Details of the Drug

General Information of Drug (ID: DME4RA8)

Drug Name
Amodiaquine
Synonyms
Amodiachin; Amodiachinum; Amodiaquin; Amodiaquina; Amodiaquinum; Basoquin; CQA; Camochin; Camoquin; Camoquinal; Camoquine; Flavoquin; Flavoquine; Miaquin; Sunoquine; Amodiaquine hydrochloride; Amodiaquine USP24; SN 10751; AMODIAQUINE, FLAVOQUINE; Amodiaquina [INN-Spanish]; Amodiaquinum [INN-Latin]; CAM-AQ 1; CAM-AQI; Cam-AQ1; Camoquin (TN); Flavoquine (TN); SN 10,751; WR-002977; Amodiaquine (USAN/INN); Amodiaquine [USAN:INN:BAN]; Amodiaquine, ring-closed; S. N. 10751
Indication
Disease Entry ICD 11 Status REF
Malaria 1F40-1F45 Approved [1]
Middle East Respiratory Syndrome (MERS) 1D64 Preclinical [2]
Severe acute respiratory syndrome (SARS) 1D65 Preclinical [2]
Therapeutic Class
Antimalarials
Affected Organisms
Plasmodium
ATC Code
P01BA06: Amodiaquine
P01BA: Aminoquinolines
P01B: ANTIMALARIALS
P01: ANTIPROTOZOALS
P: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 355.9
Logarithm of the Partition Coefficient (xlogp) 2.6
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 4
ADMET Property
Absorption
The drug is rapidly absorbed following oral administration []
Bioavailability
75% of drug becomes completely available to its intended biological destination(s) [3]
Clearance
The drug present in the plasma can be removed from the body at the rate of 217 mL/min/kg [4]
Half-life
The concentration or amount of drug in body reduced by one-half in 5.2 +/-1.7 (range 0.4 - 5.5) minutes [4]
Metabolism
The drug is metabolized via the hepatic []
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 17.4 L/kg [4]
Chemical Identifiers
Formula
C20H22ClN3O
IUPAC Name
4-[(7-chloroquinolin-4-yl)amino]-2-(diethylaminomethyl)phenol
Canonical SMILES
CCN(CC)CC1=C(C=CC(=C1)NC2=C3C=CC(=CC3=NC=C2)Cl)O
InChI
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
Cross-matching ID
PubChem CID
2165
ChEBI ID
CHEMBL682
CAS Number
86-42-0
UNII
220236ED28
DrugBank ID
DB00613
TTD ID
D04NQI
VARIDT ID
DR00976
INTEDE ID
DR0102
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Histamine N-methyltransferase (HNMT) TT2B6EV HNMT_HUMAN Inhibitor [5]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 1A1 (CYP1A1) DE6OQ3W CP1A1_HUMAN Substrate [6]
Cytochrome P450 1B1 (CYP1B1) DE9QHP6 CP1B1_HUMAN Substrate [6]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [7]
Glutathione S-transferase mu-4 (GSTM4) DERQ52Z GSTM4_HUMAN Substrate [8]
Cytochrome P450 102A1 (cyp102) DE4OGUF CPXB_BACMB Substrate [9]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cyclin-dependent kinase inhibitor 1 (CDKN1A) OTQWHCZE CDN1A_HUMAN Gene/Protein Processing [10]
Cytochrome P450 2C19 (CYP2C19) OTFMJYYE CP2CJ_HUMAN Gene/Protein Processing [11]
Hepatocyte growth factor receptor (MET) OT7K55MU MET_HUMAN Gene/Protein Processing [12]
Proepiregulin (EREG) OTRM4NQY EREG_HUMAN Gene/Protein Processing [12]
PTB-containing, cubilin and LRP1-interacting protein (PID1) OT5YJ7FI PCLI1_HUMAN Gene/Protein Processing [12]
Retinoblastoma-associated protein (RB1) OTQJUJMZ RB_HUMAN Post-Translational Modifications [10]
Transcription factor E2F1 (E2F1) OTLKYBBC E2F1_HUMAN Gene/Protein Processing [10]
Tumor necrosis factor-inducible gene 6 protein (TNFAIP6) OT1SLUZH TSG6_HUMAN Gene/Protein Processing [12]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Drug information of Amodiaquine, 2008. eduDrugs.
2 Repurposing of clinically developed drugs for treatment of Middle East respiratory syndrome coronavirus infection. Antimicrob Agents Chemother. 2014 Aug;58(8):4885-93.
3 Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 Effect of amodiaquine, a histamine N-methyltransferase inhibitor, on, Propionibacterium acnes and lipopolysaccharide-induced hepatitis in mice. Eur J Pharmacol. 2007 Mar 8;558(1-3):179-84.
6 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.
7 Amodiaquine metabolism is impaired by common polymorphisms in CYP2C8: implications for malaria treatment in Africa. Clin Pharmacol Ther. 2007 Aug;82(2):197-203.
8 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.
9 The bacterial P450 BM3: a prototype for a biocatalyst with human P450 activities. Trends Biotechnol. 2007 Jul;25(7):289-98.
10 The antimalarial amodiaquine causes autophagic-lysosomal and proliferative blockade sensitizing human melanoma cells to starvation- and chemotherapy-induced cell death. Autophagy. 2013 Dec;9(12):2087-102. doi: 10.4161/auto.26506. Epub 2013 Oct 8.
11 Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s. Drug Metab Dispos. 2001 Jan;29(1):30-5.
12 An in vitro coculture system of human peripheral blood mononuclear cells with hepatocellular carcinoma-derived cells for predicting drug-induced liver injury. Arch Toxicol. 2021 Jan;95(1):149-168. doi: 10.1007/s00204-020-02882-4. Epub 2020 Aug 20.