Drug Information
| General Information | ||||||
|---|---|---|---|---|---|---|
| Drug ID |
DR00319
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| Drug Name |
Citalopram
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| Synonyms |
1,3-Dihydro-1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-5-isobenzofurancarbonitrile; 1,3-dihydro[3,4]benzofuran-5-carbonitrile; 1-(3-(Dimethylamino)propyl)-1-(p-fluorophenyl)-5-phthalancarbonitrile; 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile; 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-carbonitrile; AE-641/00603021; Akarin; Akarin (TN); Celapram; Celapram (TN); Celexa; Celexa (TN); Celius; Celius (TN); Ciazil; Ciazil (TN); Cilift; Cilift (TN); Cipram; Cipram (TN); Cipramil (TN); Ciprapine; Ciprapine (TN); Citabax; Citabax (TN); Citadur; Citadur (TN); Citalec; Citalec (TN); Citalopram (USP/INN); Citalopram [Celexa]; Citalopram [INN:BAN]; Citalopramum; Citalopramum [INN-Latin]; Citaxin (TN); Citol (TN); Citopam; Citopam (TN); Citox (TN); Citrol (TN); Cytalopram; Dalsan; Dalsan (TN); Humorup; Lu 10-171; Lu-10-171; Nitalapram; Oropram; Pramcit; Recital; Recital (TN); Seropram; Seropram (TN); Talam; Talam (TN); Talohexal; Temperax; Vodelax; Zentius; Zentius (TN); Zetalo; Zetalo (TN); [3H]Citalopram
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| Drug Type |
Small molecular drug
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| Indication | Depression [ICD11:6A8Z] | Approved | [1] | |||
| Therapeutic Class |
Antidepressants
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| Structure |
|
 |
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| 3D MOL | 2D MOL | |||||
| Formula |
C20H21FN2O
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| Canonical SMILES |
CN(C)CCCC1(C2=C(CO1)C=C(C=C2)C#N)C3=CC=C(C=C3)F
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| InChI |
InChI=1S/C20H21FN2O/c1-23(2)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-24-20/h4-9,12H,3,10-11,14H2,1-2H3
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| InChIKey |
WSEQXVZVJXJVFP-UHFFFAOYSA-N
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| CAS Number |
CAS 59729-33-8
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| Pharmaceutical Properties | Molecular Weight | 324.4 | Topological Polar Surface Area | 36.3 | ||
| Heavy Atom Count | 24 | Rotatable Bond Count | 5 | |||
| Hydrogen Bond Donor Count | 0 | Hydrogen Bond Acceptor Count | 4 | |||
| XLogP |
3.2
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| PubChem CID | ||||||
| PubChem SID |
103177051
,104170209
,104301562
,121362384
,124570949
,124749575
,124879738
,124879739
,125353996
,126440716
,126525331
,126630818
,126657311
,126666544
,127275913
,127275914
,127275915
,14826333
,24723457
,29221926
,4445124
,46508746
,47656601
,47730750
,47879631
,48253450
,48415786
,48493834
,49699144
,49985355
,50104852
,51092001
,53788845
,56313600
,56413158
,57321451
,7978955
,80123691
,80953770
,8151789
,85209895
,855965
,85787315
,87690083
,90340852
,92307844
,92309285
,92711474
,9775
,99418031
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| ChEBI ID |
ChEBI:3723
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| TTD Drug ID | ||||||
| DT(s) Transporting This Drug | 1-Oct | Transporter Info | Organic cation transporter 1 | Substrate | [2] | |
| MRP1 | Transporter Info | Multidrug resistance-associated protein 1 | Substrate | [3] | ||
| P-GP | Transporter Info | P-glycoprotein 1 | Substrate | [4] | ||
| Drug-Transporter Activity Data | ||||||
| Drug-Transporter Activity Data | MRP1 | Transporter Info | Km =1.99 microM | Human embryonic kidney cells (HEK293)-MRP1 | [3] | |
| References | ||||||
| 1 | Citalopram was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019) | |||||
| 2 | Organic cation transporters and their pharmacokinetic and pharmacodynamic consequences. Drug Metab Pharmacokinet. 2008;23(4):243-53. | |||||
| 3 | MRP1 polymorphisms associated with citalopram response in patients with major depression. J Clin Psychopharmacol. 2010 Apr;30(2):116-25. | |||||
| 4 | ABCB1 gene polymorphisms are associated with fatal intoxications involving venlafaxine but not citalopram. Int J Legal Med. 2013 May;127(3):579-86. | |||||
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