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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:44 UTC
HMDB IDHMDB0014751
Secondary Accession Numbers
  • HMDB14751
Metabolite Identification
Common NameAmodiaquine
DescriptionAmodiaquine is only found in individuals that have used or taken this drug. It is a 4-aminoquinoquinoline compound with anti-inflammatory properties. [PubChem]The mechanism of plasmodicidal action of amodiaquine is not completely certain. Like other quinoline derivatives, it is thought to inhibit heme polymerase activity. This results in accumulation of free heme, which is toxic to the parasites. The drug binds the free heme preventing the parasite from converting it to a form less toxic. This drug-heme complex is toxic and disrupts membrane function.
Structure
Data?1582753217
Synonyms
ValueSource
AmodiaquinaChEBI
AmodiaquinumChEBI
AmodiaquinHMDB
Amodiaquine usp24HMDB
Amodiaquine, ring-closedHMDB
CamoquinHMDB
FlavoquineHMDB
Hydrochloride, amodiaquineHMDB
Roussel brand OF amodiaquine hydrochlorideHMDB
AmodiachinHMDB
Amodiaquine hydrochlorideHMDB
CamoquineHMDB
Chemical FormulaC20H22ClN3O
Average Molecular Weight355.861
Monoisotopic Molecular Weight355.145140048
IUPAC Name4-[(7-chloroquinolin-4-yl)amino]-2-[(diethylamino)methyl]phenol
Traditional Nameamodiaquine
CAS Registry Number86-42-0
SMILES
CCN(CC)CC1=C(O)C=CC(NC2=C3C=CC(Cl)=CC3=NC=C2)=C1
InChI Identifier
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)
InChI KeyOVCDSSHSILBFBN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 4-aminoquinolines. These are organic compounds containing an amino group attached to the 4-position of a quinoline ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassAminoquinolines and derivatives
Direct Parent4-aminoquinolines
Alternative Parents
Substituents
  • Chloroquinoline
  • Haloquinoline
  • 4-aminoquinoline
  • Aminophenol
  • P-aminophenol
  • Phenylmethylamine
  • Benzylamine
  • Aniline or substituted anilines
  • Aminopyridine
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Aryl chloride
  • Monocyclic benzene moiety
  • Aryl halide
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Tertiary amine
  • Tertiary aliphatic amine
  • Secondary amine
  • Azacycle
  • Amine
  • Organochloride
  • Organohalogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point208 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0088 g/LNot Available
LogP3.7Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available191.937http://allccs.zhulab.cn/database/detail?ID=AllCCS00000940
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0088 g/LALOGPS
logP4.83ALOGPS
logP3.76ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)9.12ChemAxon
pKa (Strongest Basic)10.23ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area48.39 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity103.29 m³·mol⁻¹ChemAxon
Polarizability38.89 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+191.54530932474
DeepCCS[M-H]-189.11530932474
DeepCCS[M-2H]-223.61930932474
DeepCCS[M+Na]+199.90930932474
AllCCS[M+H]+184.232859911
AllCCS[M+H-H2O]+181.232859911
AllCCS[M+NH4]+187.032859911
AllCCS[M+Na]+187.832859911
AllCCS[M-H]-186.232859911
AllCCS[M+Na-2H]-185.732859911
AllCCS[M+HCOO]-185.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AmodiaquineCCN(CC)CC1=C(O)C=CC(NC2=C3C=CC(Cl)=CC3=NC=C2)=C14392.0Standard polar33892256
AmodiaquineCCN(CC)CC1=C(O)C=CC(NC2=C3C=CC(Cl)=CC3=NC=C2)=C13077.9Standard non polar33892256
AmodiaquineCCN(CC)CC1=C(O)C=CC(NC2=C3C=CC(Cl)=CC3=NC=C2)=C13384.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Amodiaquine,1TMS,isomer #1CCN(CC)CC1=CC(NC2=CC=NC3=CC(Cl)=CC=C23)=CC=C1O[Si](C)(C)C3190.0Semi standard non polar33892256
Amodiaquine,1TMS,isomer #2CCN(CC)CC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C)=CC=C1O3023.9Semi standard non polar33892256
Amodiaquine,2TMS,isomer #1CCN(CC)CC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C)=CC=C1O[Si](C)(C)C3024.2Semi standard non polar33892256
Amodiaquine,2TMS,isomer #1CCN(CC)CC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C)=CC=C1O[Si](C)(C)C2938.5Standard non polar33892256
Amodiaquine,2TMS,isomer #1CCN(CC)CC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C)=CC=C1O[Si](C)(C)C3483.6Standard polar33892256
Amodiaquine,1TBDMS,isomer #1CCN(CC)CC1=CC(NC2=CC=NC3=CC(Cl)=CC=C23)=CC=C1O[Si](C)(C)C(C)(C)C3389.3Semi standard non polar33892256
Amodiaquine,1TBDMS,isomer #2CCN(CC)CC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C(C)(C)C)=CC=C1O3230.9Semi standard non polar33892256
Amodiaquine,2TBDMS,isomer #1CCN(CC)CC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C3397.2Semi standard non polar33892256
Amodiaquine,2TBDMS,isomer #1CCN(CC)CC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C3353.8Standard non polar33892256
Amodiaquine,2TBDMS,isomer #1CCN(CC)CC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C3619.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Amodiaquine GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-5039000000-deb48fd096e8eab878052017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Amodiaquine GC-MS (1 TMS) - 70eV, Positivesplash10-03di-7009800000-7089f4eec8e0b64bba2c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Amodiaquine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Amodiaquine LC-ESI-qTof , Positive-QTOFsplash10-0570-3940000000-2d4500c74767ebc68cf02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Amodiaquine LC-ESI-qTof , Positive-QTOFsplash10-001i-1390000000-e476bc93f0f2236bccdc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Amodiaquine , positive-QTOFsplash10-0570-3940000000-2d4500c74767ebc68cf02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Amodiaquine , positive-QTOFsplash10-001i-1390000000-e476bc93f0f2236bccdc2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amodiaquine 10V, Positive-QTOFsplash10-0a4i-0039000000-62adbcf1b80da6582ca12016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amodiaquine 20V, Positive-QTOFsplash10-001i-1393000000-c73e48e7cfd7d390ddfa2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amodiaquine 40V, Positive-QTOFsplash10-0kcs-2190000000-8de404d259f2e431ba082016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amodiaquine 10V, Negative-QTOFsplash10-0udi-1009000000-c665029b31d3d0ae731b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amodiaquine 20V, Negative-QTOFsplash10-0udi-4119000000-d9ade9d08becc9d7fe952016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amodiaquine 40V, Negative-QTOFsplash10-00dl-9111000000-e7bdd6a9f825f1429a1e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amodiaquine 10V, Positive-QTOFsplash10-0a59-0089000000-228889052bdf8049fae32021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amodiaquine 20V, Positive-QTOFsplash10-001i-0090000000-d45ee7ba1c5cd27865fa2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amodiaquine 40V, Positive-QTOFsplash10-053r-0290000000-333fe4ea622efd6132be2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amodiaquine 10V, Negative-QTOFsplash10-0udi-0019000000-398809cbbc619aca88782021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amodiaquine 20V, Negative-QTOFsplash10-0f89-1089000000-3e1ecc2c9b62f80738452021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amodiaquine 40V, Negative-QTOFsplash10-00lr-2290000000-6c33a84366a5268dd9dd2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00613 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00613 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00613
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2080
KEGG Compound IDC07626
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAmodiaquine
METLIN IDNot Available
PubChem Compound2165
PDB IDCQA
ChEBI ID2674
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Harrison AC, Kitteringham NR, Clarke JB, Park BK: The mechanism of bioactivation and antigen formation of amodiaquine in the rat. Biochem Pharmacol. 1992 Apr 1;43(7):1421-30. [PubMed:1567466 ]
  2. Jewell H, Maggs JL, Harrison AC, O'Neill PM, Ruscoe JE, Park BK: Role of hepatic metabolism in the bioactivation and detoxication of amodiaquine. Xenobiotica. 1995 Feb;25(2):199-217. [PubMed:7618347 ]

Enzymes

General function:
Involved in histamine N-methyltransferase activity
Specific function:
Inactivates histamine by N-methylation. Plays an important role in degrading histamine and in regulating the airway response to histamine.
Gene Name:
HNMT
Uniprot ID:
P50135
Molecular weight:
6045.9
References
  1. Yokoyama A, Mori S, Takahashi HK, Kanke T, Wake H, Nishibori M: 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. Epub 2006 Nov 22. [PubMed:17222819 ]
  2. Nowak JZ, Zandarowska E: Effect of amodiaquine on histamine level and histamine-methyltransferase activity in the rat brain. Arch Immunol Ther Exp (Warsz). 1980;28(6):927-30. [PubMed:6789797 ]
  3. Barth H, Lorenz W, Troidl H: Effect of amodiaquine on gastric histamine methyltransferase and on histamine-stimulated gastric secretion. Br J Pharmacol. 1975 Nov;55(3):321-7. [PubMed:1203620 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Molecular weight:
60845.33
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Molecular weight:
58164.815
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular weight:
55824.275
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Li XQ, Bjorkman A, Andersson TB, Ridderstrom M, Masimirembwa CM: 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. [PubMed:11805197 ]
  3. Walsky RL, Obach RS: Validated assays for human cytochrome P450 activities. Drug Metab Dispos. 2004 Jun;32(6):647-60. [PubMed:15155557 ]