Explore a selection of our essential drug information below, or:
Overview
- Description
- A medication used to treat depression.
- Description
- A medication used to treat depression.
- DrugBank ID
- DB00215
- Type
- Small Molecule
Identification
- Summary
Citalopram is a selective serotonin reuptake inhibitor (SSRI) used in the treatment of depression.
- Brand Names
- Celexa, Ctp
- Generic Name
- Citalopram
- DrugBank Accession Number
- DB00215
- Background
Citalopram is an antidepressant belonging to the class of selective serotonin-reuptake inhibitors (SSRIs) widely used to treat the symptoms of depression. It is a racemic bicyclic phthalate derivate and is the only compound with a tertiary amine and 2 nitrogen-containing metabolites among all SSRIs.12,13 Citalopram enhances serotonergic transmission through the inhibition of serotonin reuptake, and among all the SSRIs, citalopram appears to be the most selective toward serotonin reuptake inhibition.12,13 Specifically, it has a very minimal effect on dopamine and norepinephrine transportation and virtually no affinity for muscarinic, histaminergic, or GABAergic receptors.12
Citalopram was approved by the FDA in 1998 for the treatment of depression in adults 18 years or older.18
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Citalopram (DB00215)
- Weight
- Average: 324.3919
Monoisotopic: 324.163791509 - Chemical Formula
- C20H21FN2O
- Synonyms
- Citalopram
- Citalopramum
- Nitalapram
- External IDs
- Lu 10-171
Pharmacology
- Indication
Citalopram is approved by the FDA for treating adults with major depressive disorder.19 It has also been used off-label to treat various diseases, including but not limited to sexual dysfunction, ethanol abuse, psychiatric conditions such as obsessive-compulsive disorder (OCD), social anxiety disorder, panic disorder, and diabetic neuropathy.16,1,2,11
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Alcohol abuse ••• ••••• Treatment of Anorexia nervosa ••• ••••• Treatment of Binge eating disorder (bed) ••• ••••• Treatment of Bulimia nervosa ••• ••••• Symptomatic treatment of Depression •••••••••••• ••••• •••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Citalopram belongs to a class of antidepressants known as selective serotonin reuptake inhibitors (SSRIs). It has been found to relieve or manage symptoms of depression, anxiety, eating disorders and obsessive-compulsive disorder among other mood disorders. The antidepressant, anti-anxiety, and other actions of citalopram are linked to its inhibition of CNS central uptake of serotonin.19 Serotonergic abnormalities have been reported in patients with mood disorders. Behavioral and neuropsychological effects of serotonin include the regulation of mood, perception, reward, anger, aggression, appetite, memory, sexuality, and attention, as examples. The onset of action for depression is approximately 1 to 4 weeks. The complete response may take 8-12 weeks after initiation of citalopram.16
In vitro studies demonstrate that citalopram is a strong and selective inhibitor of neuronal serotonin reuptake and has weak effects on norepinephrine and dopamine central reuptake. The chronic administration of citalopram has been shown to downregulate central norepinephrine receptors, similar to other drugs effective in the treatment of major depressive disorder. Citalopram does not inhibit monoamine oxidase.4
- Mechanism of action
The mechanism of action of citalopram is unclear but is presumed to be related to potentiation of serotonergic activity in the central nervous system (CNS) resulting from its inhibition of CNS neuronal reuptake of serotonin (5-HT), potentially through the inhibition of the serotonin transporter (solute carrier family 6 member 4, SLC6A4).19,8
Citalopram binds with significantly less affinity to histamine, acetylcholine, and norepinephrine receptors than tricyclic antidepressant drugs. Particularly, citalopram has no or very low affinity for 5-HT1A, 5-HT2A, dopamine D1 and D2, α1-, α2-, and β-adrenergic, histamine H1, gamma aminobutyric acid (GABA), muscarinic cholinergic, and benzodiazepine receptors.19
Target Actions Organism ASodium-dependent serotonin transporter inhibitorHumans NHistamine H1 receptor binderHumans - Absorption
The single- and multiple-dose pharmacokinetics of citalopram are linear and dose-proportional in a dose range of 10 to 40 mg/day. Biotransformation of citalopram is mainly hepatic, with a mean terminal half-life of about 35 hours. With once daily dosing, steady state plasma concentrations are achieved within approximately one week. At steady state, the extent of accumulation of citalopram in plasma, based on the half-life, is expected to be 2.5 times the plasma concentrations observed after a single dose.19
Following a single oral dose (40 mg tablet) of citalopram, peak blood levels occur at about 4 hours. The absolute bioavailability of citalopram was about 80% relative to an intravenous dose, and absorption is not affected by food.19
- Volume of distribution
The volume of distribution of citalopram is about 12 L/kg.19
- Protein binding
The binding of citalopram (CT), demethylcitalopram (DCT) and didemethylcitalopram (DDCT) to human plasma proteins is about 80%.19
- Metabolism
Citalopram is metabolized mainly in the liver via N-demethylation to its main metabolite, demethylcitalopram by CYP2C19 and CYP3A4. 5,8,19 Other metabolites include didemethylcitalopram via CYP2D6 metabolism, citalopram N-oxide and propionic acid derivative via monoamine oxidase enzymes A and B and aldehyde oxidase.5,19 Citalopram metabolites exert little pharmacologic activity in comparison to the parent drug and are not likely to contribute to the clinical effect of citalopram.4
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- Route of elimination
Approximately 12 to 23% of an oral dose of citalopram is found unchanged in the urine, while 10% is found in feces.8 Following intravenous administrations of citalopram, the fraction of the drug recovered in the urine as citalopram and DCT was about 10% and 5%, respectively.19
- Half-life
The mean terminal half-life of citalopram is about 35 hours.21
- Clearance
The systemic clearance of citalopram was 330 mL/min, with approximately 20% of that due to renal clearance.19
- Adverse Effects
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Based on data from published observational studies, exposure to SSRIs, particularly in the month before delivery, has been associated with a less than 2-fold increase in the risk of postpartum hemorrhage.19
Available data from published epidemiologic studies and postmarketing reports with citalopram use in pregnancy have not established an increased risk of major birth defects or miscarriage. Published studies demonstrated that citalopram levels in both cord blood and amniotic fluid are similar to those observed in maternal serum. There are risks of persistent pulmonary hypertension of the newborn (PPHN) and/or poor neonatal adaptation with exposure to selective serotonin reuptake inhibitors (SSRIs), including citalopram, during pregnancy. There also are risks associated with untreated depression in pregnancy.19
Citalopram was administered orally to pregnant rats during the period of organogenesis at doses of 32, 56, and 112 mg/kg/day, which are approximately 8, 14, and 27 times the Maximum Recommended Human Dose (MRHD) of 40 mg, based on mg/m2 body surface area. Citalopram caused maternal toxicity of CNS clinical signs and decreased weight gain at 112 mg/kg/day, which is 27 times the MRHD. At this maternally toxic dose, citalopram decreased embryo/fetal growth and survival and increased fetal abnormalities (including cardiovascular and skeletal defects). The no observed adverse effect level (NOAEL) for maternal and embryofetal toxicity is 56 mg/kg/day, which is approximately 14 times the MRHD.19
Citalopram was administered orally to pregnant rabbits during the period of organogenesis at doses up to 16 mg/kg/day, which is approximately 8 times the MRHD of 40 mg, based on mg/m2 body surface area. No maternal or embryofetal toxicity was observed. The NOAEL for maternal and embryofetal toxicity is 16 mg/kg/day, which is approximately 8 times the MRHD.19
Citalopram was administered orally to pregnant rats during late gestation and lactation periods at doses of 4.8, 12.8, and 32 mg/kg/day, which are approximately 1, 3, and 8 times the MRHD of 40 mg, based on mg/m2 body surface area. Citalopram increased offspring mortality during the first 4 days of birth and decreased offspring growth at 32 mg/kg/day, which is approximately 8 times the MRHD. The NOAEL for developmental toxicity is 12.8 mg/kg/day, which is approximately 3 times the MRHD. In a separate study, similar effects on offspring mortality and growth were seen when dams were treated throughout gestation and early lactation at doses ≥ 24 mg/kg/day, which is approximately 6 times the MRHD. A NOAEL was not determined in that study.19
SSRIs, including citalopram, have been associated with cases of clinically significant hyponatremia in elderly patients, who may be at greater risk for this adverse reaction.19
The following have been reported with citalopram tablet overdosage: • Seizures, which may be delayed, and altered mental status including coma.19 • Cardiovascular toxicity, which may be delayed, including QRS and QTc interval prolongation, wide complex tachyarrhythmias, and torsade de pointes. Hypertension is most commonly seen, but hypotension can rarely be seen alone or with co‐ingestants including alcohol.19 • Serotonin syndrome (patients with a multiple drug overdosage with other pro-serotonergic drugs may have a higher risk).19
Prolonged cardiac monitoring is recommended in citalopram overdosage ingestions due to the arrhythmia risk. Gastrointestinal decontamination with activated charcoal should be considered in patients who present early after a citalopram overdose. Consider contacting a Poison Center (1‐800‐221‐2222) or a medical toxicologist for additional overdosage management recommendations.19
Citalopram increased the incidence of small intestine carcinoma in rats treated for 24 months at doses of 8 and 24 mg/kg/day in the diet, which are approximately 2 and 6 times the Maximum Recommended Human Dose (MRHD) of 40 mg, respectively, based on mg/m2 body surface area. A no-effect level (NOEL) for this finding was not established. Citalopram did not increase the incidence of tumors in mice treated for 18 months at doses up to 240 mg/kg/day in the diet, which is approximately 30 times the MRDH of 40 mg based on mg/m2 body surface area.19
Citalopram was mutagenic in the in vitro bacterial reverse mutation assay (Ames test) in 2 of 5 bacterial strains (Salmonella TA98 and TA1537) in the absence of metabolic activation. It was clastogenic in the in vitro Chinese hamster lung cell assay for chromosomal aberrations in the presence and absence of metabolic activation. Citalopram was not mutagenic in the in vitro mammalian forward gene mutation assay (HPRT) in mouse lymphoma cells or in in vitro/in vivo unscheduled DNA synthesis (UDS) assay in rat liver. It was not clastogenic in the in vitro chromosomal aberration assay in human lymphocytes or in two in vivo mouse micronucleus assays.19
Citalopram was administered orally to female and male rats at doses of 32, 48, and 72 mg/kg/day prior to and throughout mating and continuing to gestation. These doses are approximately 8, 12, and 17 times the MRHD of 40 mg based on mg/m2 body surface area. Mating and fertility were decreased at doses ≥ 32 mg/kg/day, which is approximately 8 times the MRHD. Gestation duration was increased to 48 mg/kg/day, which is approximately 12 times the MRHD.19
- Pathways
Pathway Category Citalopram Action Pathway Drug action Citalopram Metabolism Pathway Drug metabolism - Pharmacogenomic Effects/ADRs
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Glutamate receptor ionotropic, kainate 2 --- (C;C) C Allele, homozygote ADR Directly Studied Patients with this genotype have increased frequency of suicidal ideation with citalopram Details Glutamate receptor 3 --- (G;G) / (G;A) G allele ADR Directly Studied Patients with this genotype have increased frequency of suicidal ideation with citalopram Details Multidrug resistance protein 1 --- (C;C) / (C;T) C Allele Effect Directly Studied Patients with this genotype have an increased likelihood of remission when using citalopram to treat major depressive disorder Details 5-hydroxytryptamine receptor 2A --- (A;A) A Allele Effect Directly Studied Patients with this genotype have an increased likelihood of responding to citalopram when treating major depressive disorder Details Glutamate receptor ionotropic, kainate 4 --- (C;C) C Allele Effect Directly Studied Patients with this genotype have an increased likelihood of responding to citalopram when treating major depressive disorder Details Cyclic AMP-responsive element-binding protein 1 --- (T;T) T allele, homozygous ADR Directly Studied Male patients with this genotype have an increased risk of (condition: suicide) with (drug: citalopram). Details Cytochrome P450 2C19 CYP2C19*2A Not Available 681G>A ADR Inferred Poor drug metabolizer, increased risk of QT prolongation. For individual with two non-functional alleles, dose reduction or alternative drug recommended. Details Cytochrome P450 2C19 CYP2C19*2B Not Available 681G>A ADR Inferred Poor drug metabolizer, increased risk of QT prolongation. For individual with two non-functional alleles, dose reduction or alternative drug recommended. Details Cytochrome P450 2C19 CYP2C19*3 Not Available 636G>A ADR Inferred Poor drug metabolizer, increased risk of QT prolongation. For individual with two non-functional alleles, dose reduction or alternative drug recommended. Details Cytochrome P450 2C19 CYP2C19*4 Not Available 1A>G ADR Inferred Poor drug metabolizer, increased risk of QT prolongation. For individual with two non-functional alleles, dose reduction or alternative drug recommended. Details Cytochrome P450 2C19 CYP2C19*5 Not Available 1297C>T ADR Inferred Poor drug metabolizer, increased risk of QT prolongation. For individual with two non-functional alleles, dose reduction or alternative drug recommended. Details Cytochrome P450 2C19 CYP2C19*6 Not Available 395G>A ADR Inferred Poor drug metabolizer, increased risk of QT prolongation. For individual with two non-functional alleles, dose reduction or alternative drug recommended. Details Cytochrome P450 2C19 CYP2C19*7 Not Available 19294T>A ADR Inferred Poor drug metabolizer, increased risk of QT prolongation. For individual with two non-functional alleles, dose reduction or alternative drug recommended. Details Cytochrome P450 2C19 CYP2C19*22 Not Available 557G>C / 991A>G ADR Inferred Poor drug metabolizer, increased risk of QT prolongation. For individual with two non-functional alleles, dose reduction or alternative drug recommended. Details Cytochrome P450 2C19 CYP2C19*24 Not Available 99C>T / 991A>G … show all ADR Inferred Poor drug metabolizer, increased risk of QT prolongation. For individual with two non-functional alleles, dose reduction or alternative drug recommended. Details Cytochrome P450 2C19 CYP2C19*35 Not Available 12662A>G ADR Inferred Poor drug metabolizer, increased risk of QT prolongation. For individual with two non-functional alleles, dose reduction or alternative drug recommended. Details
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when 1,2-Benzodiazepine is combined with Citalopram. Abametapir The serum concentration of Citalopram can be increased when it is combined with Abametapir. Abatacept The metabolism of Citalopram can be increased when combined with Abatacept. Abciximab The risk or severity of bleeding can be increased when Abciximab is combined with Citalopram. Abemaciclib The metabolism of Abemaciclib can be decreased when combined with Citalopram. - Food Interactions
- Avoid alcohol.
- Avoid St. John's Wort. Co-administration of St. John's Wort with citalopram can increase the risk of serotonin syndrome.
- Take with or without food. The absorption is unaffected by food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Citalopram hydrobromide I1E9D14F36 59729-32-7 WIHMBLDNRMIGDW-UHFFFAOYSA-N - Product Images
- International/Other Brands
- Akarin / Celapram / Ciazil / Cilift / Cipram / Cipramil / Ciprapine / Citabax / Citadur / Citalec / Citol / Citopam / Citox / Citrol / Dalsan / Elopram / Humorup / Oropram / Pramcit / Recital / Seropram / Talam / Talohexal / Temperax / Vodelax / Zentius / Zetalo
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Act Citalopram Tablet 40 mg Oral Sunovion 2004-01-21 2022-04-27 Canada 
Act Citalopram Tablet 30 mg Oral Sumitomo Pharma America, Inc. Not applicable Not applicable Canada Act Citalopram Tablet 20 mg Oral Sunovion 2004-01-21 2022-04-27 Canada Celexa Tablet 40 mg/1 Oral Physicians Total Care, Inc. 2001-09-05 Not applicable US 
Celexa Tablet, film coated 10 mg/1 Oral Allergan, Inc. 1998-07-17 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Abbott-citalopram Tablet 10 mg Oral Abbott 2014-03-17 2015-12-31 Canada Abbott-citalopram Tablet 40 mg Oral Abbott 2014-03-12 2015-12-31 Canada Abbott-citalopram Tablet 20 mg Oral Abbott 2014-03-12 2015-12-31 Canada Accel-citalopram Tablets Tablet 20 mg Oral Accel Pharma Inc 2013-07-02 2020-03-20 Canada Accel-citalopram Tablets Tablet 10 mg Oral Accel Pharma Inc 2013-03-21 2020-03-20 Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Sentralopram AM-10 Citalopram hydrobromide (10 mg/1) + Choline (250 mg/1) Kit Oral Physician Therapeutics Llc 2011-07-07 Not applicable US
Categories
- ATC Codes
- N06AB04 — Citalopram
- Drug Categories
- Amines
- Antidepressive Agents
- Antidepressive Agents Indicated for Depression
- Antidepressive Agents, Second-Generation
- Benzofurans
- Central Nervous System Agents
- Central Nervous System Depressants
- Combined Inhibitors of Serotonin/Norepinephrine Reuptake
- Cytochrome P-450 CYP1A2 Inhibitors
- Cytochrome P-450 CYP1A2 Inhibitors (weak)
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 Inhibitors (weak)
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (weak)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Heterocyclic Compounds, Fused-Ring
- Highest Risk QTc-Prolonging Agents
- Hypoglycemia-Associated Agents
- Monoamine Oxidase A Substrates
- Nervous System
- Neurotransmitter Agents
- Neurotransmitter Uptake Inhibitors
- Nitriles
- P-glycoprotein inhibitors
- P-glycoprotein substrates
- Propylamines
- Psychoanaleptics
- Psychotropic Drugs
- QTc Prolonging Agents
- Selective Serotonin Reuptake Inhibitors
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin 5-HT2 Receptor Antagonists
- Serotonin Agents
- Serotonin Modulators
- Serotonin Receptor Antagonists
- Vasodilating Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylbutylamines. These are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Phenylbutylamines
- Direct Parent
- Phenylbutylamines
- Alternative Parents
- Isocoumarans / Fluorobenzenes / Aralkylamines / Aryl fluorides / Trialkylamines / Oxacyclic compounds / Nitriles / Dialkyl ethers / Organopnictogen compounds / Organofluorides show 1 more
- Substituents
- Amine / Aralkylamine / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Carbonitrile / Dialkyl ether / Ether / Fluorobenzene / Halobenzene show 15 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- organofluorine compound, tertiary amino compound, 2-benzofurans, nitrile, cyclic ether (CHEBI:77397)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 0DHU5B8D6V
- CAS number
- 59729-33-8
- InChI Key
- WSEQXVZVJXJVFP-UHFFFAOYSA-N
- 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
- IUPAC Name
- 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile
- SMILES
- CN(C)CCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1
References
- Synthesis Reference
Hans Petersen, "Method for the preparation of citalopram." U.S. Patent US6229026, issued December, 1992.
US6229026- General References
- Sindrup SH, Bjerre U, Dejgaard A, Brøsen K, Aaes-Jørgensen T, Gram LF: The selective serotonin reuptake inhibitor citalopram relieves the symptoms of diabetic neuropathy Clin Pharmacol Ther. 1992 Nov;52(5):547-52. [Article]
- Atmaca M, Kuloglu M, Tezcan E, Semercioz A: The efficacy of citalopram in the treatment of premature ejaculation: a placebo-controlled study. Int J Impot Res. 2002 Dec;14(6):502-5. [Article]
- Andersen G, Vestergaard K, Riis JO: Citalopram for post-stroke pathological crying. Lancet. 1993 Oct 2;342(8875):837-9. [Article]
- Baumann P: Pharmacology and pharmacokinetics of citalopram and other SSRIs. Int Clin Psychopharmacol. 1996 Mar;11 Suppl 1:5-11. [Article]
- Bezchlibnyk-Butler K, Aleksic I, Kennedy SH: Citalopram--a review of pharmacological and clinical effects. J Psychiatry Neurosci. 2000 May;25(3):241-54. [Article]
- Sheeler RD, Ackerman MJ, Richelson E, Nelson TK, Staab JP, Tangalos EG, Dieser LM, Cunningham JL: Considerations on safety concerns about citalopram prescribing. Mayo Clin Proc. 2012 Nov;87(11):1042-5. doi: 10.1016/j.mayocp.2012.07.009. Epub 2012 Sep 24. [Article]
- McElroy SL, Hudson JI, Malhotra S, Welge JA, Nelson EB, Keck PE Jr: Citalopram in the treatment of binge-eating disorder: a placebo-controlled trial J Clin Psychiatry. 2003 Jul;64(7):807-13. [Article]
- Sangkuhl K, Klein TE, Altman RB: PharmGKB summary: citalopram pharmacokinetics pathway. Pharmacogenet Genomics. 2011 Nov;21(11):769-72. doi: 10.1097/FPC.0b013e328346063f. [Article]
- Fassino S, Leombruni P, Daga G, Brustolin A, Migliaretti G, Cavallo F, Rovera G: Efficacy of citalopram in anorexia nervosa: a pilot study. Eur Neuropsychopharmacol. 2002 Oct;12(5):453-9. doi: 10.1016/s0924-977x(02)00058-5. [Article]
- Leombruni P, Amianto F, Delsedime N, Gramaglia C, Abbate-Daga G, Fassino S: Citalopram versus fluoxetine for the treatment of patients with bulimia nervosa: a single-blind randomized controlled trial. Adv Ther. 2006 May-Jun;23(3):481-94. doi: 10.1007/BF02850170. [Article]
- Naranjo CA, Poulos CX, Bremner KE, Lanctot KL: Citalopram decreases desirability, liking, and consumption of alcohol in alcohol-dependent drinkers. Clin Pharmacol Ther. 1992 Jun;51(6):729-39. doi: 10.1038/clpt.1992.85. [Article]
- Pollock BG: Citalopram: a comprehensive review. Expert Opin Pharmacother. 2001 Apr;2(4):681-98. doi: 10.1517/14656566.2.4.681. [Article]
- Baumann P: Pharmacokinetic-pharmacodynamic relationship of the selective serotonin reuptake inhibitors. Clin Pharmacokinet. 1996 Dec;31(6):444-69. [Article]
- https://www.ncbi.nlm.nih.gov/books/NBK482222/ (2018). Stat Pearls [Internet]. NIH Stat Pearls.
- MSDS citalopram [Link]
- NIH Stat Pearls: Citalopram [Link]
- AAFP: Off-label Applications for SSRIs [Link]
- Celexa Information, FDA [Link]
- FDA Approved Drug Products: CELEXA (citalopram) tablets, for oral use (August 2023) [Link]
- DailyMed Label: SENTRALOPRAM AM-10 (citalopram hydrobromide, choline) oral kit [Link]
- Citalopram FDA label [Link]
- Health Canada Approved Drug Proucts: ACT CITALOPRAM (Citalopram) tablets, for oral use [Link]
- Celexa Monograph [File]
- External Links
- Human Metabolome Database
- HMDB0005038
- KEGG Drug
- D07704
- KEGG Compound
- C07572
- PubChem Compound
- 2771
- PubChem Substance
- 46508746
- ChemSpider
- 2669
- BindingDB
- 25870
- 2556
- ChEBI
- 77397
- ChEMBL
- CHEMBL549
- Therapeutic Targets Database
- DAP000118
- PharmGKB
- PA449015
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Citalopram
- FDA label
- Download (190 KB)
- MSDS
- Download (379 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Acute Kidney Injury (AKI) / Depression 1 somestatus stop reason just information to hide Not Available Completed Not Available Alcohol Use Disorders (AUD) / Major Depressive Disorder (MDD) 1 somestatus stop reason just information to hide Not Available Completed Not Available Antidepressants / Pharmacokinetics / Pregnancy 1 somestatus stop reason just information to hide Not Available Completed Not Available Breast Cancer / Depression / Hot Flashes / Psychosocial Effects of Cancer and Its Treatment 1 somestatus stop reason just information to hide Not Available Completed Not Available Healthy Volunteers (HV) 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Alphapharm party ltd
- Forest laboratories inc
- Apotex inc richmond hill
- Aurobindo pharma ltd inc
- Roxane laboratories inc
- Silarx pharmaceuticals inc
- Biovail laboratories international srl
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- Corepharma llc
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- Epic pharma llc
- Glenmark generics ltd
- Invagen pharmaceuticals inc
- Ivax pharmaceuticals inc sub teva pharmaceuticals usa
- Matrix laboratories inc
- Mutual pharmaceutical co inc
- Mylan pharmaceuticals inc
- Natco pharma ltd
- Pliva inc
- Sandoz inc
- Taro pharmaceuticals usa inc
- Teva pharmaceuticals usa
- Torrent pharmaceuticals ltd
- Watson laboratories inc
- Packagers
- Actavis Group
- Advanced Pharmaceutical Services Inc.
- Aidarex Pharmacuticals LLC
- Amerisource Health Services Corp.
- Amkas Laboratories Inc.
- Amneal Pharmaceuticals
- Apotex Inc.
- A-S Medication Solutions LLC
- Atlantic Biologicals Corporation
- Aurobindo Pharma Ltd.
- Aurolife Pharma LLC
- Blu Pharmaceuticals LLC
- Bryant Ranch Prepack
- Camber Pharmaceuticals Inc.
- Caraco Pharmaceutical Labs
- Cardinal Health
- Cipla Ltd.
- Cobalt Pharmaceuticals Inc.
- Comprehensive Consultant Services Inc.
- Corepharma LLC
- Coupler Enterprises Inc.
- Cypress Pharmaceutical Inc.
- Dept Health Central Pharmacy
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- Doctor Reddys Laboratories Ltd.
- Eon Labs
- Forest Laboratories Inc.
- Forest Pharmaceuticals
- Glenmark Generics Ltd.
- Greenstone LLC
- Heartland Repack Services LLC
- Innoviant Pharmacy Inc.
- International Laboratories Inc.
- InvaGen Pharmaceuticals Inc.
- Inwood Labs
- Kali Laboratories Inc.
- Lake Erie Medical and Surgical Supply
- Legacy Pharmaceuticals Packaging LLC
- Lundbeck Inc.
- Major Pharmaceuticals
- Matrix Laboratories Ltd.
- Medvantx Inc.
- Murfreesboro Pharmaceutical Nursing Supply
- Mylan
- Nucare Pharmaceuticals Inc.
- Palmetto Pharmaceuticals Inc.
- PD-Rx Pharmaceuticals Inc.
- Perrigo Co.
- Physicians Total Care Inc.
- Pliva Inc.
- Preferred Pharmaceuticals Inc.
- Prepackage Specialists
- Prepak Systems Inc.
- Rebel Distributors Corp.
- Remedy Repack
- Resource Optimization and Innovation LLC
- Roxane Labs
- Silarx Pharmaceuticals
- Southwood Pharmaceuticals
- Stat Rx Usa
- Teva Pharmaceutical Industries Ltd.
- Torrent Pharmaceuticals
- Va Cmop Dallas
- Vangard Labs Inc.
- W and D Distributing Co.
- Dosage Forms
Form Route Strength Tablet Oral 49.960 mg Tablet Oral 24.98 mg Tablet Oral 6.355 mg Tablet Oral 20 mg Tablet Oral 40 mg Injection, solution, concentrate Intravenous Capsule Oral 30 mg/1 Solution Oral 20 mg/10mL Tablet, film coated Oral 10 MG Tablet, film coated Oral 30 MG Solution / drops Oral Tablet, film coated Oral Tablet, coated Oral 20 MG Tablet, coated Oral 40 MG Injection, solution, concentrate Intravenous 40 MG/ML Solution / drops Oral 40 MG/ML Tablet, film coated Oral 20 MG Tablet, film coated Oral 40 MG Solution Oral 20 MG/ML Capsule Oral 10 mg/1 Capsule Oral 20 mg/1 Capsule Oral 40 mg/1 Solution Oral 10 mg/5mL Tablet Oral 10 mg/1 Tablet Oral 20 mg/1 Tablet Oral 40 mg/301 Tablet Oral 40 mg/1 Tablet, film coated Oral 10 mg/1 Tablet, film coated Oral 20 mg/1 Tablet, film coated Oral 40 mg/1 Tablet Oral 20.000 mg Tablet Oral 30 mg Injection, solution, concentrate Intravenous; Parenteral 40 MG/ML Tablet Oral 25.000 mg Tablet Oral 26.240 mg Tablet Oral 20.0000 mg Tablet Oral 10 mg Injection, solution, concentrate Intravenous 20 mg/0.5ml Kit Oral Injection, solution, concentrate Parenteral 20 mg/0.5ml Injection, solution, concentrate Parenteral 40 mg/ml Tablet Oral 20.00 mg Tablet Oral 24.99 mg - Prices
Unit description Cost Unit Citalopram Hydrobromide 10 mg/5ml Solution 240ml Bottle 122.28USD bottle Celexa 40 mg tablet 3.88USD tablet Celexa 20 mg tablet 3.72USD tablet Celexa 10 mg tablet 3.57USD tablet Citalopram Hydrobromide 40 mg tablet 2.89USD tablet Citalopram Hydrobromide 20 mg tablet 2.8USD tablet Citalopram Hydrobromide 10 mg tablet 2.68USD tablet Citalopram hbr 40 mg tablet 2.53USD tablet Citalopram hbr 20 mg tablet 2.43USD tablet Citalopram hbr 10 mg tablet 2.33USD tablet Celexa 20 mg Tablet 1.47USD tablet Celexa 40 mg Tablet 1.47USD tablet Ctp 30 30 mg Tablet 0.99USD tablet Apo-Citalopram 20 mg Tablet 0.82USD tablet Apo-Citalopram 40 mg Tablet 0.82USD tablet Citalopram 20 mg Tablet 0.82USD tablet Citalopram 40 mg Tablet 0.82USD tablet Citalopram-Odan 20 mg Tablet 0.82USD tablet Citalopram-Odan 40 mg Tablet 0.82USD tablet Co Citalopram 20 mg Tablet 0.82USD tablet Co Citalopram 40 mg Tablet 0.82USD tablet Jamp-Citalopram 20 mg Tablet 0.82USD tablet Jamp-Citalopram 40 mg Tablet 0.82USD tablet Mint-Citalopram 20 mg Tablet 0.82USD tablet Mint-Citalopram 40 mg Tablet 0.82USD tablet Mylan-Citalopram 20 mg Tablet 0.82USD tablet Mylan-Citalopram 40 mg Tablet 0.82USD tablet Ng Citalopram 20 mg Tablet 0.82USD tablet Ng Citalopram 40 mg Tablet 0.82USD tablet Novo-Citalopram 20 mg Tablet 0.82USD tablet Novo-Citalopram 40 mg Tablet 0.82USD tablet Phl-Citalopram 20 mg Tablet 0.82USD tablet Phl-Citalopram 40 mg Tablet 0.82USD tablet Pms-Citalopram 20 mg Tablet 0.82USD tablet Pms-Citalopram 40 mg Tablet 0.82USD tablet Ran-Citalo 20 mg Tablet 0.82USD tablet Ran-Citalo 40 mg Tablet 0.82USD tablet Ran-Citalopram 20 mg Tablet 0.82USD tablet Ran-Citalopram 40 mg Tablet 0.82USD tablet Ratio-Citalopram 20 mg Tablet 0.82USD tablet Ratio-Citalopram 40 mg Tablet 0.82USD tablet Sandoz Citalopram 20 mg Tablet 0.82USD tablet Sandoz Citalopram 40 mg Tablet 0.82USD tablet Pms-Citalopram 10 mg Tablet 0.47USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region CA2353693 No 2003-07-22 2021-07-24 Canada CA2049368 No 2001-10-23 2011-08-16 Canada
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 182-188 https://www.chemicalbook.com/ChemicalProductProperty_US_CB2736240.aspx boiling point (°C) 347-358 http://datasheets.scbt.com/sc-201123.pdf water solubility Sparingly soluble https://www.chemicalbook.com/ChemicalProductProperty_US_CB2736240.aspx logP 3.76 http://www.t3db.ca/toxins/T3D2715 logS -4.7 http://www.t3db.ca/toxins/T3D2715 pKa 9.78 http://www.t3db.ca/toxins/T3D2715 - Predicted Properties
Property Value Source Water Solubility 0.00588 mg/mL ALOGPS logP 3.58 ALOGPS logP 3.76 Chemaxon logS -4.7 ALOGPS pKa (Strongest Basic) 9.78 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 36.26 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 94.02 m3·mol-1 Chemaxon Polarizability 35.3 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9966 Blood Brain Barrier + 0.9729 Caco-2 permeable + 0.6099 P-glycoprotein substrate Substrate 0.7597 P-glycoprotein inhibitor I Non-inhibitor 0.6361 P-glycoprotein inhibitor II Inhibitor 0.9789 Renal organic cation transporter Inhibitor 0.6993 CYP450 2C9 substrate Non-substrate 0.8401 CYP450 2D6 substrate Substrate 0.8919 CYP450 3A4 substrate Substrate 0.7407 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Inhibitor 0.8949 CYP450 2D6 inhibitor Non-inhibitor 0.5054 CYP450 2C19 inhibitor Inhibitor 0.8994 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5223 Ames test Non AMES toxic 0.7602 Carcinogenicity Non-carcinogens 0.7452 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.9054 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7735 hERG inhibition (predictor II) Inhibitor 0.8994
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 189.5986377 predictedDarkChem Lite v0.1.0 [M-H]- 180.40004 predictedDeepCCS 1.0 (2019) [M+H]+ 190.3072377 predictedDarkChem Lite v0.1.0 [M+H]+ 182.75804 predictedDeepCCS 1.0 (2019) [M+Na]+ 190.4356377 predictedDarkChem Lite v0.1.0 [M+Na]+ 188.94392 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Serotonin transporter that cotransports serotonin with one Na(+) ion in exchange for one K(+) ion and possibly one proton in an overall electroneutral transport cycle. Transports serotonin across the plasma membrane from the extracellular compartment to the cytosol thus limiting serotonin intercellular signaling (PubMed:10407194, PubMed:12869649, PubMed:21730057, PubMed:27049939, PubMed:27756841, PubMed:34851672). Essential for serotonin homeostasis in the central nervous system. In the developing somatosensory cortex, acts in glutamatergic neurons to control serotonin uptake and its trophic functions accounting for proper spatial organization of cortical neurons and elaboration of sensory circuits. In the mature cortex, acts primarily in brainstem raphe neurons to mediate serotonin uptake from the synaptic cleft back into the pre-synaptic terminal thus terminating serotonin signaling at the synapse (By similarity). Modulates mucosal serotonin levels in the gastrointestinal tract through uptake and clearance of serotonin in enterocytes. Required for enteric neurogenesis and gastrointestinal reflexes (By similarity). Regulates blood serotonin levels by ensuring rapid high affinity uptake of serotonin from plasma to platelets, where it is further stored in dense granules via vesicular monoamine transporters and then released upon stimulation (PubMed:17506858, PubMed:18317590). Mechanistically, the transport cycle starts with an outward-open conformation having Na1(+) and Cl(-) sites occupied. The binding of a second extracellular Na2(+) ion and serotonin substrate leads to structural changes to outward-occluded to inward-occluded to inward-open, where the Na2(+) ion and serotonin are released into the cytosol. Binding of intracellular K(+) ion induces conformational transitions to inward-occluded to outward-open and completes the cycle by releasing K(+) possibly together with a proton bound to Asp-98 into the extracellular compartment. Na1(+) and Cl(-) ions remain bound throughout the transport cycle (PubMed:10407194, PubMed:12869649, PubMed:21730057, PubMed:27049939, PubMed:27756841, PubMed:34851672). Additionally, displays serotonin-induced channel-like conductance for monovalent cations, mainly Na(+) ions. The channel activity is uncoupled from the transport cycle and may contribute to the membrane resting potential or excitability (By similarity)
- Specific Function
- actin filament binding
- Gene Name
- SLC6A4
- Uniprot ID
- P31645
- Uniprot Name
- Sodium-dependent serotonin transporter
- Molecular Weight
- 70324.165 Da
References
- Sangkuhl K, Klein TE, Altman RB: PharmGKB summary: citalopram pharmacokinetics pathway. Pharmacogenet Genomics. 2011 Nov;21(11):769-72. doi: 10.1097/FPC.0b013e328346063f. [Article]
- Coleman JA, Green EM, Gouaux E: X-ray structures and mechanism of the human serotonin transporter. Nature. 2016 Apr 21;532(7599):334-9. doi: 10.1038/nature17629. Epub 2016 Apr 6. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Binder
- General Function
- G-protein-coupled receptor for histamine, a biogenic amine that functions as an immune modulator and a neurotransmitter (PubMed:33828102, PubMed:8280179). Through the H1 receptor, histamine mediates the contraction of smooth muscles and increases capillary permeability due to contraction of terminal venules. Also mediates neurotransmission in the central nervous system and thereby regulates circadian rhythms, emotional and locomotor activities as well as cognitive functions (By similarity)
- Specific Function
- G protein-coupled serotonin receptor activity
- Gene Name
- HRH1
- Uniprot ID
- P35367
- Uniprot Name
- Histamine H1 receptor
- Molecular Weight
- 55783.61 Da
References
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Brosen K, Naranjo CA: Review of pharmacokinetic and pharmacodynamic interaction studies with citalopram. Eur Neuropsychopharmacol. 2001 Aug;11(4):275-83. [Article]
- Rasmussen BB, Brosen K: Is therapeutic drug monitoring a case for optimizing clinical outcome and avoiding interactions of the selective serotonin reuptake inhibitors? Ther Drug Monit. 2000 Apr;22(2):143-54. [Article]
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
- Pelkonen O, Maenpaa J, Taavitsainen P, Rautio A, Raunio H: Inhibition and induction of human cytochrome P450 (CYP) enzymes. Xenobiotica. 1998 Dec;28(12):1203-53. [Article]
- Sangkuhl K, Klein TE, Altman RB: PharmGKB summary: citalopram pharmacokinetics pathway. Pharmacogenet Genomics. 2011 Nov;21(11):769-72. doi: 10.1097/FPC.0b013e328346063f. [Article]
- von Moltke LL, Greenblatt DJ, Grassi JM, Granda BW, Venkatakrishnan K, Duan SX, Fogelman SM, Harmatz JS, Shader RI: Citalopram and desmethylcitalopram in vitro: human cytochromes mediating transformation, and cytochrome inhibitory effects. Biol Psychiatry. 1999 Sep 15;46(6):839-49. [Article]
- FDA Approved Drug Products: CELEXA (citalopram) tablets, for oral use (August 2023) [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position (PubMed:18577768). Catalyzes the epoxidation of double bonds of PUFA (PubMed:19965576, PubMed:20972997). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine. Hydroxylates fenbendazole at the 4' position (PubMed:23959307)
- Specific Function
- (R)-limonene 6-monooxygenase activity
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55944.565 Da
References
- Brosen K, Naranjo CA: Review of pharmacokinetic and pharmacodynamic interaction studies with citalopram. Eur Neuropsychopharmacol. 2001 Aug;11(4):275-83. [Article]
- Rasmussen BB, Brosen K: Is therapeutic drug monitoring a case for optimizing clinical outcome and avoiding interactions of the selective serotonin reuptake inhibitors? Ther Drug Monit. 2000 Apr;22(2):143-54. [Article]
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
- Pelkonen O, Maenpaa J, Taavitsainen P, Rautio A, Raunio H: Inhibition and induction of human cytochrome P450 (CYP) enzymes. Xenobiotica. 1998 Dec;28(12):1203-53. [Article]
- von Moltke LL, Greenblatt DJ, Grassi JM, Granda BW, Venkatakrishnan K, Duan SX, Fogelman SM, Harmatz JS, Shader RI: Citalopram and desmethylcitalopram in vitro: human cytochromes mediating transformation, and cytochrome inhibitory effects. Biol Psychiatry. 1999 Sep 15;46(6):839-49. [Article]
- Olesen OV, Linnet K: Studies on the stereoselective metabolism of citalopram by human liver microsomes and cDNA-expressed cytochrome P450 enzymes. Pharmacology. 1999 Dec;59(6):298-309. doi: 10.1159/000028333. [Article]
- Flockhart Table of Drug Interactions [Link]
- Citalopram FDA label [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
- Specific Function
- anandamide 11,12 epoxidase activity
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:11555828, PubMed:12865317). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2 (PubMed:11555828, PubMed:12865317). Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). May act as a major enzyme for all-trans retinoic acid biosynthesis in the liver. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). Primarily catalyzes stereoselective epoxidation of the last double bond of polyunsaturated fatty acids (PUFA), displaying a strong preference for the (R,S) stereoisomer (PubMed:19965576). Catalyzes bisallylic hydroxylation and omega-1 hydroxylation of PUFA (PubMed:9435160). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195). Plays a role in the oxidative metabolism of xenobiotics. Catalyzes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin (PubMed:14725854). Metabolizes caffeine via N3-demethylation (Probable)
- Specific Function
- aromatase activity
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58406.915 Da
References
- von Moltke LL, Greenblatt DJ, Grassi JM, Granda BW, Venkatakrishnan K, Duan SX, Fogelman SM, Harmatz JS, Shader RI: Citalopram and desmethylcitalopram in vitro: human cytochromes mediating transformation, and cytochrome inhibitory effects. Biol Psychiatry. 1999 Sep 15;46(6):839-49. [Article]
- Citalopram FDA [File]
- MedSafe NZ Data Sheet, Citalopram [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Catalyzes the oxidative deamination of primary and some secondary amine such as neurotransmitters, with concomitant reduction of oxygen to hydrogen peroxide and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues (PubMed:18391214, PubMed:20493079, PubMed:24169519, PubMed:8316221). Preferentially oxidizes serotonin (PubMed:20493079, PubMed:24169519). Also catalyzes the oxidative deamination of kynuramine to 3-(2-aminophenyl)-3-oxopropanal that can spontaneously condense to 4-hydroxyquinoline (By similarity)
- Specific Function
- aliphatic amine oxidase activity
- Gene Name
- MAOA
- Uniprot ID
- P21397
- Uniprot Name
- Amine oxidase [flavin-containing] A
- Molecular Weight
- 59681.27 Da
References
- 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. doi: 10.1016/s0006-2952(98)00008-2. [Article]
- Sangkuhl K, Klein TE, Altman RB: PharmGKB summary: citalopram pharmacokinetics pathway. Pharmacogenet Genomics. 2011 Nov;21(11):769-72. doi: 10.1097/FPC.0b013e328346063f. [Article]
- Bezchlibnyk-Butler K, Aleksic I, Kennedy SH: Citalopram--a review of pharmacological and clinical effects. J Psychiatry Neurosci. 2000 May;25(3):241-54. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Catalyzes the oxidative deamination of primary and some secondary amines such as neurotransmitters, and exogenous amines including the tertiary amine, neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP), with concomitant reduction of oxygen to hydrogen peroxide and participates in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues (PubMed:11049757, PubMed:11134050, PubMed:20493079, PubMed:8316221, PubMed:8665924). Preferentially degrades benzylamine and phenylethylamine (PubMed:11049757, PubMed:11134050, PubMed:20493079, PubMed:8316221, PubMed:8665924)
- Specific Function
- aliphatic amine oxidase activity
- Gene Name
- MAOB
- Uniprot ID
- P27338
- Uniprot Name
- Amine oxidase [flavin-containing] B
- Molecular Weight
- 58762.475 Da
References
- Bezchlibnyk-Butler K, Aleksic I, Kennedy SH: Citalopram--a review of pharmacological and clinical effects. J Psychiatry Neurosci. 2000 May;25(3):241-54. [Article]
- 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. doi: 10.1016/s0006-2952(98)00008-2. [Article]
- Sangkuhl K, Klein TE, Altman RB: PharmGKB summary: citalopram pharmacokinetics pathway. Pharmacogenet Genomics. 2011 Nov;21(11):769-72. doi: 10.1097/FPC.0b013e328346063f. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Oxidase with broad substrate specificity, oxidizing aromatic azaheterocycles, such as N1-methylnicotinamide, N-methylphthalazinium and phthalazine, as well as aldehydes, such as benzaldehyde, retinal, pyridoxal, and vanillin. Plays a key role in the metabolism of xenobiotics and drugs containing aromatic azaheterocyclic substituents. Participates in the bioactivation of prodrugs such as famciclovir, catalyzing the oxidation step from 6-deoxypenciclovir to penciclovir, which is a potent antiviral agent. Is probably involved in the regulation of reactive oxygen species homeostasis. May be a prominent source of superoxide generation via the one-electron reduction of molecular oxygen. May also catalyze nitric oxide (NO) production via the reduction of nitrite to NO with NADH or aldehyde as electron donor. May play a role in adipogenesis
- Specific Function
- 2 iron, 2 sulfur cluster binding
- Gene Name
- AOX1
- Uniprot ID
- Q06278
- Uniprot Name
- Aldehyde oxidase
- Molecular Weight
- 147916.735 Da
References
- Sangkuhl K, Klein TE, Altman RB: PharmGKB summary: citalopram pharmacokinetics pathway. Pharmacogenet Genomics. 2011 Nov;21(11):769-72. doi: 10.1097/FPC.0b013e328346063f. [Article]
- 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. doi: 10.1016/s0006-2952(98)00008-2. [Article]
- Bezchlibnyk-Butler K, Aleksic I, Kennedy SH: Citalopram--a review of pharmacological and clinical effects. J Psychiatry Neurosci. 2000 May;25(3):241-54. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- ATP-dependent translocase ABCB1
- Molecular Weight
- 141477.255 Da
References
- Weiss J, Dormann SM, Martin-Facklam M, Kerpen CJ, Ketabi-Kiyanvash N, Haefeli WE: Inhibition of P-glycoprotein by newer antidepressants. J Pharmacol Exp Ther. 2003 Apr;305(1):197-204. [Article]
- Uhr M, Tontsch A, Namendorf C, Ripke S, Lucae S, Ising M, Dose T, Ebinger M, Rosenhagen M, Kohli M, Kloiber S, Salyakina D, Bettecken T, Specht M, Putz B, Binder EB, Muller-Myhsok B, Holsboer F: Polymorphisms in the drug transporter gene ABCB1 predict antidepressant treatment response in depression. Neuron. 2008 Jan 24;57(2):203-9. doi: 10.1016/j.neuron.2007.11.017. [Article]
- Uhr M, Grauer MT: abcb1ab P-glycoprotein is involved in the uptake of citalopram and trimipramine into the brain of mice. J Psychiatr Res. 2003 May-Jun;37(3):179-85. [Article]
Drug created at June 13, 2005 13:24 / Updated at November 09, 2024 06:13