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Identification
NameCitalopram
Accession NumberDB00215  (APRD00147)
Typesmall molecule
Groupsapproved
Description

Citalopram hydrobromide belongs to a class of antidepressant agents known as selective serotonin-reuptake inhibitors (SSRIs). Citalopram and its N-demethylated metabolites exist as a racemic mixture but its effects are largely due to the S-enantiomer, S-citalopram and S-demthylcitalopram. Despite distinct structural differences between compounds in this class, SSRIs possess similar pharmacological activity. As with other antidepressant agents, several weeks of therapy may be required before a clinical effect is seen. SSRIs are potent inhibitors of neuronal serotonin reuptake. They have little to no effect on norepinephrine or dopamine reuptake and do not antagonize α- or β-adrenergic, dopamine D2 or histamine H1 receptors. During acute use, SSRIs block serotonin reuptake and increase serotonin stimulation of somatodendritic 5-HT1A and terminal autoreceptors. Chronic use leads to desensitization of somatodendritic 5-HT1A and terminal autoreceptors. The overall clinical effect of increased mood and decreased anxiety is thought to be due to adaptive changes in neuronal function that leads to enhanced serotonergic neurotransmission. Side effects include dry mouth, nausea, dizziness, drowsiness, sexual dysfunction and headache. Side effects generally occur within the first two weeks of therapy and are usually less severe and frequent than those observed with tricyclic antidepressants. Citalopram is approved for treatment of depression. Unlabeled indications include mild dementia-associated agitation in nonpsychotic patients, smoking cessation, ethanol abuse, obsessive-compulsive disorder (OCD) in children, and diabetic neuropathy. Citalopram has the fewest drug-drug interactions of the SSRIs.

Structure
Thumb
Synonyms
SynonymLanguageCode
Nitalapram Not AvailableNot Available
Salts
Name/CAS Structure Properties
Citalopram Hydrobromide
59729-32-7
Thumb
  • InChI Key: WIHMBLDNRMIGDW-UHFFFAOYNA-N
  • Monoisotopic Mass: 404.089954188
  • Average Mass: 405.304
DBSALT000027
Brand names
NameCompany
AkarinNot Available
CelapramNot Available
CelexaForest Laboratories
CiazilNot Available
CiliftNot Available
CipramNot Available
CipramilNot Available
CiprapineNot Available
CitabaxNot Available
CitalecNot Available
CitolNot Available
CitopamNot Available
CitoxNot Available
CitrolNot Available
DalsanNot Available
ElopramNot Available
HumorupNot Available
OropramNot Available
PramcitNot Available
RecitalNot Available
SeropramNot Available
TalamNot Available
TalohexalNot Available
TemperaxNot Available
VodelaxNot Available
ZentiusNot Available
ZetaloNot Available
Brand mixturesNot Available
Categories
CAS number59729-33-8
WeightAverage: 324.3919
Monoisotopic: 324.163791509
Chemical FormulaC20H21FN2O
InChI KeyInChIKey=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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassBenzofurans
SubclassNot Available
Direct parentBenzofurans
Alternative parentsBenzonitriles; Fluorobenzenes; Aryl Fluorides; Tertiary Amines; Nitriles; Polyamines; Dialkyl Ethers; Organofluorides
Substituentsbenzonitrile; fluorobenzene; aryl halide; benzene; aryl fluoride; tertiary amine; carbonitrile; ether; nitrile; polyamine; dialkyl ether; organohalogen; organofluoride; amine; organonitrogen compound
Classification descriptionThis compound belongs to the benzofurans. These are organic compounds containing a benzene ring fused to a furan.
Pharmacology
IndicationFor the treatment of depression. Unlabeled indications include: treatment of mild dementia-associated agitation in nonpsychotic patients, smoking cessation, ethanol abuse, obsessive-compulsive disorder (OCD) in children, and diabetic neuropathy.
PharmacodynamicsCitalopram is one of a class of antidepressants known as selective serotonin reuptake inhibitors (SSRIs). It is used to treat the depression associated with mood disorders. It is also used on occassion in the treatment of body dysmorphic disorder and anxiety. The antidepressant, antiobsessive-compulsive, and antibulimic actions of citalopram are presumed to be linked to its inhibition of CNS neuronal uptake of serotonin. In vitro studies show that citalopram is a potent and selective inhibitor of neuronal serotonin reuptake and has only very weak effects on norepinephrine and dopamine neuronal reuptake. Citalopram has no significant affinity for adrenergic (α1, α2, β), cholinergic, GABA, dopaminergic, histaminergic, serotonergic (5HT1A, 5HT1B, 5HT2), or benzodiazepine receptors; antagonism of such receptors has been hypothesized to be associated with various anticholinergic, sedative, and cardiovascular effects for other psychotropic drugs. The chronic administration of citalopram was found to downregulate brain norepinephrine receptors, as has been observed with other drugs effective in the treatment of major depressive disorder. Citalopram does not inhibit monoamine oxidase.
Mechanism of actionThe antidepressant, antiobsessive-compulsive, and antibulimic actions of citalopram are presumed to be linked to its inhibition of CNS neuronal uptake of serotonin. Citalopram blocks the reuptake of serotonin at the serotonin reuptake pump of the neuronal membrane, enhancing the actions of serotonin on 5HT1A autoreceptors. SSRIs bind with significantly less affinity to histamine, acetylcholine, and norepinephrine receptors than tricyclic antidepressant drugs.
AbsorptionRapidly 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.
Volume of distribution
  • 12 L/kg
    Citalopram is highly lipophilic and likely widely distributed throughout the body, including the blood-brain-barrier. However, its metabolite, demethylcitalopram does not cross the barrier well.
Protein bindingCitalopram, dimethylcitalopram, and didemethylcitalopram is 80% bound to plasma proteins.
Metabolism

Citalopram is metabolized mainly in the liver via <i>N</i>-demethylation to its principle metabolite, demethylcitalopram. Other metabolites include didemethylcitalopram, citalopram <i>N</i>-oxide, and a deaminated propionic acid derivative. However, the predominant entity in plasma is unchanged citalopram. Cytochrome P450 (CYP) 3A4 and 2C19 isozymes appear to be principally involved in producing demethylcitalopram. Demethylcitalopram appears to be further <i>N</i>-demethylated by CYP2D6 to didemethylcitalopram. Citalopram metabolites possess little pharmacologic activity in comparison to their parent compound and do not likely contribute to the clinical effect of the drug.

SubstrateEnzymesProduct
Citalopram
Citalopram N-oxideDetails
Citalopram
N-DesmethylcitalopramDetails
Citalopram
    Citalopram propionic acidDetails
    N-Desmethylcitalopram
    N,N-DidesmethylcitalopramDetails
    Route of elimination12-23% of an oral dose of citalopram is recovered unchanged in the urine, while 10% of the dose is recovered in the feces.
    Half life35 hours
    Clearance

    The systemic clearance of citalopram was 330 mL/min, with approximately 20% of that due to renal clearance.

    ToxicitySymptoms most often accompanying citalopram overdose, alone or in combination with other drugs and/or alcohol, included dizziness, sweating, nausea, vomiting, tremor, somnolence, and sinus tachycardia. In more rare cases, observed symptoms included amnesia, confusion, coma, convulsions, hyperventilation, cyanosis, rhabdomyolysis, and ECG changes (including QTc prolongation, nodal rhythm, ventricular arrhythmia, and very rare cases of torsade de pointes). Acute renal failure has been very rarely reported accompanying overdose. Withdrawal symptoms include flu-like symptoms, insomnia, nausea, imbalance, sensory changes and hyperactivity.
    Affected organisms
    • Humans and other mammals
    PathwaysNot Available
    SNP Mediated Effects
    Interacting Gene/EnzymeSNP RS IDAllele nameDefining changeEffectReference(s)
    Multidrug resistance protein 1
    Gene symbol: ABCB1
    UniProt: P08183
    rs2032583 Not AvailableC AlleleImproved response to antidepressant medication17913323
    5-hydroxytryptamine receptor 2A
    Gene symbol: HTR2A
    UniProt: P28223
    rs7997012 Not AvailableA AlleleImproved response to antidepressant medication16642436
    Glutamate receptor ionotropic, kainate 4
    Gene symbol: GRIK4
    UniProt: Q16099
    rs1954787 Not AvailableC AlleleImproved response to antidepressant medication17671280
    5-hydroxytryptamine receptor 1A
    Gene symbol: HTR1A
    UniProt: P08908
    rs6295 Not AvailableG AlleleHomozygosity for the rs6295 G allele is associated with lower response rate in patients treated for major depression19829169
    SNP Mediated Adverse Drug Reactions
    Interacting Gene/EnzymeSNP RS IDAllele nameDefining changeAdverse ReactionReference(s)
    Glutamate receptor ionotropic, kainate 2
    Gene symbol: GRIK2
    UniProt: Q13002
    rs2518224 Not AvailableC Allele, homozygoteIncreased suicidal thoughts17898344
    Glutamate receptor 3
    Gene symbol: GRIA3
    UniProt: P42263
    rs4825476 Not AvailableG Allele, homozygoteIncreased suicidal thoughts17898344
    Cyclic AMP-responsive element-binding protein 1
    Gene symbol: CREB1
    UniProt: P16220
    rs4675690 Not AvailableT AlleleElevated suicide risk17548750
    Cyclic AMP-responsive element-binding protein 1
    Gene symbol: CREB1
    UniProt: P16220
    rs7569963 Not AvailableA AlleleElevated suicide risk17548750
    ADMET
    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 substrate Inhibitor 0.8949
    CYP450 2D6 substrate Non-inhibitor 0.5054
    CYP450 2C19 substrate Inhibitor 0.8994
    CYP450 3A4 substrate 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
    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
    Dosage forms
    FormRouteStrength
    SolutionOral10 mg/5 ml
    TabletOral10 mg, 20 mg, 40 mg
    Prices
    Unit descriptionCostUnit
    Citalopram Hydrobromide 10 mg/5ml Solution 240ml Bottle122.28USDbottle
    Celexa 40 mg tablet3.88USDtablet
    Celexa 20 mg tablet3.72USDtablet
    Celexa 10 mg tablet3.57USDtablet
    Citalopram Hydrobromide 40 mg tablet2.89USDtablet
    Citalopram Hydrobromide 20 mg tablet2.8USDtablet
    Citalopram Hydrobromide 10 mg tablet2.68USDtablet
    Citalopram hbr 40 mg tablet2.53USDtablet
    Citalopram hbr 20 mg tablet2.43USDtablet
    Citalopram hbr 10 mg tablet2.33USDtablet
    Celexa 20 mg Tablet1.47USDtablet
    Celexa 40 mg Tablet1.47USDtablet
    Ctp 30 30 mg Tablet0.99USDtablet
    Apo-Citalopram 20 mg Tablet0.82USDtablet
    Apo-Citalopram 40 mg Tablet0.82USDtablet
    Citalopram 20 mg Tablet0.82USDtablet
    Citalopram 40 mg Tablet0.82USDtablet
    Citalopram-Odan 20 mg Tablet0.82USDtablet
    Citalopram-Odan 40 mg Tablet0.82USDtablet
    Co Citalopram 20 mg Tablet0.82USDtablet
    Co Citalopram 40 mg Tablet0.82USDtablet
    Jamp-Citalopram 20 mg Tablet0.82USDtablet
    Jamp-Citalopram 40 mg Tablet0.82USDtablet
    Mint-Citalopram 20 mg Tablet0.82USDtablet
    Mint-Citalopram 40 mg Tablet0.82USDtablet
    Mylan-Citalopram 20 mg Tablet0.82USDtablet
    Mylan-Citalopram 40 mg Tablet0.82USDtablet
    Ng Citalopram 20 mg Tablet0.82USDtablet
    Ng Citalopram 40 mg Tablet0.82USDtablet
    Novo-Citalopram 20 mg Tablet0.82USDtablet
    Novo-Citalopram 40 mg Tablet0.82USDtablet
    Phl-Citalopram 20 mg Tablet0.82USDtablet
    Phl-Citalopram 40 mg Tablet0.82USDtablet
    Pms-Citalopram 20 mg Tablet0.82USDtablet
    Pms-Citalopram 40 mg Tablet0.82USDtablet
    Ran-Citalo 20 mg Tablet0.82USDtablet
    Ran-Citalo 40 mg Tablet0.82USDtablet
    Ran-Citalopram 20 mg Tablet0.82USDtablet
    Ran-Citalopram 40 mg Tablet0.82USDtablet
    Ratio-Citalopram 20 mg Tablet0.82USDtablet
    Ratio-Citalopram 40 mg Tablet0.82USDtablet
    Sandoz Citalopram 20 mg Tablet0.82USDtablet
    Sandoz Citalopram 40 mg Tablet0.82USDtablet
    Pms-Citalopram 10 mg Tablet0.47USDtablet
    DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
    Patents
    CountryPatent NumberApprovedExpires (estimated)
    Canada23536932003-07-222021-07-24
    Canada20493682001-10-232011-08-16
    Properties
    Statesolid
    Experimental Properties
    PropertyValueSource
    melting point182-183 °CNot Available
    water solubilitySparingly soluble FDA label
    logP3.5Not Available
    Predicted Properties
    PropertyValueSource
    water solubility5.88e-03 g/lALOGPS
    logP3.58ALOGPS
    logP3.76ChemAxon
    logS-4.7ALOGPS
    pKa (strongest basic)9.78ChemAxon
    physiological charge1ChemAxon
    hydrogen acceptor count3ChemAxon
    hydrogen donor count0ChemAxon
    polar surface area36.26ChemAxon
    rotatable bond count5ChemAxon
    refractivity94.02ChemAxon
    polarizability35.4ChemAxon
    number of rings3ChemAxon
    bioavailability1ChemAxon
    rule of fiveYesChemAxon
    Ghose filterYesChemAxon
    Veber's ruleYesChemAxon
    MDDR-like ruleNoChemAxon
    Spectra
    Spectra
    References
    Synthesis Reference

    Hans Petersen, “Method for the preparation of citalopram.” U.S. Patent US6229026, issued December, 1992.

    US6229026
    General Reference
    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
    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
    3. Andersen G, Vestergaard K, Riis JO: Citalopram for post-stroke pathological crying. Lancet. 1993 Oct 2;342(8875):837-9. Pubmed
    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
    5. Baumann P: Pharmacology and pharmacokinetics of citalopram and other SSRIs. Int Clin Psychopharmacol. 1996 Mar;11 Suppl 1:5-11. Pubmed
    6. FDA label
    7. Hyttel J, Bogeso KP, Perregaard J, Sanchez C: The pharmacological effect of citalopram residues in the (S)-(+)-enantiomer. J Neural Transm Gen Sect. 1992;88(2):157-60. Pubmed
    8. Caccia S: Metabolism of the newer antidepressants. An overview of the pharmacological and pharmacokinetic implications. Clin Pharmacokinet. 1998 Apr;34(4):281-302. Pubmed
    External Links
    ResourceLink
    KEGG DrugD07704
    KEGG CompoundC07572
    PubChem Compound2771
    PubChem Substance46508746
    ChemSpider2669
    BindingDB25870
    ChEBI3723
    ChEMBLCHEMBL549
    Therapeutic Targets DatabaseDAP000118
    PharmGKBPA449015
    Drug Product Database2248051
    RxListhttp://www.rxlist.com/cgi/generic/citalo.htm
    Drugs.comhttp://www.drugs.com/citalopram.html
    WikipediaCitalopram
    ATC CodesN06AB04N06AB10
    AHFS Codes
    • 28:16.04.20
    PDB EntriesNot Available
    FDA labelshow(148 KB)
    MSDSNot Available
    Interactions
    Drug Interactions
    Drug
    AcenocoumarolThe SSRI, citalopram, increases the effect of anticoagulant, acenocoumarol.
    AlmotriptanIncreased risk of CNS adverse effects
    AnisindioneThe SSRI, citalopram, increases the effect of anticoagulant, anisindione.
    ArtemetherAdditive QTc-prolongation may occur. Concomitant therapy should be avoided.
    CarvedilolThe SSRI, citalopram, may increase the bradycardic effect of the beta-blocker, carvedilol.
    ClarithromycinPossible serotoninergic syndrome with this combination
    ClozapineThe antidepressant increases the effect of clozapine
    DesvenlafaxineIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
    DicoumarolThe SSRI, citalopram, increases the effect of anticoagulant, dicumarol.
    EletriptanIncreased risk of CNS adverse effects
    ErythromycinPossible serotoninergic syndrome with this combination
    EtravirineCitalopram, when used concomitantly with etravirine (a CYP2C19 inhibitor), may experience an increase in serum concentration. It is recommended to maintain the dose of citalopram below 20mg/day, and to monitor for toxicity. The symptoms which often accompany citalopram overdose are dizziness, sweating, nausea, vomiting, tremor, somnolence,sinus tachycardia,amnesia, confusion, coma, convulsions, hyperventilation, cyanosis, rhabdomyolysis, acute renal failure, and ECG changes (including QTc prolongation, nodal rhythm, ventricular arrhythmia, and torsade de pointes).
    FrovatriptanIncreased risk of CNS adverse effects
    Ginkgo bilobaAdditive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
    IsocarboxazidPossible severe adverse reaction with this combination
    JosamycinPossible serotoninergic sydrome with this combination
    KetoprofenConcomitant therapy may result in additive antiplatelet effects and increase the risk of bleeding. Monitor for increased risk of bleeding during concomitant therapy.
    LinezolidCombination associated with possible serotoninergic syndrome
    LumefantrineAdditive QTc-prolongation may occur. Concomitant therapy should be avoided.
    MetoprololThe SSRI, citalopram, may increase the bradycardic effect of the beta-blocker, metoprolol.
    MoclobemidePossible serotoninergic syndrome
    NaratriptanIncreased risk of CNS adverse effects
    OxycodoneIncreased risk of serotonin syndrome
    PhenelzinePossible severe adverse reaction with this combination
    PimozideThe SSRI, citalopram, may increase the effect and toxicity of pimozide.
    PropranololThe SSRI, citalopram, may increase the bradycardic effect of the beta-blocker, propranolol.
    RasagilinePossible severe adverse reaction with this combination
    RizatriptanIncreased risk of CNS adverse effects
    SelegilinePossible severe adverse reaction with this combination
    SibutramineRisk of serotoninergic syndrome
    St. John's WortSt. John's Wort increases the effect and toxicity of the SSRI, citalopram.
    SumatriptanIncreased risk of CNS adverse effects
    TelithromycinTelithromycin may reduce clearance of Citalopram. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Citalopram if Telithromycin is initiated, discontinued or dose changed.
    Tiaprofenic acidAdditive antiplatelet effects increase the risk of bleeding. Consider alternate therapy or monitor for increased bleeding.
    TiclopidineTiclopidine may decrease the metabolism and clearance of Citalopram. Consider alternate therapy or monitor for adverse/toxic effects of Citalopram if Ticlopidine is initiated, discontinued or dose changed.
    TolmetinIncreased antiplatelet effects may enhance the risk of bleeding. Alternate therapy may be considered or monitor for inreased bleeding during concomitant therapy.
    TramadolThe use of two serotonin modulators, such as citalopram and tramadol, may increase the risk of serotonin syndrome. Consider alternate therapy or monitor for serotonin syndrome during concomitant therapy.
    TranylcypromineIncreased risk of serotonin syndrome. Concomitant therapy should be avoided. A significant washout period, dependent on the half-lives of the agents, should be employed between therapies.
    TrazodoneIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
    TreprostinilThe prostacyclin analogue, Treprostinil, increases the risk of bleeding when combined with the antiplatelet agent, Citalopram. Monitor for increased bleeding during concomitant thearpy.
    TrimipramineThe SSRI, Citalopram, may decrease the metabolism and clearance of Trimipramine. Increased risk of serotonin syndrome. Monitor for changes in Trimipramine efficacy and toxicity if Citalopram is initiated, discontinued or dose changed.
    TriprolidineThe CNS depressants, Triprolidine and Citalopram, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
    TroleandomycinPossible serotoninergic syndrome with this combination
    VenlafaxineIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
    VoriconazoleVoriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of citalopram by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of citalopram if voriconazole is initiated, discontinued or dose changed.
    WarfarinThe SSRI, citalopram, increases the effect of anticoagulant, warfarin.
    ZiprasidoneAdditive QTc-prolongation may occur increasing the risk of life-threatening ventricular arrhythmias and torsade de pointes. Concomitant therapy should be avoided.
    ZolmitriptanThe use of two serotonin modulators, such as zolmitriptan and citalopram, may increase the risk of serotonin syndrome. Consider alternate therapy or monitor for serotonin syndrome during concomitant therapy.
    ZuclopenthixolAdditive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
    Zuclopenthixol acetateAdditive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
    Zuclopenthixol decanoateAdditive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
    Food Interactions
    • Avoid alcohol.
    • Avoid St.John's Wort.
    • Take without regard to meals.

    1. Sodium-dependent serotonin transporter

    Kind: protein

    Organism: Human

    Pharmacological action: yes

    Actions: inhibitor

    Components

    Name UniProt ID Details
    Sodium-dependent serotonin transporter P31645 Details

    References:

    1. Eriksson E, Engberg G, Bing O, Nissbrandt H: Effects of mCPP on the extracellular concentrations of serotonin and dopamine in rat brain. Neuropsychopharmacology. 1999 Mar;20(3):287-96. Pubmed
    2. Maines LW, Keck BJ, Smith JE, Lakoski JM: Corticosterone regulation of serotonin transporter and 5-HT1A receptor expression in the aging brain. Synapse. 1999 Apr;32(1):58-66. Pubmed
    3. Vicentic A, Battaglia G, Carroll FI, Kuhar MJ: Serotonin transporter production and degradation rates: studies with RTI-76. Brain Res. 1999 Sep 11;841(1-2):1-10. Pubmed
    4. Dugar A, Keck BJ, Maines LW, Miller S, Njai R, Lakoski JM: Compensatory responses in the aging hippocampal serotonergic system following neurodegenerative injury with 5,7-dihydroxytryptamine. Synapse. 2001 Feb;39(2):109-21. Pubmed
    5. Dutta AK, Fei XS, Beardsley PM, Newman JL, Reith ME: Structure-activity relationship studies of 4-[2-(diphenylmethoxy)ethyl]-1-benzylpiperidine derivatives and their N-analogues: evaluation of O-and N-analogues and their binding to monoamine transporters. J Med Chem. 2001 Mar 15;44(6):937-48. Pubmed
    6. Plenge P, Wiborg O: High- and low-affinity binding of S-citalopram to the human serotonin transporter mutated at 20 putatively important amino acid positions. Neurosci Lett. 2005 Aug 5;383(3):203-8. Epub 2005 Apr 25. Pubmed
    7. Schloss P, Betz H: Heterogeneity of antidepressant binding sites on the recombinant rat serotonin transporter SERT1. Biochemistry. 1995 Oct 3;34(39):12590-5. Pubmed
    8. Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. Pubmed
    9. Zhong H, Hansen KB, Boyle NJ, Han K, Muske G, Huang X, Egebjerg J, Sanchez C: An allosteric binding site at the human serotonin transporter mediates the inhibition of escitalopram by R-citalopram: kinetic binding studies with the ALI/VFL-SI/TT mutant. Neurosci Lett. 2009 Oct 25;462(3):207-12. Epub 2009 Jul 16. Pubmed
    10. Rasmussen TN, Plenge P, Bay T, Egebjerg J, Gether U: A single nucleotide polymorphism in the human serotonin transporter introduces a new site for N-linked glycosylation. Neuropharmacology. 2009 Sep;57(3):287-94. Epub 2009 Jun 3. Pubmed

    2. Histamine H1 receptor

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: binder

    Components

    Name UniProt ID Details
    Histamine H1 receptor P35367 Details

    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

    3. Alpha-1A adrenergic receptor

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: binder

    Components

    Name UniProt ID Details
    Alpha-1A adrenergic receptor P35348 Details

    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

    4. Muscarinic acetylcholine receptor M1

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: binder

    Components

    Name UniProt ID Details
    Muscarinic acetylcholine receptor M1 P11229 Details

    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

    1. Cytochrome P450 3A4

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: substrate

    Components

    Name UniProt ID Details
    Cytochrome P450 3A4 P08684 Details

    References:

    1. Brosen K, Naranjo CA: Review of pharmacokinetic and pharmacodynamic interaction studies with citalopram. Eur Neuropsychopharmacol. 2001 Aug;11(4):275-83. Pubmed
    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
    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
    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
    5. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
    6. Lexicomp

    2. Cytochrome P450 2C19

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: substrate inhibitor

    Components

    Name UniProt ID Details
    Cytochrome P450 2C19 P33261 Details

    References:

    1. Brosen K, Naranjo CA: Review of pharmacokinetic and pharmacodynamic interaction studies with citalopram. Eur Neuropsychopharmacol. 2001 Aug;11(4):275-83. Pubmed
    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
    3. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
    4. 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
    5. 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
    6. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
    7. Lexicomp.

    3. Cytochrome P450 2D6

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: substrate inhibitor

    Components

    Name UniProt ID Details
    Cytochrome P450 2D6 P10635 Details

    References:

    1. Baumann P: Pharmacokinetic-pharmacodynamic relationship of the selective serotonin reuptake inhibitors. Clin Pharmacokinet. 1996 Dec;31(6):444-69. Pubmed
    2. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
    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
    4. Lexicomp

    4. Cytochrome P450 2E1

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: substrate

    Components

    Name UniProt ID Details
    Cytochrome P450 2E1 P05181 Details

    References:

    1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

    5. Cytochrome P450 1A2

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: inhibitor

    Components

    Name UniProt ID Details
    Cytochrome P450 1A2 P05177 Details

    References:

    1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
    2. Lexicomp

    6. Cytochrome P450 2B6

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: inhibitor

    Components

    Name UniProt ID Details
    Cytochrome P450 2B6 P20813 Details

    References:

    1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
    2. Lexicomp

    1. Multidrug resistance protein 1

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: substrate inhibitor

    Components

    Name UniProt ID Details
    Multidrug resistance protein 1 P08183 Details

    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
    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

    2. Sodium-dependent dopamine transporter

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: substrate inhibitor

    Components

    Name UniProt ID Details
    Sodium-dependent dopamine transporter Q01959 Details

    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

    3. Sodium-dependent noradrenaline transporter

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: substrate inhibitor

    Components

    Name UniProt ID Details
    Sodium-dependent noradrenaline transporter P23975 Details

    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

    4. Sodium-dependent serotonin transporter

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: substrate inhibitor

    Components

    Name UniProt ID Details
    Sodium-dependent serotonin transporter P31645 Details

    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

    Comments
    Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:08