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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: Beilstein:19337;   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 19918
    role 19894
      application 19729
        NMR chemical shift reference compound 17992
          ammonia 17848
            organic amino compound 17848
              aromatic amine 15440
                aminoquinoline 1743
                  primaquine 22
Path 2
Term Annotations click to browse term
  CHEBI ontology 19918
    subatomic particle 19916
      composite particle 19916
        hadron 19916
          baryon 19916
            nucleon 19916
              atomic nucleus 19916
                atom 19916
                  main group element atom 19866
                    main group molecular entity 19866
                      s-block molecular entity 19698
                        hydrogen molecular entity 19684
                          hydrides 19159
                            inorganic hydride 18151
                              pnictogen hydride 18140
                                nitrogen hydride 18046
                                  azane 17849
                                    ammonia 17848
                                      organic amino compound 17848
                                        polyamine 9031
                                          diamine 8966
                                            N-substituted diamine 318
                                              primaquine 22
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