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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 ISO Citalopram results in increased expression of ABCC2 protein CTD PMID:12524417 NCBI chr 1:242,664,657...242,723,239
Ensembl chr 1:242,664,657...242,723,238
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 chr13:45,658,872...45,695,821
Ensembl chr13:45,658,872...45,695,801
JBrowse link
G Ahr aryl hydrocarbon receptor multiple interactions
decreases expression
ISO 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 6:52,234,089...52,271,568
Ensembl chr 6:52,234,089...52,271,568
JBrowse link
G Akt1 AKT serine/threonine kinase 1 multiple interactions ISO Citalopram inhibits the reaction [convulxin results in increased phosphorylation of AKT1 protein] CTD PMID:30592962 NCBI chr 6:131,713,716...131,735,319
Ensembl chr 6:131,713,720...131,733,921
JBrowse link
G Casp3 caspase 3 multiple interactions ISO Citalopram results in increased cleavage of and results in increased activity of CASP3 protein CTD PMID:10487422 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648
JBrowse link
G Cat catalase decreases expression ISO Citalopram results in decreased expression of CAT protein CTD PMID:15309392 NCBI chr 3:89,842,393...89,874,577
Ensembl chr 3:89,842,399...89,874,478
JBrowse link
G Cnr1 cannabinoid receptor 1 decreases expression EXP Citalopram results in decreased expression of CNR1 protein CTD PMID:28866072 NCBI chr 5:48,408,543...48,436,099
Ensembl chr 5:48,408,574...48,435,099
JBrowse link
G Cnr2 cannabinoid receptor 2 increases expression EXP Citalopram results in increased expression of CNR2 protein CTD PMID:28866072 NCBI chr 5:148,125,222...148,151,548
Ensembl chr 5:148,125,604...148,151,548
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 9:65,903,511...65,972,562
Ensembl chr 9:65,903,547...65,970,816
JBrowse link
G Cyp19a1 cytochrome P450, family 19, subfamily a, polypeptide 1 decreases activity ISO Citalopram results in decreased activity of CYP19A1 protein CTD PMID:26162595 NCBI chr 8:54,553,165...54,580,758
Ensembl chr 8:54,553,165...54,580,758
JBrowse link
G Cyp2c6v1 cytochrome P450, family 2, subfamily C, polypeptide 6, variant 1 decreases methylation ISO CYP2C19 protein polymorphism results in decreased methylation of Citalopram; CYP2C19 protein results in decreased methylation of Citalopram analog CTD PMID:9110356 PMID:12975335 NCBI chr 1:237,938,521...237,976,238
Ensembl chr 1:237,693,094...238,057,596
JBrowse link
G Cyp2d4 cytochrome P450, family 2, subfamily d, polypeptide 4 decreases methylation ISO CYP2D6 protein results in decreased methylation of Citalopram analog CTD PMID:9110356 NCBI chr 7:113,882,584...113,891,754
Ensembl chr 7:113,881,618...113,891,759
JBrowse link
G Cyp3a2 cytochrome P450, family 3, subfamily a, polypeptide 2 decreases methylation ISO CYP3A4 protein results in decreased methylation of Citalopram analog CTD PMID:9110356 NCBI chr12:9,207,986...9,230,038
Ensembl chr12:9,015,383...9,285,008
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 3:10,488,260...10,505,245
Ensembl chr 3:10,488,260...10,505,248
JBrowse link
G Dnmt1 DNA methyltransferase 1 affects expression EXP Citalopram affects the expression of DNMT1 mRNA CTD PMID:21682946 NCBI chr 8:19,440,611...19,486,659
Ensembl chr 8:19,440,611...19,486,659
JBrowse link
G Dnmt3a DNA methyltransferase 3 alpha affects expression EXP Citalopram affects the expression of DNMT3A mRNA CTD PMID:21682946 NCBI chr 6:26,791,517...26,902,161
Ensembl chr 6:26,822,609...26,896,687
JBrowse link
G Fabp1 fatty acid binding protein 1 increases expression ISO Citalopram results in increased expression of FABP1 mRNA CTD PMID:17567588 NCBI chr 4:103,191,015...103,194,791
Ensembl chr 4:103,191,006...103,194,788
JBrowse link
G Fcer1g Fc epsilon receptor Ig multiple interactions ISO Citalopram inhibits the reaction [convulxin promotes the reaction [FCER1G protein binds to SYK protein]] CTD PMID:30592962 NCBI chr13:83,649,447...83,654,215
Ensembl chr13:83,649,449...83,671,443
JBrowse link
G Gdpd3 glycerophosphodiester phosphodiesterase domain containing 3 increases expression ISO Citalopram results in increased expression of GDPD3 mRNA CTD PMID:17567588 NCBI chr 1:181,373,505...181,383,063
Ensembl chr 1:181,366,626...181,383,063
JBrowse link
G Gria1 glutamate ionotropic receptor AMPA type subunit 1 affects response to substance ISO GRIA1 polymorphism affects the susceptibility to Citalopram CTD PMID:19295509 NCBI chr10:41,210,713...41,527,283
Ensembl chr10:41,210,713...41,527,283
JBrowse link
G Gria3 glutamate ionotropic receptor AMPA type subunit 3 affects response to substance ISO GRIA3 polymorphism affects the susceptibility to Citalopram CTD PMID:19295509 NCBI chr  X:120,238,515...120,504,106
Ensembl chr  X:120,238,534...120,504,096
JBrowse link
G Grik2 glutamate ionotropic receptor kainate type subunit 2 affects response to substance ISO GRIK2 polymorphism affects the susceptibility to Citalopram CTD PMID:19295509 NCBI chr20:52,135,325...52,833,061
Ensembl chr20:52,133,851...52,838,375
JBrowse link
G Grin2b glutamate ionotropic receptor NMDA type subunit 2B decreases expression EXP Citalopram results in decreased expression of GRIN2B protein CTD PMID:23260230 NCBI chr 4:168,580,824...169,044,110
Ensembl chr 4:168,599,546...169,042,279
JBrowse link
G Grin3a glutamate ionotropic receptor NMDA type subunit 3A affects response to substance ISO GRIN3A polymorphism affects the susceptibility to Citalopram CTD PMID:19295509 NCBI chr 5:64,006,847...64,206,408
Ensembl chr 5:64,009,980...64,206,085
JBrowse link
G Hmgcs1 3-hydroxy-3-methylglutaryl-CoA synthase 1 increases expression ISO Citalopram results in increased expression of HMGCS1 mRNA CTD PMID:16324787 NCBI chr 2:51,649,368...51,667,100
Ensembl chr 2:51,649,497...51,667,100
JBrowse link
G Htr1b 5-hydroxytryptamine receptor 1B decreases expression EXP Citalopram results in decreased expression of HTR1B protein CTD PMID:18157704 NCBI chr 8:82,513,572...82,534,892
Ensembl chr 8:82,517,360...82,534,549
JBrowse link
G Htr2c 5-hydroxytryptamine receptor 2C affects binding ISO Citalopram binds to HTR2C protein CTD PMID:18083778 NCBI chr  X:110,640,777...110,870,288
Ensembl chr  X:110,641,153...110,870,287
JBrowse link
G Inhbe inhibin subunit beta E increases expression ISO Citalopram results in increased expression of INHBE mRNA CTD PMID:17567588 NCBI chr 7:63,177,558...63,178,983
Ensembl chr 7:63,176,219...63,179,172
JBrowse link
G Lat linker for activation of T cells multiple interactions ISO Citalopram inhibits the reaction [convulxin results in increased phosphorylation of LAT protein] CTD PMID:30592962 NCBI chr 1:180,936,536...180,941,561
Ensembl chr 1:180,936,534...180,941,578
JBrowse link
G Npvf neuropeptide VF precursor affects expression ISO Citalopram affects the expression of NPVF mRNA CTD PMID:20381503 NCBI chr 4:79,712,520...79,716,236
Ensembl chr 4:79,712,520...79,716,236
JBrowse link
G Nr3c1 nuclear receptor subfamily 3, group C, member 1 multiple interactions ISO Citalopram inhibits the reaction [Dexamethasone results in increased expression of NR3C1 mRNA] CTD PMID:24316275 NCBI chr18:31,271,681...31,393,320
Ensembl chr18:31,271,681...31,393,375
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 chr17:5,558,992...5,870,299
Ensembl chr17:5,559,043...5,869,136
JBrowse link
G Nupr1 nuclear protein 1, transcriptional regulator increases expression ISO Citalopram results in increased expression of NUPR1 mRNA CTD PMID:17567588 NCBI chr 1:181,213,292...181,215,327 JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 increases cleavage ISO Citalopram results in increased cleavage of PARP1 protein CTD PMID:10487422 NCBI chr13:92,307,593...92,339,406
Ensembl chr13:92,307,586...92,339,404
JBrowse link
G Pomc proopiomelanocortin increases expression ISO Citalopram results in increased expression of POMC protein CTD PMID:20414043 NCBI chr 6:26,939,844...26,945,666
Ensembl chr 6:26,939,837...26,945,664
JBrowse link
G Prkcd protein kinase C, delta multiple interactions ISO Citalopram inhibits the reaction [convulxin results in increased phosphorylation of PRKCD protein] CTD PMID:30592962 NCBI chr16:5,769,226...5,807,214
Ensembl chr16:5,769,215...5,799,352
JBrowse link
G Prl prolactin affects secretion
multiple interactions
increases expression
ISO 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 chr17:37,859,999...37,870,062
Ensembl chr17:37,860,007...37,870,062
JBrowse link
G S100a10 S100 calcium binding protein A10 affects expression EXP Citalopram affects the expression of S100A10 mRNA CTD PMID:21682946 NCBI chr 2:179,221,012...179,229,659
Ensembl chr 2:179,220,887...179,229,661
JBrowse link
G Scd stearoyl-CoA desaturase increases expression ISO Citalopram results in increased expression of SCD mRNA CTD PMID:16324787 NCBI chr 1:243,269,745...243,282,878
Ensembl chr 1:243,269,747...243,282,562
JBrowse link
G Serpina3n serine (or cysteine) peptidase inhibitor, clade A, member 3N increases expression ISO Citalopram results in increased expression of SERPINA3 mRNA CTD PMID:17567588 NCBI chr 6:123,323,632...123,331,166
Ensembl chr 6:123,323,629...123,332,433
JBrowse link
G Slc2a3 solute carrier family 2 member 3 decreases expression ISO Citalopram results in decreased expression of SLC2A3 mRNA CTD PMID:17567588 NCBI chr 4:155,960,944...156,026,000
Ensembl chr 4:155,960,946...156,025,472
JBrowse link
G Slc32a1 solute carrier family 32 member 1 decreases expression EXP Citalopram results in decreased expression of SLC32A1 protein CTD PMID:20707986 NCBI chr 3:147,267,373...147,271,842
Ensembl chr 3:147,267,373...147,271,844
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 chr 7:38,553,055...38,607,239
Ensembl chr 7:38,553,196...38,607,239
JBrowse link
G Slc6a3 solute carrier family 6 member 3 multiple interactions
affects response to substance
ISO 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 1:29,709,443...29,750,413
Ensembl chr 1:29,709,443...29,750,413
JBrowse link
G Slc6a4 solute carrier family 6 member 4 multiple interactions
affects response to substance
ISO 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 chr10:61,824,208...61,858,924
Ensembl chr10:61,826,123...61,858,384
JBrowse link
G Srebf1 sterol regulatory element binding transcription factor 1 multiple interactions ISO Citalopram results in increased cleavage of and results in increased activity of SREBF1 protein CTD PMID:16324787 NCBI chr10:45,007,637...45,029,650
Ensembl chr10:45,007,637...45,029,650
JBrowse link
G Srebf2 sterol regulatory element binding transcription factor 2 multiple interactions ISO Citalopram results in increased cleavage of and results in increased activity of SREBF2 protein CTD PMID:16324787 NCBI chr 7:113,663,202...113,720,850
Ensembl chr 7:113,663,202...113,720,848
JBrowse link
G Syk spleen associated tyrosine kinase multiple interactions ISO 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 chr17:12,604,615...12,678,437
Ensembl chr17:12,604,619...12,661,410
JBrowse link
G Taar1 trace-amine-associated receptor 1 multiple interactions ISO 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 1:21,517,742...21,518,740
Ensembl chr 1:21,517,258...21,532,084
JBrowse link
G Tagln transgelin decreases expression ISO Citalopram results in decreased expression of TAGLN mRNA CTD PMID:17567588 NCBI chr 8:46,224,939...46,230,413
Ensembl chr 8:46,222,472...46,230,668
JBrowse link

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  CHEBI ontology 20089
    role 20042
      biological role 20011
        xenobiotic 18699
          citalopram 50
Path 2
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  CHEBI ontology 20089
    subatomic particle 20058
      composite particle 20058
        hadron 20088
          baryon 20088
            nucleon 20088
              atomic nucleus 20088
                atom 20058
                  main group element atom 19960
                    main group molecular entity 19960
                      s-block molecular entity 19784
                        hydrogen molecular entity 19777
                          hydrides 19115
                            inorganic hydride 17901
                              pnictogen hydride 17884
                                nitrogen hydride 17773
                                  azane 17503
                                    ammonia 17521
                                      organic amino compound 17521
                                        tertiary amino compound 8860
                                          1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile 50
                                            (R)-citalopram 50
                                              citalopram 50
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