Identification

Name
Citalopram
Accession Number
DB00215  (APRD00147)
Type
Small Molecule
Groups
Approved
Description

Citalopram belongs to a class of antidepressant agents known as selective serotonin-reuptake inhibitors (SSRIs). In spite of structural differences between compounds in this class, the SSRIs possess similar pharmacological activity. As with other antidepressant agents, several weeks of therapy may be indicated before a clinical effect is noticed. SSRIs are potent inhibitors of serotonin reuptake in the neurons. 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 usage, SSRIs inhibit 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 general 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 [5].

Structure
Thumb
Synonyms
  • Citadur
  • Nitalapram
External IDs
Lu 10-171
Product Ingredients
IngredientUNIICASInChI Key
Citalopram HydrobromideI1E9D14F3659729-32-7WIHMBLDNRMIGDW-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act CitalopramTablet40 mgOralActavis Pharma Company2004-01-21Not applicableCanada
Act CitalopramTablet20 mgOralActavis Pharma Company2004-01-21Not applicableCanada
Act CitalopramTablet30 mgOralActavis Pharma CompanyNot applicableNot applicableCanada
CelexaTablet20 mg/1OralPhysicians Total Care, Inc.2000-11-28Not applicableUs
CelexaTablet, film coated40 mg/1OralAllergan, Inc.1998-07-17Not applicableUs
CelexaTablet, film coated40 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2011-11-172014-12-31Us
CelexaTablet, film coated20 mg/1OralAllergan, Inc.1998-07-17Not applicableUs
CelexaTablet40 mg/1OralPhysicians Total Care, Inc.2001-09-05Not applicableUs
CelexaTablet10 mg/1OralPhysicians Total Care, Inc.2004-01-30Not applicableUs
CelexaTablet, film coated10 mg/1OralAllergan, Inc.1998-07-17Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Abbott-citalopramTablet10 mgOralAbbott2014-03-172015-12-31Canada
Abbott-citalopramTablet40 mgOralAbbott2014-03-122015-12-31Canada
Abbott-citalopramTablet20 mgOralAbbott2014-03-122015-12-31Canada
Accel-citalopram TabletsTablet20 mgOralAccel Pharma Inc2013-07-02Not applicableCanada
Accel-citalopram TabletsTablet10 mgOralAccel Pharma Inc2013-03-21Not applicableCanada
Accel-citalopram TabletsTablet40 mgOralAccel Pharma Inc2013-07-02Not applicableCanada
Ag-citalopramTablet10 mgOralAngita Pharma Inc.2014-08-14Not applicableCanada
Ag-citalopramTablet40 mgOralAngita Pharma Inc.2014-09-14Not applicableCanada
Ag-citalopramTablet20 mgOralAngita Pharma Inc.2014-09-14Not applicableCanada
Apo-citalopramTablet20 mgOralApotex Corporation2004-01-21Not applicableCanada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Sentralopram AM-10Citalopram Hydrobromide (10 mg/1) + Choline (250 mg/1)KitPhysician Therapeutics Llc2011-07-07Not applicableUs
International/Other Brands
Akarin / Celapram / Ciazil / Cilift / Cipram / Cipramil / Ciprapine / Citabax / Citalec / Citol / Citopam / Citox / Citrol / Dalsan / Elopram / Humorup / Oropram / Pramcit / Recital / Seropram / Talam / Talohexal / Temperax / Vodelax / Zentius / Zetalo
Categories
UNII
0DHU5B8D6V
CAS number
59729-33-8
Weight
Average: 324.3919
Monoisotopic: 324.163791509
Chemical Formula
C20H21FN2O
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

Pharmacology

Indication

For the treatment of depression. Off-label indications include: treatment of mild dementia-associated agitation in nonpsychotic patients, smoking cessation, ethanol abuse, obsessive-compulsive disorder (OCD) in children, and diabetic neuropathy [Label].

Associated Conditions
Pharmacodynamics

Citalopram belongs to a class of antidepressants known as selective serotonin reuptake inhibitors (SSRIs). It is used to treat depression, anxiety, eating disorders and obsessive-compulsive disorder among other mood disorders. The antidepressant, anti-anxiety, and antibulimic actions of citalopram are linked to its inhibition of CNS central uptake of serotonin [Label]. In vitro studies demonstrate that citalopram is a potent 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, as has been noted with 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]. Studies suggest that citalopram is a highly selective serotonin reuptake inhibitor (SSRI) with little effect on norepinephrine (NE) and dopamine (DA) central reuptake [Label].

Citalopram binds with significantly less affinity to histamine, acetylcholine, and norepinephrine receptors than tricyclic antidepressant drugs [Label].

TargetActionsOrganism
ASodium-dependent serotonin transporter
inhibitor
Human
UHistamine H1 receptor
binder
Human
UAlpha-1A adrenergic receptor
binder
Human
UMuscarinic acetylcholine receptor M1
binder
Human
U5-hydroxytryptamine receptor 2C
antagonist
Human
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 cross the blood-brain-barrier well [Label]
Protein binding

Citalopram, dimethylcitalopram, and didemethylcitalopram is 80% bound to plasma proteins [Label].

Metabolism

Citalopram is metabolized mainly in the liver via N-demethylation to its main metabolite, demethylcitalopram. Other metabolites include didemethylcitalopram, citalopram N-oxide, and a deaminated propionic acid derivative. However, the drug in plasma is found mainly unchanged as citalopram. Cytochrome P450 (CYP) 3A4 and 2C19 isozymes appear to be principally involved in producing demethylcitalopram. Demethylcitalopram appears to be further N-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 [5].

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.

After a single dose of citalopram, peak blood concentrations occur at approximately 4 hours. The bioavailability of this drug was about 80%, compared to an IV dose [Label]. The volume of distribution of citalopram is about 12 L/kg and c

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

35 hours [Label].

Clearance

The systemic clearance of citalopram is 330 mL/min, with approximately 20% renal clearance [Label]

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].

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Citalopram Metabolism PathwayDrug metabolism
Citalopram Action PathwayDrug action
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;A) / (G;G)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
DrugInteraction
(R)-warfarinThe risk or severity of hemorrhage can be increased when Citalopram is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of hemorrhage can be increased when Citalopram is combined with (S)-Warfarin.
2,4-thiazolidinedioneThe risk or severity of hypoglycemia can be increased when Citalopram is combined with 2,4-thiazolidinedione.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when Citalopram is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with Citalopram.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Citalopram.
3,5-diiodothyropropionic acidThe therapeutic efficacy of 3,5-diiodothyropropionic acid can be decreased when used in combination with Citalopram.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Citalopram.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Citalopram.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Citalopram.
Food Interactions
  • Avoid alcohol.
  • Avoid St.John's Wort.
  • Take without regard to meals.

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. 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:1632943]
  7. Caccia S: Metabolism of the newer antidepressants. An overview of the pharmacological and pharmacokinetic implications. Clin Pharmacokinet. 1998 Apr;34(4):281-302. [PubMed:9571301]
  8. MSDS citalopram [Link]
External Links
Human Metabolome Database
HMDB0005038
KEGG Drug
D07704
KEGG Compound
C07572
PubChem Compound
2771
PubChem Substance
46508746
ChemSpider
2669
BindingDB
25870
ChEBI
77397
ChEMBL
CHEMBL549
Therapeutic Targets Database
DAP000118
PharmGKB
PA449015
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Citalopram
ATC Codes
N06AB04 — Citalopram
AHFS Codes
  • 28:16.04.20 — Selective-serotonin Reuptake Inhibitors
FDA label
Download (148 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedSupportive CareMajor Depressive Disorder (MDD) / Neoplasms1
0Not Yet RecruitingTreatmentDepression; Psychoneurotic / Pain NOS1
0Not Yet RecruitingTreatmentDepression / Depressive Disorders / Depressive Symptoms1
0RecruitingTreatmentMajor Depressive Disorder (MDD)1
1CompletedNot AvailableAutism Spectrum Conditions/Disorders1
1CompletedNot AvailableDepression / Human Immunodeficiency Virus (HIV)1
1CompletedNot AvailableHealthy Volunteers7
1CompletedBasic ScienceAlcohol Dependence1
1CompletedBasic ScienceDepression1
1CompletedTreatmentDepressive Disorder and Anxiety Disorders1
1CompletedTreatmentHealthy Volunteers4
1CompletedTreatmentHealthy Young and Older Adults1
1RecruitingBasic ScienceUnipolar Depression1
1, 2WithdrawnTreatmentAcute Coronary Syndromes (ACS)1
2Active Not RecruitingTreatmentCitalopram / Major Depressive Disorder (MDD)1
2Active Not RecruitingTreatmentMajor Depressive Disorder (MDD)1
2CompletedNot AvailableNormal Volunteers1
2CompletedTreatmentAlcohol Abuse / Alcohol Dependence1
2CompletedTreatmentAttention Deficit and Disruptive Behavior Disorders / Attention Deficit Disorder With Hyperactivity (ADHD) / Mental Disorders Diagnosed in Childhood / Moods Disorders1
2CompletedTreatmentAutistic Disorder1
2CompletedTreatmentBereavement / Complicated Grief1
2CompletedTreatmentBorderline Personality Disorder (BPD) / Depression Not Otherwise Specified / Dysthymic Disorder / Major Depressive Disorder (MDD)1
2CompletedTreatmentChorea / Executive Dysfunction / Huntington's Disease (HD)1
2CompletedTreatmentDementias1
2CompletedTreatmentDependence, Cocaine3
2CompletedTreatmentDepression2
2CompletedTreatmentDepression / Major Depressive Disorder (MDD)2
2CompletedTreatmentIrritable Bowel Syndrome (IBS)1
2CompletedTreatmentMajor Depressive Disorder (MDD)1
2CompletedTreatmentStroke, Ischemic / Strokes1
2TerminatedTreatmentCocaine Abuse / Opiate Dependence1
2WithdrawnNot AvailableDepression1
2, 3CompletedTreatmentBipolar Disorder (BD) / Depression, Bipolar1
2, 3CompletedTreatmentDepression1
2, 3CompletedTreatmentDepression / Suicide, Attempted1
2, 3CompletedTreatmentMajor Depressive Disorder (MDD)1
2, 3Unknown StatusTreatmentAbdominal Pain (AP) / Feeling Anxious1
3CompletedPreventionDepression / Hepatitis C Viral Infection / Human Immunodeficiency Virus (HIV) Infections1
3CompletedSupportive CareBone Mineral Density Quantitative Trait Locus 71
3CompletedSupportive CareCancer, Breast / Menopausal Hot Flushes / Psychosocial Effects of Cancer and Its Treatment1
3CompletedTreatmentAcute Agitation / Alzheimer's Disease (AD)1
3CompletedTreatmentAlzheimer's Disease (AD) / Dementia, Vascular / Dementias1
3CompletedTreatmentDepression / Depressive Disorders1
3CompletedTreatmentMajor Depressive Disorder (MDD)3
3RecruitingTreatmentMajor Depressive Disorder (MDD)1
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
3WithdrawnTreatmentMajor Depressive Disorder (MDD)1
4CompletedNot AvailableAlcohol Use Disorder (AUD) / Major Depressive Disorder (MDD)1
4CompletedNot AvailableInjuries, Whiplash1
4CompletedHealth Services ResearchObsessive Compulsive Disorder (OCD)1
4CompletedOtherHealthy Controls / Major Depressive Disorder (MDD)1
4CompletedPreventionDepression / Hepatitis C Viral Infection1
4CompletedSupportive CareFriedreich's Ataxia1
4CompletedTreatmentAntidepressant Activity in Healthy Volunteers1
4CompletedTreatmentDementias2
4CompletedTreatmentDepression5
4CompletedTreatmentDepression / Mild Cognitive Impairment (MCI)1
4CompletedTreatmentDepression / Traumatic Brain Injury (TBI)1
4CompletedTreatmentDepressive illness1
4CompletedTreatmentFrontotemporal Dementia1
4CompletedTreatmentMajor Depressive Disorder (MDD)3
4CompletedTreatmentNegative Symptoms / Schizophrenic Disorders1
4CompletedTreatmentSchizophrenic Disorders1
4CompletedTreatmentSchizophrenic Disorders / Schizophreniform Disorder1
4CompletedTreatmentSleep disorders and disturbances1
4Not Yet RecruitingTreatmentGastro-esophageal Reflux Disease (GERD)1
4RecruitingNot AvailableDepressive Disorders / Lactation1
4RecruitingBasic ScienceBipolar Disorder (BD)1
4RecruitingBasic ScienceMajor Depressive Disorder (MDD)1
4RecruitingTreatmentAnxiety Disorders / Obsessive Compulsive Disorder (OCD) / Psychiatric Disorder NOS1
4RecruitingTreatmentChest Pain Rule Out Myocardial Infarction1
4RecruitingTreatmentStrokes1
4TerminatedTreatmentAcute Coronary Syndromes (ACS) / Major Depressive Episode1
4TerminatedTreatmentDepression / Relapsing Remitting Multiple Sclerosis (RRMS)1
4TerminatedTreatmentMajor Depressive Disorder With Psychotic Features1
4Unknown StatusNot AvailableMajor Depressive Disorder (MDD)1
4Unknown StatusTreatmentBorderline Personality Disorder (BPD) / Suicide1
4Unknown StatusTreatmentDepression1
4Unknown StatusTreatmentMajor Depressive Disorder (MDD)2
4Unknown StatusTreatmentSchizophrenic Disorders1
4WithdrawnTreatmentComorbidity / Feeling Anxious / Major Depressive Disorder (MDD)1
Not AvailableActive Not RecruitingNot AvailableCancer, Breast / Depression / Menopausal Hot Flushes / Psychosocial Effects of Cancer and Its Treatment1
Not AvailableCompletedNot AvailableAcute Kidney Injury (AKI) / Depression1
Not AvailableCompletedNot AvailableHealthy Volunteers1
Not AvailableCompletedNot AvailableMajor Depressive Disorder (MDD) / Major Depressive Disorder, Bipolar I and Bipolar II1
Not AvailableCompletedBasic ScienceAlcohol Dependence / Stress1
Not AvailableCompletedBasic ScienceAntidepressive Agents, Second-Generation1
Not AvailableCompletedBasic ScienceCognitive Performance in Major Depression1
Not AvailableCompletedBasic ScienceHealthy Volunteers1
Not AvailableCompletedBasic ScienceMDMA Mechanism of Action1
Not AvailableCompletedBasic ScienceMajor Depressive Disorder (MDD)1
Not AvailableCompletedOtherHealthy Young and Elderly Volunteers1
Not AvailableCompletedTreatmentAlzheimer's Disease (AD)1
Not AvailableCompletedTreatmentCardiovascular Disease (CVD) / Heart Diseases1
Not AvailableCompletedTreatmentDepression2
Not AvailableCompletedTreatmentDepression / Feeling Anxious1
Not AvailableCompletedTreatmentDepression / Major Depressive Disorder (MDD)1
Not AvailableCompletedTreatmentDepression / Malignancies / Palliative Care / Psychiatric Disorder NOS1
Not AvailableCompletedTreatmentSchizophrenic Disorders1
Not AvailableEnrolling by InvitationNot AvailableBipolar Disorder (BD)1
Not AvailableNot Yet RecruitingNot AvailableGastro-esophageal Reflux Disease (GERD)1
Not AvailableRecruitingNot AvailableObesity, Morbid1
Not AvailableRecruitingOtherObsessive Compulsive Disorder (OCD)1
Not AvailableRecruitingTreatmentAlcohol-Related Disorders / Brain Injury / Depression / Disease, Chronic / Mild Cognitive Impairment (MCI) / Pain NOS / Posttraumatic Stress Disorders / Quality of Life / Substance-Related Disorders / Suicidal Thoughts / Wounds and Injuries1
Not AvailableTerminatedTreatmentDepression / Depressive Disorders / Moods Disorders1
Not AvailableUnknown StatusNot AvailableFatigue Syndrome, Chronic / Fibromyalgia / Rheumatoid Arthritis1
Not AvailableUnknown StatusNot AvailablePrurigo Nodularis1
Not AvailableUnknown StatusTreatmentAsthma Bronchial1
Not AvailableUnknown StatusTreatmentTraumatic Brain Injury (TBI)1
Not AvailableUnknown StatusTreatmentTreatment Resistant Depression (TRD)1
Not AvailableWithdrawnHealth Services ResearchShort Bowel Syndrome (SBS)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
TabletOral20 mg
TabletOral40 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
TabletOral30 mg
TabletOral10 mg
Kit
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
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Pms-Citalopram 40 mg Tablet0.82USD tablet
Ran-Citalo 20 mg Tablet0.82USD tablet
Ran-Citalo 40 mg Tablet0.82USD tablet
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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)
CA2353693No2003-07-222021-07-24Canada
CA2049368No2001-10-232011-08-16Canada

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)182-183 °C[L1355]
water solubilitySparingly soluble FDA label
logP3.5Not Available
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

Taxonomy

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
Phenylbutylamine / Isocoumaran / Fluorobenzene / Halobenzene / Aralkylamine / Aryl halide / Aryl fluoride / Tertiary amine / Tertiary aliphatic amine / Oxacycle
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organofluorine compound, tertiary amino compound, 2-benzofurans, nitrile, cyclic ether (CHEBI:77397)

Targets

Kind
Protein
Organism
Human
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. 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:10063489]
  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:10188639]
  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:10546982]
  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:11180498]
  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:11300876]
  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:15955412]
  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:7548008]
  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:9537821]
  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. doi: 10.1016/j.neulet.2009.07.030. Epub 2009 Jul 16. [PubMed:19616061]
  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. doi: 10.1016/j.neuropharm.2009.05.009. Epub 2009 Jun 3. [PubMed:19500602]
  11. 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Binder
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
Molecular Weight
51486.005 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Binder
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
Molecular Weight
51420.375 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-...
Gene Name
HTR2C
Uniprot ID
P28335
Uniprot Name
5-hydroxytryptamine receptor 2C
Molecular Weight
51820.705 Da
References
  1. Chanrion B, Mannoury la Cour C, Gavarini S, Seimandi M, Vincent L, Pujol JF, Bockaert J, Marin P, Millan MJ: Inverse agonist and neutral antagonist actions of antidepressants at recombinant and native 5-hydroxytryptamine2C receptors: differential modulation of cell surface expression and signal transduction. Mol Pharmacol. 2008 Mar;73(3):748-57. Epub 2007 Dec 14. [PubMed:18083778]

Enzymes

Kind
Protein
Organism
Human
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. 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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  6. 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
Human
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. 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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  6. 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]
  7. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
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. 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]
  3. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
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. 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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. 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]
  3. Citalopram FDA [File]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid 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 oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Walsky RL, Astuccio AV, Obach RS: Evaluation of 227 drugs for in vitro inhibition of cytochrome P450 2B6. J Clin Pharmacol. 2006 Dec;46(12):1426-38. [PubMed:17101742]

Transporters

Kind
Protein
Organism
Human
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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Monoamine transmembrane transporter activity
Specific Function
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A3
Uniprot ID
Q01959
Uniprot Name
Sodium-dependent dopamine transporter
Molecular Weight
68494.255 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Norepinephrine:sodium symporter activity
Specific Function
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A2
Uniprot ID
P23975
Uniprot Name
Sodium-dependent noradrenaline transporter
Molecular Weight
69331.42 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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. 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]

Drug created on June 13, 2005 07:24 / Updated on November 20, 2018 13:19