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

General Information of Drug (ID: DR0102)
Drug Name
Amodiaquine
Synonyms
Amodiachin; Amodiachinum; Amodiaquin; Amodiaquina; Amodiaquina [INN-Spanish]; Amodiaquine USP24; Amodiaquine hydrochloride; Amodiaquine, ring-closed; Amodiaquinum; Amodiaquinum [INN-Latin]; CAM-AQI; Cam-AQ1; Camochin; Camoquin; Camoquin Hcl; Camoquinal; Camoquine; Flavoquine; Miaquin; S. N. 10751; SN 10,751; amodiaquine; 4-[(7-CHLOROQUINOLIN-4-YL)AMINO]-2-[(DIETHYLAMINO)METHYL]PHENOL; 86-42-0; C20H22ClN3O; CHEBI:2674; NSC 13453; Phenol, 4-[(7-chloro-4-quinolinyl)amino]-2-[(diethylamino)methyl]-; UNII-220236ED28
Indication Malaria [ICD11: 1F40] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 355.9 Topological Polar Surface Area 48.4
Heavy Atom Count 25 Rotatable Bond Count 6
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
2165
PubChem SID
9828 ; 77901 ; 598064 ; 4621370 ; 7886759 ; 7978694 ; 8151472 ; 10537079 ; 10589213 ; 11466337 ; 11467457 ; 11486233 ; 15374079 ; 17397079 ; 29221344 ; 46393825 ; 46506940 ; 47291303 ; 47440457 ; 47589170 ; 47810953 ; 47959956 ; 48415557 ; 49698430 ; 49956414 ; 50085969 ; 53789783 ; 53801183 ; 57321182 ; 76179602 ; 81062056 ; 81093107 ; 84974934 ; 92712423 ; 103190631 ; 103973209 ; 104299796 ; 105086070 ; 124596739 ; 124659480 ; 124801466 ; 124951249 ; 125358735 ; 126630109 ; 126678259 ; 128866127 ; 131333557 ; 134337988 ; 134970939 ; 135702891
ChEBI ID
ChEBI:2674
CAS Number
86-42-0
TTD Drug ID
D04NQI
Formula
C20H22ClN3O
Canonical SMILES
CCN(CC)CC1=C(C=CC(=C1)NC2=C3C=CC(=CC3=NC=C2)Cl)O
InChI
1S/C20H22ClN3O/c1-3-24(4-2)13-14-11-16(6-8-20(14)25)23-18-9-10-22-19-12-15(21)5-7-17(18)19/h5-12,25H,3-4,13H2,1-2H3,(H,22,23)
InChIKey
OVCDSSHSILBFBN-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
Amodiaquine metabolite AQCYS DM001567 N. A. Unclear 1 [6]
Amodiaquine metabolite AQGT DM001566 N. A. Unclear 1 [6]
Amodiaquine metabolite BISDEAQ DM001568
181536
Unclear 1 [6]
Amodiaquine metabolite CARBOXYLIC ACID DM001569
353545
Unclear 1 [6]
Desethylamodiaquine DM001565
122068
Oxidation - N-Deethylation 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002802 Amodiaquine Desethylamodiaquine Oxidation - N-Deethylation CYP2C8 [4]
MR002803 Amodiaquine Amodiaquine metabolite AQGT Unclear Unclear [6]
MR002804 Amodiaquine Amodiaquine metabolite AQCYS Unclear Unclear [6]
MR002805 Amodiaquine Amodiaquine metabolite BISDEAQ Unclear Unclear [6]
MR002806 Amodiaquine Amodiaquine metabolite CARBOXYLIC ACID Unclear Unclear [6]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 102A1 (cyp102) DME1075 Bacillus megaterium
CPXB_BACMB
1.14.14.1
[2]
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[3]
Cytochrome P450 1B1 (CYP1B1) DME0023 Homo sapiens
CP1B1_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[4]
Glutathione S-transferase mu-4 (GSTM4) DME0613 Homo sapiens
GSTM4_HUMAN
2.5.1.18
[5]
References
1 Biowaiver monographs for immediate release solid oral dosage forms: amodiaquine hydrochloride. J Pharm Sci. 2012 Dec;101(12):4390-401.
2 The bacterial P450 BM3: a prototype for a biocatalyst with human P450 activities. Trends Biotechnol. 2007 Jul;25(7):289-98.
3 Amodiaquine clearance and its metabolism to N-desethylamodiaquine is mediated by CYP2C8: a new high affinity and turnover enzyme-specific probe substrate. J Pharmacol Exp Ther. 2002 Feb;300(2):399-407.
4 Cardiovascular concentration-effect relationships of amodiaquine and its metabolite desethylamodiaquine: Clinical and preclinical studies. Br J Clin Pharmacol. 2023 Mar;89(3):1176-1186. doi: 10.1111/bcp.15569.
5 Human glutathione S-transferases- and NAD(P)H:quinone oxidoreductase 1-catalyzed inactivation of reactive quinoneimines of amodiaquine and N-desethylamodiaquine: possible implications for susceptibility to amodiaquine-induced liver toxicity. Toxicol Lett. 2017 Jun 5;275:83-91.
6 Role of hepatic metabolism in the bioactivation and detoxication of amodiaquine Xenobiotica. 1995 Feb;25(2):199-217. doi: 10.3109/00498259509061845.

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