteOral
    Strength200mg
    Market StatusPrescription
    CompanyAmedra Pharms

    2 of 2  
    Drug NameAlbenza
    PubMed HealthAlbendazole (By mouth)
    Drug ClassesAnthelmintic
    Drug LabelALBENZA (albendazole) is an orally administered broad-spectrum anthelmintic. Chemically, it is methyl 5-(propylthio)-2-benzimidazolecarbamate. Its molecular formula is C12H15N3O2S. Its molecular weight is 265.34. It has the following chemical structu...
    Active IngredientAlbendazole
    Dosage FormTablet
    RouteOral
    Strength200mg
    Market StatusPrescription
    CompanyAmedra Pharms

    4.2 Therapeutic Uses

    Mesh Headings: anthelmintics, anticestodalagents, antiprotozoal agents

    National Library of Medicine, SIS; ChemIDplus Record for Albendazole (54965-21-8). Available from, as of April 13, 2006: https://chem.sis.nlm.nih.gov/chemidplus/chemidlite.jsp

    Albendazole is a benzimidazole carbamate, used for the treatment of gastrointestinal infestations with roundworms, lungworms and tapeworms and adult flukes of Fasciola hepatica.

    European Medicines Agency (EMEA), The European Agency for the Evaluation of Medicinal Products, Veterinary Medicines Evaluation Unit, Committee for Veterinary Medicinal Products; Albendazole, Summary Report(3). EMEA/MRL/865/03-Final (June 2004). Available from, as of July 25, 2006: https://www.ema.europa.eu/ema/index.jsp?curl=pages/document_library/landing/document_library_search.jsp&murl=menus/document_library/document_library.jsp&mid

    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.

    Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1126

    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.

    Ullmann's Encyclopedia of Industrial Chemistry. 6th ed.Vol 1: Federal Republic of Germany: Wiley-VCH Verlag GmbH & Co. 2003 to Present, p. V. 3 185 (2003)

    For more Therapeutic Uses (Complete) data for ALBENDAZOLE (21 total), please visit the HSDB record page.

    4.3 Drug Warning

    Leukopenia has occurred in less than 1% of patients receiving albendazole, and rarely, granulocytopenia, pancytopenia, agranulocytosis, or thrombocytopenia have been reported. Therefore, blood counts should be performed at the start of, and every 2 weeks during, each 28-day treatment cycle. The manufacturer states that if decreases in the total leukocyte count occur, treatment with albendazole may be continued if the decreases are modest and do not progress.

    McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 46

    Because albendazole has been associated with mild to moderate increases of hepatic enzymes in about 16% of patients receiving the drug in clinical trials, and may cause hepatotoxicity, liver function tests should be performed prior to each course of albendazole therapy and at least every 2 weeks during treatment with the drug. If clinically important increases in liver function test results occur, albendazole should be discontinued. The drug can be reinstituted when liver enzymes return to pretreatment levels, but laboratory tests should be performed frequently during repeat therapy.

    McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 46

    Albendazole may cause harm to the fetus and should be used during pregnancy only if the benefits justify the risk to the fetus and only in clinical circumstances where no alternative management is appropriate. Women of childbearing age should begin treatment only after a negative pregnancy test, and should be cautioned against becoming pregnant while receiving albendazole or within 1 month of completing treatment with the drug.

    McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 46

    Teratogenic in animals (rats and rabbits) and is not recommended in pregnancy or in infants younger than 2 years.

    Haddad, L.M. (Ed). Clinical Management of Poisoning and Drug Overdose 3rd Edition. Saunders, Philadelphia, PA. 1998., p. 714

    For more Drug Warnings (Complete) data for ALBENDAZOLE (9 total), please visit the HSDB record page.

    4.4 Drug Indication

    For the treatment of parenchymal neurocysticercosis due to active lesions caused by larval forms of the pork tapeworm, Taenia solium and for the treatment of cystic hydatid disease of the liver, lung, and peritoneum, caused by the larval form of the dog tapeworm, Echinococcus granulosus.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Albendazole is a broad-spectrum anthelmintic. The principal mode of action for albendazole is by its inhibitory effect on tubulin polymerization which results in the loss of cytoplasmic microtubules.

    5.2 MeSH Pharmacological Classification

    Anthelmintics

    Agents that kill parasitic worms. They are used therapeutically in the treatment of HELMINTHIASIS in man and animal. (See all compounds classified as Anthelmintics.)

    Anticestodal Agents

    Agents used to treat tapeworm infestations in man or animals. (See all compounds classified as Anticestodal Agents.)

    Tubulin Modulators

    Agents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES. (See all compounds classified as Tubulin Modulators.)

    Antiprotozoal Agents

    Substances that are destructive to protozoans. (See all compounds classified as Antiprotozoal Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    ALBENDAZOLE
    5.3.2 FDA UNII
    F4216019LN
    5.3.3 Pharmacological Classes
    Cytochrome P450 1A Inducers [MoA]; Anthelmintic [EPC]
    5.4 ATC Code

    P - Antiparasitic products, insecticides and repellents

    P02 - Anthelmintics

    P02C - Antinematodal agents

    P02CA - Benzimidazole derivatives

    P02CA03 - Albendazole

    5.5 Absorption, Distribution and Excretion

    Absorption

    Poorly absorbed from the gastrointestinal tract due to its low aqueous solubility. Oral bioavailability appears to be enhanced when coadministered with a fatty meal (estimated fat content 40 g)

    Route of Elimination

    Albendazole is rapidly converted in the liver to the primary metabolite, albendazole sulfoxide, which is further metabolized to albendazole sulfone and other primary oxidative metabolites that have been identified in human urine. Urinary excretion of albendazole sulfoxide is a minor elimination pathway with less than 1% of the dose recovered in the urine. Biliary elimination presumably accounts for a portion of the elimination as evidenced by biliary concentrations of albendazole sulfoxide similar to those achieved in plasma.

    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.

    Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1126

    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

    McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 46

    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.

    Joint FAO/WHO Expert Committee on Food Additives; WHO Food Additive Series 25: Toxicological Evaluation of Ceratin Veterinary Drug Residues in Food: Albendazole (1990). Available from, as of July 17, 2006: https://www.inchem.org/documents/jecfa/jecmono/v25je01.htm

    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.

    Joint FAO/WHO Expert Committee on Food Additives; WHO Food Additive Series 25: Toxicological Evaluation of Ceratin Veterinary Drug Residues in Food: Albendazole (1990). Available from, as of July 17, 2006: https://www.inchem.org/documents/jecfa/jecmono/v25je01.htm

    For more Absorption, Distribution and Excretion (Complete) data for ALBENDAZOLE (9 total), please visit the HSDB record page.

    5.6 Metabolism/Metabolites

    Hepatic. Rapidly converted in the liver to the primary metabolite, albendazole sulfoxide, which is further metabolized to albendazole sulfone and other primary oxidative metabolites that have been identified in human urine.

    Albendazole is converted first to a sulfoxide and then to a sulfone. All of these reactions are catalyzed by flavin monooxygenases (FMO) and/or cytochrome P450. Both enzymes are efficient catalysts of S-oxygenation ...

    Klaassen, C.D. (ed). Casarett and Doull's Toxicology. The Basic Science of Poisons. 6th ed. New York, NY: McGraw-Hill, 2001., p. 176

    Albendazole is metabolized in the liver to an active metabolite, albendazole sulfoxide, which accounts for detectable plasma concentrations of the drug; systemic anthelmintic activity of the drug has been attributed to this metabolite.

    McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 47

    Albendazole ... 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 and has a highly variable plasma half-life ranging from about 4 to 15 hr. It is well distributed into various tissues, including hydatid cysts, where it reaches a concn of about one-fifth that in plasma. This probably explains why albendazole is more effective than mebendazole for treating hydatid cyst disease. Formation of albendazole sulfoxide is catalyzed by both microsomal flavin monooxygenase and isoforms of cytochrome P450 in the liver and possibly also in the intestine. Hepatic flavin monooxygenase activity appears associated with (+) albendazole sulfoxide formation, whereas cytochromes P450 preferentially produce the (-) sulfoxide metabolite. 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 and plasma half-life of the bioactive (+) sulfoxide metabolite. Induction of enzymes involved in sulfone formation from the (+) sulfoxide could account for some of the wide variation noted in plasma half-lives of albendazole sulfoxide. Indeed, in animal models, benzimidazoles can induce their own metabolism. Albendazole metabolites are excreted mainly in the urine.

    Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1126

    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.

    Joint FAO/WHO Expert Committee on Food Additives; WHO Food Additive Series 25: Toxicological Evaluation of Ceratin Veterinary Drug Residues in Food: Albendazole (1990). Available from, as of July 17, 2006: https://www.inchem.org/documents/jecfa/jecmono/v25je01.htm

    For more Metabolism/Metabolites (Complete) data for ALBENDAZOLE (12 total), please visit the HSDB record page.

    Albendazole has known human metabolites that include Albendazole oxide.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.7 Biological Half-Life

    Terminal elimination half-life ranges from 8 to 12 hours (single dose, 400mg).

    Albendazole ... is rapidly metabolized ... to albendazole sulfoxide, which ... has a highly variable plasma half-life ranging from about 4 to 15 hr ... Both /(+) and (-)/ sulfoxide derivatives are oxidized further to the nonchiral sulfone metabolite ... This reaction favors the (-) sulfoxide and probably becomes rate limiting in determining ... plasma half-life of the bioactive (+) sulfoxide metabolite. Induction of enzymes involved in sulfone formation from the (+) sulfoxide could account for some of the wide variation noted in plasma half-lives of albendazole sulfoxide.

    Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1126

    5.8 Mechanism of Action

    Albendazole causes degenerative alterations in the tegument and intestinal cells of the worm by diminishing its energy production, ultimately leading to immobilization and death of the parasite. It works by binding to the colchicine-sensitive site of tubulin, thus inhibiting its polymerization or assembly into microtubules. As cytoplasmic microtubules are critical in promoting glucose uptake in larval and adult stages of the susceptible parasites, the glycogen stores of the parasites are depleted. 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.

    Benzimidazoles produce many biochemical changes in susceptible nematodes, eg, inhibition of mitochondrial fumarate reductase, reduced glucose transport, and uncoupling of oxidative phosphorylation ... /but/ the primary action ... /should be/ to inhibit microtubule polymerization by binding to beta-tubulin. The selective toxicity of these agents derives from the fact that specific, high-affinity binding to parasite beta-tubulin occurs at much lower concn than does binding to the mammalian protein ... Benzimidazole-resistant Haemonchus contortus display reduced high-affinity drug binding to beta-tubulin and alterations in beta-tubulin isotype gene expression that correlate with drug resistance ... Two identified mechanisms of drug resistance in nematodes involve both a progressive loss of "susceptible" beta-tubulin gene isotypes together with emergence of a "resistant" isotype with a conserved point mutation that encodes a tyrosine instead of phenylalanine at position 200 of beta-tubulin. While this mutation may not be required for benzimidazole resistance in all parasites, eg, Giardia lamblia, benzimidazole resistance in parasitic nematodes is unlikely to be overcome by novel benzimidazole analogs, because tyrosine also is present at position 200 of human beta-tubulin. /Benzimidazoles/

    Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1126

    Although the exact mechanism of action of albendazole has not been fully elucidated, the principal anthelmintic effect of benzimidazoles, including albendazole, appears to be the specific, high-affinity binding of the drug to free beta-tubulin in parasite cells, resulting in selective inhibition of parasite microtubule polymerization, and inhibition of microtubule-dependent uptake of glucose. Benzimidazole drugs bind to the beta-tubulin of parasites at much lower concentrations than to mammalian beta-tubulin protein; the drugs do not inhibit glucose uptake in mammals, and do not appear to have any effect on blood glucose concentrations in humans

    McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 47

    The mode of action of albendazole is by binding strongly with the tubulin in the cells of nematodes. The intestinal cells of the nematode are particularly affected, resulting in a loss of absorptive function which causes the nematodes to starve to death.

    European Medicines Agency (EMEA), The European Agency for the Evaluation of Medicinal Products, Veterinary Medicines Evaluation Unit, Committee for Veterinary Medicinal Products; Albendazole, Summary Report(3). EMEA/MRL/865/03-Final (June 2004). Available from, as of July 25, 2006: https://www.ema.europa.eu/ema/index.jsp?curl=pages/document_library/landing/document_library_search.jsp&murl=menus/document_library/document_library.jsp&mid

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    DMF Review : N/A

    Rev. Date :

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    DMF Number : 17754

    Submission : 2004-11-08

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    Marketing Category : BULK INGREDIENT

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    ABOUT THIS PAGE

    Looking for 54965-21-8 / Albendazole API manufacturers, exporters & distributors?

    Albendazole manufacturers, exporters & distributors 1

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    PharmaCompass offers a list of Albendazole API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Albendazole manufacturer or Albendazole supplier for your needs.

    Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Albendazole manufacturer or Albendazole supplier.

    PharmaCompass also assists you with knowing the Albendazole API Price utilized in the formulation of products. Albendazole API Price is not always fixed or binding as the Albendazole Price is obtained through a variety of data sources. The Albendazole Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

    API | Excipient name

    Albendazole

    Synonyms

    54965-21-8, Albenza, Eskazole, Zentel, Valbazen, Proftril

    Cas Number

    54965-21-8

    Unique Ingredient Identifier (UNII)

    F4216019LN

    About Albendazole

    A benzimidazole broad-spectrum anthelmintic structurally related to MEBENDAZOLE that is effective against many diseases. (From Martindale, The Extra Pharmacopoeia, 30th ed, p38)

    Albendazole (JAN/USP/INN) Manufacturers

    A Albendazole (JAN/USP/INN) manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Albendazole (JAN/USP/INN), including repackagers and relabelers. The FDA regulates Albendazole (JAN/USP/INN) manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Albendazole (JAN/USP/INN) API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

    click here to find a list of Albendazole (JAN/USP/INN) manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

    Albendazole (JAN/USP/INN) Suppliers

    A Albendazole (JAN/USP/INN) supplier is an individual or a company that provides Albendazole (JAN/USP/INN) active pharmaceutical ingredient (API) or Albendazole (JAN/USP/INN) finished formulations upon request. The Albendazole (JAN/USP/INN) suppliers may include Albendazole (JAN/USP/INN) API manufacturers, exporters, distributors and traders.

    click here to find a list of Albendazole (JAN/USP/INN) suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

    Albendazole (JAN/USP/INN) USDMF

    A Albendazole (JAN/USP/INN) DMF (Drug Master File) is a document detailing the whole manufacturing process of Albendazole (JAN/USP/INN) active pharmaceutical ingredient (API) in detail. Different forms of Albendazole (JAN/USP/INN) DMFs exist exist since differing nations have different regulations, such as Albendazole (JAN/USP/INN) USDMF, ASMF (EDMF), JDMF, CDMF, etc.

    A Albendazole (JAN/USP/INN) DMF submitted to regulatory agencies in the US is known as a USDMF. Albendazole (JAN/USP/INN) USDMF includes data on Albendazole (JAN/USP/INN)'s chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Albendazole (JAN/USP/INN) USDMF is kept confidential to protect the manufacturer’s intellectual property.

    click here to find a list of Albendazole (JAN/USP/INN) suppliers with USDMF on PharmaCompass.

    Albendazole (JAN/USP/INN) CEP

    A Albendazole (JAN/USP/INN) CEP of the European Pharmacopoeia monograph is often referred to as a Albendazole (JAN/USP/INN) Certificate of Suitability (COS). The purpose of a Albendazole (JAN/USP/INN) CEP is to show that the European Pharmacopoeia monograph adequately controls the purity of Albendazole (JAN/USP/INN) EP produced by a given manufacturer. Suppliers of raw materials can prove the suitability of Albendazole (JAN/USP/INN) to their clients by showing that a Albendazole (JAN/USP/INN) CEP has been issued for it. The manufacturer submits a Albendazole (JAN/USP/INN) CEP (COS) as part of the market authorization procedure, and it takes on the role of a Albendazole (JAN/USP/INN) CEP holder for the record. Additionally, the data presented in the Albendazole (JAN/USP/INN) CEP (COS) is managed confidentially and offers a centralized system acknowledged by numerous nations, exactly like the Albendazole (JAN/USP/INN) DMF.

    A Albendazole (JAN/USP/INN) CEP (COS) is recognised by all 36 nations that make up the European Pharmacopoeia Convention. Albendazole (JAN/USP/INN) CEPs may be accepted in nations that are not members of the Ph. Eur. at the discretion of the authorities there.

    click here to find a list of Albendazole (JAN/USP/INN) suppliers with CEP (COS) on PharmaCompass.

    Albendazole (JAN/USP/INN) WC

    A Albendazole (JAN/USP/INN) written confirmation (Albendazole (JAN/USP/INN) WC) is an official document issued by a regulatory agency to a Albendazole (JAN/USP/INN) manufacturer, verifying that the manufacturing facility of a Albendazole (JAN/USP/INN) active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting Albendazole (JAN/USP/INN) APIs or Albendazole (JAN/USP/INN) finished pharmaceutical products to another nation, regulatory agencies frequently require a Albendazole (JAN/USP/INN) WC (written confirmation) as part of the regulatory process.

    click here to find a list of Albendazole (JAN/USP/INN) suppliers with Written Confirmation (WC) on PharmaCompass.

    Albendazole (JAN/USP/INN) NDC

    National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Albendazole (JAN/USP/INN) as an active pharmaceutical ingredient (API).

    Finished drug products

    The FDA updates the NDC directory daily. The NDC numbers for Albendazole (JAN/USP/INN) API and other APIs are published in this directory by the FDA.

    Unfinished drugs

    The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

    Pharmaceutical companies that manufacture Albendazole (JAN/USP/INN) as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

    Compounded drug products

    The NDC directory also contains data on finished compounded human drug products that contain Albendazole (JAN/USP/INN) and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Albendazole (JAN/USP/INN) NDC to their finished compounded human drug products, they may choose to do so.

    click here to find a list of Albendazole (JAN/USP/INN) suppliers with NDC on PharmaCompass.

    Albendazole (JAN/USP/INN) GMP

    Albendazole (JAN/USP/INN) Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

    GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

    PharmaCompass offers a list of Albendazole (JAN/USP/INN) GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Albendazole (JAN/USP/INN) GMP manufacturer or Albendazole (JAN/USP/INN) GMP API supplier for your needs.

    Albendazole (JAN/USP/INN) CoA

    A Albendazole (JAN/USP/INN) CoA (Certificate of Analysis) is a formal document that attests to Albendazole (JAN/USP/INN)'s compliance with Albendazole (JAN/USP/INN) specifications and serves as a tool for batch-level quality control.

    Albendazole (JAN/USP/INN) CoA mostly includes findings from lab analyses of a specific batch. For each Albendazole (JAN/USP/INN) CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

    Albendazole (JAN/USP/INN) may be tested according to a variety of international standards, such as European Pharmacopoeia (Albendazole (JAN/USP/INN) EP), Albendazole (JAN/USP/INN) JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Albendazole (JAN/USP/INN) USP).

    Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
    For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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