Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0055)
Drug Name
Albendazole
Synonyms
Albendazol; Albendazol [INN-Spanish]; Albendazolum; Albendazolum [INN-Latin]; Albenza; Bilutac; Eskazole; Proftril; SK&F 62979; SK&F-62979; SKF 62979; SKF-62979; Valbazen; Zental; Zentel; albendazole; (5-(Propylthio)-1H-benzimidazol-2-yl)carbamic acid methyl ester; 5-(Propylthio)-2-carbomethoxyaminobenzimidazole; 54965-21-8; Methyl 5-(propylthio)-2-benzimidazolecarbamate; Methyl [5-(Propylthio)benzimidazol-2-yl]carbamate; methyl N-[6-(propylsulfanyl)-1H-1,3-benzodiazol-2-yl]carbamate
Indication Giardiasis [ICD11: 1A31] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 265.33 Topological Polar Surface Area 92.3
Heavy Atom Count 18 Rotatable Bond Count 5
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
2082
PubChem SID
4909 ; 129996 ; 603014 ; 855809 ; 3154181 ; 5010055 ; 5590332 ; 6318023 ; 7847202 ; 7978654 ; 8144956 ; 8150054 ; 8151416 ; 10321635 ; 10589336 ; 11112790 ; 11242363 ; 11335879 ; 11361118 ; 11364426 ; 11366988 ; 11369550 ; 11373940 ; 11377712 ; 11462090 ; 11466275 ; 11467395 ; 11485989 ; 11492016 ; 11495346 ; 11521860 ; 11528637 ; 12014008 ; 14823901 ; 16704067 ; 24890894 ; 25623359 ; 25751296 ; 26612535 ; 26679872 ; 26746999 ; 26747000 ; 26751522 ; 29221262 ; 46506472 ; 47216788 ; 47291149 ; 47296872 ; 47296873 ; 47742180
ChEBI ID
ChEBI:16664
CAS Number
54965-21-8
TTD Drug ID
D00KVO
Formula
C12H15N3O2S
Canonical SMILES
CCCSC1=CC2=C(C=C1)N=C(N2)NC(=O)OC
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)
InChIKey
HXHWSAZORRCQMX-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
(+) albendazole sulfoxide DM000022
13805917
Oxidation - Oxidation 1 [5] , [6] , [7] , [8]
(-) albendazole sulfoxide DM000025
13805918
Oxidation - Oxidation 1 [5] , [6] , [7] , [8]
Hydroxyalbendazole DM000026
131841459
Oxidation - Hydroxylation 1 [9]
Unclear DM009999 N. A. Oxidation - Oxidation 1 [10]
Unclear DM009999 N. A. Oxidation - Oxidation 1 [4]
Albendazole sulfone DM000023
53174
Oxidation - Oxidation 2 [6] , [7] , [8]
Albendazole-2-aminosulfone DM000024
88125
Oxidation - Deacetylation 2 [11] , [12]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000109 Albendazole (+) albendazole sulfoxide Oxidation - Oxidation FMO [5], [6], [7], [8]
MR000110 Albendazole (-) albendazole sulfoxide Oxidation - Oxidation CYP2J2 ... [5], [6], [7], [8]
MR000111 Albendazole Hydroxyalbendazole Oxidation - Hydroxylation CYP2J2 [9]
MR000112 Albendazole . Oxidation - Oxidation CYP3A4 [10]
MR000105 (+) albendazole sulfoxide Albendazole sulfone Oxidation - Oxidation FMO [6], [7], [8]
MR000106 (+) albendazole sulfoxide Albendazole-2-aminosulfone Oxidation - Deacetylation Unclear [11], [12]
MR000107 (-) albendazole sulfoxide Albendazole sulfone Oxidation - Oxidation CYP2J2 ... [6], [7], [8]
MR000108 (-) albendazole sulfoxide Albendazole-2-aminosulfone Oxidation - Deacetylation Unclear [11], [12]
⏷ Show the Full List of 8 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2J2 (CYP2J2) DME0031 Homo sapiens
CP2J2_HUMAN
1.14.14.24
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3]
References
1 Albendazole was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Cytochrome P450 1A1/2 induction by antiparasitic drugs: dose-dependent increase in ethoxyresorufin O-deethylase activity and mRNA caused by quinine, primaquine and albendazole in HepG2 cells. Eur J Clin Pharmacol. 2002 Nov;58(8):537-42.
3 Danazol inhibits cytochrome P450 2J2 activity in a substrate-independent manner. Drug Metab Dispos. 2015 Aug;43(8):1250-3.
4 Identification of human cytochrome P(450)s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data. Eur J Clin Pharmacol. 2003 Sep;59(5-6):429-42.
5 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
6 Nanocrystal Suspensions for Enhancing the Oral Absorption of Albendazole. Nanomaterials (Basel). 2022 Sep 1;12(17):3032. doi: 10.3390/nano12173032.
7 Multi-residue methodology for quantification of antiparasitics in hen eggs by LC-MS/MS: development, validation and application to 348 samples from Brazil. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2022 Aug;39(8):1412-1423. doi: 10.1080/19440049.2022.2093984.
8 Improvement of Albendazole Bioavailability with Menbutone Administration in Sheep. Animals (Basel). 2022 Feb 14;12(4):463. doi: 10.3390/ani12040463.
9 CYP2J2 and CYP2C19 are the major enzymes responsible for metabolism of albendazole and fenbendazole in human liver microsomes and recombinant P450 assay systems. Antimicrob Agents Chemother. 2013 Nov;57(11):5448-56.
10 Effect of clotrimazole on microsomal metabolism and pharmacokinetics of albendazole J Pharm Pharmacol. 2003 Jun;55(6):757-64. doi: 10.1211/002235703765951357.
11 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:
12 Secretion into Milk of the Main Metabolites of the Anthelmintic Albendazole Is Mediated by the ABCG2/BCRP Transporter. Antimicrob Agents Chemother. 2022 Jul 19;66(7):e0006222. doi: 10.1128/aac.00062-22.

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