Human Metabolome Database Version 3.5

Showing metabocard for Citalopram (HMDB05038)

Record Information
Version 3.5
Creation Date 2006-10-17 05:25:30 -0600
Update Date 2013-02-08 17:13:49 -0700
HMDB ID HMDB05038
Secondary Accession Numbers None
Metabolite Identification
Common Name Citalopram
Description Citalopram is an antidepressant drug used to treat depression associated with mood disorders. It is also used on occasion in the treatment of body dysmorphic disorder and anxiety; Citalopram belongs to a class of drugs known as selective serotonin reuptake inhibitors (SSRIs). It is sold under the brand-names Celexa (U.S., Forest Laboratories, Inc.), Cipramil, Seropram (Europe and Australia) and Ciazil (Australia); A furancarbonitrile that is one of the serotonin uptake inhibitors used as an antidepressant. The drug is also effective in reducing ethanol uptake in alcoholics and is used in depressed patients who also suffer from tardive dyskinesia in preference to tricyclic antidepressants, which aggravate this condition; Citalopram is an antidepressant drug used to treat depression associated with mood disorders. It is also used on occasion in the treatment of body dysmorphic disorder and anxiety. Citalopram belongs to a class of drugs known as selective serotonin reuptake inhibitors (SSRIs).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Bonitrile
  2. Celexa
  3. Citalopram hydrobromide
  4. Nitalapram
Chemical Formula C20H21FN2O
Average Molecular Weight 324.3919
Monoisotopic Molecular Weight 324.163791509
IUPAC Name 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile
Traditional IUPAC Name citalopram
CAS Registry Number 59729-33-8
SMILES CN(C)CCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1
InChI Identifier 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
InChI Key WSEQXVZVJXJVFP-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Phenylbutylamines
Sub Class N/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • citalopram(ChEBI)
Substituents
  • Aryl Fluoride
  • Benzofuran
  • Benzonitrile
  • Dialkyl Ether
  • Dihydrofuran
  • Fluorobenzene
  • Nitrile
  • Organofluoride
  • Tertiary Aliphatic Amine (Trialkylamine)
Direct Parent Phenylbutylamines
Ontology
Status Expected and Not Quantified
Origin
  • Drug
Biofunction Not Available
Application Not Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 178 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
LogP 3.58 ALOGPS
LogP 3.76 ChemAxon
LogS -4.74 ALOGPS
pKa (strongest basic) 9.78 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 36.26 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 94.02 ChemAxon
Polarizability 35.21 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
1H NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations Not Available
Tissue Location
  • Liver
  • Brain
  • Platelet
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023605
KNApSAcK ID Not Available
Chemspider ID 2669 Link_out
KEGG Compound ID C07572 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Citalopram Link_out
NuGOwiki Link HMDB05038 Link_out
Metagene Link HMDB05038 Link_out
METLIN ID 1781 Link_out
PubChem Compound 2771 Link_out
PDB ID Not Available
ChEBI ID 3723 Link_out
References
Synthesis Reference Petersen, Hans; Bogeso, Klaus Peter; Bech Sommer, Michael. Lundbeck A/S, Method for the preparation of citalopram. PCT Int. Appl. (1998), 16 pp.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Gleason OC, Yates WR, Isbell MD, Philipsen MA: An open-label trial of citalopram for major depression in patients with hepatitis C. J Clin Psychiatry. 2002 Mar;63(3):194-8. Pubmed: 11926717 Link_out
  2. Blardi P, de Lalla A, Urso R, Auteri A, Dell'Erba A, Bossini L, Castrogiovanni P: Activity of citalopram on adenosine and serotonin circulating levels in depressed patients. J Clin Psychopharmacol. 2005 Jun;25(3):262-6. Pubmed: 15876907 Link_out
  3. Bhagwagar Z, Hafizi S, Cowen PJ: Acute citalopram administration produces correlated increases in plasma and salivary cortisol. Psychopharmacology (Berl). 2002 Aug;163(1):118-20. Epub 2002 Jun 27. Pubmed: 12185409 Link_out
  4. Nikisch G, Mathe AA, Czernik A, Eap CB, Jimenez-Vasquez P, Brawand-Amey M, Baumann P: Stereoselective metabolism of citalopram in plasma and cerebrospinal fluid of depressive patients: relationship with 5-HIAA in CSF and clinical response. J Clin Psychopharmacol. 2004 Jun;24(3):283-90. Pubmed: 15118482 Link_out
  5. Anastos N, McIntyre IM, Lynch MJ, Drummer OH: Postmortem concentrations of citalopram. J Forensic Sci. 2002 Jul;47(4):882-4. Pubmed: 12137000 Link_out
  6. Horak EL, Jenkins AJ: Postmortem tissue distribution of olanzapine and citalopram in a drug intoxication. J Forensic Sci. 2005 May;50(3):679-81. Pubmed: 15932107 Link_out
  7. Lapatto-Reiniluoto O, Kivisto KT, Neuvonen PJ: Effect of activated charcoal alone or given after gastric lavage in reducing the absorption of diazepam, ibuprofen and citalopram. Br J Clin Pharmacol. 1999 Aug;48(2):148-53. Pubmed: 10417490 Link_out
  8. Worm K, Dragsholt C, Simonsen KW, Kringsholm B: [Citalopram in forensic samples. Citalopram concentrations in samples from legal autopsies and from living persons in connection with traffic accidents or cases of violence in Denmark 1989-1996] Ugeskr Laeger. 1999 Jul 26;161(30):4291-2. Pubmed: 10439690 Link_out
  9. Jensen PN, Olesen OV, Bertelsen A, Linnet K: Citalopram and desmethylcitalopram concentrations in breast milk and in serum of mother and infant. Ther Drug Monit. 1997 Apr;19(2):236-9. Pubmed: 9108657 Link_out
  10. Schmidt K, Olesen OV, Jensen PN: Citalopram and breast-feeding: serum concentration and side effects in the infant. Biol Psychiatry. 2000 Jan 15;47(2):164-5. Pubmed: 10664835 Link_out
  11. Rochat B, Kosel M, Boss G, Testa B, Gillet M, Baumann P: Stereoselective biotransformation of the selective serotonin reuptake inhibitor citalopram and its demethylated metabolites by monoamine oxidases in human liver. Biochem Pharmacol. 1998 Jul 1;56(1):15-23. Pubmed: 9698084 Link_out
  12. Kristoffersen L, Bugge A, Lundanes E, Slordal L: Simultaneous determination of citalopram, fluoxetine, paroxetine and their metabolites in plasma and whole blood by high-performance liquid chromatography with ultraviolet and fluorescence detection. J Chromatogr B Biomed Sci Appl. 1999 Nov 12;734(2):229-46. Pubmed: 10595721 Link_out
  13. Nordeng H, Bergsholm YK, Bohler E, Spigset O: [The transfer of selective serotonin reuptake inhibitors to human milk] Tidsskr Nor Laegeforen. 2001 Jan 20;121(2):199-203. Pubmed: 11475200 Link_out
  14. Plenge P, Mellerup ET: [3H]citalopram binding to brain and platelet membranes of human and rat. J Neurochem. 1991 Jan;56(1):248-52. Pubmed: 1824783 Link_out
  15. Nikisch G, Mathe AA, Czernik A, Thiele J, Bohner J, Eap CB, Agren H, Baumann P: Long-term citalopram administration reduces responsiveness of HPA axis in patients with major depression: relationship with S-citalopram concentrations in plasma and cerebrospinal fluid (CSF) and clinical response. Psychopharmacology (Berl). 2005 Oct;181(4):751-60. Epub 2005 Sep 29. Pubmed: 15988572 Link_out
  16. Spigset O, Hagg S, Stegmayr B, Dahlqvist R: Citalopram pharmacokinetics in patients with chronic renal failure and the effect of haemodialysis. Eur J Clin Pharmacol. 2000 Dec;56(9-10):699-703. Pubmed: 11214779 Link_out
  17. Anderer P, Saletu B, Semlitsch HV, Pascual-Marqui RD: Perceptual and cognitive event-related potentials in neuropsychopharmacology: methodological aspects and clinical applications (pharmaco-ERP topography and tomography). Methods Find Exp Clin Pharmacol. 2002;24 Suppl C:121-37. Pubmed: 12575494 Link_out
  18. Kosel M, Gnerre C, Voirol P, Amey M, Rochat B, Bouras C, Testa B, Baumann P: In vitro biotransformation of the selective serotonin reuptake inhibitor citalopram, its enantiomers and demethylated metabolites by monoamine oxidase in rat and human brain preparations. Mol Psychiatry. 2002;7(2):181-8. Pubmed: 11840311 Link_out
  19. Spigset O, Wilhelmsson C, Mjorndal T, Eriksson S: Low serum sodium concentrations during treatment with citalopram in elderly patients: relationship to serum citalopram levels and to platelet serotonin 5-HT2A receptor status. J Clin Psychopharmacol. 2000 Oct;20(5):582-4. Pubmed: 11001247 Link_out

Enzymes
Name: Amine oxidase [flavin-containing] B
Reactions:
Citalopram + Oxygen + Water unknown Citalopram aldehyde + Dimethylamine + Hydrogen peroxide details
Gene Name: MAOB
Uniprot ID: P27338 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Amine oxidase [flavin-containing] A
Reactions:
Citalopram + Oxygen + Water unknown Citalopram aldehyde + Dimethylamine + Hydrogen peroxide details
Gene Name: MAOA
Uniprot ID: P21397 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A4
Reactions: Not Available
Gene Name: CYP3A4
Uniprot ID: P08684 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C9
Reactions: Not Available
Gene Name: CYP2C9
Uniprot ID: P11712 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C19
Reactions: Not Available
Gene Name: CYP2C19
Uniprot ID: P33261 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2E1
Reactions: Not Available
Gene Name: CYP2E1
Uniprot ID: P05181 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A43
Reactions: Not Available
Gene Name: CYP3A43
Uniprot ID: Q9HB55 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1B1
Reactions: Not Available
Gene Name: CYP1B1
Uniprot ID: Q16678 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2D6
Reactions: Not Available
Gene Name: CYP2D6
Uniprot ID: P10635 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C18
Reactions: Not Available
Gene Name: CYP2C18
Uniprot ID: P33260 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2F1
Reactions: Not Available
Gene Name: CYP2F1
Uniprot ID: P24903 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 4X1
Reactions: Not Available
Gene Name: CYP4X1
Uniprot ID: Q8N118 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2B6
Reactions: Not Available
Gene Name: CYP2B6
Uniprot ID: P20813 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A5
Reactions: Not Available
Gene Name: CYP3A5
Uniprot ID: P20815 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2A13
Reactions: Not Available
Gene Name: CYP2A13
Uniprot ID: Q16696 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A7
Reactions: Not Available
Gene Name: CYP3A7
Uniprot ID: P24462 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 4B1
Reactions: Not Available
Gene Name: CYP4B1
Uniprot ID: P13584 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 4Z1
Reactions: Not Available
Gene Name: CYP4Z1
Uniprot ID: Q86W10 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1A2
Reactions: Not Available
Gene Name: CYP1A2
Uniprot ID: P05177 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 19A1
Reactions: Not Available
Gene Name: CYP19A1
Uniprot ID: P11511 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C8
Reactions: Not Available
Gene Name: CYP2C8
Uniprot ID: P10632 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2S1
Reactions: Not Available
Gene Name: CYP2S1
Uniprot ID: Q96SQ9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2J2
Reactions: Not Available
Gene Name: CYP2J2
Uniprot ID: P51589 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2A7
Reactions: Not Available
Gene Name: CYP2A7
Uniprot ID: P20853 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2A6
Reactions: Not Available
Gene Name: CYP2A6
Uniprot ID: P11509 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450, family 1, subfamily A, polypeptide 1
Reactions: Not Available
Gene Name: CYP1A1
Uniprot ID: A0N0X8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2D6
Reactions: Not Available
Gene Name: CYP2D6
Uniprot ID: Q6NWU0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Transporters
Name: Sodium-dependent serotonin transporter
Reactions: Not Available
Gene Name: SLC6A4
Uniprot ID: P31645 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA