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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:citalopram
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Accession:CHEBI:3723 term browser browse the term
Definition:A racemate comprising equimolar amounts of (R)-citalopram and its enantiomer, escitalopram. It is used as an antidepressant, although only escitalopram is active.
Synonyms:exact_synonym: rac-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile
 related_synonym: 1,3-dihydro-1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-5-isobenzofurancarbonitrile;   1-(3-(dimethylamino)propyl)-1-(p-fluorophenyl)-5-phthalancarbonitrile;   Cipram;   Citadur;   Formula=C20H21FN2O;   Lu 10-171;   Nitalapram;   citalopramum
 xref: Beilstein:1397373;   CAS:59729-33-8;   DrugBank:DB00215;   HMDB:HMDB0005038;   KEGG:C07572;   KEGG:D07704
 xref_mesh: MESH:D015283
 xref: PMID:11336616;   PMID:18213744;   PMID:18219053;   PMID:19747949;   PMID:20825390;   Patent:DE2657013;   Patent:EP0171943;   Patent:EP1506963;   Patent:US4136193;   Reaxys:1397373;   Wikipedia:Citalopram


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citalopram term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G ABCC2 ATP binding cassette subfamily C member 2 increases expression EXP Citalopram results in increased expression of ABCC2 protein CTD PMID:12524417 NCBI chr10:99,782,640...99,852,594
Ensembl chr10:99,782,640...99,852,594 		JBrowse link
G ADORA1 adenosine A1 receptor multiple interactions ISO [Citalopram co-treated with Caffeine deficiency] results in increased expression of ADORA1 mRNA; [Citalopram co-treated with Caffeine] results in decreased expression of ADORA1 mRNA CTD PMID:29107002 NCBI chr 1:203,127,726...203,167,405
Ensembl chr 1:203,090,654...203,167,405 		JBrowse link
G AHR aryl hydrocarbon receptor multiple interactions
decreases expression		 EXP Citalopram inhibits the reaction [Tetrachlorodibenzodioxin results in increased expression of AHR mRNA]
Citalopram results in decreased expression of AHR mRNA		 CTD PMID:24316275 NCBI chr 7:17,298,652...17,346,147
Ensembl chr 7:16,916,359...17,346,152 		JBrowse link
G AKT1 AKT serine/threonine kinase 1 multiple interactions EXP Citalopram inhibits the reaction [convulxin results in increased phosphorylation of AKT1 protein] CTD PMID:30592962 NCBI chr14:104,769,349...104,795,748
Ensembl chr14:104,769,349...104,795,759 		JBrowse link
G CASP3 caspase 3 multiple interactions EXP Citalopram results in increased cleavage of and results in increased activity of CASP3 protein CTD PMID:10487422 NCBI chr 4:184,627,696...184,649,447
Ensembl chr 4:184,627,696...184,650,062 		JBrowse link
G CAT catalase decreases expression EXP Citalopram results in decreased expression of CAT protein CTD PMID:15309392 NCBI chr11:34,438,934...34,472,060
Ensembl chr11:34,438,934...34,472,060 		JBrowse link
G CNR1 cannabinoid receptor 1 decreases expression ISO Citalopram results in decreased expression of CNR1 protein CTD PMID:28866072 NCBI chr 6:88,139,864...88,167,349
Ensembl chr 6:88,139,864...88,166,347 		JBrowse link
G CNR2 cannabinoid receptor 2 increases expression ISO Citalopram results in increased expression of CNR2 protein CTD PMID:28866072 NCBI chr 1:23,870,515...23,913,362
Ensembl chr 1:23,870,515...23,913,362 		JBrowse link
G CREB1 cAMP responsive element binding protein 1 multiple interactions ISO Citalopram results in decreased phosphorylation of and results in decreased activity of CREB1 protein CTD PMID:20122921 NCBI chr 2:207,529,962...207,605,988
Ensembl chr 2:207,529,737...207,605,988 		JBrowse link
G CYP19A1 cytochrome P450 family 19 subfamily A member 1 decreases activity EXP Citalopram results in decreased activity of CYP19A1 protein CTD PMID:26162595 NCBI chr15:51,208,057...51,338,596
Ensembl chr15:51,208,057...51,338,601 		JBrowse link
G CYP2C19 cytochrome P450 family 2 subfamily C member 19 decreases methylation EXP CYP2C19 protein polymorphism results in decreased methylation of Citalopram; CYP2C19 protein results in decreased methylation of Citalopram analog CTD PMID:9110356 PMID:12975335 NCBI chr10:94,762,681...94,855,547
Ensembl chr10:94,762,681...94,855,547 		JBrowse link
G CYP2D6 cytochrome P450 family 2 subfamily D member 6 decreases methylation EXP CYP2D6 protein results in decreased methylation of Citalopram analog CTD PMID:9110356 NCBI chr22:42,126,499...42,130,810
Ensembl chr22:42,126,499...42,130,865 		JBrowse link
G CYP3A4 cytochrome P450 family 3 subfamily A member 4 decreases methylation EXP CYP3A4 protein results in decreased methylation of Citalopram analog CTD PMID:9110356 NCBI chr 7:99,756,967...99,784,184
Ensembl chr 7:99,756,960...99,784,248 		JBrowse link
G DBH dopamine beta-hydroxylase multiple interactions ISO DBH protein promotes the reaction [Citalopram results in increased abundance of Serotonin] CTD PMID:15148402 NCBI chr 9:133,636,363...133,659,329
Ensembl chr 9:133,636,363...133,659,329 		JBrowse link
G DNMT1 DNA methyltransferase 1 affects expression ISO Citalopram affects the expression of DNMT1 mRNA CTD PMID:21682946 NCBI chr19:10,133,346...10,194,953
Ensembl chr19:10,133,342...10,231,286 		JBrowse link
G DNMT3A DNA methyltransferase 3 alpha affects expression ISO Citalopram affects the expression of DNMT3A mRNA CTD PMID:21682946 NCBI chr 2:25,227,874...25,342,590
Ensembl chr 2:25,227,855...25,342,590 		JBrowse link
G FABP1 fatty acid binding protein 1 increases expression EXP Citalopram results in increased expression of FABP1 mRNA CTD PMID:17567588 NCBI chr 2:88,122,982...88,128,062
Ensembl chr 2:88,122,982...88,128,062 		JBrowse link
G FCER1G Fc epsilon receptor Ig multiple interactions EXP Citalopram inhibits the reaction [convulxin promotes the reaction [FCER1G protein binds to SYK protein]] CTD PMID:30592962 NCBI chr 1:161,215,295...161,219,245
Ensembl chr 1:161,215,234...161,220,699 		JBrowse link
G GDPD3 glycerophosphodiester phosphodiesterase domain containing 3 increases expression EXP Citalopram results in increased expression of GDPD3 mRNA CTD PMID:17567588 NCBI chr16:30,104,810...30,113,537
Ensembl chr16:30,104,810...30,113,537 		JBrowse link
G GRIA1 glutamate ionotropic receptor AMPA type subunit 1 affects response to substance EXP GRIA1 polymorphism affects the susceptibility to Citalopram CTD PMID:19295509 NCBI chr 5:153,489,615...153,813,869
Ensembl chr 5:153,489,615...153,813,869 		JBrowse link
G GRIA3 glutamate ionotropic receptor AMPA type subunit 3 affects response to substance EXP GRIA3 polymorphism affects the susceptibility to Citalopram CTD PMID:19295509 NCBI chr  X:123,184,278...123,490,915
Ensembl chr  X:123,184,153...123,490,915 		JBrowse link
G GRIK2 glutamate ionotropic receptor kainate type subunit 2 affects response to substance EXP GRIK2 polymorphism affects the susceptibility to Citalopram CTD PMID:19295509 NCBI chr 6:101,393,708...102,070,083
Ensembl chr 6:100,962,701...102,081,622 		JBrowse link
G GRIN2B glutamate ionotropic receptor NMDA type subunit 2B decreases expression ISO Citalopram results in decreased expression of GRIN2B protein CTD PMID:23260230 NCBI chr12:13,537,337...13,982,134
Ensembl chr12:13,437,942...13,982,002 		JBrowse link
G GRIN3A glutamate ionotropic receptor NMDA type subunit 3A affects response to substance EXP GRIN3A polymorphism affects the susceptibility to Citalopram CTD PMID:19295509 NCBI chr 9:101,569,352...101,738,647
Ensembl chr 9:101,569,352...101,738,647 		JBrowse link
G HMGCS1 3-hydroxy-3-methylglutaryl-CoA synthase 1 increases expression EXP Citalopram results in increased expression of HMGCS1 mRNA CTD PMID:16324787 NCBI chr 5:43,287,470...43,313,412
Ensembl chr 5:43,287,470...43,313,512 		JBrowse link
G HTR1B 5-hydroxytryptamine receptor 1B decreases expression ISO Citalopram results in decreased expression of HTR1B protein CTD PMID:18157704 NCBI chr 6:77,460,924...77,463,491
Ensembl chr 6:77,460,924...77,463,491 		JBrowse link
G HTR2C 5-hydroxytryptamine receptor 2C affects binding EXP Citalopram binds to HTR2C protein CTD PMID:18083778 NCBI chr  X:114,584,086...114,910,061
Ensembl chr  X:114,584,078...114,910,061 		JBrowse link
G INHBE inhibin subunit beta E increases expression EXP Citalopram results in increased expression of INHBE mRNA CTD PMID:17567588 NCBI chr12:57,455,307...57,458,025
Ensembl chr12:57,452,323...57,459,280 		JBrowse link
G LAT linker for activation of T cells multiple interactions EXP Citalopram inhibits the reaction [convulxin results in increased phosphorylation of LAT protein] CTD PMID:30592962 NCBI chr16:28,984,803...28,990,784
Ensembl chr16:28,984,826...28,990,784 		JBrowse link
G NPVF neuropeptide VF precursor affects expression ISO Citalopram affects the expression of NPVF mRNA CTD PMID:20381503 NCBI chr 7:25,224,570...25,228,486
Ensembl chr 7:25,224,570...25,228,486 		JBrowse link
G NR3C1 nuclear receptor subfamily 3 group C member 1 multiple interactions EXP Citalopram inhibits the reaction [Dexamethasone results in increased expression of NR3C1 mRNA] CTD PMID:24316275 NCBI chr 5:143,277,931...143,435,512
Ensembl chr 5:143,277,931...143,435,512 		JBrowse link
G NTRK2 neurotrophic receptor tyrosine kinase 2 multiple interactions ISO Citalopram results in increased phosphorylation of and results in increased activity of NTRK2 protein CTD PMID:21666748 NCBI chr 9:84,668,522...85,027,054
Ensembl chr 9:84,668,375...85,095,751 		JBrowse link
G NUPR1 nuclear protein 1, transcriptional regulator increases expression EXP Citalopram results in increased expression of NUPR1 mRNA CTD PMID:17567588 NCBI chr16:28,532,708...28,538,974
Ensembl chr16:28,532,708...28,539,008 		JBrowse link
G PARP1 poly(ADP-ribose) polymerase 1 increases cleavage EXP Citalopram results in increased cleavage of PARP1 protein CTD PMID:10487422 NCBI chr 1:226,360,691...226,408,093
Ensembl chr 1:226,360,210...226,408,154 		JBrowse link
G POMC proopiomelanocortin increases expression EXP Citalopram results in increased expression of POMC protein CTD PMID:20414043 NCBI chr 2:25,160,860...25,168,580
Ensembl chr 2:25,160,853...25,168,903 		JBrowse link
G PRKCD protein kinase C delta multiple interactions EXP Citalopram inhibits the reaction [convulxin results in increased phosphorylation of PRKCD protein] CTD PMID:30592962 NCBI chr 3:53,161,209...53,192,717
Ensembl chr 3:53,156,009...53,192,717 		JBrowse link
G PRL prolactin affects secretion
multiple interactions
increases expression		 EXP Citalopram affects the secretion of PRL protein
SLC6A4 polymorphism inhibits the reaction [Citalopram affects the secretion of PRL protein]
Citalopram results in increased expression of PRL protein		 CTD PMID:17000009 PMID:19153152 NCBI chr 6:22,287,246...22,302,835
Ensembl chr 6:22,287,244...22,302,826 		JBrowse link
G S100A10 S100 calcium binding protein A10 affects expression ISO Citalopram affects the expression of S100A10 mRNA CTD PMID:21682946 NCBI chr 1:151,982,915...151,993,859
Ensembl chr 1:151,982,915...151,993,859 		JBrowse link
G SCD stearoyl-CoA desaturase increases expression EXP Citalopram results in increased expression of SCD mRNA CTD PMID:16324787 NCBI chr10:100,347,233...100,364,826
Ensembl chr10:100,347,233...100,364,826 		JBrowse link
G SERPINA3 serpin family A member 3 increases expression EXP Citalopram results in increased expression of SERPINA3 mRNA CTD PMID:17567588 NCBI chr14:94,612,391...94,624,053
Ensembl chr14:94,612,384...94,624,055 		JBrowse link
G SLC2A3 solute carrier family 2 member 3 decreases expression EXP Citalopram results in decreased expression of SLC2A3 mRNA CTD PMID:17567588 NCBI chr12:7,919,230...7,936,187
Ensembl chr12:7,919,230...8,019,007 		JBrowse link
G SLC32A1 solute carrier family 32 member 1 decreases expression ISO Citalopram results in decreased expression of SLC32A1 protein CTD PMID:20707986 NCBI chr20:38,724,486...38,729,372
Ensembl chr20:38,724,486...38,729,372 		JBrowse link
G SLC6A15 solute carrier family 6 member 15 multiple interactions ISO [Citalopram co-treated with Caffeine] results in decreased expression of SLC6A15 mRNA CTD PMID:29107002 NCBI chr12:84,859,491...84,912,799
Ensembl chr12:84,859,491...84,913,629 		JBrowse link
G SLC6A3 solute carrier family 6 member 3 multiple interactions
affects response to substance		 ISO
EXP		 SLC6A3 mutant form promotes the reaction [Citalopram results in increased abundance of Dopamine]
[SLC6A3 protein polymorphism affects the susceptibility to Citalopram] which affects the uptake of Dopamine; Citalopram inhibits the reaction [SLC6A3 protein results in increased uptake of Dopamine]		 CTD PMID:14691264 PMID:31009648 NCBI chr 5:1,392,794...1,445,440
Ensembl chr 5:1,392,794...1,445,440 		JBrowse link
G SLC6A4 solute carrier family 6 member 4 multiple interactions
affects response to substance		 EXP Citalopram binds to and results in decreased activity of SLC6A4 protein; Citalopram inhibits the reaction [convulxin promotes the reaction [SLC6A4 protein binds to SYK protein]]; Citalopram inhibits the reaction [SLC6A4 protein promotes the reaction [Dopamine results in increased activity of TAAR1 protein]]; Citalopram inhibits the reaction [SLC6A4 protein promotes the reaction [Methamphetamine results in increased activity of TAAR1 protein]]; Citalopram inhibits the reaction [SLC6A4 protein promotes the reaction [Octopamine results in increased activity of TAAR1 protein]]; Citalopram inhibits the reaction [SLC6A4 protein promotes the reaction [tryptamine results in increased activity of TAAR1 protein]]; Citalopram inhibits the reaction [SLC6A4 protein promotes the reaction [Tyramine results in increased activity of TAAR1 protein]]; SLC6A4 polymorphism inhibits the reaction [Citalopram affects the secretion of PRL protein]
SLC6A4 promoter polymorphism affects the susceptibility to Citalopram		 CTD PMID:14624186 PMID:16272152 PMID:17000009 PMID:17234900 PMID:30592962 NCBI chr17:30,194,319...30,235,697
Ensembl chr17:30,194,319...30,236,002 		JBrowse link
G SREBF1 sterol regulatory element binding transcription factor 1 multiple interactions EXP Citalopram results in increased cleavage of and results in increased activity of SREBF1 protein CTD PMID:16324787 NCBI chr17:17,811,334...17,836,986
Ensembl chr17:17,810,399...17,837,002 		JBrowse link
G SREBF2 sterol regulatory element binding transcription factor 2 multiple interactions EXP Citalopram results in increased cleavage of and results in increased activity of SREBF2 protein CTD PMID:16324787 NCBI chr22:41,833,105...41,907,305
Ensembl chr22:41,833,105...41,907,306 		JBrowse link
G SYK spleen associated tyrosine kinase multiple interactions EXP Citalopram inhibits the reaction [convulxin promotes the reaction [FCER1G protein binds to SYK protein]]; Citalopram inhibits the reaction [convulxin promotes the reaction [SLC6A4 protein binds to SYK protein]]; Citalopram inhibits the reaction [convulxin results in increased phosphorylation of SYK protein] CTD PMID:30592962 NCBI chr 9:90,801,600...90,898,549
Ensembl chr 9:90,801,787...90,898,549 		JBrowse link
G TAAR1 trace amine associated receptor 1 multiple interactions EXP Citalopram inhibits the reaction [SLC6A4 protein promotes the reaction [Dopamine results in increased activity of TAAR1 protein]]; Citalopram inhibits the reaction [SLC6A4 protein promotes the reaction [Methamphetamine results in increased activity of TAAR1 protein]]; Citalopram inhibits the reaction [SLC6A4 protein promotes the reaction [Octopamine results in increased activity of TAAR1 protein]]; Citalopram inhibits the reaction [SLC6A4 protein promotes the reaction [tryptamine results in increased activity of TAAR1 protein]]; Citalopram inhibits the reaction [SLC6A4 protein promotes the reaction [Tyramine results in increased activity of TAAR1 protein]] CTD PMID:17234900 NCBI chr 6:132,643,312...132,659,182
Ensembl chr 6:132,643,312...132,659,182 		JBrowse link
G TAGLN transgelin decreases expression EXP Citalopram results in decreased expression of TAGLN mRNA CTD PMID:17567588 NCBI chr11:117,199,294...117,207,465
Ensembl chr11:117,199,370...117,207,464 		JBrowse link
Term paths to the root
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Term Annotations click to browse term
  CHEBI ontology 26050
    role 25966
      biological role 25945
        xenobiotic 20379
          citalopram 50
Path 2
Term Annotations click to browse term
  CHEBI ontology 26050
    subatomic particle 26025
      composite particle 26025
        hadron 26025
          baryon 26025
            nucleon 26025
              atomic nucleus 26025
                atom 26025
                  main group element atom 25850
                    main group molecular entity 25850
                      s-block molecular entity 25171
                        hydrogen molecular entity 24769
                          hydrides 22979
                            inorganic hydride 20497
                              pnictogen hydride 20438
                                nitrogen hydride 20214
                                  azane 19958
                                    ammonia 19957
                                      organic amino compound 19957
                                        tertiary amino compound 10438
                                          1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile 50
                                            (R)-citalopram 50
                                              citalopram 50
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