Identification

Name
Citalopram
Accession Number
DB00215
Description

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
Thumb
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.

Associated Conditions
Contraindications & Blackbox Warnings
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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 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.

TargetActionsOrganism
ASodium-dependent serotonin transporter
inhibitor
Humans
NHistamine H1 receptor
binder
Humans
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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Toxicity

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.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Citalopram Action PathwayDrug action
Citalopram Metabolism PathwayDrug metabolism
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Glutamate receptor ionotropic, kainate 2---(C;C)C Allele, homozygoteADR Directly StudiedPatients with this genotype have increased frequency of suicidal ideation with citalopramDetails
Glutamate receptor 3---(G;G) / (G;A)G alleleADR Directly StudiedPatients with this genotype have increased frequency of suicidal ideation with citalopramDetails
Multidrug resistance protein 1---(C;C) / (C;T)C AlleleEffect Directly StudiedPatients with this genotype have an increased likelihood of remission when using citalopram to treat major depressive disorderDetails
5-hydroxytryptamine receptor 2A---(A;A)A AlleleEffect Directly StudiedPatients with this genotype have an increased likelihood of responding to citalopram when treating major depressive disorderDetails
Glutamate receptor ionotropic, kainate 4---(C;C)C AlleleEffect Directly StudiedPatients with this genotype have an increased likelihood of responding to citalopram when treating major depressive disorderDetails
Cyclic AMP-responsive element-binding protein 1---(T;T)T allele, homozygousADR Directly StudiedMale patients with this genotype have an increased risk of (condition: suicide) with (drug: citalopram).Details
Cytochrome P450 2C19CYP2C19*2ANot Available681G>AADR InferredPoor drug metabolizer, increased risk of QT prolongation. For individual with two non-functional alleles, dose reduction or alternative drug recommended.Details
Cytochrome P450 2C19CYP2C19*2BNot Available681G>AADR InferredPoor drug metabolizer, increased risk of QT prolongation. For individual with two non-functional alleles, dose reduction or alternative drug recommended.Details
Cytochrome P450 2C19CYP2C19*3Not Available636G>AADR InferredPoor drug metabolizer, increased risk of QT prolongation. For individual with two non-functional alleles, dose reduction or alternative drug recommended.Details
Cytochrome P450 2C19CYP2C19*4Not Available1A>GADR InferredPoor drug metabolizer, increased risk of QT prolongation. For individual with two non-functional alleles, dose reduction or alternative drug recommended.Details
Cytochrome P450 2C19CYP2C19*5Not Available1297C>TADR InferredPoor drug metabolizer, increased risk of QT prolongation. For individual with two non-functional alleles, dose reduction or alternative drug recommended.Details
Cytochrome P450 2C19CYP2C19*6Not Available395G>AADR InferredPoor drug metabolizer, increased risk of QT prolongation. For individual with two non-functional alleles, dose reduction or alternative drug recommended.Details
Cytochrome P450 2C19CYP2C19*7Not Available19294T>AADR InferredPoor drug metabolizer, increased risk of QT prolongation. For individual with two non-functional alleles, dose reduction or alternative drug recommended.Details
Cytochrome P450 2C19CYP2C19*22Not Available557G>C / 991A>GADR InferredPoor drug metabolizer, increased risk of QT prolongation. For individual with two non-functional alleles, dose reduction or alternative drug recommended.Details
Cytochrome P450 2C19CYP2C19*24Not Available99C>T / 991A>G  … show all ADR InferredPoor drug metabolizer, increased risk of QT prolongation. For individual with two non-functional alleles, dose reduction or alternative drug recommended.Details
Cytochrome P450 2C19CYP2C19*35Not Available12662A>GADR InferredPoor 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.
DrugInteraction
AbaloparatideThe therapeutic efficacy of Abaloparatide can be decreased when used in combination with Citalopram.
AbametapirThe serum concentration of Citalopram can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Citalopram can be increased when combined with Abatacept.
AbciximabThe risk or severity of hemorrhage can be increased when Citalopram is combined with Abciximab.
AbirateroneThe serum concentration of Citalopram can be increased when it is combined with Abiraterone.
AcalabrutinibThe metabolism of Acalabrutinib can be decreased when combined with Citalopram.
AcarboseThe risk or severity of hypoglycemia can be increased when Citalopram is combined with Acarbose.
AcebutololThe risk or severity of QTc prolongation can be increased when Acebutolol is combined with Citalopram.
AceclofenacThe risk or severity of gastrointestinal bleeding can be increased when Citalopram is combined with Aceclofenac.
AcemetacinThe risk or severity of gastrointestinal bleeding can be increased when Citalopram is combined with Acemetacin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Avoid alcohol.
  • Avoid St. John's Wort.
  • Take with or without food. The absorption is unaffected by food.

Products

Product Ingredients
IngredientUNIICASInChI Key
Citalopram hydrobromideI1E9D14F3659729-32-7WIHMBLDNRMIGDW-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
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act CitalopramTabletOralSunovion2004-01-21Not applicableCanada flag
Act CitalopramTabletOralSunovion2004-01-21Not applicableCanada flag
Act CitalopramTabletOralSunovionNot applicableNot applicableCanada flag
CelexaTablet, film coated20 mg/1OralAllergan, Inc.1998-07-17Not applicableUS flag
CelexaTablet, film coated40 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2011-11-172014-12-31US flag
CelexaTablet20 mg/1OralPhysicians Total Care, Inc.2000-11-28Not applicableUS flag
CelexaTablet, film coated10 mg/1OralAllergan, Inc.1998-07-17Not applicableUS flag
CelexaTablet, film coated40 mg/1OralAllergan, Inc.1998-07-17Not applicableUS flag
CelexaTablet10 mg/1OralPhysicians Total Care, Inc.2004-01-30Not applicableUS flag
CelexaTablet40 mg/1OralPhysicians Total Care, Inc.2001-09-05Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Abbott-citalopramTabletOralAbbott2014-03-122015-12-31Canada flag
Abbott-citalopramTabletOralAbbott2014-03-172015-12-31Canada flag
Abbott-citalopramTabletOralAbbott2014-03-122015-12-31Canada flag
Accel-citalopram TabletsTabletOralAccel Pharma Inc2013-03-212020-03-20Canada flag
Accel-citalopram TabletsTabletOralAccel Pharma Inc2013-07-022020-03-20Canada flag
Accel-citalopram TabletsTabletOralAccel Pharma Inc2013-07-022020-03-20Canada flag
Ag-citalopramTabletOralAngita Pharma Inc.2014-09-14Not applicableCanada flag
Ag-citalopramTabletOralAngita Pharma Inc.2014-08-14Not applicableCanada flag
Ag-citalopramTabletOralAngita Pharma Inc.2014-09-14Not applicableCanada flag
Apo-citalopramTabletOralApotex Corporation2004-01-21Not applicableCanada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Sentralopram AM-10Citalopram hydrobromide (10 mg/1) + Choline (250 mg/1)KitOralPhysician Therapeutics Llc2011-07-07Not applicableUS flag

Categories

ATC Codes
N06AB04 — Citalopram
Drug Categories
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)

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
  1. Sindrup SH, Bjerre U, Dejgaard A, Brosen K, Aaes-Jorgensen T, Gram LF: The selective serotonin reuptake inhibitor citalopram relieves the symptoms of diabetic neuropathy. Clin Pharmacol Ther. 1992 Nov;52(5):547-52. [PubMed:1424428]
  2. 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. [PubMed:12494286]
  3. Andersen G, Vestergaard K, Riis JO: Citalopram for post-stroke pathological crying. Lancet. 1993 Oct 2;342(8875):837-9. [PubMed:8104273]
  4. 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. [PubMed:16430968]
  5. Baumann P: Pharmacology and pharmacokinetics of citalopram and other SSRIs. Int Clin Psychopharmacol. 1996 Mar;11 Suppl 1:5-11. [PubMed:8732438]
  6. 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. [PubMed:9571301]
  7. Bezchlibnyk-Butler K, Aleksic I, Kennedy SH: Citalopram--a review of pharmacological and clinical effects. J Psychiatry Neurosci. 2000 May;25(3):241-54. [PubMed:10863884]
  8. 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. [PubMed:11206593]
  9. 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. [PubMed:23018033]
  10. 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. [PubMed:10863887]
  11. 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. [PubMed:9466233]
  12. 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. [PubMed:12934982]
  13. Sangkuhl K, Klein TE, Altman RB: PharmGKB summary: citalopram pharmacokinetics pathway. Pharmacogenet Genomics. 2011 Nov;21(11):769-72. doi: 10.1097/FPC.0b013e328346063f. [PubMed:21546862]
  14. https://www.ncbi.nlm.nih.gov/books/NBK482222/ (2018). Stat Pearls [Internet]. NIH Stat Pearls.
  15. MSDS citalopram [Link]
  16. NIH Stat Pearls: Citalopram [Link]
  17. AAFP: Off-label Applications for SSRIs [Link]
  18. Celexa Information, FDA [Link]
  19. Celexa Monograph [File]
Human Metabolome Database
HMDB0005038
KEGG Drug
D07704
KEGG Compound
C07572
PubChem Compound
2771
PubChem Substance
46508746
ChemSpider
2669
BindingDB
25870
RxNav
2556
ChEBI
77397
ChEMBL
CHEMBL549
Therapeutic Targets Database
DAP000118
PharmGKB
PA449015
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Citalopram
AHFS Codes
  • 28:16.04.20 — Selective-serotonin Reuptake Inhibitors
FDA label
Download (190 KB)
MSDS
Download (379 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingBasic ScienceMajor Depressive Disorder (MDD)1
4CompletedBasic ScienceBipolar Disorder (BD)1
4CompletedHealth Services ResearchObsessive Compulsive Disorder (OCD)1
4CompletedOtherDepression1
4CompletedOtherHealthy Controls / Major Depressive Disorder (MDD)1
4CompletedSupportive CareFriedreich's Ataxia1
4CompletedTreatmentAntidepressant Activity in Healthy Volunteers1
4CompletedTreatmentAnxiety Disorders / Obsessive Compulsive Disorder (OCD) / Psychiatric Disorder NOS1
4CompletedTreatmentBorderline Personality Disorder (BPD) / Suicide1
4CompletedTreatmentCitalopram / Major Depressive Disorder (MDD)1

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
FormRouteStrength
Tablet, film coated20 mg
Tablet, film coated40 mg
TabletOral
Tablet
Tablet, film coatedOral20 MG
Tablet, film coatedOral40 MG
SolutionOral20 mg/10mL
TabletOral10 mg
TabletOral20 mg
TabletOral40 mg
Tablet, film coatedOral10 MG
Tablet, film coatedOral30 MG
Solution / dropsOral40 MG/ML
Tablet, coated20 MG
Tablet, coated40 MG
CapsuleOral10 mg/1
CapsuleOral20 mg/1
CapsuleOral40 mg/1
SolutionOral10 mg/5mL
TabletOral10 mg/1
TabletOral20 mg/1
TabletOral40 mg/301
TabletOral40 mg/1
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral20 mg/1
Tablet, film coatedOral40 mg/1
Tablet, coatedOral20 MG
Tablet, coatedOral40 MG
Tablet, coatedOral10 MG
Tablet, film coated10 mg
Injection, solution, concentrateIntravenous40 MG/ML
Tablet40 MG
KitOral
Prices
Unit descriptionCostUnit
Citalopram Hydrobromide 10 mg/5ml Solution 240ml Bottle122.28USD bottle
Celexa 40 mg tablet3.88USD tablet
Celexa 20 mg tablet3.72USD tablet
Celexa 10 mg tablet3.57USD tablet
Citalopram Hydrobromide 40 mg tablet2.89USD tablet
Citalopram Hydrobromide 20 mg tablet2.8USD tablet
Citalopram Hydrobromide 10 mg tablet2.68USD tablet
Citalopram hbr 40 mg tablet2.53USD tablet
Citalopram hbr 20 mg tablet2.43USD tablet
Citalopram hbr 10 mg tablet2.33USD tablet
Celexa 20 mg Tablet1.47USD tablet
Celexa 40 mg Tablet1.47USD tablet
Ctp 30 30 mg Tablet0.99USD tablet
Apo-Citalopram 20 mg Tablet0.82USD tablet
Apo-Citalopram 40 mg Tablet0.82USD tablet
Citalopram 20 mg Tablet0.82USD tablet
Citalopram 40 mg Tablet0.82USD tablet
Citalopram-Odan 20 mg Tablet0.82USD tablet
Citalopram-Odan 40 mg Tablet0.82USD tablet
Co Citalopram 20 mg Tablet0.82USD tablet
Co Citalopram 40 mg Tablet0.82USD tablet
Jamp-Citalopram 20 mg Tablet0.82USD tablet
Jamp-Citalopram 40 mg Tablet0.82USD tablet
Mint-Citalopram 20 mg Tablet0.82USD tablet
Mint-Citalopram 40 mg Tablet0.82USD tablet
Mylan-Citalopram 20 mg Tablet0.82USD tablet
Mylan-Citalopram 40 mg Tablet0.82USD tablet
Ng Citalopram 20 mg Tablet0.82USD tablet
Ng Citalopram 40 mg Tablet0.82USD tablet
Novo-Citalopram 20 mg Tablet0.82USD tablet
Novo-Citalopram 40 mg Tablet0.82USD tablet
Phl-Citalopram 20 mg Tablet0.82USD tablet
Phl-Citalopram 40 mg Tablet0.82USD tablet
Pms-Citalopram 20 mg Tablet0.82USD tablet
Pms-Citalopram 40 mg Tablet0.82USD tablet
Ran-Citalo 20 mg Tablet0.82USD tablet
Ran-Citalo 40 mg Tablet0.82USD tablet
Ran-Citalopram 20 mg Tablet0.82USD tablet
Ran-Citalopram 40 mg Tablet0.82USD tablet
Ratio-Citalopram 20 mg Tablet0.82USD tablet
Ratio-Citalopram 40 mg Tablet0.82USD tablet
Sandoz Citalopram 20 mg Tablet0.82USD tablet
Sandoz Citalopram 40 mg Tablet0.82USD tablet
Pms-Citalopram 10 mg Tablet0.47USD tablet
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Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
CA2353693No2003-07-222021-07-24Canada flag
CA2049368No2001-10-232011-08-16Canada flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)182-188https://www.chemicalbook.com/ChemicalProductProperty_US_CB2736240.aspx
boiling point (°C)347-358http://datasheets.scbt.com/sc-201123.pdf
water solubilitySparingly soluble https://www.chemicalbook.com/ChemicalProductProperty_US_CB2736240.aspx
logP3.76http://www.t3db.ca/toxins/T3D2715
logS-4.7http://www.t3db.ca/toxins/T3D2715
pKa9.78http://www.t3db.ca/toxins/T3D2715
Predicted Properties
PropertyValueSource
Water Solubility0.00588 mg/mLALOGPS
logP3.58ALOGPS
logP3.76ChemAxon
logS-4.7ALOGPS
pKa (Strongest Basic)9.78ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area36.26 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity94.02 m3·mol-1ChemAxon
Polarizability35.4 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9966
Blood Brain Barrier+0.9729
Caco-2 permeable+0.6099
P-glycoprotein substrateSubstrate0.7597
P-glycoprotein inhibitor INon-inhibitor0.6361
P-glycoprotein inhibitor IIInhibitor0.9789
Renal organic cation transporterInhibitor0.6993
CYP450 2C9 substrateNon-substrate0.8401
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateSubstrate0.7407
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorInhibitor0.8949
CYP450 2D6 inhibitorNon-inhibitor0.5054
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5223
Ames testNon AMES toxic0.7602
CarcinogenicityNon-carcinogens0.7452
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.9054 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7735
hERG inhibition (predictor II)Inhibitor0.8994
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0a4i-9110000000-5b1fde1b7a58929c7f2d
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0009000000-589e7ae88aee7da0e0bd
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0029000000-8fd40dc922da5ab2c8b0
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03di-0291000000-c60cbea4e4e6acbb4599
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00l2-0290000000-f2131534473e56b3c8a7
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00mk-0390000000-e6cd61150feeca1d2867
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0291000000-ff658bd6b54adccbaf03
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0009000000-67fa40aabd862948aaf3
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0129000000-60abdaff2f5d8f72e271
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0bt9-0981000000-1eba423765a46f1dd6b9
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0980000000-514f2e0bb73903b25b90
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0970000000-f27f46e3a573498d9f9b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0980000000-5ba355c707bc5008c067
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0009000000-a115136f2084cc2a6a47
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0129000000-474ae50db9e74e5a31be
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0bt9-0981000000-011dbb85d8e791486397
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0970000000-99aedc452f996b9c9113
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0980000000-c8734dde2a469350af7c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0970000000-cff11d70160f94e8fc2e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0391000000-e7862ea10a18e5771adc
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0980000000-d24616414bd7fc5e1182
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0970000000-1c68a33d62afa4612071
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0394000000-f3c86fb3bf5bc7669307
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0390000000-5c227e85878c48f06a42
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-0239000000-900cc91bba3c1f9f3674
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Targets

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
  1. Sangkuhl K, Klein TE, Altman RB: PharmGKB summary: citalopram pharmacokinetics pathway. Pharmacogenet Genomics. 2011 Nov;21(11):769-72. doi: 10.1097/FPC.0b013e328346063f. [PubMed:21546862]
  2. 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. [PubMed:27049939]
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
  1. Bareggi SR, Mundo E, Dell'Osso B, Altamura AC: The use of escitalopram beyond major depression: pharmacological aspects, efficacy and tolerability in anxiety disorders. Expert Opin Drug Metab Toxicol. 2007 Oct;3(5):741-53. [PubMed:17916059]
  2. Citalopram MedSafe NZ Data Sheet [File]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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
  1. Brosen K, Naranjo CA: Review of pharmacokinetic and pharmacodynamic interaction studies with citalopram. Eur Neuropsychopharmacol. 2001 Aug;11(4):275-83. [PubMed:11532381]
  2. 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. [PubMed:10774624]
  3. 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. [PubMed:19515014]
  4. 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. [PubMed:9890159]
  5. Sangkuhl K, Klein TE, Altman RB: PharmGKB summary: citalopram pharmacokinetics pathway. Pharmacogenet Genomics. 2011 Nov;21(11):769-72. doi: 10.1097/FPC.0b013e328346063f. [PubMed:21546862]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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
  1. Brosen K, Naranjo CA: Review of pharmacokinetic and pharmacodynamic interaction studies with citalopram. Eur Neuropsychopharmacol. 2001 Aug;11(4):275-83. [PubMed:11532381]
  2. 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. [PubMed:10774624]
  3. 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. [PubMed:19515014]
  4. 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. [PubMed:9890159]
  5. 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. [PubMed:10494454]
  6. 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. [PubMed:10575324]
  7. Flockhart Table of Drug Interactions [Link]
  8. Citalopram FDA label [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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
  1. Baumann P: Pharmacokinetic-pharmacodynamic relationship of the selective serotonin reuptake inhibitors. Clin Pharmacokinet. 1996 Dec;31(6):444-69. [PubMed:8968657]
  2. Flockhart Table of Drug Interactions [Link]
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
  1. 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. [PubMed:10494454]
  2. Citalopram FDA [File]
  3. MedSafe NZ Data Sheet, Citalopram [File]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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
  1. 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. [PubMed:12649369]
  2. 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. [PubMed:18215618]
  3. 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. [PubMed:12650738]

Drug created on June 13, 2005 07:24 / Updated on October 19, 2020 07:46

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