NAV

Sertraline

Identification

Summary

Sertraline is a selective serotonin reuptake inhibitor (SSRI) indicated to treat major depressive disorder, social anxiety disorder and many other psychiatric conditions.

Brand Names
Zoloft
Generic Name
Sertraline
DrugBank Accession Number
DB01104
Background

Sertraline is a popular antidepressant medication commonly known as a selective serotonin reuptake inhibitor (SSRI), and is similar to drugs such as Citalopram and Fluoxetine. Despite marked structural differences between compounds in this drug class, SSRIs exert similar pharmacological effects.

Several weeks of therapy with sertraline may be required before beneficial effects are noticed. Sertraline displays enhanced safety or tolerability than other classes of antidepressants, which frequently cause high levels of drowsiness, dizziness, blurred vision, and other undesirable effects.6,10,19

Type
Small Molecule
Groups
Approved
Structure
3D
Similar Structures
Weight
Average: 306.23
Monoisotopic: 305.073804963
Chemical Formula
C17H17Cl2N
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
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Pharmacology

Indication

Sertraline is indicated for the management of major depressive disorder (MDD), post-traumatic stress disorder (PTSD), obsessive-compulsive disorder (OCD), panic disorder (PD), premenstrual dysphoric disorder (PMDD), and social anxiety disorder (SAD).21 Common off-label uses for sertraline include the prevention of post stroke depression11, generalized anxiety disorder (GAD), fibromyalgia, premature ejaculation, migraine prophylaxis, diabetic neuropathy, and neurocardiogenic syncope.23

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofBinge eating disorder••• •••••
Treatment ofBulimia nervosa••• •••••
Treatment ofGeneralized anxiety disorder••• •••••
Treatment ofMajor depressive disorder•••••••••••••••••
Treatment ofObsessive-compulsive disorder••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Sertraline improves or relieves the symptoms of depression, OCD, post-traumatic stress disorder, obsessive-compulsive disorder, panic disorder, and premenstrual dysphoric disorder via the inhibition of serotonin reuptake.10,21 Clinical studies have shown that it improves cognition in depressed patients.6 It has less sedative, anticholinergic, and cardiovascular effects than the tricyclic antidepressant drugs because it does not exert significant anticholinergic, antihistamine, or adrenergic (alpha1, alpha2, beta) blocking activity.5 The onset of action and beneficial effects are usually noticed after 4-6 weeks, for reasons that are not fully understood and currently under investigation.17,27

Mechanism of action

Sertraline selectively inhibits the reuptake of serotonin (5-HT) at the presynaptic neuronal membrane, thereby increasing serotonergic activity. This results in an increased synaptic concentration of serotonin in the CNS, which leads to numerous functional changes associated with enhanced serotonergic neurotransmission.19,21 These changes are believed to be responsible for the antidepressant action and beneficial effects in obsessive-compulsive (and other anxiety related disorders). It has been hypothesized that obsessive-compulsive disorder, like depression, is also caused by the disregulation of serotonin.16

In animal studies, chronic administration of sertraline results in down-regulation of brain norepinephrine receptors.21 Sertraline displays affinity for sigma-1 and 2 receptor binding sites13, but binds with stronger affinity to sigma-1 binding sites.12 In vitro, sertraline shows little to no affinity for GABA, dopaminergic, serotonergic (5HT1A, 5HT1B, 5HT2), or benzodiazepine receptors.21 It exerts weak inhibitory actions on the neuronal uptake of norepinephrine and dopamine5 and exhibits no inhibitory effects on the monoamine oxidase enzyme.21

TargetActionsOrganism
ASodium-dependent serotonin transporter
inhibitor
binder
downregulator
Humans
USodium-dependent dopamine transporter
inhibitor
binder
Humans
USigma receptor
inhibitor
binder
Humans
USodium-dependent noradrenaline transporter
inhibitor
downregulator
Humans
UEquilibrative nucleoside transporter 4Not AvailableHumans
Absorption

Following once-daily administration of 50 to 200 mg for two weeks, the mean peak plasma concentrations (Cmax) of sertraline occurred between 4.5 to 8.4 hours after administration, and measured at 20 to 55 μg/L.6,21 Steady-state concentrations are reached after 1 week following once-daily administration, and vary greatly depending on the patient.7,21 Bioavailability has been estimated to be above 44%. The area under the curve in healthy volunteers after a 100mg dose of sertraline was 456 μg × h/mL in one study.7

Effects of food on absorption

The effects of food on the bioavailability of the sertraline tablet and oral concentrate were studied in subjects given a single dose with and without food. For the tablet, AUC was slightly increased when sertraline was administered with food, the Cmax was 25% greater, and the time to peak plasma concentration was shortened by about 2.5 hours. For the oral concentrate preparation of sertraline, peak concentration was prolonged by approximately 1 hour with the ingestion of food.21

Volume of distribution

Sertraline is widely distributed, and its volume of distribution is estimated to be more than 20L/kg.6 Post-mortem studies in humans have measured liver tissue concentrations of 3.9–20 mg/kg for sertraline and between 1.4 to 11 mg/kg for its active metabolite, N-desmethyl-sertraline (DMS).7 Studies have also determined sertraline distributes into the brain, plasma, and serum.7

Protein binding

Sertraline is highly bound to serum proteins, at about 98%-99%.15,21

Metabolism

Sertraline is heavily metabolized in the liver and has one major active metabolite. It undergoes N-demethylation to form N-desmethylsertraline, which is much less potent in its pharmacological activity than sertraline.7 In addition to N-demethylation, sertraline metabolism involves N-hydroxylation, oxidative deamination, and finally, glucuronidation.21 The metabolism of sertraline is mainly catalyzed by CYP3A4 and CYP2B6, with some activity accounted for by CYP2C19 and CYP2D6.6,22

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Route of elimination

Since sertraline is extensively metabolized, excretion of unchanged drug in the urine is a minor route of elimination, with 12-14% of unchanged sertraline excreted in the feces.6,7,21

Half-life

The elimination half-life of sertraline is approximately 26 hours.6,21 One reference mentions an elimination half-life ranging from 22-36 hours.7

Clearance

In pharmacokinetic studies, the clearance of a 200mg dose of sertraline in studies of both young and elderly patients ranged between 1.09 ± 0.38 L/h/kg - 1.35 ± 0.67 L/h/kg.7

Adverse Effects
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Toxicity

The LD50 of sertraline is >2000 mg/kg in rats according to the FDA label.25 One other references indicates an oral LD50 of in mice and rats of 419 - 548 mg/kg and 1327 - 1591mg/kg, respectively.MSDS

The most common signs and symptoms associated with a non-fatal sertraline overdose are somnolence, vomiting, tachycardia, nausea, dizziness, agitation, and tremor.21 No cases of fatal overdose with only sertraline have been reported. Most fatal cases are associated with the ingestion of sertraline with other drugs.18 Consequences of a sertraline overdose may include serotonin syndrome, hypertension, hypotension, syncope, stupor, coma, bradycardia, bundle branch block, QT-prolongation, torsade de pointes, delirium, hallucinations, and pancreatitis.21

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
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 Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Integrate drug-drug
interactions in your software
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when 1,2-Benzodiazepine is combined with Sertraline.
AbametapirThe serum concentration of Sertraline can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Sertraline can be increased when combined with Abatacept.
AbciximabThe risk or severity of bleeding can be increased when Sertraline is combined with Abciximab.
AbirateroneThe metabolism of Sertraline can be decreased when combined with Abiraterone.
Food Interactions
  • Avoid St. John's Wort.
  • Take with or without food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Sertraline hydrochlorideUTI8907Y6X79559-97-0BLFQGGGGFNSJKA-XHXSRVRCSA-N
Product Images
International/Other Brands
Lustral
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act SertralineCapsule25 mgOralActavis Pharma Company2006-11-082018-07-09Canada flag
Act SertralineCapsule100 mgOralActavis Pharma Company2006-11-082018-07-09Canada flag
Act SertralineCapsule50 mgOralActavis Pharma Company2006-11-082018-07-09Canada flag
M-sertralineCapsule100 mgOralMantra Pharma Inc2023-03-20Not applicableCanada flag
M-sertralineCapsule50 mgOralMantra Pharma Inc2023-03-20Not applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ag-sertralineCapsule25 mgOralAngita Pharma Inc.2018-09-06Not applicableCanada flag
Ag-sertralineCapsule100 mgOralAngita Pharma Inc.2018-09-06Not applicableCanada flag
Ag-sertralineCapsule50 mgOralAngita Pharma Inc.2018-09-06Not applicableCanada flag
Apo-sertralineCapsule50 mgOralApotex Corporation1999-09-01Not applicableCanada flag
Apo-sertralineCapsule25 mgOralApotex Corporation1999-09-01Not applicableCanada flag

Categories

ATC Codes
N06AB06 — Sertraline
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1,2-dichlorobenzene / Amine / Aralkylamine / Aromatic homopolycyclic compound / Aryl chloride / Aryl halide / Chlorobenzene / Halobenzene / Hydrocarbon derivative / Monocyclic benzene moiety
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
secondary amino compound, dichlorobenzene, tetralins (CHEBI:9123)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
QUC7NX6WMB
CAS number
79617-96-2
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

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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  5. Shelton RC: The role of sertraline in the management of depression. Clin Ther. 1994 Sep-Oct;16(5):768-82; discussion 767. [Article]
  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. [Article]
  7. DeVane CL, Liston HL, Markowitz JS: Clinical pharmacokinetics of sertraline. Clin Pharmacokinet. 2002;41(15):1247-66. doi: 10.2165/00003088-200241150-00002. [Article]
  8. Cooper JM, Duffull SB, Saiao AS, Isbister GK: The pharmacokinetics of sertraline in overdose and the effect of activated charcoal. Br J Clin Pharmacol. 2015 Feb;79(2):307-15. doi: 10.1111/bcp.12500. [Article]
  9. Lau GT, Horowitz BZ: Sertraline overdose. Acad Emerg Med. 1996 Feb;3(2):132-6. doi: 10.1111/j.1553-2712.1996.tb03400.x. [Article]
  10. Cipriani A, La Ferla T, Furukawa TA, Signoretti A, Nakagawa A, Churchill R, McGuire H, Barbui C: Sertraline versus other antidepressive agents for depression. Cochrane Database Syst Rev. 2010 Jan 20;(1):CD006117. doi: http://dx.doi.org/10.1002/14651858.CD006117. [Article]
  11. Feng R, Wang P, Gao C, Yang J, Chen Z, Yang Y, Jiao J, Li M, Fu B, Li L, Zhang Z, Wang S: Effect of sertraline in the treatment and prevention of poststroke depression: A meta-analysis. Medicine (Baltimore). 2018 Dec;97(49):e13453. doi: 10.1097/MD.0000000000013453. [Article]
  12. 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. [Article]
  13. 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. [Article]
  14. Doogan DP, Caillard V: Sertraline: a new antidepressant. J Clin Psychiatry. 1988 Aug;49 Suppl:46-51. [Article]
  15. Kristensen JH, Ilett KF, Dusci LJ, Hackett LP, Yapp P, Wojnar-Horton RE, Roberts MJ, Paech M: Distribution and excretion of sertraline and N-desmethylsertraline in human milk. Br J Clin Pharmacol. 1998 May;45(5):453-7. doi: 10.1046/j.1365-2125.1998.00705.x. [Article]
  16. Pittenger C, Bloch MH, Williams K: Glutamate abnormalities in obsessive compulsive disorder: neurobiology, pathophysiology, and treatment. Pharmacol Ther. 2011 Dec;132(3):314-32. doi: 10.1016/j.pharmthera.2011.09.006. Epub 2011 Sep 22. [Article]
  17. Erb SJ, Schappi JM, Rasenick MM: Antidepressants Accumulate in Lipid Rafts Independent of Monoamine Transporters to Modulate Redistribution of the G Protein, Galphas. J Biol Chem. 2016 Sep 16;291(38):19725-19733. doi: 10.1074/jbc.M116.727263. Epub 2016 Jul 18. [Article]
  18. Barbey JT, Roose SP: SSRI safety in overdose. J Clin Psychiatry. 1998;59 Suppl 15:42-8. [Article]
  19. 46. (2012). In Rang and Dale's Pharmacology (7th ed., pp. 573-574). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
  20. EMA Label: Zoloft; INN: sertraline [Link]
  21. FDA Approved Drug Products: Zoloft (sertraline hydrochloride) for oral use [Link]
  22. Zoloft, PDR [Link]
  23. AAFP: Off-label Applications for SSRIs [Link]
  24. Sertraline, pubchem [Link]
  25. Sertraline, Pfizer SDS [Link]
  26. Sertraline pathway [Link]
  27. Psychology Today article [Link]
Human Metabolome Database
HMDB0005010
KEGG Drug
D02360
KEGG Compound
C07246
PubChem Compound
68617
PubChem Substance
46505341
ChemSpider
61881
BindingDB
50028094
RxNav
36437
ChEBI
9123
ChEMBL
CHEMBL809
ZINC
ZINC000001853550
Therapeutic Targets Database
DAP000051
PharmGKB
PA451333
PDBe Ligand
SRE
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Sertraline
PDB Entries
3gwu / 4mm5 / 4mmb / 6awo / 6awq / 6f6n
MSDS
Download (47.6 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceMajor Depressive Disorder (MDD)1
4CompletedHealth Services ResearchObsessive Compulsive Disorder (OCD)1
4CompletedOtherHealthy Controls / Major Depressive Disorder (MDD)1
4CompletedOtherHealthy Subjects (HS)1
4CompletedOtherObsessive Compulsive Disorder (OCD)1

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
TabletOral55.96 mg
CapsuleOral50.0000 mg
CapsuleOral50 mg
Tablet, film coatedOral50.0 mg
TabletOral50.00 mg
Tablet, coatedOral25 mg
Tablet, film coatedOral25 mg
CapsuleOral25 mg / cap
TabletOral100 mg
Tablet, coatedOral56 mg
TabletOral50 mg
CapsuleOral100.000 mg
CapsuleOral
Tablet, film coatedOral100 mg
TabletOral5000000 mg
TabletOral50.000 mg
Tablet, film coatedOral150 MG
Tablet, film coatedOral200 MG
Tablet, coatedOral5000000 mg
CapsuleOral150 mg/1
CapsuleOral200 mg/1
Tablet, film coatedOral
Tablet, film coatedOral55.95 MG
ConcentrateOral20 mg/1mL
SolutionOral20 mg/1mL
Solution, concentrateOral20 mg/1mL
TabletOral
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, extended releaseOral100 mg/1
Tablet, extended releaseOral25 mg/1
Tablet, extended releaseOral50 mg/1
Tablet, film coatedOral100 mg/1
Tablet, film coatedOral25 mg/1
Tablet, film coatedOral50 mg/1
Tablet, coatedOral55.96 mg
Tablet, delayed releaseOral100 mg
TabletOral56.000 mg
TabletOral55.953 mg
Tablet, film coatedOral56 Mg
SolutionOral20 mg
CapsuleOral100 mg
CapsuleOral25 mg
Solution, concentrateOral20 MG/ML
Tablet, coatedOral100 mg
Tablet, coatedOral50 mg
SolutionOral20 mg/mL
Tablet, film coatedOral50 mg
Tablet, orally disintegratingOral25 mg
Tablet, orally disintegratingOral50 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
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Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US4962128No1990-10-092009-11-02US flag
CA2029065No1994-11-082010-10-31Canada flag
US6727283Yes2004-04-272020-04-11US flag
US7067555Yes2006-06-272020-04-11US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)245-246https://www.trc-canada.com/product-detail/?CatNum=S280000&CAS=79559-97-0&Chemical_Name=Sertraline
boiling point (°C)416.3±45.0 °C http://www.chemspider.com/Chemical-Structure.61881.html
water solubility3.8mg/mLhttp://www.inchem.org/documents/pims/pharm/pim177.htm
logP5.51http://foodb.ca/compounds/FDB023583
logS-6.3http://www.t3db.ca/toxins/T3D2985
pKa9.16https://www.ncbi.nlm.nih.gov/pubmed/16848750
Predicted Properties
PropertyValueSource
Water Solubility0.000145 mg/mLALOGPS
logP5.06ALOGPS
logP5.15Chemaxon
logS-6.3ALOGPS
pKa (Strongest Basic)9.56Chemaxon
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-MSsplash10-004j-0490000000-724d07a27d5e8d538495
Mass Spectrum (Electron Ionization)MSsplash10-00b9-2890000000-d53a90b04ec8457ad2f1
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-056r-0098000000-f03ca4b7178e85623709
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0019000000-1f106e0311893f9b11f6
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a6r-0079000000-a377087e24173fde2184
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0019000000-1230260ef8ce4ba89327
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-06rj-0891000000-0ebaf9dd895d31570a9f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9011000000-04a78b2a37df726d9dfa
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-166.5034035
predicted
DarkChem Lite v0.1.0
[M-H]-168.69624
predicted
DeepCCS 1.0 (2019)
[M+H]+167.5262035
predicted
DarkChem Lite v0.1.0
[M+H]+171.05423
predicted
DeepCCS 1.0 (2019)
[M+Na]+166.8793035
predicted
DarkChem Lite v0.1.0
[M+Na]+177.47963
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Sodium-dependent serotonin transporter
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
Binder
Downregulator
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
Details2. Sodium-dependent dopamine transporter
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Binder
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. [Article]
  2. Ghanizadeh A: Sertraline-associated hair loss. J Drugs Dermatol. 2008 Jul;7(7):693-4. [Article]
  3. Lemke MR: [Antidepressant effects of dopamine agonists. Experimental and clinical findings]. Nervenarzt. 2007 Jan;78(1):31-8. [Article]
  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. [Article]
  5. Goodnick PJ, Goldstein BJ: Selective serotonin reuptake inhibitors in affective disorders--I. Basic pharmacology. J Psychopharmacol. 1998;12(3 Suppl B):S5-20. [Article]
Details3. Sigma receptor (Protein Group)
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Binder
General Function
Steroid binding
Specific Function
Receptor for progesterone.
Components:
NameUniProt ID
Membrane-associated progesterone receptor component 1O00264
Sigma non-opioid intracellular receptor 1Q99720
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. [Article]
  2. Fishback JA, Robson MJ, Xu YT, Matsumoto RR: Sigma receptors: potential targets for a new class of antidepressant drug. Pharmacol Ther. 2010 Sep;127(3):271-82. doi: 10.1016/j.pharmthera.2010.04.003. Epub 2010 May 11. [Article]
Details4. Sodium-dependent noradrenaline transporter
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Downregulator
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. 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. [Article]
  2. Sorensen L, Andersen J, Thomsen M, Hansen SM, Zhao X, Sandelin A, Stromgaard K, Kristensen AS: Interaction of antidepressants with the serotonin and norepinephrine transporters: mutational studies of the S1 substrate binding pocket. J Biol Chem. 2012 Dec 21;287(52):43694-707. doi: 10.1074/jbc.M112.342212. Epub 2012 Oct 19. [Article]
Details5. Equilibrative nucleoside transporter 4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Nucleoside transmembrane transporter activity
Specific Function
Functions as a polyspecific organic cation transporter, efficiently transporting many organic cations such as monoamine neurotransmitters 1-methyl-4-phenylpyridinium and biogenic amines including s...
Gene Name
SLC29A4
Uniprot ID
Q7RTT9
Uniprot Name
Equilibrative nucleoside transporter 4
Molecular Weight
58058.005 Da
References
  1. Daws LC: Unfaithful neurotransmitter transporters: focus on serotonin uptake and implications for antidepressant efficacy. Pharmacol Ther. 2009 Jan;121(1):89-99. doi: 10.1016/j.pharmthera.2008.10.004. Epub 2008 Oct 29. [Article]
  2. Zhou M, Engel K, Wang J: Evidence for significant contribution of a newly identified monoamine transporter (PMAT) to serotonin uptake in the human brain. Biochem Pharmacol. 2007 Jan 1;73(1):147-54. doi: 10.1016/j.bcp.2006.09.008. Epub 2006 Sep 14. [Article]
  3. Haenisch B, Bonisch H: Interaction of the human plasma membrane monoamine transporter (hPMAT) with antidepressants and antipsychotics. Naunyn Schmiedebergs Arch Pharmacol. 2010 Jan;381(1):33-9. doi: 10.1007/s00210-009-0479-8. Epub 2009 Dec 10. [Article]

Enzymes

Details1. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. 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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  5. 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. [Article]
  6. Klotz U: Interaction potential of lercanidipine, a new vasoselective dihydropyridine calcium antagonist. Arzneimittelforschung. 2002;52(3):155-61. doi: 10.1055/s-0031-1299873. [Article]
Details2. Cytochrome P450 2D6
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Baumann P: Pharmacokinetic-pharmacodynamic relationship of the selective serotonin reuptake inhibitors. Clin Pharmacokinet. 1996 Dec;31(6):444-69. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  5. Flockhart Table of Drug Interactions [Link]
  6. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
Details3. Cytochrome P450 2C19
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. 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. [Article]
  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. [Article]
  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. [Article]
  4. Catterson ML, Preskorn SH: Pharmacokinetics of selective serotonin reuptake inhibitors: clinical relevance. Pharmacol Toxicol. 1996 Apr;78(4):203-8. [Article]
  5. Yuce-Artun N, Baskak B, Ozel-Kizil ET, Ozdemir H, Uckun Z, Devrimci-Ozguven H, Suzen HS: Influence of CYP2B6 and CYP2C19 polymorphisms on sertraline metabolism in major depression patients. Int J Clin Pharm. 2016 Apr;38(2):388-94. doi: 10.1007/s11096-016-0259-8. Epub 2016 Jan 30. [Article]
  6. Zoloft, PDR [Link]
Details4. Cytochrome P450 2C9
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Curator comments
The effects of sertraline on CYP2C9 have been demonstrated as minimal according to the cited references.
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. [Article]
  2. Schmider J, Greenblatt DJ, von Moltke LL, Karsov D, Shader RI: Inhibition of CYP2C9 by selective serotonin reuptake inhibitors in vitro: studies of phenytoin p-hydroxylation. Br J Clin Pharmacol. 1997 Nov;44(5):495-8. doi: 10.1046/j.1365-2125.1997.00601.x. [Article]
  3. Tremaine LM, Wilner KD, Preskorn SH: A study of the potential effect of sertraline on the pharmacokinetics and protein binding of tolbutamide. Clin Pharmacokinet. 1997;32 Suppl 1:31-6. [Article]
  4. Apseloff G, Wilner KD, Gerber N, Tremaine LM: Effect of sertraline on protein binding of warfarin. Clin Pharmacokinet. 1997;32 Suppl 1:37-42. [Article]
  5. Flockhart Table of Drug Interactions [Link]
  6. Zoloft, PDR [Link]
Details5. Cytochrome P450 2B6
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  3. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
  4. Yuce-Artun N, Baskak B, Ozel-Kizil ET, Ozdemir H, Uckun Z, Devrimci-Ozguven H, Suzen HS: Influence of CYP2B6 and CYP2C19 polymorphisms on sertraline metabolism in major depression patients. Int J Clin Pharm. 2016 Apr;38(2):388-94. doi: 10.1007/s11096-016-0259-8. Epub 2016 Jan 30. [Article]
  5. Molnari JC, Hassan HE, Myers AL: Effects of sertraline on the pharmacokinetics of bupropion and its major metabolite, hydroxybupropion, in mice. Eur J Drug Metab Pharmacokinet. 2012 Mar;37(1):57-63. doi: 10.1007/s13318-011-0065-6. Epub 2011 Sep 17. [Article]
  6. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
Details6. Amine oxidase [flavin-containing] B
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Curator comments
This enzyme action is based on the results of in vitro studies.
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. [Article]
Details7. Amine oxidase [flavin-containing] A
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Curator comments
This enzyme action is based on the results of in vitro studies.
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. [Article]
Details8. CYP2B protein
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
Curator comments
Data in the literature is limited regarding this enzyme. One study found that sertraline was a CYP2B inducer in rats. The relevance to humans is unknown.
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. [Article]
Details9. Cytochrome P450 2E1
Kind
Protein
Organism
Humans
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. Sertraline pathway [Link]

Carriers

Details1. Serum albumin
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
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. [Article]

Transporters

Details1. P-glycoprotein 1
Kind
Protein
Organism
Humans
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. [Article]
  2. Kapoor A, Iqbal M, Petropoulos S, Ho HL, Gibb W, Matthews SG: Effects of sertraline and fluoxetine on p-glycoprotein at barrier sites: in vivo and in vitro approaches. PLoS One. 2013;8(2):e56525. doi: 10.1371/journal.pone.0056525. Epub 2013 Feb 28. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55