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 belongs to a class of antidepressant agents known as selective serotonin-reuptake inhibitors (SSRIs) and is widely used to treat the symptoms of depression. Its chemical structure is unrelated to that of other SSRIs or of tricyclic, tetracyclic, or other prescribed antidepressants Label. Citalopram is also known as Celexa, and available in tablet and solution forms Label. This drug was initially approved by the FDA in 1998 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
For the treatment of depression, as indicated by the FDA label Label. Off-label indications include but are not limited to: treatment of sexual dysfunction, post-stroke behavioural changes, ethanol abuse, obsessive-compulsive disorder (OCD) in children, and diabetic neuropathy Label, 1, 2, 3, 4, 10, 11, 12.
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- Contraindications & Blackbox Warnings
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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 Label. Serotonergic abnormalities have been reported in patients with mood disorders. Behavioral and neuropsychological of 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 5.
- Mechanism of action
The mechanism of action of citalopram results from its inhibition of CNS neuronal reuptake of serotonin (5-HT) Label. The molecular target for citalopram is the serotonin transporter (solute carrier family 6 member 4, SLC6A4), inhibiting its serotonin reuptake in the synaptic cleft 13.
Citalopram binds with significantly less affinity to histamine, acetylcholine, and norepinephrine receptors than tricyclic antidepressant drugs Label. This drug has no or neglible 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. Antagonism of muscarinic, histaminergic, and adrenergic receptors is thought to be associated with several anticholinergic, sedative, and cardiovascular effects of other psychotropic drugs Label.
Target Actions Organism ASodium-dependent serotonin transporter inhibitorHumans NHistamine H1 receptor binderHumans - Absorption
Rapidly and well absorbed from the GI tract. Peak plasma concentrations occur within 4 hours of a single orally administered dose. Bioavailability is 80% following oral administration. Food does not affect absorption Label.
- Volume of distribution
12 L/kg Label
Citalopram is highly lipophilic and likely widely distributed throughout the body, including the blood-brain-barrier. However, its metabolite, demethylcitalopram does not penetrate the blood-brain-barrier well Label.
- Protein binding
Citalopram, dimethylcitalopram, and didemethylcitalopram are 80% bound to plasma proteins Label.
- Metabolism
Citalopram is metabolized mainly in the liver via N-demethylation to its main metabolite, demethylcitalopram by CYP2C19 and CYP3A4 7. Other metabolites include didemethylcitalopram via CYP2D6 metabolism, and citalopram N-oxide via monoamine oxidase enzymes and aldehyde oxidase. It is a deaminated propionic acid derivative 7.
After a single dose of citalopram, peak blood concentrations occur at approximately 4 hours Label. This drug in is found mainly unchanged in the plasma as citalopram. Cytochrome P450 (CYP) 3A4 and 2C19 isozymes appear to be heavily involved in producing demethylcitalopram. Demethylcitalopram appears to be further N-demethylated by CYP2D6 to didemethylcitalopram. Citalopram metabolites exert little pharmacologic activity in comparison to the parent drug and are not likely to contribute to the clinical effect of citalopram 5.
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- Route of elimination
12-23% of an oral dose of citalopram is found unchanged in the urine, while 10% of the dose is found in the faeces Label.
- Half-life
About 35 hours Label.
- Clearance
The systemic clearance of citalopram is 330 mL/min, with approximately 20% renal clearance Label.
- Adverse Effects
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Oral (Human) LD: 56 mg/kg Intraperitoneal (Mouse) LD50: 179 mg/kg
Acute toxicity
Symptoms of toxicity include dizziness, sweating, nausea, vomiting, tremor, somnolence, and sinus tachycardia. Rarely, symptoms included amnesia, confusion, coma, convulsions, hyperventilation, cyanosis, rhabdomyolysis, and ECG changes (including QTc prolongation, nodal rhythm, ventricular arrhythmia, and extremely rare cases of cardiac torsade de pointes) may occur. Acute renal failure has been a rare occurrence 5.
In cases of overdose, establish and maintain the airway to ensure adequate ventilation and oxygen delivery. Due to the large volume of distribution of citalopram, forced diuresis, dialysis, hemoperfusion, and exchange transfusion are unlikely to be of benefit. Gastric evacuation by lavage and use of activated charcoal should be considered. Careful observation and cardiac and vital sign monitoring are advised, in addition to supportive care. With the large volume of distribution of citalopram, forced diuresis, dialysis, hemoperfusion, and exchange transfusion are unlikely to be of benefit Label.
Pregnancy
This drug is categorized as pregnancy category C. In animal reproduction studies, citalopram has been shown to have adverse effects on embryo/fetal and postnatal development, which includes teratogenic effects when given at doses higher than human therapeutic doses. There are no sufficient and well-controlled studies in pregnant women; therefore, citalopram should be used during pregnancy only in cases where the potential benefit justifies the possible risk to the fetus Label.
Pregnancy-Nonteratogenic Effects
Neonates exposed to celexa and other SSRIs or SNRIs, late in the third trimester, have undergone complications requiring prolonged hospitalization, respiratory support, and parenteral feeding. Complications such as these can arise immediately upon delivery Label.
Nursing Mothers
Citalopram is excreted in human breast milk. There have been two reports of infants demonstrating high levels of somnolence, reduced feeding, and weight loss associated with breastfeeding from a mother taking citalopram. In one specific case, the infant was reported to recover completely after the discontinuation of citalopram. In the second case, no follow-up information was available for assessment. The decision whether to continue or discontinue either nursing or celexa should consider the risks of citalopram exposure for the infant versus the benefits of celexa treatment for the mother Label.
- 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 hemorrhage can be increased when Citalopram is combined with Abciximab. Abemaciclib The metabolism of Abemaciclib can be decreased when combined with Citalopram. Abiraterone The metabolism of Citalopram can be decreased when combined with Abiraterone. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Citalopram. Acalabrutinib The metabolism of Acalabrutinib can be decreased when combined with Citalopram. Acarbose The risk or severity of hypoglycemia can be increased when Citalopram is combined with Acarbose. Acebutolol The metabolism of Acebutolol can be decreased when combined with Citalopram. 
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- Avoid alcohol.
- Avoid St. John's Wort.
- 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 30 mg Oral Sunovion Not applicable Not applicable Canada 
Act Citalopram Tablet 40 mg Oral Sunovion 2004-01-21 2022-04-27 Canada Act Citalopram Tablet 20 mg Oral Sunovion 2004-01-21 2022-04-27 Canada Celexa Tablet 10 mg/1 Oral Physicians Total Care, Inc. 2004-01-30 Not applicable US 
Celexa Tablet, film coated 20 mg/1 Oral Allergan, Inc. 1998-07-17 Not applicable US 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 Celexa Solution 10 mg/5mL Oral FOREST PHARMACEUTICALS, INC. 2007-11-16 2007-11-16 US Celexa Tablet 20 mg/1 Oral Physicians Total Care, Inc. 2000-11-28 Not applicable US Celexa Tablet, film coated 40 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 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 Abbott-citalopram Tablet 10 mg Oral Abbott 2014-03-17 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 Accel-citalopram Tablets Tablet 40 mg Oral Accel Pharma Inc 2013-07-02 2020-03-20 Canada Ag-citalopram Tablet 40 mg Oral Angita Pharma Inc. 2014-09-14 Not applicable Canada Ag-citalopram Tablet 20 mg Oral Angita Pharma Inc. 2014-09-14 Not applicable Canada Ag-citalopram Tablet 10 mg Oral Angita Pharma Inc. 2014-08-14 Not applicable Canada Ag-citalopram Tablets Tablet 10 mg Oral Angita Pharma Inc. Not applicable Not applicable 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
- 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]
- Clayton A, Keller A, McGarvey EL: Burden of phase-specific sexual dysfunction with SSRIs. J Affect Disord. 2006 Mar;91(1):27-32. Epub 2006 Jan 20. [Article]
- Baumann P: Pharmacology and pharmacokinetics of citalopram and other SSRIs. Int Clin Psychopharmacol. 1996 Mar;11 Suppl 1:5-11. [Article]
- Caccia S: Metabolism of the newer antidepressants. An overview of the pharmacological and pharmacokinetic implications. Clin Pharmacokinet. 1998 Apr;34(4):281-302. doi: 10.2165/00003088-199834040-00002. [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]
- Keller MB: Citalopram therapy for depression: a review of 10 years of European experience and data from U.S. clinical trials. J Clin Psychiatry. 2000 Dec;61(12):896-908. [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]
- Naranjo CA, Knoke DM, Bremner KE: Variations in response to citalopram in men and women with alcohol dependence. J Psychiatry Neurosci. 2000 May;25(3):269-75. [Article]
- Thomsen PH: Child and adolescent obsessive-compulsive disorder treated with citalopram: findings from an open trial of 23 cases. J Child Adolesc Psychopharmacol. 1997;7(3):157-66. doi: 10.1089/cap.1997.7.157. [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]
- 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]
- 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
Phase Status Purpose Conditions Count 4 Completed Basic Science Bipolar Disorder (BD) 1 4 Completed Health Services Research Obsessive Compulsive Disorder (OCD) 1 4 Completed Other Depression 1 4 Completed Other Healthy Controls / Major Depressive Disorder (MDD) 1 4 Completed Supportive Care Friedreich's Ataxia 1 4 Completed Treatment Antidepressant Activity in Healthy Volunteers 1 4 Completed Treatment Anxiety Disorders / Obsessive Compulsive Disorder (OCD) / Psychiatric Disorder NOS 1 4 Completed Treatment Borderline Personality Disorder (BPD) / Suicide 1 4 Completed Treatment Citalopram / Major Depressive Disorder (MDD) 1 4 Completed Treatment Dementia 2
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
- Actavis elizabeth llc
- Amneal pharmaceuticals ny llc
- Apotex inc etobicoke site
- Aurobindo pharma ltd
- Caraco pharmaceutical laboratories ltd
- Corepharma llc
- Dr reddys laboratories ltd
- 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 20 mg Tablet Oral 40 mg Injection, solution, concentrate Intravenous Capsule Oral 30 mg/1 Solution Oral 20 mg/10mL Tablet, film coated Oral Tablet, film coated Oral 30 MG Solution / drops 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, film coated Oral 10 MG Tablet Oral 30 mg Injection, solution, concentrate Intravenous; Parenteral 40 MG/ML 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 - 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
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Serotonin:sodium symporter activity
- Specific Function
- Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into t...
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Binder
- General Function
- Histamine receptor activity
- Specific Function
- In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
- Gene Name
- HRH1
- Uniprot ID
- P35367
- Uniprot Name
- Histamine H1 receptor
- Molecular Weight
- 55783.61 Da
References
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- 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 im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 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
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 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]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- 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 June 02, 2023 16:39