Details
Stereochemistry | ACHIRAL |
Molecular Formula | C12H15N3O2S |
Molecular Weight | 265.331 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCSC1=CC=C2N=C(NC(=O)OC)NC2=C1
InChI
InChIKey=HXHWSAZORRCQMX-UHFFFAOYSA-N
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)
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11386684
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11386684
ALBENZA (albendazole) is an orally administered anthelmintic drug. Chemically, it is methyl 5¬ (propylthio)-2-benzimidazolecarbamate, is indicated to treatment of parenchymal neurocysticercosis due to active lesions caused by larval forms of the pork tapeworm, Taenia solium. In addition, treatment of cystic hydatid disease of the liver, lung, and peritoneum, caused by the larval form of the dog tapeworm, Echinococcus granulosus. Albendazole binds to the colchicine-sensitive site of β-tubulin inhibiting their polymerization into microtubules. The decrease in microtubules in the intestinal cells of the parasites decreases their absorptive function, especially the uptake of glucose by the adult and larval forms of the parasites, and depletes glycogen storage. Insufficient glucose results in insufficient energy for the production of adenosine trisphosphate (ATP) and the parasite eventually dies. Albendazole developed in 1975. It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system. The incidence of side effects reported in the published literature is very low, with only gastrointestinal side effects occurring with an overall frequency of just >1% . Albendazole's unique broad-spectrum activity is exemplified in the overall cure rates calculated from studies employing the recommended doses for hookworm (78% in 68 studies: 92%, for A. duodenale in 23 studies and 75% for N. americanus in 30 studies), A. lumbricoides (95% in 64 studies), T. trichiura (48% in 57 studies), E. vermicularis (98% in 27 studies), S. stercoralis (62% in 19 studies), H. nana (68% in 11 studies), and Taenia spp. (85% in 7 studies).
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=19915628
Curator's Comment: Albendazole penetrates blood–brain barrier, with concentrations in CSF reaching 50% of that found in plasma
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2364705 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11980387 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | ALBENZA Approved UseALBENZA is an anthelmintic drug indicated for: Treatment of parenchymal neurocysticercosis due to active lesions caused by larval forms of the pork tapeworm, Taenia solium. (1.1) Treatment of cystic hydatid disease of the liver, lung, and peritoneum, caused by the larval form of the dog tapeworm, Echinococcus granulosus. (1.2) 1.1 Neurocysticercosis ALBENZA is indicated for the treatment of parenchymal neurocysticercosis due to active lesions caused by larval forms of the pork tapeworm, Taenia solium. 1.2 Hydatid Disease ALBENZA is indicated for the treatment of cystic hydatid disease of the liver, lung, and peritoneum, caused by the larval form of the dog tapeworm, Echinococcus granulosus. Launch Date8.3445121E11 |
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Curative | ALBENZA Approved UseALBENZA is an anthelmintic drug indicated for: Treatment of parenchymal neurocysticercosis due to active lesions caused by larval forms of the pork tapeworm, Taenia solium. (1.1) Treatment of cystic hydatid disease of the liver, lung, and peritoneum, caused by the larval form of the dog tapeworm, Echinococcus granulosus. (1.2) 1.1 Neurocysticercosis ALBENZA is indicated for the treatment of parenchymal neurocysticercosis due to active lesions caused by larval forms of the pork tapeworm, Taenia solium. 1.2 Hydatid Disease ALBENZA is indicated for the treatment of cystic hydatid disease of the liver, lung, and peritoneum, caused by the larval form of the dog tapeworm, Echinococcus granulosus. Launch Date8.3445121E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
39.61 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12784319 |
800 mg 1 times / day steady-state, oral dose: 800 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ALBENDAZOLE SULFONE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1310 ng/mL |
400 mg 2 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ALBENDAZOLE OXIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED |
|
707.37 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12784319 |
800 mg 1 times / day steady-state, oral dose: 800 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ALBENDAZOLE OXIDE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
284.55 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12784319 |
800 mg 1 times / day steady-state, oral dose: 800 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ALBENDAZOLE SULFONE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
3713.96 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12784319 |
800 mg 1 times / day steady-state, oral dose: 800 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ALBENDAZOLE OXIDE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
11.91 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12784319 |
800 mg 1 times / day steady-state, oral dose: 800 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ALBENDAZOLE SULFONE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
8 h |
400 mg 2 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ALBENDAZOLE OXIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED |
|
11.43 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12784319 |
800 mg 1 times / day steady-state, oral dose: 800 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ALBENDAZOLE OXIDE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
30% |
400 mg 2 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ALBENDAZOLE OXIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED |
Doses
Dose | Population | Adverse events |
---|---|---|
1200 mg 2 times / day multiple, oral MTD Dose: 1200 mg, 2 times / day Route: oral Route: multiple Dose: 1200 mg, 2 times / day Sources: Page: p.600 |
unhealthy, 25–81 n = 9 Health Status: unhealthy Condition: Advanced cancer Age Group: 25–81 Sex: M+F Population Size: 9 Sources: Page: p.600 |
Disc. AE: Neutropenic sepsis... AEs leading to discontinuation/dose reduction: Neutropenic sepsis (grade 5, 11%) Sources: Page: p.600 |
3200 mg 1 times / day multiple, oral Highest studied dose Dose: 3200 mg, 1 times / day Route: oral Route: multiple Dose: 3200 mg, 1 times / day Sources: Page: p.57-58 |
unhealthy, 38 n = 1 Health Status: unhealthy Condition: Neurocysticercosis Age Group: 38 Sex: F Population Size: 1 Sources: Page: p.57-58 |
Disc. AE: Parkinsonism aggravated... AEs leading to discontinuation/dose reduction: Parkinsonism aggravated Sources: Page: p.57-58 |
16 g single, oral (total daily dose) Overdose Dose: 16 g Route: oral Route: single Dose: 16 g Sources: Page: p.10 |
unhealthy n = 1 Health Status: unhealthy Condition: Hydatid Disease Population Size: 1 Sources: Page: p.10 |
|
400 mg 2 times / day multiple, oral Recommended Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: Page: p.6 |
unhealthy Health Status: unhealthy Condition: Hydatid Disease|Neurocysticercosis Sources: Page: p.6 |
Disc. AE: Granulocytopenia, Pancytopenia... Other AEs: Bone marrow depression, Aplastic anemia... AEs leading to discontinuation/dose reduction: Granulocytopenia (grade 5) Other AEs:Pancytopenia (grade 5) Bone marrow depression Sources: Page: p.6Aplastic anemia Agranulocytosis Disorder fetal |
400 mg 2 times / day multiple, oral Recommended Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: Page: p.9 |
unhealthy Health Status: unhealthy Condition: Hydatid Disease Sources: Page: p.9 |
Disc. AE: Hepatic dysfunction NOS... AEs leading to discontinuation/dose reduction: Hepatic dysfunction NOS (3.8%) Sources: Page: p.9 |
400 mg 2 times / day multiple, oral Recommended Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: Page: p.9 |
unhealthy Health Status: unhealthy Condition: Hydatid Disease|Neurocysticercosis Sources: Page: p.9 |
Disc. AE: Leukopenia... AEs leading to discontinuation/dose reduction: Leukopenia (0.7%) Sources: Page: p.9 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Neutropenic sepsis | grade 5, 11% Disc. AE |
1200 mg 2 times / day multiple, oral MTD Dose: 1200 mg, 2 times / day Route: oral Route: multiple Dose: 1200 mg, 2 times / day Sources: Page: p.600 |
unhealthy, 25–81 n = 9 Health Status: unhealthy Condition: Advanced cancer Age Group: 25–81 Sex: M+F Population Size: 9 Sources: Page: p.600 |
Parkinsonism aggravated | Disc. AE | 3200 mg 1 times / day multiple, oral Highest studied dose Dose: 3200 mg, 1 times / day Route: oral Route: multiple Dose: 3200 mg, 1 times / day Sources: Page: p.57-58 |
unhealthy, 38 n = 1 Health Status: unhealthy Condition: Neurocysticercosis Age Group: 38 Sex: F Population Size: 1 Sources: Page: p.57-58 |
Agranulocytosis | 400 mg 2 times / day multiple, oral Recommended Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: Page: p.6 |
unhealthy Health Status: unhealthy Condition: Hydatid Disease|Neurocysticercosis Sources: Page: p.6 |
|
Aplastic anemia | 400 mg 2 times / day multiple, oral Recommended Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: Page: p.6 |
unhealthy Health Status: unhealthy Condition: Hydatid Disease|Neurocysticercosis Sources: Page: p.6 |
|
Bone marrow depression | 400 mg 2 times / day multiple, oral Recommended Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: Page: p.6 |
unhealthy Health Status: unhealthy Condition: Hydatid Disease|Neurocysticercosis Sources: Page: p.6 |
|
Disorder fetal | 400 mg 2 times / day multiple, oral Recommended Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: Page: p.6 |
unhealthy Health Status: unhealthy Condition: Hydatid Disease|Neurocysticercosis Sources: Page: p.6 |
|
Granulocytopenia | grade 5 Disc. AE |
400 mg 2 times / day multiple, oral Recommended Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: Page: p.6 |
unhealthy Health Status: unhealthy Condition: Hydatid Disease|Neurocysticercosis Sources: Page: p.6 |
Pancytopenia | grade 5 Disc. AE |
400 mg 2 times / day multiple, oral Recommended Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: Page: p.6 |
unhealthy Health Status: unhealthy Condition: Hydatid Disease|Neurocysticercosis Sources: Page: p.6 |
Hepatic dysfunction NOS | 3.8% Disc. AE |
400 mg 2 times / day multiple, oral Recommended Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: Page: p.9 |
unhealthy Health Status: unhealthy Condition: Hydatid Disease Sources: Page: p.9 |
Leukopenia | 0.7% Disc. AE |
400 mg 2 times / day multiple, oral Recommended Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: Page: p.9 |
unhealthy Health Status: unhealthy Condition: Hydatid Disease|Neurocysticercosis Sources: Page: p.9 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/11901088/ Page: - |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/020666Orig1s000rev.pdf#page=183 Page: 183.0 |
yes |
Drug as victim
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/28220623/ Page: - |
PubMed
Title | Date | PubMed |
---|---|---|
Susceptibility of avian hosts to experimental Gymnophalloides seoi infection. | 2001 Apr |
|
Primary echinococcosis of the sternocleidomastoid muscle. | 2001 Apr |
|
[Disseminated strongyloidiasis]. | 2001 Apr 28 |
|
Ocular and orbital cysticercosis. | 2001 Aug |
|
Ivermectin treatment of a traveler who returned from Peru with cutaneous gnathostomiasis. | 2001 Aug 15 |
|
Chemotherapy of enterobiasis (oxyuriasis). | 2001 Feb |
|
Laparoscopic surgery in hepatic hydatid cysts: a technical improvement. | 2001 Feb |
|
The development and survival of three species of coprophagous insect after feeding on the faeces of sheep treated with controlled-release formulations of ivermectin or albendazole. | 2001 Feb |
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Pharmacokinetics of netobimin and microsomal metabolism of albendazole in infected gerbils with Echinococcus granulosus. | 2001 Feb |
|
Primary muscle hydatidosis of the thigh: management of a complicated case with combination adjunctive albendazole and praziquantel chemotherapy. | 2001 Feb 1 |
|
[Migrating swellings from Asia: gnathostomiasis]. | 2001 Feb 17 |
|
The effect of albendazole on Oesophagostomum bifurcum infection and pathology in children from rural northern Ghana. | 2001 Jan |
|
Strongyloides stercoralis eggs in the stools during anticancer therapy. | 2001 Jul-Aug |
|
Retroperitoneal localization of hydatid cyst disease. | 2001 Jul-Aug |
|
Treatment of ocular toxocariasis with albendazole. | 2001 Jun |
|
Intestinal helminth infections, anaemia and labour productivity of female tea pluckers in Bangladesh. | 2001 Jun |
|
Seizure recurrence in children with focal seizures and single small enhancing computed tomographic lesions: prognostic factors on long-term follow-up. | 2001 Jun |
|
Late onset temporal lobe epilepsy with MRI evidence of mesial temporal sclerosis following acute neurocysticercosis: case report. | 2001 Jun |
|
An unusual cause of renal colic: hydatiduria. | 2001 Jun |
|
Control of anthelmintic resistant endoparasites in a commercial sheep flock through parasite community replacement. | 2001 Jun 12 |
|
Successful treatment of metronidazole- and albendazole-resistant giardiasis with nitazoxanide in a patient with acquired immunodeficiency syndrome. | 2001 Jun 15 |
|
Activity of oxyclozanide, nitroxynil, clorsulon and albendazole against adult triclabendazole-resistant Fasciola hepatica. | 2001 Jun 9 |
|
Two imported cases of cutaneous larva migrans. | 2001 Mar |
|
Towards the eradication of hookworm in an isolated Australian community. | 2001 Mar 10 |
|
The epidemiology of gastrointestinal nematodes of dairy cattle in central Kenya. | 2001 May |
|
[Orthopedic aspects of osseous echinococcosis--radiologic diagnosis, current surgery and drug therapy aspects]. | 2001 May-Jun |
Patents
Sample Use Guides
Patients weighing 60 kg or greater, 400 mg twice daily; less than 60 kg, 15 mg/kg/day in divided doses twice daily (maximum total daily dose 800 mg). Hydatid disease: 28-day cycle followed by 14-day albendazole-free
interval for a total of 3 cycles.
Neurocysticercosis: 8 to 30 days.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19846910
The antiproliferative effect of Albendazole (ABZ) on parent PTX-sensitive 1A9 and PTX-resistant sub-line 1A9PTX22 cells (human ovarian cancer)were compared to those induced by colchicine and paclitaxel (PTX). Cells were exposed to drugs for 3 days (colchicine) or 5 days (ABZ and PTX). The results demonstrate the inhibitory effect on 1A9 and 1A9PTX22 cells by ABZ (IC50=237 nM ± 3.65 and 351 nM ± 90 respectively).
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
94295
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WHO-ESSENTIAL MEDICINES LIST |
6.1.1
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CFR |
21 CFR 520.38A
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WHO-ATC |
P02CA03
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CFR |
21 CFR 520.38
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NCI_THESAURUS |
C250
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WHO-VATC |
QP52AC11
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CFR |
21 CFR 520.38B
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CFR |
21 CFR 556.34
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FDA ORPHAN DRUG |
94195
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LIVERTOX |
NBK548360
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NDF-RT |
N0000175481
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WHO-ESSENTIAL MEDICINES LIST |
6.1.2
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F4216019LN
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16664
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F4216019LN
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m1473
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PRIMARY | Merck Index | ||
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1012553
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220008
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7444
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2082
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430
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DB00518
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100000087712
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54965-21-8
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ALBENDAZOLE
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ALBENDAZOLE
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PRIMARY | Description: A white or almost white powder. Solubility: Practically insoluble in water; soluble in glacial acetic acid R; slightly soluble in acetone R, very slightly soluble in ethanol (~750 g/l) TS. Category: Anthelminthic. Storage: Albendazole should be kept in a well-closed container, protected from light. Additional information: Melting temperature, about 210?C, with decomposition. Requirement: Albendazole contains not less than 98.0% and not more than 101.0% of C12H15N3O2S, calculated with reference to the dried substance. | ||
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D015766
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N0000191624
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PRIMARY | Cytochrome P450 1A Inducers [MoA] | ||
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C47384
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3967
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SUB05295MIG
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CHEMBL1483
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albendazole
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103
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DTXSID0022563
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Albendazole
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259-414-7
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE INACTIVE (PARENT)