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

General Information of Drug (ID: DR0899)
Drug Name
Ivermectin
Synonyms Ivermectin B1a; Avermectin H2B1a; 22,23-Dihydroavermectin B1a; Dihydroavermectin B1a; IVERMECTIN; 70288-86-7; 71827-03-7; 91Y2202OUW; CHEBI:63941; UNII-91Y2202OUW
Indication Onchocerciasis [ICD11: 1F6A] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 875.1 Topological Polar Surface Area 170
Heavy Atom Count 62 Rotatable Bond Count 8
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 14
Cross-matching ID
PubChem CID
6321424
ChEBI ID
CHEBI:63941
CAS Number
71827-03-7
TTD Drug ID
D09YHJ
Formula
C48H74O14
Canonical SMILES
CCC(C)C1C(CCC2(O1)CC3CC(O2)CC=C(C(C(C=CC=C4COC5C4(C(C=C(C5O)C)C(=O)O3)O)C)OC6CC(C(C(O6)C)OC7CC(C(C(O7)C)O)OC)OC)C)C
InChI
1S/C48H74O14/c1-11-25(2)43-28(5)17-18-47(62-43)23-34-20-33(61-47)16-15-27(4)42(26(3)13-12-14-32-24-55-45-40(49)29(6)19-35(46(51)58-34)48(32,45)52)59-39-22-37(54-10)44(31(8)57-39)60-38-21-36(53-9)41(50)30(7)56-38/h12-15,19,25-26,28,30-31,33-45,49-50,52H,11,16-18,20-24H2,1-10H3/b13-12+,27-15+,32-14+/t25-,26-,28-,30-,31-,33+,34-,35-,36-,37-,38-,39-,40+,41-,42-,43+,44-,45+,47+,48+/m0/s1
InChIKey
AZSNMRSAGSSBNP-XPNPUAGNSA-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
3''-O-Desmethyl-ivermectin B1a DM001048
155491110
Oxidation - O-Demethylation 1 [3]
3''-O-Desmethyl-ivermectin B1b DM001050
155491046
Oxidation - O-Demethylation 1 [3]
3''\O\demethyl, 4\hydroxymethyl ivermectin DM001049 N. A. Unclear 1 [3]
Ivermectin metabolite M2 DM001052 N. A. Unclear 1 [3]
Ivermectin metabolite M3 DM001051
155491213
Oxidation - Hydroxylation 1 [3]
3''\O\demethyl, 4\hydroxymethyl ivermectin DM001049 N. A. Unclear 2 [3] , [4] , [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001287 Ivermectin 3''-O-Desmethyl-ivermectin B1a Oxidation - O-Demethylation CYP3A4 [3]
MR001288 Ivermectin 3''\O\demethyl, 4\hydroxymethyl ivermectin Unclear CYP3A4 [3]
MR001289 Ivermectin 3''-O-Desmethyl-ivermectin B1b Oxidation - O-Demethylation CYP3A4 [3]
MR001290 Ivermectin Ivermectin metabolite M3 Oxidation - Hydroxylation CYP3A4 [3]
MR001291 Ivermectin Ivermectin metabolite M2 Unclear Unclear [3]
MR001284 3''-O-Desmethyl-ivermectin B1a 3''\O\demethyl, 4\hydroxymethyl ivermectin Unclear Unclear [3], [4], [5]
MR001285 3''-O-Desmethyl-ivermectin B1b 3''\O\demethyl, 4\hydroxymethyl ivermectin Unclear Unclear [3], [4], [5]
MR001286 Ivermectin metabolite M3 3''\O\demethyl, 4\hydroxymethyl ivermectin Unclear Unclear [3], [4], [5]
⏷ 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 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
References
1 Ivermectin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Identification of cytochrome P4503A4 as the major enzyme responsible for the metabolism of ivermectin by human liver microsomes. Xenobiotica. 1998 Mar;28(3):313-21.
3 Identification of the metabolites of ivermectin in humans Pharmacol Res Perspect. 2021 Feb;9(1):e00712. doi: 10.1002/prp2.712.
4 Ivermectin metabolites reduce Anopheles survival. Sci Rep. 2023 May 19;13(1):8131. doi: 10.1038/s41598-023-34719-2.
5 Pharmacokinetics of ivermectin metabolites and their activity against Anopheles stephensi mosquitoes. Malar J. 2023 Jun 24;22(1):194. doi: 10.1186/s12936-023-04624-0.

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