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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:primaquine
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Accession:CHEBI:8405 term browser browse the term
Definition:An N-substituted diamine that is pentane-1,4-diamine substituted by a 6-methoxyquinolin-8-yl group at the N(4) position. It is a drug used in the treatment of malaria and Pneumocystis pneumonia.
Synonyms:exact_synonym: N(4)-(6-methoxyquinolin-8-yl)pentane-1,4-diamine
 related_synonym: 6-Methoxy-8-(4-amino-1-methylbutylamino)quinoline;   8-((4-Amino-1-methylbutyl)amino)-6-methoxyquinoline;   8-(4-Amino-1-methylbutylamino)-6-methoxyquinoline;   Formula=C15H21N3O;   InChI=1S/C15H21N3O/c1-11(5-3-7-16)18-14-10-13(19-2)9-12-6-4-8-17-15(12)14/h4,6,8-11,18H,3,5,7,16H2,1-2H3;   InChIKey=INDBQLZJXZLFIT-UHFFFAOYSA-N;   Neo-Quipenyl;   Primachin;   Primachinum;   Primaquin;   SMILES=COc1cc(NC(C)CCCN)c2ncccc2c1;   primaquina;   primaquinum
 alt_id: CHEBI:110389
 xref: CAS:90-34-6;   DrugBank:DB01087;   Drug_Central:2266;   Gmelin:751542;   HMDB:HMDB0015219;   KEGG:C07627;   KEGG:D08420;   LINCS:LSM-1649
 xref_mesh: MESH:D011319
 xref: PMID:10928454;   PMID:11303037;   PMID:12036132;   PMID:14917959;   PMID:15494911;   PMID:16537060;   PMID:17253504;   PMID:18930565;   PMID:19114311;   PMID:2210868;   PMID:28279180;   PMID:28289025;   PMID:8920977;   Reaxys:19337;   Wikipedia:Primaquine


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primaquine term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcb11 ATP binding cassette subfamily B member 11 decreases activity ISO Primaquine results in decreased activity of ABCB11 protein CTD PMID:20829430 NCBI chr 3:54,016,854...54,112,797
Ensembl chr 3:54,017,127...54,112,730 		JBrowse link
G Abcb4 ATP binding cassette subfamily B member 4 decreases activity ISO Primaquine results in decreased activity of ABCB4 protein CTD PMID:28437613 NCBI chr 4:25,150,998...25,209,489
Ensembl chr 4:25,151,953...25,209,202 		JBrowse link
G Ahr aryl hydrocarbon receptor multiple interactions
increases activity		 ISO
EXP		 Primaquine binds to and results in increased activity of AHR protein
[Primaquine results in increased activity of AHR protein] which results in increased expression of CYP1A1 mRNA; AHR protein promotes the reaction [Primaquine results in increased expression of CYP1A1 protein]; Primaquine binds to and results in increased activity of AHR protein; Primaquine inhibits the reaction [Tetrachlorodibenzodioxin binds to AHR protein]		 CTD PMID:11259546 PMID:14742684 NCBI chr 6:52,234,089...52,271,568
Ensembl chr 6:52,234,089...52,271,568 		JBrowse link
G Cftr CF transmembrane conductance regulator multiple interactions EXP Primaquine inhibits the reaction [Cyclic AMP affects the localization of and results in increased activity of CFTR protein] CTD PMID:12529251 NCBI chr 4:46,561,269...46,728,759
Ensembl chr 4:46,560,885...46,728,756 		JBrowse link
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 increases activity
increases expression
multiple interactions
decreases degradation
increases response to substance
decreases activity		 ISO
EXP		 Primaquine results in increased activity of CYP1A1 promoter; Primaquine results in increased activity of CYP1A1 protein
Primaquine results in increased expression of CYP1A1 mRNA; Primaquine results in increased expression of CYP1A1 protein
[Primaquine results in increased activity of AHR protein] which results in increased expression of CYP1A1 mRNA; AHR protein promotes the reaction [Primaquine results in increased expression of CYP1A1 protein]; Primaquine binds to and results in decreased activity of CYP1A1 protein
Primaquine results in decreased degradation of CYP1A1 protein
CYP1A1 protein results in increased susceptibility to Primaquine
Primaquine results in decreased activity of CYP1A1 protein		 CTD PMID:9860486 PMID:11259546 PMID:12451431 PMID:12623754 PMID:14742684 More... NCBI chr 8:58,096,021...58,102,130
Ensembl chr 8:58,096,077...58,102,125 		JBrowse link
G Cyp1a2 cytochrome P450, family 1, subfamily a, polypeptide 2 increases activity
affects metabolic processing
increases expression
multiple interactions
increases metabolic processing		 ISO Primaquine results in increased activity of CYP1A2 promoter
CYP1A2 protein affects the metabolism of Primaquine
Primaquine results in increased expression of CYP1A2 mRNA
[CYP1A2 protein results in increased expression of HBG2 protein] which affects the susceptibility to Primaquine
CYP1A2 protein results in increased metabolism of Primaquine		 CTD PMID:12451431 PMID:12623754 PMID:12920490 PMID:17954527 PMID:18502397 More... NCBI chr 8:58,075,367...58,082,255
Ensembl chr 8:58,075,367...58,082,312 		JBrowse link
G Cyp1b1 cytochrome P450, family 1, subfamily b, polypeptide 1 increases expression
decreases activity		 ISO Primaquine results in increased expression of CYP1B1 mRNA
Primaquine results in decreased activity of CYP1B1 protein		 CTD PMID:12623754 PMID:33814510 NCBI chr 6:15,342,312...15,350,886
Ensembl chr 6:15,342,344...15,350,917 		JBrowse link
G Cyp2b3 cytochrome P450, family 2, subfamily b, polypeptide 3 multiple interactions
increases metabolic processing		 ISO [CYP2B6 protein results in increased expression of HBG2 protein] which affects the susceptibility to Primaquine
CYP2B6 protein results in increased metabolism of Primaquine		 CTD PMID:19616568 NCBI chr 1:81,652,762...81,732,153
Ensembl chr 1:81,652,787...81,732,143 		JBrowse link
G Cyp2d4 cytochrome P450, family 2, subfamily d, polypeptide 4 multiple interactions
affects metabolic processing
increases metabolic processing
increases response to substance		 ISO [CYP2D6 protein results in increased expression of HBG2 protein] which affects the susceptibility to Primaquine
CYP2D6 protein affects the metabolism of Primaquine
CYP2D6 protein results in increased metabolism of Primaquine
CYP2D6 protein results in increased susceptibility to Primaquine		 CTD PMID:12920490 PMID:19616568 PMID:26477383 NCBI chr 7:113,882,584...113,891,754
Ensembl chr 7:113,881,618...113,891,759 		JBrowse link
G Cyp2e1 cytochrome P450, family 2, subfamily e, polypeptide 1 increases metabolic processing
multiple interactions		 ISO CYP2E1 protein results in increased metabolism of Primaquine
[CYP2E1 protein results in increased expression of HBG2 protein] which affects the susceptibility to Primaquine		 CTD PMID:19616568 NCBI chr 1:195,840,330...195,850,728
Ensembl chr 1:195,840,058...195,864,023 		JBrowse link
G Cyp3a2 cytochrome P450, family 3, subfamily a, polypeptide 2 increases metabolic processing
multiple interactions		 ISO CYP3A4 protein results in increased metabolism of Primaquine
[CYP3A4 protein results in increased expression of HBG2 protein] which affects the susceptibility to Primaquine		 CTD PMID:19616568 NCBI chr12:9,207,978...9,230,064
Ensembl chr12:9,015,383...9,285,008 		JBrowse link
G Egf epidermal growth factor multiple interactions ISO Primaquine inhibits the reaction [EGF protein results in increased uptake of and results in increased degradation of EGFR protein] CTD PMID:23125191 NCBI chr 2:218,219,408...218,302,359
Ensembl chr 2:218,219,415...218,302,064 		JBrowse link
G Egfr epidermal growth factor receptor multiple interactions ISO Primaquine inhibits the reaction [EGF protein results in increased uptake of and results in increased degradation of EGFR protein] CTD PMID:23125191 NCBI chr14:91,176,979...91,349,722
Ensembl chr14:91,177,067...91,344,382 		JBrowse link
G Ereg epiregulin increases expression ISO Primaquine results in increased expression of EREG mRNA CTD PMID:32816093 NCBI chr14:17,027,287...17,041,062
Ensembl chr14:17,027,287...17,041,062 		JBrowse link
G F3 coagulation factor III, tissue factor increases expression ISO Primaquine results in increased expression of F3 protein CTD PMID:25569083 NCBI chr 2:209,827,061...209,838,666
Ensembl chr 2:209,826,959...209,838,668 		JBrowse link
G G6pd glucose-6-phosphate dehydrogenase affects response to substance
decreases response to substance		 ISO G6PD protein affects the susceptibility to Primaquine
G6PD protein results in decreased susceptibility to Primaquine		 CTD PMID:19616568 PMID:22330256 NCBI chr  X:152,201,081...152,220,863
Ensembl chr  X:152,201,098...152,220,801 		JBrowse link
G Il1a interleukin 1 alpha decreases expression ISO Primaquine results in decreased expression of IL1A mRNA CTD PMID:32816093 NCBI chr 3:116,526,601...116,537,055
Ensembl chr 3:116,526,604...116,536,822 		JBrowse link
G Il1b interleukin 1 beta decreases expression ISO Primaquine results in decreased expression of IL1B mRNA CTD PMID:32816093 NCBI chr 3:116,577,005...116,583,386
Ensembl chr 3:116,577,010...116,583,415 		JBrowse link
G Il24 interleukin 24 decreases expression ISO Primaquine results in decreased expression of IL24 mRNA CTD PMID:32816093 NCBI chr13:42,353,089...42,358,487
Ensembl chr13:42,353,090...42,358,487 		JBrowse link
G Nqo2 N-ribosyldihydronicotinamide:quinone dehydrogenase 2 multiple interactions ISO Primaquine binds to and results in decreased activity of NQO2 protein CTD PMID:15078100 NCBI chr17:30,909,482...30,938,725
Ensembl chr17:30,909,187...30,938,320 		JBrowse link
G Slc22a2 solute carrier family 22 member 2 multiple interactions ISO Primaquine inhibits the reaction [SLC22A2 protein results in increased uptake of 4-(4-dimethylaminostyryl)-1-methylpyridinium] CTD PMID:21599003 NCBI chr 1:48,121,061...48,163,268
Ensembl chr 1:48,121,061...48,163,268 		JBrowse link
G Slpi secretory leukocyte peptidase inhibitor increases expression ISO Primaquine results in increased expression of SLPI mRNA CTD PMID:32816093 NCBI chr 3:153,082,208...153,084,457
Ensembl chr 3:153,082,369...153,084,453 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19899
    role 19869
      application 19713
        NMR chemical shift reference compound 18091
          ammonia 17890
            organic amino compound 17890
              aromatic amine 15506
                aminoquinoline 1753
                  primaquine 22
Path 2
Term Annotations click to browse term
  CHEBI ontology 19899
    subatomic particle 19897
      composite particle 19897
        hadron 19897
          baryon 19897
            nucleon 19897
              atomic nucleus 19897
                atom 19897
                  main group element atom 19835
                    main group molecular entity 19835
                      s-block molecular entity 19669
                        hydrogen molecular entity 19651
                          hydrides 19162
                            inorganic hydride 18183
                              pnictogen hydride 18173
                                nitrogen hydride 18086
                                  azane 17891
                                    ammonia 17890
                                      organic amino compound 17890
                                        polyamine 9030
                                          diamine 8965
                                            N-substituted diamine 320
                                              primaquine 22
paths to the root