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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.

Term:amodiaquine
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Accession:CHEBI:2674 term browser browse the term
Definition:A quinoline having a chloro group at the 7-position and an aryl amino group at the 4-position.
Synonyms:exact_synonym: 4-[(7-chloroquinolin-4-yl)amino]-2-[(diethylamino)methyl]phenol
 related_synonym: Formula=C20H22ClN3O;   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;   SMILES=CCN(CC)Cc1cc(Nc2ccnc3cc(Cl)ccc23)ccc1O;   amodiaquina;   amodiaquinum
 xref: Beilstein:300962;   CAS:86-42-0;   DrugBank:DB00613;   Drug_Central:186;   KEGG:C07626;   KEGG:D02922;   LINCS:LSM-4042
 xref_mesh: MESH:D000655
 xref: PDBeChem:CQA;   PMID:11044276;   PMID:11971651;   PMID:17046445;   PMID:17222819;   PMID:18419816;   PMID:18855526;   PMID:19024339;   PMID:19245687;   PMID:26206402;   PMID:26597254;   PMID:26647924;   PMID:26735991;   PMID:26851641;   PMID:26900802;   PMID:26930583;   PMID:27031231;   PMID:8885219;   Patent:US2474821;   Reaxys:300962;   Wikipedia:Amodiaquine
 cyclic_relationship: is_conjugate_base_of CHEBI:131327


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amodiaquine term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Ache acetylcholinesterase multiple interactions ISO Amodiaquine analog inhibits the reaction [Paraoxon results in decreased activity of ACHE protein]; Amodiaquine inhibits the reaction [Paraoxon results in decreased activity of ACHE protein] CTD PMID:29614332 NCBI chr12:22,472,358...22,477,052
Ensembl chr12:22,472,358...22,478,753
JBrowse link
G Bax BCL2 associated X, apoptosis regulator multiple interactions
increases expression
ISO [Ketoconazole inhibits the reaction [CYP3A4 protein results in increased susceptibility to Amodiaquine]] which results in increased expression of BAX protein; [Rifampin inhibits the reaction [CYP2C8 protein results in increased susceptibility to Amodiaquine]] which results in increased expression of BAX protein
Amodiaquine results in increased expression of BAX protein
CTD PMID:31629065 NCBI chr 1:101,451,801...101,457,207
Ensembl chr 1:101,451,802...101,457,207
JBrowse link
G Bche butyrylcholinesterase multiple interactions ISO Amodiaquine inhibits the reaction [Paraoxon results in decreased activity of BCHE protein] CTD PMID:29614332 NCBI chr 2:171,104,476...171,196,186
Ensembl chr 2:171,100,140...171,196,395
JBrowse link
G Bcl2 BCL2, apoptosis regulator decreases expression
multiple interactions
ISO Amodiaquine results in decreased expression of BCL2 protein
[Ketoconazole inhibits the reaction [CYP3A4 protein results in increased susceptibility to Amodiaquine]] which results in decreased expression of BCL2 protein; [Rifampin inhibits the reaction [CYP2C8 protein results in increased susceptibility to Amodiaquine]] which results in decreased expression of BCL2 protein
CTD PMID:31629065 NCBI chr13:26,605,426...26,769,374
Ensembl chr13:26,605,426...26,769,374
JBrowse link
G Casp3 caspase 3 increases cleavage ISO Amodiaquine results in increased cleavage of CASP3 protein CTD PMID:31629065 NCBI chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
JBrowse link
G Ccnd1 cyclin D1 affects expression ISO Amodiaquine affects the expression of CCND1 protein CTD PMID:24113242 NCBI chr 1:218,090,750...218,100,447
Ensembl chr 1:218,090,750...218,100,325
JBrowse link
G Cdkn1a cyclin-dependent kinase inhibitor 1A affects expression ISO Amodiaquine affects the expression of CDKN1A mRNA; Amodiaquine affects the expression of CDKN1A protein CTD PMID:24113242 NCBI chr20:6,348,422...6,358,864
Ensembl chr20:6,351,458...6,358,864
JBrowse link
G Ctla4 cytotoxic T-lymphocyte-associated protein 4 multiple interactions ISO CTLA4 protein affects the reaction [[PDCD1 protein co-treated with TGFB1 protein] affects the reaction [Amodiaquine results in increased expression of GPT protein]]; CTLA4 protein affects the reaction [PDCD1 protein affects the reaction [[LY6C1 protein co-treated with LY6G protein] affects the reaction [Amodiaquine results in increased expression of GPT protein]]] CTD PMID:29938495 NCBI chr 9:67,699,397...67,706,068
Ensembl chr 9:67,699,379...67,706,065
JBrowse link
G Ctsb cathepsin B decreases activity ISO Amodiaquine results in decreased activity of CTSB protein CTD PMID:24113242 NCBI chr15:46,316,741...46,337,613
Ensembl chr15:46,316,741...46,337,612
JBrowse link
G Ctsd cathepsin D decreases activity ISO Amodiaquine results in decreased activity of CTSD protein CTD PMID:24113242 NCBI chr 1:215,541,570...215,553,446
Ensembl chr 1:215,541,542...215,553,451
JBrowse link
G Ctsl cathepsin L decreases activity ISO Amodiaquine results in decreased activity of CTSL protein CTD PMID:24113242 NCBI chr17:1,873,105...1,879,266
Ensembl chr17:1,872,848...1,879,279
JBrowse link
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 increases activity
multiple interactions
decreases response to substance
increases metabolic processing
ISO Amodiaquine results in increased activity of CYP1A1 protein
[CYP1A1 protein results in increased metabolism of Amodiaquine] which results in increased abundance of desethylamodiaquine
CYP1A1 protein results in decreased susceptibility to Amodiaquine
CTD PMID:12451431, PMID:31629065 NCBI chr 8:62,472,087...62,478,122
Ensembl chr 8:62,472,095...62,478,147
JBrowse link
G Cyp1a2 cytochrome P450, family 1, subfamily a, polypeptide 2 decreases activity
increases metabolic processing
multiple interactions
ISO Amodiaquine results in decreased activity of CYP1A2 protein
CYP1A2 protein results in increased metabolism of Amodiaquine
[CYP1A2 protein results in increased metabolism of Amodiaquine] which results in increased abundance of desethylamodiaquine; [Gemfibrozil results in decreased activity of CYP1A2 protein] which results in decreased metabolism of Amodiaquine; [Trimethoprim results in decreased activity of CYP1A2 protein] which results in decreased metabolism of Amodiaquine
CTD PMID:11124226, PMID:26599973, PMID:31629065 NCBI chr 8:62,451,360...62,458,244
Ensembl chr 8:62,451,329...62,458,301
JBrowse link
G Cyp1b1 cytochrome P450, family 1, subfamily b, polypeptide 1 decreases response to substance
increases metabolic processing
multiple interactions
ISO CYP1B1 protein results in decreased susceptibility to Amodiaquine
CYP1B1 protein results in increased metabolism of Amodiaquine
[CYP1B1 protein results in increased metabolism of Amodiaquine] which results in increased abundance of desethylamodiaquine
CTD PMID:31629065 NCBI chr 6:2,308,179...2,316,739
Ensembl chr 6:2,307,808...2,316,722
JBrowse link
G Cyp2b3 cytochrome P450, family 2, subfamily b, polypeptide 3 multiple interactions
increases metabolic processing
ISO [CYP2B6 protein results in increased metabolism of Amodiaquine] which results in increased abundance of desethylamodiaquine CTD PMID:31629065 NCBI chr 1:83,163,103...83,236,615
Ensembl chr 1:83,163,079...83,236,615
JBrowse link
G Cyp2c24 cytochrome P450, family 2, subfamily c, polypeptide 24 increases metabolic processing
multiple interactions
ISO CYP2C18 protein results in increased metabolism of Amodiaquine
[CYP2C18 protein results in increased metabolism of Amodiaquine] which results in increased abundance of desethylamodiaquine
CTD PMID:31629065 NCBI chr 1:258,074,797...258,139,176
Ensembl chr 1:258,074,860...258,139,176
JBrowse link
G Cyp2c6v1 cytochrome P450, family 2, subfamily C, polypeptide 6, variant 1 decreases activity
increases metabolic processing
multiple interactions
ISO Amodiaquine results in decreased activity of CYP2C19 protein
CYP2C19 protein results in increased metabolism of Amodiaquine
[CYP2C19 protein results in increased metabolism of Amodiaquine] which results in increased abundance of desethylamodiaquine
CTD PMID:11124226, PMID:31629065 NCBI chr 1:147,713,879...147,814,410
Ensembl chr 1:147,713,892...147,888,007
JBrowse link
G Cyp2c79 cytochrome P450, family 2, subfamily c, polypeptide 79 multiple interactions
increases response to substance
affects metabolic processing
increases metabolic processing
ISO [5-bromotryptamine analog results in decreased activity of CYP2C8 protein] which results in decreased metabolism of Amodiaquine; [5-chlorotryptamine analog results in decreased activity of CYP2C8 protein] which results in decreased metabolism of Amodiaquine; [5-fluorotryptamine analog results in decreased activity of CYP2C8 protein] which results in decreased metabolism of Amodiaquine; [CYP2C8 protein results in increased metabolism of Amodiaquine] which results in increased abundance of and results in increased secretion of desethylamodiaquine; [CYP2C8 protein results in increased metabolism of Amodiaquine] which results in increased abundance of desethylamodiaquine; [CYP2C8 protein results in increased metabolism of Amodiaquine] which results in increased chemical synthesis of amodiaquine quinoneimine; [CYP2C8 protein results in increased metabolism of Amodiaquine] which results in increased chemical synthesis of desethylamodiaquine; [CYP2C8 protein results in increased susceptibility to Amodiaquine] which results in increased phosphorylation of MAPK1 protein; [CYP2C8 protein results in increased susceptibility to Amodiaquine] which results in increased phosphorylation of MAPK3 protein; [CYP2C8 protein results in increased susceptibility to Amodiaquine] which results in increased phosphorylation of MAPK8 protein; [Gemfibrozil co-treated with Amodiaquine] results in decreased activity of CYP2C8 protein; [Rifampin inhibits the reaction [CYP2C8 protein results in increased susceptibility to Amodiaquine]] which results in decreased expression of BCL2 protein; [Rifampin inhibits the reaction [CYP2C8 protein results in increased susceptibility to Amodiaquine]] which results in decreased expression of MCL1 protein; [Rifampin inhibits the reaction [CYP2C8 protein results in increased susceptibility to Amodiaquine]] which results in increased expression of BAX protein; [Tryptamines analog results in decreased activity of CYP2C8 protein] which results in decreased metabolism of Amodiaquine; Felodipine inhibits the reaction [CYP2C8 protein results in increased metabolism of Amodiaquine]; Rifampin inhibits the reaction [CYP2C8 protein results in increased susceptibility to Amodiaquine]
CYP2C8 protein affects the metabolism of Amodiaquine
CTD PMID:12920490, PMID:15155557, PMID:15601807, PMID:15626586, PMID:15771232, PMID:17286541, PMID:17565714, PMID:22634058, PMID:26599973, PMID:28119166, PMID:28478157, PMID:31629065 NCBI chr 1:147,236,480...147,307,988 JBrowse link
G Cyp2d4 cytochrome P450, family 2, subfamily d, polypeptide 4 increases metabolic processing
multiple interactions
ISO CYP2D6 protein results in increased metabolism of Amodiaquine
[CYP2D6 protein results in increased metabolism of Amodiaquine] which results in increased abundance of desethylamodiaquine; [CYP2D6 protein results in increased metabolism of Amodiaquine] which results in increased chemical synthesis of amodiaquine quinoneimine
CTD PMID:28478157, PMID:31629065 NCBI chr 7:123,599,264...123,608,436
Ensembl chr 7:123,599,266...123,608,436
JBrowse link
G Cyp2e1 cytochrome P450, family 2, subfamily e, polypeptide 1 multiple interactions
increases metabolic processing
ISO [CYP2E1 protein results in increased metabolism of Amodiaquine] which results in increased abundance of desethylamodiaquine CTD PMID:31629065 NCBI chr 1:213,511,892...213,522,195
Ensembl chr 1:213,511,874...213,535,542
JBrowse link
G Cyp3a9 cytochrome P450, family 3, subfamily a, polypeptide 9 increases metabolic processing
multiple interactions
ISO CYP3A5 protein results in increased metabolism of Amodiaquine
[CYP3A5 protein results in increased metabolism of Amodiaquine] which results in increased abundance of desethylamodiaquine
CTD PMID:31629065 NCBI chr12:19,074,288...19,114,491
Ensembl chr12:19,074,583...19,114,399
JBrowse link
G E2f1 E2F transcription factor 1 affects expression ISO Amodiaquine affects the expression of E2F1 mRNA; Amodiaquine affects the expression of E2F1 protein CTD PMID:24113242 NCBI chr 3:150,062,895...150,073,721
Ensembl chr 3:150,047,826...150,073,721
JBrowse link
G Gpt glutamic--pyruvic transaminase multiple interactions ISO [LY6C1 protein co-treated with LY6G protein] affects the reaction [Amodiaquine results in increased expression of GPT protein]; [PDCD1 protein co-treated with LAG3 protein] affects the reaction [Amodiaquine results in increased expression of GPT protein]; [PDCD1 protein co-treated with TGFB1 protein] affects the reaction [Amodiaquine results in increased expression of GPT protein]; CTLA4 protein affects the reaction [[PDCD1 protein co-treated with TGFB1 protein] affects the reaction [Amodiaquine results in increased expression of GPT protein]]; CTLA4 protein affects the reaction [PDCD1 protein affects the reaction [[LY6C1 protein co-treated with LY6G protein] affects the reaction [Amodiaquine results in increased expression of GPT protein]]]; PDCD1 protein affects the reaction [[LY6C1 protein co-treated with LY6G protein] affects the reaction [Amodiaquine results in increased expression of GPT protein]] CTD PMID:29938495 NCBI chr 7:117,759,083...117,761,932
Ensembl chr 7:117,759,083...117,761,931
JBrowse link
G Lag3 lymphocyte activating 3 multiple interactions ISO [PDCD1 protein co-treated with LAG3 protein] affects the reaction [Amodiaquine results in increased expression of GPT protein] CTD PMID:29938495 NCBI chr 4:157,425,644...157,433,700
Ensembl chr 4:157,425,644...157,433,467
JBrowse link
G Mapk1 mitogen activated protein kinase 1 multiple interactions ISO [CYP2C8 protein results in increased susceptibility to Amodiaquine] which results in increased phosphorylation of MAPK1 protein; [CYP3A4 protein results in increased susceptibility to Amodiaquine] which results in increased phosphorylation of MAPK1 protein CTD PMID:31629065 NCBI chr11:88,203,863...88,273,301
Ensembl chr11:88,211,599...88,273,254
JBrowse link
G Mapk3 mitogen activated protein kinase 3 multiple interactions ISO [CYP2C8 protein results in increased susceptibility to Amodiaquine] which results in increased phosphorylation of MAPK3 protein; [CYP3A4 protein results in increased susceptibility to Amodiaquine] which results in increased phosphorylation of MAPK3 protein CTD PMID:31629065 NCBI chr 1:198,192,773...198,198,975
Ensembl chr 1:198,192,773...198,198,975
JBrowse link
G Mapk8 mitogen-activated protein kinase 8 multiple interactions ISO [CYP2C8 protein results in increased susceptibility to Amodiaquine] which results in increased phosphorylation of MAPK8 protein; [CYP3A4 protein results in increased susceptibility to Amodiaquine] which results in increased phosphorylation of MAPK8 protein CTD PMID:31629065 NCBI chr16:9,620,854...9,709,342
Ensembl chr16:9,625,177...9,709,347
JBrowse link
G Mcl1 MCL1 apoptosis regulator, BCL2 family member decreases expression
multiple interactions
ISO Amodiaquine results in decreased expression of MCL1 protein
[Ketoconazole inhibits the reaction [CYP3A4 protein results in increased susceptibility to Amodiaquine]] which results in decreased expression of MCL1 protein; [Rifampin inhibits the reaction [CYP2C8 protein results in increased susceptibility to Amodiaquine]] which results in decreased expression of MCL1 protein
CTD PMID:31629065 NCBI chr 2:197,786,212...197,788,992 JBrowse link
G Mpo myeloperoxidase affects response to substance ISO MPO protein affects the susceptibility to Amodiaquine CTD PMID:24588327 NCBI chr10:75,087,892...75,098,260
Ensembl chr10:75,087,892...75,098,260
JBrowse link
G Nqo2 N-ribosyldihydronicotinamide:quinone reductase 2 multiple interactions ISO Amodiaquine inhibits the reaction [NQO2 protein results in increased reduction of Vitamin K 3] CTD PMID:29281794 NCBI chr17:32,131,847...32,158,559
Ensembl chr17:32,132,347...32,158,538
JBrowse link
G Pdcd1 programmed cell death 1 multiple interactions ISO [PDCD1 protein co-treated with LAG3 protein] affects the reaction [Amodiaquine results in increased expression of GPT protein]; [PDCD1 protein co-treated with TGFB1 protein] affects the reaction [Amodiaquine results in increased expression of GPT protein]; CTLA4 protein affects the reaction [[PDCD1 protein co-treated with TGFB1 protein] affects the reaction [Amodiaquine results in increased expression of GPT protein]]; CTLA4 protein affects the reaction [PDCD1 protein affects the reaction [[LY6C1 protein co-treated with LY6G protein] affects the reaction [Amodiaquine results in increased expression of GPT protein]]]; PDCD1 protein affects the reaction [[LY6C1 protein co-treated with LY6G protein] affects the reaction [Amodiaquine results in increased expression of GPT protein]] CTD PMID:29938495 NCBI chr 9:101,305,742...101,319,937
Ensembl chr 9:101,307,764...101,319,845
JBrowse link
G Rb1 RB transcriptional corepressor 1 affects phosphorylation ISO Amodiaquine affects the phosphorylation of RB1 protein CTD PMID:24113242 NCBI chr15:55,081,582...55,209,060
Ensembl chr15:55,083,140...55,209,342
JBrowse link
G Tgfb1 transforming growth factor, beta 1 multiple interactions ISO [PDCD1 protein co-treated with TGFB1 protein] affects the reaction [Amodiaquine results in increased expression of GPT protein]; CTLA4 protein affects the reaction [[PDCD1 protein co-treated with TGFB1 protein] affects the reaction [Amodiaquine results in increased expression of GPT protein]] CTD PMID:29938495 NCBI chr 1:82,480,875...82,497,196
Ensembl chr 1:82,480,195...82,497,199
JBrowse link
G Tp53 tumor protein p53 increases activity
affects expression
ISO Amodiaquine results in increased activity of TP53 protein
Amodiaquine affects the expression of TP53 protein
CTD PMID:12082016, PMID:24113242 NCBI chr10:56,186,299...56,198,449
Ensembl chr10:56,187,020...56,198,449
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19792
    role 19738
      application 19385
        pro-agent 8831
          prodrug 8620
            amodiaquine 34
              amodiaquine hydrochloride 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19792
    subatomic particle 19788
      composite particle 19788
        hadron 19788
          baryon 19788
            nucleon 19788
              atomic nucleus 19788
                atom 19788
                  main group element atom 19675
                    main group molecular entity 19675
                      s-block molecular entity 19420
                        hydrogen molecular entity 19411
                          hydrides 18460
                            inorganic hydride 17430
                              pnictogen hydride 17402
                                nitrogen hydride 17245
                                  azane 16962
                                    ammonia 16961
                                      organic amino compound 16960
                                        aromatic amine 13634
                                          aminoquinoline 1683
                                            amodiaquine 34
                                              amodiaquine hydrochloride 0
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