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
Accession: CHEBI:3723
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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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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
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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
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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
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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
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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
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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
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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
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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
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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
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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 8:54,552,978...54,580,375
Ensembl chr 8:54,553,165...54,580,758
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Cyp2c6
cytochrome P450, family 2, subfamily C, polypeptide 6
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
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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
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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 chr12:9,207,978...9,230,064
Ensembl chr12:9,015,383...9,285,008
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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
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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
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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
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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
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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...83,654,248
Ensembl chr13:83,649,449...83,671,443
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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
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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
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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
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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
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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
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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
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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
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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...82,534,670
Ensembl chr 8:82,517,360...82,534,549
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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
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Inhbe
inhibin subunit beta E
increases expression
ISO
Citalopram results in increased expression of INHBE mRNA
CTD
PMID:17567588
NCBI chr 7:63,176,221...63,179,209
Ensembl chr 7:63,176,219...63,179,172
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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
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Npvf
neuropeptide VF precursor
affects expression
ISO
Citalopram affects the expression of NPVF mRNA
CTD
PMID:20381503
NCBI chr 4:79,712,358...79,716,275
Ensembl chr 4:79,712,520...79,716,236
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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
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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
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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
Ensembl chr 1:181,213,368...181,215,281
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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
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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
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Prkcd
protein kinase C, delta
multiple interactions
ISO
Citalopram inhibits the reaction [convulxin results in increased phosphorylation of PRKCD protein]
CTD
PMID:30592962
NCBI chr16:5,769,217...5,799,380
Ensembl chr16:5,769,215...5,799,352
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Prl
prolactin
affects secretion increases expression multiple interactions
ISO
Citalopram affects the secretion of PRL protein Citalopram results in increased expression of PRL protein SLC6A4 polymorphism inhibits the reaction [Citalopram affects the secretion of PRL protein]
CTD
PMID:17000009 PMID:19153152
NCBI chr17:37,859,999...37,870,062
Ensembl chr17:37,860,007...37,870,062
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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
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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
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Serpina3n
serpin family A member 3N
increases expression
ISO
Citalopram results in increased expression of SERPINA3 mRNA
CTD
PMID:17567588
NCBI chr 6:123,323,623...123,331,181
Ensembl chr 6:123,323,629...123,332,433
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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
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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
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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
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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 [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
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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
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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
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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
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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
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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
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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
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