Identification

Name
Sertraline
Accession Number
DB01104  (APRD00175, DB08567)
Type
Small Molecule
Groups
Approved
Description

Sertraline hydrochloride belongs to a class of antidepressant agents known as selective serotonin-reuptake inhibitors (SSRIs). 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 [7]. 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 (see Toxicity section below for a more detailed listing of side effects). Compared to other agents in this class, sertraline may cause greater diarrheal and male sexual dysfunction effects [5]. Sertraline displays a better safety or tolerability profile than other classes of antidepressants [6]. Side effects generally occur within the first two weeks of therapy and are usually less severe and frequent than those observed with tricyclic antidepressants or monoamine oxidase inhibitors [7]. Sertraline has shown therapeutic effectiveness as a treatment for major depressive disorder [1], obsessive-compulsive disorder (OCD) [2], panic disorder, post-traumatic stress disorder (PTSD) [3], premenstrual dysphoric disorder (PMDD) [4] and social anxiety disorder (social phobia).

Structure
Thumb
Synonyms
  • (+)-Sertraline
  • (1S-cis)-1,2,3,4-tetrahydro-4-(3,4-dichlorophenyl)-N-methyl-1-naphthalenamine
  • (1S,4S)-sertraline
  • cis-(+)-sertraline
  • Sertralina
  • Sertraline
  • Sertralinum
External IDs
CP 51974
Product Ingredients
IngredientUNIICASInChI Key
Sertraline hydrochlorideUTI8907Y6X79559-97-0BLFQGGGGFNSJKA-XHXSRVRCSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act SertralineCapsule100 mgOralActavis Pharma Company2006-11-08Not applicableCanada
Act SertralineCapsule50 mgOralActavis Pharma Company2006-11-08Not applicableCanada
Act SertralineCapsule25 mgOralActavis Pharma Company2006-11-08Not applicableCanada
Q-sertralineCapsule25 mgOralQd Pharmaceuticals Ulc2012-02-032015-08-21Canada
Q-sertralineCapsule100 mgOralQd Pharmaceuticals Ulc2012-02-032015-08-21Canada
Q-sertralineCapsule50 mgOralQd Pharmaceuticals Ulc2012-02-032015-08-21Canada
Sandoz SertralineCapsule100 mgOralSandoz Canada Incorporated2002-02-13Not applicableCanada
Sandoz SertralineCapsule50 mgOralSandoz Canada Incorporated2002-02-13Not applicableCanada
Sandoz SertralineCapsule25 mgOralSandoz Canada Incorporated2002-02-13Not applicableCanada
SertralineCapsule100 mgOralCobalt LaboratoriesNot applicableNot applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-sertralineCapsule25 mgOralApotex Corporation1999-09-01Not applicableCanada
Apo-sertralineCapsule100 mgOralApotex Corporation1999-09-01Not applicableCanada
Apo-sertralineCapsule50 mgOralApotex Corporation1999-09-01Not applicableCanada
Auro-sertralineCapsule25 mgOralAuro Pharma Inc2012-10-18Not applicableCanada
Auro-sertralineCapsule100 mgOralAuro Pharma Inc2012-10-18Not applicableCanada
Auro-sertralineCapsule50 mgOralAuro Pharma Inc2012-10-18Not applicableCanada
Bio-sertralineCapsule100 mgOralBiomed Pharma2016-12-08Not applicableCanada
Bio-sertralineCapsule50 mgOralBiomed Pharma2016-11-23Not applicableCanada
Bio-sertralineCapsule25 mgOralBiomed Pharma2016-11-23Not applicableCanada
Dom-sertralineCapsule100 mgOralDominion Pharmacal2002-05-31Not applicableCanada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Sertraline HydrochlorideSertraline hydrochloride (25 mg/1)TabletOralWatson Pharmaceuticals2008-05-16Not applicableUs
Sertraline HydrochlorideSertraline hydrochloride (25 mg/1)Tablet, film coatedOralCobalt Pharmaceuticals2007-08-02Not applicableUs
Sertraline HydrochlorideSertraline hydrochloride (50 mg/1)TabletOralActavis Elizabeth LLC2009-04-07Not applicableUs
Sertraline HydrochlorideSertraline hydrochloride (100 mg/1)TabletOralWatson Pharmaceuticals2008-05-16Not applicableUs
Sertraline HydrochlorideSertraline hydrochloride (100 mg/1)Tablet, film coatedOralCobalt Pharmaceuticals2007-08-02Not applicableUs
Sertraline HydrochlorideSertraline hydrochloride (50 mg/1)TabletOralActavis Elizabeth LLC2009-04-07Not applicableUs
Sertraline HydrochlorideSertraline hydrochloride (50 mg/1)TabletOralWatson Pharmaceuticals2008-05-16Not applicableUs
Sertraline HydrochlorideSertraline hydrochloride (50 mg/1)Tablet, film coatedOralCobalt Pharmaceuticals2007-08-02Not applicableUs
Sertraline HydrochlorideSertraline hydrochloride (25 mg/1)TabletOralActavis Elizabeth LLC2009-04-07Not applicableUs
International/Other Brands
Lustral
Categories
UNII
QUC7NX6WMB
CAS number
79617-96-2
Weight
Average: 306.23
Monoisotopic: 305.073804963
Chemical Formula
C17H17Cl2N
InChI Key
VGKDLMBJGBXTGI-SJCJKPOMSA-N
InChI
InChI=1S/C17H17Cl2N/c1-20-17-9-7-12(13-4-2-3-5-14(13)17)11-6-8-15(18)16(19)10-11/h2-6,8,10,12,17,20H,7,9H2,1H3/t12-,17-/m0/s1
IUPAC Name
(1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine
SMILES
CN[C@H]1CC[C@@H](C2=CC(Cl)=C(Cl)C=C2)C2=CC=CC=C12

Pharmacology

Indication

For the management of major depressive disorder (MDD), posttraumatic stress disorder (PTSD), obsessive-compulsive disorder (OCD), panic disorder (PD) with or without agoraphobia, premenstrual dysphoric disorder (PMDD), and social anxiety disorder (SAD) [Label].

It may be used for premature ejaculation and vascular headaches as off-label indications.

Associated Conditions
Pharmacodynamics

Sertraline, an antidepressant drug similar to citalopram, fluoxetine, and paroxetine, is of the selective serotonin reuptake inhibitor (SSRI) type. Sertraline has one active metabolite and, like the other SSRIs, have less sedative, anticholinergic, and cardiovascular effects than the tricyclic antidepressant drugs because it does not have clinically important anticholinergic, antihistamine, or adrenergic (alpha1, alpha2, beta) blocking activity [5]. In vitro, sertraline has no significant affinity for GABA, dopaminergic, serotonergic (5HT1A, 5HT1B, 5HT2), or benzodiazepine receptors [Label]. It mediates a weak inhibitory actions on the neuronal uptake of norepinephrine or dopamine [5] and exhibits no inhibitory action on monoamine oxidase [Label]. In animal studies, chronic administration of sertraline resulted in down-regulation of brain norepinephrine receptors [Label]. Sertraline displays affinity for sigma-1 and 2 receptor binding sites [A31941], but binds with more affinity to sigma-1 binding sites. The Ki for sigma 2 sites was > 1000 nM [A31940]. The pharmacological role of sigma receptors in the mechanism of action of sertraline is unclear.

Mechanism of action

The exact mechanism of action sertraline is not fully known, but the drug appears to selectively inhibit the reuptake of serotonin at the presynaptic membrane. This results in an increased synaptic concentration of serotonin in the CNS, which leads to numerous functional changes associated with enhanced serotonergic neurotransmission [Label]. It is suggested that these modifications are responsible for the antidepressant action observed during long term administration of antidepressants. It has also been hypothesized that obsessive-compulsive disorder is caused by the dysregulation of serotonin, as it is treated by sertraline, and the drug corrects this imbalance.

TargetActionsOrganism
ASodium-dependent serotonin transporter
inhibitor
Human
USodium-dependent dopamine transporter
inhibitor
Human
USigma receptor
antagonist
Human
Absorption

Following once-daily administration over the range of 50 to 200 mg for 14 days, mean peak plasma concentrations (Cmax) of sertraline occurred between 4.5 to 8.4 hours post-administration [Label]. The steady-state concentrations are reached after 1 week following once-daily administration, and approximately two-fold accumulation up to steady-state concentrations is observed [Label]. The single dose bioavailability of sertraline tablets is approximately equal to an equivalent dose of sertraline oral solution [Label].

The effects of food on the bioavailability of the sertraline tablet and oral concentrate were studied in subjects administered a single dose with and without food. For the tablet, AUC was slightly increased when drug was administered with food but the Cmax was 25% greater, while the time to reach peak plasma concentration (Tmax) decreased from 8 hours post-dosing to 5.5 hours. For the oral concentrate, Tmax was slightly prolonged from 5.9 hours to 7.0 hours with food.

Volume of distribution
Not Available
Protein binding

In vitro protein binding studies indicate that sertraline is highly bound to serum proteins (98%) in the range of 20 to 500 ng/mL [Label], predominantly to albumin and α1-acid glycoprotein [6].

Metabolism

Extensively metabolized in the liver. Sertraline metabolism involves N-demethylation, N-hydroxylation, oxidative deamination, and glucuronidation of sertraline carbamic acid. Sertraline undergoes N-demethylation to form N-desmethylsertraline, which retains substantially less pharmacological activity than its parent compound [Label]. This metabolic pathway is primarily catalyzed by cytochrome P450 (CYP) 2B6, with CYP2C19, CYP3A4 and CYP2D6 contributing to a lesser extent. Both sertraline and N-desmethylsertraline undergo oxidative deamination and subsequent reduction, hydroxylation, and glucuronide conjugation [Label]. Deamination occurs via CYP3A4 and CYP2C19. In vitro studies have shown that monoamine oxidase A and B may also catalyze sertraline deamination. Sertraline N-carbamoyl glucuronidation has also been observed in human liver microsomes.

Route of elimination

Sertraline and its metabolites are excreted via both renal and fecal elimination. In a study of radiolabeled sertraline involving two healthy male subjects, about 40-45% of total radioactivity was observed in 9 days post-administration [Label] with negligible amount (<0.2%) of unchanged parent compound detected [8]. For the same period, 40-45% of total radioactivity was also accounted for in feces, where 12-14% of the radioactivity was unchanged sertraline [Label].

Half life

The elimination half-life of sertraline is approximately 25-26 hours. The elimination half-life of desmethylsertraline is approximately 62-104 hours [Label].

Clearance
Not Available
Toxicity

The most common signs and symptoms associated with non-fatal sertraline overdosage were somnolence, vomiting, tachycardia, nausea, dizziness, agitation and tremor. No cases of fatal overdosage with only sertraline have been reported. Other important signs of overdose include bradycardia, bundle branch block, coma, convulsions, delirium, hallucinations, hypertension, hypotension, manic reaction, pancreatitis, QT-interval prolongation, Torsade de Pointes, serotonin syndrome, stupor, and syncope [Label]. Oral LD50 of sertraline in mice and rats are 419 - 548 mg/kg and 1327 - 1591mg/kg, respectively [MSDS].

In a lifetime carcinogenicity studies on mice and rats, there was no significant evidence of sertraline-induced carcinogenic effects despite observable dose-related increases in liver adenomas in male mice receiving sertraline at 10-40 mg/kg and an increase in follicular adenomas of the thyroid in female rats receiving sertraline at 40 mg/kg [Label]. There was an increase in uterine adenocarcinomas in rats receiving sertraline at 10-40 mg/kg, however this effect was not understood to be drug-related [Label]. There were no signs of genotoxicity nor impairment of fertility in bacterial assays and animal studies [Label].

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2C19CYP2C19*2Not Available681G>AEffect Directly StudiedThe presence of this polymorphism in CYP2C19 is associated with poor metabolism of sertraline.Details
Cytochrome P450 2C19CYP2C19*3Not Available636G>AEffect Directly StudiedThe presence of this polymorphism in CYP2C19 is associated with reduced or poor metabolism of sertraline.Details
Cytochrome P450 2C19CYP2C19*2ANot Available681G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*2BNot Available681G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*4Not Available1A>GEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*5Not Available1297C>TEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*6Not Available395G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*7Not Available19294T>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*22Not Available557G>C / 991A>GEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*24Not Available99C>T / 991A>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*35Not Available12662A>GEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinSertraline may increase the antiplatelet activities of (R)-warfarin.
(S)-WarfarinSertraline may increase the antiplatelet activities of (S)-Warfarin.
2,4-thiazolidinedioneThe risk or severity of hypoglycemia can be increased when Sertraline is combined with 2,4-thiazolidinedione.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when Sertraline is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of serotonin syndrome can be increased when Sertraline is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of serotonin syndrome can be increased when Sertraline is combined with 3,4-Methylenedioxyamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of serotonin syndrome can be increased when Sertraline is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-hydroxycoumarinSertraline may increase the antiplatelet activities of 4-hydroxycoumarin.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Sertraline.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of serotonin syndrome can be increased when Sertraline is combined with 5-methoxy-N,N-dimethyltryptamine.
Food Interactions
  • Avoid alcohol.
  • Avoid St.John's Wort.
  • Avoid taking with grapefruit juice.
  • Take with food.

References

Synthesis Reference

George J. Quallich, Michael T. Williams, "Process for preparing sertraline intermediates." U.S. Patent US4839104, issued February, 1977.

US4839104
General References
  1. Fabre LF, Abuzzahab FS, Amin M, Claghorn JL, Mendels J, Petrie WM, Dube S, Small JG: Sertraline safety and efficacy in major depression: a double-blind fixed-dose comparison with placebo. Biol Psychiatry. 1995 Nov 1;38(9):592-602. [PubMed:8573661]
  2. Kronig MH, Apter J, Asnis G, Bystritsky A, Curtis G, Ferguson J, Landbloom R, Munjack D, Riesenberg R, Robinson D, Roy-Byrne P, Phillips K, Du Pont IJ: Placebo-controlled, multicenter study of sertraline treatment for obsessive-compulsive disorder. J Clin Psychopharmacol. 1999 Apr;19(2):172-6. [PubMed:10211919]
  3. Brady K, Pearlstein T, Asnis GM, Baker D, Rothbaum B, Sikes CR, Farfel GM: Efficacy and safety of sertraline treatment of posttraumatic stress disorder: a randomized controlled trial. JAMA. 2000 Apr 12;283(14):1837-44. [PubMed:10770145]
  4. Yonkers KA, Halbreich U, Freeman E, Brown C, Endicott J, Frank E, Parry B, Pearlstein T, Severino S, Stout A, Stone A, Harrison W: Symptomatic improvement of premenstrual dysphoric disorder with sertraline treatment. A randomized controlled trial. Sertraline Premenstrual Dysphoric Collaborative Study Group. JAMA. 1997 Sep 24;278(12):983-8. [PubMed:9307345]
  5. Shelton RC: The role of sertraline in the management of depression. Clin Ther. 1994 Sep-Oct;16(5):768-82; discussion 767. [PubMed:7859236]
  6. Murdoch D, McTavish D: Sertraline. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in depression and obsessive-compulsive disorder. Drugs. 1992 Oct;44(4):604-24. [PubMed:1281075]
  7. 46. (2012). In Rang and Dale's Pharmacology (7th ed., pp. 573-574). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
  8. EMA Label: Zoloft; INN: sertraline [Link]
External Links
Human Metabolome Database
HMDB0005010
KEGG Drug
D02360
KEGG Compound
C07246
PubChem Compound
68617
PubChem Substance
46505341
ChemSpider
61881
BindingDB
50028094
ChEBI
9123
ChEMBL
CHEMBL809
Therapeutic Targets Database
DAP000051
PharmGKB
PA451333
HET
SRE
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Sertraline
ATC Codes
N06AB06 — Sertraline
AHFS Codes
  • 28:16.04.20 — Selective-serotonin Reuptake Inhibitors
PDB Entries
3gwu / 4mm5 / 4mmb / 6awo / 6awq / 6f6n
FDA label
Download (724 KB)
MSDS
Download (47.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentMajor Depressive Disorder (MDD)1
1Active Not RecruitingTreatmentGlioblastomas1
1CompletedNot AvailableHealthy Volunteers9
1CompletedBasic ScienceHealthy Volunteers2
1CompletedBasic ScienceHepatitis C Infection1
1CompletedDiagnosticAlcoholism1
1CompletedDiagnosticChronic Subjective Dizziness / Vestibular Migraine1
1CompletedTreatmentDementias1
1CompletedTreatmentHealthy Male Adults1
1CompletedTreatmentHealthy Volunteers3
1CompletedTreatmentMajor Depressive Disorder (MDD)3
1RecruitingTreatmentLeukemia Acute Myeloid Leukemia (AML)1
1RecruitingTreatmentMyelodysplastic Syndromes1
1TerminatedPreventionAcute Coronary Syndromes (ACS) / Coronary Artery Disease / Depression1
1, 2Active Not RecruitingTreatmentChronic Orthostatic Intolerance / Tachycardia1
1, 2Active Not RecruitingTreatmentDepression / Parkinson's Disease (PD)1
1, 2CompletedBasic ScienceObsessive Compulsive Disorder (OCD)1
1, 2CompletedTreatmentPost-Traumatic Stress Disorder (PTSD)1
1, 2CompletedTreatmentPremenstrual Syndrome1
1, 2RecruitingTreatmentBipolar Disorder (BD) / Major Depressive Disorder (MDD)1
2Active Not RecruitingTreatmentMajor Depressive Disorder (MDD)1
2Active Not RecruitingTreatmentStress Disorders, Post-Traumatic1
2CompletedOtherMajor Depressive Disorder (MDD)1
2CompletedTreatmentAlcohol Abuse / Stress Disorders, Post-Traumatic / Substance-Related Disorders1
2CompletedTreatmentAlcohol Dependence / Alcoholism1
2CompletedTreatmentAlcoholism1
2CompletedTreatmentAlcoholism / Depression1
2CompletedTreatmentAlcoholism / Post-Traumatic Stress Disorder (PTSD)1
2CompletedTreatmentAnxiety Disorders / Depression1
2CompletedTreatmentAutism Spectrum Conditions/Disorders1
2CompletedTreatmentBipolar Disorder (BD) / Depressive Disorders1
2CompletedTreatmentCocaine-Related Disorders1
2CompletedTreatmentDependence, Cocaine / Depressive Symptoms1
2CompletedTreatmentDepression1
2CompletedTreatmentDepression / Substance-Related Disorders1
2CompletedTreatmentFragile X Syndrome (FXS)1
2CompletedTreatmentHepatitis C Viral Infection / Liver Cirrhosis, Biliary / Pruritus1
2CompletedTreatmentMajor Depressive Disorder (MDD)3
2CompletedTreatmentPostpartum Depression1
2CompletedTreatmentSocial Anxiety Disorder (SAD)1
2Not Yet RecruitingTreatmentCoccidioidomycosis1
2RecruitingTreatmentAutism Spectrum Conditions/Disorders / Feeling Anxious1
2RecruitingTreatmentMajor Depressive Disorder (MDD)2
2SuspendedTreatmentMental Retardation / Stereotyped Behavior1
2TerminatedNot AvailablePost-Traumatic Stress Disorder (PTSD)1
2TerminatedTreatmentAlcoholism / Gambling1
2TerminatedTreatmentAnxiety Disorder of Adolescence1
2TerminatedTreatmentMajor Depressive Disorder (MDD)1
2Unknown StatusTreatmentPediatric Autoimmune Neuropsychiatric Disorders Associated With Streptococcal Infections1
2, 3CompletedPreventionTraumatic Brain Injury (TBI)1
2, 3CompletedTreatmentAffective Disorders1
2, 3CompletedTreatmentAlzheimer's Disease (AD) / Depression1
2, 3CompletedTreatmentChronic Heart Failure (CHF) / Congestive Heart Failure (CHF) / Depression1
2, 3CompletedTreatmentDepression / Feeling Anxious1
2, 3CompletedTreatmentDepression / Suicide, Attempted1
2, 3CompletedTreatmentMajor Depressive Disorder (MDD)1
2, 3CompletedTreatmentPanic Disorders1
2, 3CompletedTreatmentPost-Traumatic Stress Disorder (PTSD)1
2, 3TerminatedTreatmentObsessive-Compulsive Disorder (OCD)1
3CompletedNot AvailableRoux en Y Gastric Bypass Surgery1
3CompletedPreventionDepression1
3CompletedSupportive CareBone Mineral Density Quantitative Trait Locus 71
3CompletedSupportive CareDepression / Unspecified Adult Solid Tumor, Protocol Specific1
3CompletedTreatmentAutism, Early Infantile1
3CompletedTreatmentBipolar Disorder (BD) / Depression1
3CompletedTreatmentBipolar Disorder (BD) / Depression, Bipolar1
3CompletedTreatmentBipolar Disorder (BD) / Major Depressive Disorder (MDD) / Unipolar Depression1
3CompletedTreatmentCardiovascular Disease (CVD) / Depression / Heart Diseases / Myocardial Infarction / Unstable Angina (UA)1
3CompletedTreatmentChronic Kidney Disease (CKD) / Depression1
3CompletedTreatmentDepression3
3CompletedTreatmentDepression / Depressive Disorders / Major Depressive Disorder (MDD) / Moods Disorders / Psychiatric Disorder NOS1
3CompletedTreatmentDepression / Epilepsies1
3CompletedTreatmentDepression / Feeling Anxious1
3CompletedTreatmentDepression / Heart Diseases1
3CompletedTreatmentDepressive Disorder, Treatment-Resistant / Major depressive disorder, recurrent episode2
3CompletedTreatmentMajor Depressive Disorder (MDD)3
3CompletedTreatmentMajor Depressive Disorder With Psychotic Features1
3CompletedTreatmentMajor depressive disorder, recurrent episode3
3CompletedTreatmentMeningitis, Cryptococcal / Meningitis, Fungal1
3CompletedTreatmentObsessive-Compulsive Disorder (OCD)1
3CompletedTreatmentPost-Traumatic Stress Disorder (PTSD)1
3RecruitingTreatmentDepressive Disorder, Treatment-Resistant1
3RecruitingTreatmentMajor Depressive Disorder (MDD)1
3TerminatedTreatmentAIDS-Related Opportunistic Infections / Cryptococcal infections / Cryptococcus Neoformans1
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
3TerminatedTreatmentDepression / Sleeplessness1
3TerminatedTreatmentStress Disorders, Post-Traumatic1
3Unknown StatusTreatmentAnxiety Disorders / Generalized Anxiety Disorder (GAD) / Social Phobia1
3Unknown StatusTreatmentCompulsive Behavior / Mental Retardation / Self-Injurious Behavior / Stereotyped Behavior1
4CompletedNot AvailableAnxiety Disorders1
4CompletedNot AvailableGeneralized Anxiety Disorder (GAD) / Separation Anxiety Disorder / Social Phobia1
4CompletedBasic ScienceMajor Depressive Disorder (MDD)1
4CompletedHealth Services ResearchObsessive Compulsive Disorder (OCD)1
4CompletedOtherHealthy Controls / Major Depressive Disorder (MDD)1
4CompletedPreventionDepression / Posttraumatic Stress Disorders1
4CompletedTreatmentAcute Traumatic Stress Disorders / Post-Traumatic Stress Disorder (PTSD)1
4CompletedTreatmentAlcohol Use Disorder (AUD) / PTSD1
4CompletedTreatmentAlcoholism1
4CompletedTreatmentAlcoholism / Depression1
4CompletedTreatmentAlzheimer's Disease (AD) / Depression1
4CompletedTreatmentBipolar Disorder (BD)1
4CompletedTreatmentConversion Disorder / Convulsion, Non-Epileptic / Depression / Dissociative Disorders / Stress Disorders, Post-Traumatic1
4CompletedTreatmentConversion Disorder / Convulsion, Non-Epileptic / Depression / Stress Disorders, Post-Traumatic1
4CompletedTreatmentDementias1
4CompletedTreatmentDepression9
4CompletedTreatmentDepression / Diabetes Mellitus (DM)1
4CompletedTreatmentDepression / Melancholic Depression1
4CompletedTreatmentDepression / Panic Attacks / Thoracic Pain1
4CompletedTreatmentDepression / Post Traumatic Stress Disorder (PTSD)1
4CompletedTreatmentDepressive Symptoms1
4CompletedTreatmentDiabetes Mellitus (DM) / Major Depressive Disorder (MDD)1
4CompletedTreatmentGeneralized Anxiety Disorder (GAD)1
4CompletedTreatmentHealthy Volunteers1
4CompletedTreatmentImpulse Control Disorders1
4CompletedTreatmentMajor Depressive Disorder (MDD)5
4CompletedTreatmentPanic Disorders2
4CompletedTreatmentPost-Traumatic Stress Disorder (PTSD)2
4CompletedTreatmentPosttraumatic Stress Disorders2
4CompletedTreatmentPremenstrual Dysphoric Disorder1
4CompletedTreatmentPremenstrual Syndrome1
4CompletedTreatmentSocial Phobia1
4CompletedTreatmentUnipolar Major Depressive Episode1
4Not Yet RecruitingTreatmentHigh Blood Pressure (Hypertension)1
4Not Yet RecruitingTreatmentModerate Depression / Pregnancy1
4RecruitingNot AvailableDepressive Disorders / Lactation1
4RecruitingBasic ScienceObsessive-Compulsive Disorder (OCD)1
4RecruitingDiagnosticAsthma Bronchial / Asthma: [Nos] or [Attack] / Major Depressive Disorder (MDD)1
4RecruitingHealth Services ResearchMajor Depressive Disorder (MDD)1
4RecruitingTreatmentAnxiety Disorders / Obsessive-Compulsive Disorder (OCD) / Psychiatric Disorder NOS1
4RecruitingTreatmentMajor Depressive Disorder (MDD)1
4RecruitingTreatmentMood / PMDD / Stress1
4TerminatedBasic ScienceDepression / High Blood Pressure (Hypertension)1
4TerminatedPreventionCerebrovascular Accidents / Depression1
4TerminatedPreventionPost-Traumatic Stress Disorder (PTSD)1
4TerminatedTreatmentAnxiety Disorders / Fear of open spaces / Major Depressive Disorder (MDD) / Obsessive-Compulsive Disorder (OCD) / Panic Disorders / Social Phobia1
4TerminatedTreatmentCoronary Artery Disease / Depression1
4TerminatedTreatmentEpilepsies / Feeling Anxious1
4TerminatedTreatmentGeneralised Anxiety Disorder1
4TerminatedTreatmentMajor Depressive Disorder (MDD) / Sexual Dysfunctions1
4TerminatedTreatmentMajor Depressive Disorder With Psychotic Features1
4TerminatedTreatmentPostpartum Depression1
4Unknown StatusNot AvailableMajor Depressive Disorder (MDD)1
4Unknown StatusHealth Services ResearchDepression1
4Unknown StatusTreatmentDepression1
4Unknown StatusTreatmentDepression / Dysthymic Disorder1
4Unknown StatusTreatmentMajor Depressive Disorder (MDD)2
Not AvailableActive Not RecruitingNot AvailableCancer, Breast / Depression / Menopausal Hot Flushes / Psychosocial Effects of Cancer and Its Treatment1
Not AvailableActive Not RecruitingNot AvailableMajor Depressive Disorder (MDD)1
Not AvailableActive Not RecruitingNot AvailableObsessive Compulsive Disorder (OCD)1
Not AvailableActive Not RecruitingDiagnosticGeneralized Anxiety Disorder (GAD) / Separation Anxiety Disorder / Social Phobia1
Not AvailableActive Not RecruitingTreatmentDepression1
Not AvailableCompletedNot AvailableAcute Kidney Injury (AKI) / Depression1
Not AvailableCompletedNot AvailableDepression / Depressive Disorders1
Not AvailableCompletedNot AvailableDepression / Panic Disorders2
Not AvailableCompletedNot AvailableHealthy Volunteers2
Not AvailableCompletedNot AvailablePanic Disorders1
Not AvailableCompletedNot AvailablePosttraumatic Stress Disorders1
Not AvailableCompletedBasic ScienceMajor Depressive Disorder (MDD)1
Not AvailableCompletedOtherMajor Depressive Disorder (MDD) / Treatments1
Not AvailableCompletedPreventionBipolar Disorder (BD) / Depression / Psychotic Disorder NOS / Schizophrenic Disorders1
Not AvailableCompletedScreeningAcute Coronary Syndromes (ACS) / Depressive Symptoms1
Not AvailableCompletedTreatmentDepression5
Not AvailableCompletedTreatmentDepression / Depressive Disorders1
Not AvailableCompletedTreatmentMajor Depressive Disorder (MDD)6
Not AvailableCompletedTreatmentMenopause-Hot Flashes1
Not AvailableCompletedTreatmentPostpartum Depression1
Not AvailableCompletedTreatmentSpinal Stenosis of Lumbar Region1
Not AvailableEnrolling by InvitationNot AvailableBipolar Disorder (BD)1
Not AvailableRecruitingOtherObsessive-Compulsive Disorder (OCD)1
Not AvailableRecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD) / Depression / Feeling Anxious / Interstitial Lung Disease (ILD) / Stress1
Not AvailableRecruitingTreatmentDepression / Feeling Anxious / Mild Cognitive Impairment (MCI)1
Not AvailableRecruitingTreatmentMajor Depressive Disorder (MDD)1
Not AvailableRecruitingTreatmentObsessive-Compulsive Disorder (OCD)2
Not AvailableTerminatedNot AvailableDepression / Heart Failure, Unspecified1
Not AvailableTerminatedPreventionPostpartum Depression1
Not AvailableTerminatedTreatmentAdolescent Depression1
Not AvailableUnknown StatusTreatmentDepression / Parkinson's Disease (PD)1
Not AvailableUnknown StatusTreatmentMajor Depressive Disorder (MDD)1
Not AvailableUnknown StatusTreatmentTraumatic Brain Injury (TBI)1
Not AvailableUnknown StatusTreatmentTreatment Resistant Depression (TRD)1
Not AvailableWithdrawnNot AvailableDepression1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Actavis Group
  • Advanced Pharmaceutical Services Inc.
  • Aidarex Pharmacuticals LLC
  • Amerisource Health Services Corp.
  • Apotex Inc.
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Atlantic Biologicals Corporation
  • Aurobindo Pharma Ltd.
  • Bryant Ranch Prepack
  • Camber Pharmaceuticals Inc.
  • Cardinal Health
  • Caremark LLC
  • Cobalt Pharmaceuticals Inc.
  • Comprehensive Consultant Services Inc.
  • Corepharma LLC
  • Coupler Enterprises Inc.
  • Dept Health Central Pharmacy
  • DHHS Program Support Center Supply Service Center
  • Direct Dispensing Inc.
  • Direct Pharmaceuticals Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Doctor Reddys Laboratories Ltd.
  • Eon Labs
  • Greenstone LLC
  • H.J. Harkins Co. Inc.
  • Heartland Repack Services LLC
  • Hikma Pharmaceuticals
  • Innoviant Pharmacy Inc.
  • International Laboratories Inc.
  • InvaGen Pharmaceuticals Inc.
  • Ivax Pharmaceuticals
  • Lake Erie Medical and Surgical Supply
  • Lupin Pharmaceuticals Inc.
  • Major Pharmaceuticals
  • Mckesson Corp.
  • Medvantx Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Neuman Distributors Inc.
  • Northstar Rx LLC
  • Nucare Pharmaceuticals Inc.
  • Ohm Laboratories Inc.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pfizer Inc.
  • Physicians Total Care Inc.
  • Pliva Inc.
  • Pratt Pharmaceuticals
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Professional Co.
  • Ranbaxy Laboratories
  • Rebel Distributors Corp.
  • Remedy Repack
  • Roxane Labs
  • Sandhills Packaging Inc.
  • Southwood Pharmaceuticals
  • Stat Rx Usa
  • Stat Scripts LLC
  • Teva Pharmaceutical Industries Ltd.
  • Torrent Pharmaceuticals
  • Tya Pharmaceuticals
  • UDL Laboratories
  • US Pharmaceutical Group
  • Va Cmop Dallas
  • Vangard Labs Inc.
  • West-Ward Pharmaceuticals
  • Wockhardt Ltd.
  • Zydus Pharmaceuticals
Dosage forms
FormRouteStrength
ConcentrateOral20 mg/1mL
SolutionOral20 mg/1mL
Solution, concentrateOral20 mg/1mL
TabletOral100 mg/1
TabletOral25 mg/1
TabletOral50 mg/1
Tablet, coatedOral100 mg/1
Tablet, coatedOral150 mg/1
Tablet, coatedOral200 mg/1
Tablet, coatedOral25 mg/1
Tablet, coatedOral50 mg/1
Tablet, film coatedOral100 mg/1
Tablet, film coatedOral25 mg/1
Tablet, film coatedOral50 mg/1
CapsuleOral100.0 mg
CapsuleOral25.0 mg
CapsuleOral50.0 mg
CapsuleOral25 mg
CapsuleOral100 mg
CapsuleOral50 mg
Prices
Unit descriptionCostUnit
Sertraline hcl powder480.0USD g
Zoloft 20 mg/ml Concentrate 60ml Bottle94.75USD bottle
Sertraline HCl 20 mg/ml Concentrate 60ml Bottle66.85USD bottle
Zoloft 50 mg tablet4.02USD tablet
Zoloft 100 mg tablet3.94USD tablet
Zoloft 25 mg tablet3.94USD tablet
Sertraline hcl 100 mg tablet2.77USD tablet
Sertraline hcl 25 mg tablet2.77USD tablet
Sertraline hcl 50 mg tablet2.77USD tablet
Zoloft 100 mg Capsule1.9USD capsule
Zoloft 50 mg Capsule1.81USD capsule
Apo-Sertraline 100 mg Capsule1.06USD capsule
Co Sertraline 100 mg Capsule1.06USD capsule
Mylan-Sertraline 100 mg Capsule1.06USD capsule
Novo-Sertraline 100 mg Capsule1.06USD capsule
Phl-Sertraline 100 mg Capsule1.06USD capsule
Pms-Sertraline 100 mg Capsule1.06USD capsule
Ratio-Sertraline 100 mg Capsule1.06USD capsule
Sandoz Sertraline 100 mg Capsule1.06USD capsule
Sertraline 100 mg Capsule1.06USD capsule
Apo-Sertraline 50 mg Capsule1.01USD capsule
Co Sertraline 50 mg Capsule1.01USD capsule
Mylan-Sertraline 50 mg Capsule1.01USD capsule
Novo-Sertraline 50 mg Capsule1.01USD capsule
Phl-Sertraline 50 mg Capsule1.01USD capsule
Pms-Sertraline 50 mg Capsule1.01USD capsule
Ratio-Sertraline 50 mg Capsule1.01USD capsule
Sandoz Sertraline 50 mg Capsule1.01USD capsule
Sertraline 50 mg Capsule1.01USD capsule
Zoloft 25 mg Capsule0.91USD capsule
Apo-Sertraline 25 mg Capsule0.51USD capsule
Co Sertraline 25 mg Capsule0.51USD capsule
Mylan-Sertraline 25 mg Capsule0.51USD capsule
Novo-Sertraline 25 mg Capsule0.51USD capsule
Phl-Sertraline 25 mg Capsule0.51USD capsule
Pms-Sertraline 25 mg Capsule0.51USD capsule
Ratio-Sertraline 25 mg Capsule0.51USD capsule
Sandoz Sertraline 25 mg Capsule0.51USD capsule
Sertraline 25 mg Capsule0.51USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US4962128No1992-11-022009-11-02Us
CA2029065No1994-11-082010-10-31Canada
US6727283Yes2000-04-112020-04-11Us
US7067555Yes2000-04-112020-04-11Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility3.5mg/LNot Available
logP5.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000145 mg/mLALOGPS
logP5.06ALOGPS
logP5.15ChemAxon
logS-6.3ALOGPS
pKa (Strongest Basic)9.85ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity85.74 m3·mol-1ChemAxon
Polarizability32.44 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9713
Caco-2 permeable+0.6995
P-glycoprotein substrateNon-substrate0.5858
P-glycoprotein inhibitor IInhibitor0.7333
P-glycoprotein inhibitor IINon-inhibitor0.8319
Renal organic cation transporterNon-inhibitor0.6726
CYP450 2C9 substrateNon-substrate0.71
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateSubstrate0.6304
CYP450 1A2 substrateInhibitor0.7909
CYP450 2C9 inhibitorNon-inhibitor0.9307
CYP450 2D6 inhibitorNon-inhibitor0.6469
CYP450 2C19 inhibitorInhibitor0.6839
CYP450 3A4 inhibitorNon-inhibitor0.5442
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6633
Ames testAMES toxic0.5353
CarcinogenicityNon-carcinogens0.8499
BiodegradationNot ready biodegradable0.9522
Rat acute toxicity2.5020 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9151
hERG inhibition (predictor II)Inhibitor0.7185
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)MSsplash10-00b9-2890000000-d53a90b04ec8457ad2f1
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-0091000000-10f81c7fd0a8c096039d
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-056r-0980000000-58873180fd0c95a215b3
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0bt9-0900000000-35c397f9293e114f3234
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0900000000-569e7b0694b3ef81cf90
MS/MS Spectrum - , positiveLC-MS/MSsplash10-056r-0970000000-2de49c544ebd922028dc
MS/MS Spectrum - , positiveLC-MS/MSsplash10-056r-0970000000-7753c869949091f5c066
MS/MS Spectrum - , positiveLC-MS/MSsplash10-056r-0970000000-a995c3f140efa6578777
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0bt9-2900000000-dee4675a5062129266c9
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a6r-0950000000-2a9cba59b69c41b10a59

Taxonomy

Description
This compound belongs to the class of organic compounds known as tametralines. These are compounds containing a tametraline moiety, which consists of a tetrahydronaphthalene linked to a phenyl group to form N-methyl-4-phenyl-1,2,3,4-tetrahydronaphthalen-1-amine skeleton.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Tetralins
Sub Class
Tametralines
Direct Parent
Tametralines
Alternative Parents
Dichlorobenzenes / Aralkylamines / Aryl chlorides / Dialkylamines / Organopnictogen compounds / Organochlorides / Hydrocarbon derivatives
Substituents
Tametraline / 1,2-dichlorobenzene / Chlorobenzene / Halobenzene / Aralkylamine / Aryl chloride / Aryl halide / Monocyclic benzene moiety / Secondary aliphatic amine / Secondary amine
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
secondary amino compound, dichlorobenzene, tetralins (CHEBI:9123)

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. Benmansour S, Cecchi M, Morilak DA, Gerhardt GA, Javors MA, Gould GG, Frazer A: Effects of chronic antidepressant treatments on serotonin transporter function, density, and mRNA level. J Neurosci. 1999 Dec 1;19(23):10494-501. [PubMed:10575045]
  2. Benmansour S, Owens WA, Cecchi M, Morilak DA, Frazer A: Serotonin clearance in vivo is altered to a greater extent by antidepressant-induced downregulation of the serotonin transporter than by acute blockade of this transporter. J Neurosci. 2002 Aug 1;22(15):6766-72. [PubMed:12151556]
  3. Borkowska A, Pilaczynska E, Araszkiewicz A, Rybakowski J: [The effect of sertraline on cognitive functions in patients with obsessive-compulsive disorder]. Psychiatr Pol. 2002 Nov-Dec;36(6 Suppl):289-95. [PubMed:12647451]
  4. Durham LK, Webb SM, Milos PM, Clary CM, Seymour AB: The serotonin transporter polymorphism, 5HTTLPR, is associated with a faster response time to sertraline in an elderly population with major depressive disorder. Psychopharmacology (Berl). 2004 Aug;174(4):525-9. Epub 2003 Sep 4. [PubMed:12955294]
  5. Chen F, Larsen MB, Neubauer HA, Sanchez C, Plenge P, Wiborg O: Characterization of an allosteric citalopram-binding site at the serotonin transporter. J Neurochem. 2005 Jan;92(1):21-8. [PubMed:15606893]
  6. 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]
  7. David DJ, Bourin M, Hascoet M, Colombel MC, Baker GB, Jolliet P: Comparison of antidepressant activity in 4- and 40-week-old male mice in the forced swimming test: involvement of 5-HT1A and 5-HT1B receptors in old mice. Psychopharmacology (Berl). 2001 Feb;153(4):443-9. [PubMed:11243491]
  8. Rogoz Z, Skuza G: Mechanism of synergistic action following co-treatment with pramipexole and fluoxetine or sertraline in the forced swimming test in rats. Pharmacol Rep. 2006 Jul-Aug;58(4):493-500. [PubMed:16963794]
  9. Muneoka K, Shirayama Y, Takigawa M, Shioda S: Brain region-specific effects of short-term treatment with duloxetine, venlafaxine, milnacipran and sertraline on monoamine metabolism in rats. Neurochem Res. 2009 Mar;34(3):542-55. doi: 10.1007/s11064-008-9818-2. Epub 2008 Aug 27. [PubMed:18751896]
  10. Iehle C, Delos S, Filhol O, Martin PM: Baculovirus-directed expression of human prostatic steroid 5 alpha-reductase 1 in an active form. J Steroid Biochem Mol Biol. 1993 Aug;46(2):177-82. [PubMed:8664165]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
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. 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]
  2. Ghanizadeh A: Sertraline-associated hair loss. J Drugs Dermatol. 2008 Jul;7(7):693-4. [PubMed:18664165]
  3. Lemke MR: [Antidepressant effects of dopamine agonists. Experimental and clinical findings]. Nervenarzt. 2007 Jan;78(1):31-8. [PubMed:17187269]
  4. Nemeroff CB, Owens MJ: Pharmacologic differences among the SSRIs: focus on monoamine transporters and the HPA axis. CNS Spectr. 2004 Jun;9(6 Suppl 4):23-31. [PubMed:15181382]
  5. Goodnick PJ, Goldstein BJ: Selective serotonin reuptake inhibitors in affective disorders--I. Basic pharmacology. J Psychopharmacol. 1998;12(3 Suppl B):S5-20. [PubMed:9808077]
Kind
Protein group
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Steroid binding
Specific Function
Receptor for progesterone.

Components:
References
  1. Narita N, Hashimoto K, Tomitaka S, Minabe Y: Interactions of selective serotonin reuptake inhibitors with subtypes of sigma receptors in rat brain. Eur J Pharmacol. 1996 Jun 20;307(1):117-9. [PubMed:8831113]
  2. Hashimoto K: Sigma-1 receptors and selective serotonin reuptake inhibitors: clinical implications of their relationship. Cent Nerv Syst Agents Med Chem. 2009 Sep;9(3):197-204. [PubMed:20021354]

Enzymes

Details
1. Cytochrome P450 3A4
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. Micallef J, Fakra E, Blin O: [Use of antidepressant drugs in schizophrenic patients with depression]. Encephale. 2006 Mar-Apr;32(2 Pt 1):263-9. [PubMed:16910628]
  2. Rojdmark S, von Bahr C: [Metabolic interaction between psychopharmaceuticals. Probable cause of exacerbation of hypothyroidism according to a case report]. Lakartidningen. 2002 Jun 20;99(25):2854-6. [PubMed:12143142]
  3. DeVane CL, Donovan JL, Liston HL, Markowitz JS, Cheng KT, Risch SC, Willard L: Comparative CYP3A4 inhibitory effects of venlafaxine, fluoxetine, sertraline, and nefazodone in healthy volunteers. J Clin Psychopharmacol. 2004 Feb;24(1):4-10. [PubMed:14709940]
  4. Obach RS, Cox LM, Tremaine LM: Sertraline is metabolized by multiple cytochrome P450 enzymes, monoamine oxidases, and glucuronyl transferases in human: an in vitro study. Drug Metab Dispos. 2005 Feb;33(2):262-70. Epub 2004 Nov 16. [PubMed:15547048]
  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. Gerotziafas GT, Mahe I, Elalamy I: New orally active anticoagulant agents for the prevention and treatment of venous thromboembolism in cancer patients. Ther Clin Risk Manag. 2014 Jun 13;10:423-36. doi: 10.2147/TCRM.S49063. eCollection 2014. [PubMed:24966680]
Details
2. Cytochrome P450 2D6
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. Micallef J, Fakra E, Blin O: [Use of antidepressant drugs in schizophrenic patients with depression]. Encephale. 2006 Mar-Apr;32(2 Pt 1):263-9. [PubMed:16910628]
  3. Rojdmark S, von Bahr C: [Metabolic interaction between psychopharmaceuticals. Probable cause of exacerbation of hypothyroidism according to a case report]. Lakartidningen. 2002 Jun 20;99(25):2854-6. [PubMed:12143142]
  4. Obach RS, Cox LM, Tremaine LM: Sertraline is metabolized by multiple cytochrome P450 enzymes, monoamine oxidases, and glucuronyl transferases in human: an in vitro study. Drug Metab Dispos. 2005 Feb;33(2):262-70. Epub 2004 Nov 16. [PubMed:15547048]
  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. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Details
3. Cytochrome P450 2C19
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. Micallef J, Fakra E, Blin O: [Use of antidepressant drugs in schizophrenic patients with depression]. Encephale. 2006 Mar-Apr;32(2 Pt 1):263-9. [PubMed:16910628]
  2. Rojdmark S, von Bahr C: [Metabolic interaction between psychopharmaceuticals. Probable cause of exacerbation of hypothyroidism according to a case report]. Lakartidningen. 2002 Jun 20;99(25):2854-6. [PubMed:12143142]
  3. Obach RS, Cox LM, Tremaine LM: Sertraline is metabolized by multiple cytochrome P450 enzymes, monoamine oxidases, and glucuronyl transferases in human: an in vitro study. Drug Metab Dispos. 2005 Feb;33(2):262-70. Epub 2004 Nov 16. [PubMed:15547048]
  4. 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]
  5. Catterson ML, Preskorn SH: Pharmacokinetics of selective serotonin reuptake inhibitors: clinical relevance. Pharmacol Toxicol. 1996 Apr;78(4):203-8. [PubMed:8861776]
Details
4. Cytochrome P450 2C9
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Obach RS, Cox LM, Tremaine LM: Sertraline is metabolized by multiple cytochrome P450 enzymes, monoamine oxidases, and glucuronyl transferases in human: an in vitro study. Drug Metab Dispos. 2005 Feb;33(2):262-70. Epub 2004 Nov 16. [PubMed:15547048]
  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. 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]
  4. 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
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. Obach RS, Cox LM, Tremaine LM: Sertraline is metabolized by multiple cytochrome P450 enzymes, monoamine oxidases, and glucuronyl transferases in human: an in vitro study. Drug Metab Dispos. 2005 Feb;33(2):262-70. Epub 2004 Nov 16. [PubMed:15547048]
  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]
  3. 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
Substrate
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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Primary amine oxidase activity
Specific Function
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name
MAOB
Uniprot ID
P27338
Uniprot Name
Amine oxidase [flavin-containing] B
Molecular Weight
58762.475 Da
References
  1. Obach RS, Cox LM, Tremaine LM: Sertraline is metabolized by multiple cytochrome P450 enzymes, monoamine oxidases, and glucuronyl transferases in human: an in vitro study. Drug Metab Dispos. 2005 Feb;33(2):262-70. Epub 2004 Nov 16. [PubMed:15547048]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Serotonin binding
Specific Function
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name
MAOA
Uniprot ID
P21397
Uniprot Name
Amine oxidase [flavin-containing] A
Molecular Weight
59681.27 Da
References
  1. Obach RS, Cox LM, Tremaine LM: Sertraline is metabolized by multiple cytochrome P450 enzymes, monoamine oxidases, and glucuronyl transferases in human: an in vitro study. Drug Metab Dispos. 2005 Feb;33(2):262-70. Epub 2004 Nov 16. [PubMed:15547048]
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
Not Available
Gene Name
CYP2B
Uniprot ID
Q14097
Uniprot Name
CYP2B protein
Molecular Weight
43147.81 Da
References
  1. Haduch A, Wojcikowski J, Daniel WA: Effect of selected antidepressant drugs on cytochrome P450 2B (CYP2B) in rat liver. An in vitro and in vivo study. Pharmacol Rep. 2008 Nov-Dec;60(6):957-65. [PubMed:19211989]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Curator comments
Binds but does not produce a change in protein secondary structure
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Shahlaei M, Rahimi B, Nowroozi A, Ashrafi-Kooshk MR, Sadrjavadi K, Khodarahmi R: Exploring binding properties of sertraline with human serum albumin: Combination of spectroscopic and molecular modeling studies. Chem Biol Interact. 2015 Dec 5;242:235-46. doi: 10.1016/j.cbi.2015.10.006. Epub 2015 Oct 22. [PubMed:26471709]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
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]

Drug created on June 13, 2005 07:24 / Updated on September 25, 2018 17:45