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
- 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
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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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Binge eating disorder ••• ••••• Treatment of Bulimia nervosa ••• ••••• Treatment of Generalized anxiety disorder ••• ••••• Treatment of Major depressive disorder •••••••••••• ••••• Treatment of Obsessive-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
Target Actions Organism ASodium-dependent serotonin transporter inhibitorbinderdownregulatorHumans USodium-dependent dopamine transporter inhibitorbinderHumans USigma receptor inhibitorbinderHumans USodium-dependent noradrenaline transporter inhibitordownregulatorHumans UEquilibrative nucleoside transporter 4 Not Available Humans - 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/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Cytochrome P450 2C19 CYP2C19*2 Not Available 681G>A Effect Directly Studied The presence of this polymorphism in CYP2C19 is associated with poor metabolism of sertraline. Details Cytochrome P450 2C19 CYP2C19*3 Not Available 636G>A Effect Directly Studied The presence of this polymorphism in CYP2C19 is associated with reduced or poor metabolism of sertraline. Details Cytochrome P450 2C19 CYP2C19*2A Not Available 681G>A Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2C19 CYP2C19*2B Not Available 681G>A Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2C19 CYP2C19*4 Not Available 1A>G Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2C19 CYP2C19*5 Not Available 1297C>T Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2C19 CYP2C19*6 Not Available 395G>A Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2C19 CYP2C19*7 Not Available 19294T>A Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2C19 CYP2C19*22 Not Available 557G>C / 991A>G Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2C19 CYP2C19*24 Not Available 99C>T / 991A>G … show all Effect Inferred Poor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended. Details Cytochrome P450 2C19 CYP2C19*35 Not Available 12662A>G Effect Inferred Poor 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when 1,2-Benzodiazepine is combined with Sertraline. Abametapir The serum concentration of Sertraline can be increased when it is combined with Abametapir. Abatacept The metabolism of Sertraline can be increased when combined with Abatacept. Abciximab The risk or severity of bleeding can be increased when Sertraline is combined with Abciximab. Abiraterone The metabolism of Sertraline can be decreased when combined with Abiraterone. - Food Interactions
- Avoid St. John's Wort.
- Take with or without food.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Sertraline hydrochloride UTI8907Y6X 79559-97-0 BLFQGGGGFNSJKA-XHXSRVRCSA-N - Product Images
- International/Other Brands
- Lustral
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Act Sertraline Capsule 25 mg Oral Actavis Pharma Company 2006-11-08 2018-07-09 Canada Act Sertraline Capsule 100 mg Oral Actavis Pharma Company 2006-11-08 2018-07-09 Canada Act Sertraline Capsule 50 mg Oral Actavis Pharma Company 2006-11-08 2018-07-09 Canada M-sertraline Capsule 100 mg Oral Mantra Pharma Inc 2023-03-20 Not applicable Canada M-sertraline Capsule 50 mg Oral Mantra Pharma Inc 2023-03-20 Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ag-sertraline Capsule 25 mg Oral Angita Pharma Inc. 2018-09-06 Not applicable Canada Ag-sertraline Capsule 100 mg Oral Angita Pharma Inc. 2018-09-06 Not applicable Canada Ag-sertraline Capsule 50 mg Oral Angita Pharma Inc. 2018-09-06 Not applicable Canada Apo-sertraline Capsule 50 mg Oral Apotex Corporation 1999-09-01 Not applicable Canada Apo-sertraline Capsule 25 mg Oral Apotex Corporation 1999-09-01 Not applicable Canada
Categories
- ATC Codes
- N06AB06 — Sertraline
- Drug Categories
- Agents that reduce seizure threshold
- Amines
- Antidepressive Agents
- Antidepressive Agents Indicated for Depression
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2B6 Inhibitors
- Cytochrome P-450 CYP2B6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2B6 Substrates
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 Inhibitors (moderate)
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (weak)
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP2E1 Substrates
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Drugs causing inadvertant photosensitivity
- Hypoglycemia-Associated Agents
- Membrane Transport Modulators
- Monoamine Oxidase A Substrates
- Naphthalenes
- Nervous System
- Neurotransmitter Agents
- Neurotransmitter Uptake Inhibitors
- P-glycoprotein inhibitors
- Photosensitizing Agents
- Psychoanaleptics
- Psychotropic Drugs
- Selective Serotonin Reuptake Inhibitors
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin Agents
- Serotonin Modulators
- 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
- 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]
- 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]
- 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]
- 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]
- Shelton RC: The role of sertraline in the management of depression. Clin Ther. 1994 Sep-Oct;16(5):768-82; discussion 767. [Article]
- 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]
- DeVane CL, Liston HL, Markowitz JS: Clinical pharmacokinetics of sertraline. Clin Pharmacokinet. 2002;41(15):1247-66. doi: 10.2165/00003088-200241150-00002. [Article]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- Doogan DP, Caillard V: Sertraline: a new antidepressant. J Clin Psychiatry. 1988 Aug;49 Suppl:46-51. [Article]
- 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]
- 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]
- 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]
- Barbey JT, Roose SP: SSRI safety in overdose. J Clin Psychiatry. 1998;59 Suppl 15:42-8. [Article]
- 46. (2012). In Rang and Dale's Pharmacology (7th ed., pp. 573-574). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
- EMA Label: Zoloft; INN: sertraline [Link]
- FDA Approved Drug Products: Zoloft (sertraline hydrochloride) for oral use [Link]
- Zoloft, PDR [Link]
- AAFP: Off-label Applications for SSRIs [Link]
- Sertraline, pubchem [Link]
- Sertraline, Pfizer SDS [Link]
- Sertraline pathway [Link]
- Psychology Today article [Link]
- External Links
- Human Metabolome Database
- HMDB0005010
- KEGG Drug
- D02360
- KEGG Compound
- C07246
- PubChem Compound
- 68617
- PubChem Substance
- 46505341
- ChemSpider
- 61881
- BindingDB
- 50028094
- 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);">
Phase Status Purpose Conditions Count 4 Completed Basic Science Major Depressive Disorder (MDD) 1 4 Completed Health Services Research Obsessive Compulsive Disorder (OCD) 1 4 Completed Other Healthy Controls / Major Depressive Disorder (MDD) 1 4 Completed Other Healthy Subjects (HS) 1 4 Completed Other Obsessive 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
Form Route Strength Tablet Oral 55.96 mg Capsule Oral 50.0000 mg Capsule Oral 50 mg Tablet, film coated Oral 50.0 mg Tablet Oral 50.00 mg Tablet, coated Oral 25 mg Tablet, film coated Oral 25 mg Capsule Oral 25 mg / cap Tablet Oral 100 mg Tablet, coated Oral 56 mg Tablet Oral 50 mg Capsule Oral 100.000 mg Capsule Oral Tablet, film coated Oral 100 mg Tablet Oral 5000000 mg Tablet Oral 50.000 mg Tablet, film coated Oral 150 MG Tablet, film coated Oral 200 MG Tablet, coated Oral 5000000 mg Capsule Oral 150 mg/1 Capsule Oral 200 mg/1 Tablet, film coated Oral Tablet, film coated Oral 55.95 MG Concentrate Oral 20 mg/1mL Solution Oral 20 mg/1mL Solution, concentrate Oral 20 mg/1mL Tablet Oral Tablet Oral 100 mg/1 Tablet Oral 25 mg/1 Tablet Oral 50 mg/1 Tablet, coated Oral 100 mg/1 Tablet, coated Oral 150 mg/1 Tablet, coated Oral 200 mg/1 Tablet, coated Oral 25 mg/1 Tablet, coated Oral 50 mg/1 Tablet, extended release Oral 100 mg/1 Tablet, extended release Oral 25 mg/1 Tablet, extended release Oral 50 mg/1 Tablet, film coated Oral 100 mg/1 Tablet, film coated Oral 25 mg/1 Tablet, film coated Oral 50 mg/1 Tablet, coated Oral 55.96 mg Tablet, delayed release Oral 100 mg Tablet Oral 56.000 mg Tablet Oral 55.953 mg Tablet, film coated Oral 56 Mg Solution Oral 20 mg Capsule Oral 100 mg Capsule Oral 25 mg Solution, concentrate Oral 20 MG/ML Tablet, coated Oral 100 mg Tablet, coated Oral 50 mg Solution Oral 20 mg/mL Tablet, film coated Oral 50 mg Tablet, orally disintegrating Oral 25 mg Tablet, orally disintegrating Oral 50 mg - Prices
Unit description Cost Unit Sertraline hcl powder 480.0USD g Zoloft 20 mg/ml Concentrate 60ml Bottle 94.75USD bottle Sertraline HCl 20 mg/ml Concentrate 60ml Bottle 66.85USD bottle Zoloft 50 mg tablet 4.02USD tablet Zoloft 100 mg tablet 3.94USD tablet Zoloft 25 mg tablet 3.94USD tablet Sertraline hcl 100 mg tablet 2.77USD tablet Sertraline hcl 25 mg tablet 2.77USD tablet Sertraline hcl 50 mg tablet 2.77USD tablet Zoloft 100 mg Capsule 1.9USD capsule Zoloft 50 mg Capsule 1.81USD capsule Apo-Sertraline 100 mg Capsule 1.06USD capsule Co Sertraline 100 mg Capsule 1.06USD capsule Mylan-Sertraline 100 mg Capsule 1.06USD capsule Novo-Sertraline 100 mg Capsule 1.06USD capsule Phl-Sertraline 100 mg Capsule 1.06USD capsule Pms-Sertraline 100 mg Capsule 1.06USD capsule Ratio-Sertraline 100 mg Capsule 1.06USD capsule Sandoz Sertraline 100 mg Capsule 1.06USD capsule Sertraline 100 mg Capsule 1.06USD capsule Apo-Sertraline 50 mg Capsule 1.01USD capsule Co Sertraline 50 mg Capsule 1.01USD capsule Mylan-Sertraline 50 mg Capsule 1.01USD capsule Novo-Sertraline 50 mg Capsule 1.01USD capsule Phl-Sertraline 50 mg Capsule 1.01USD capsule Pms-Sertraline 50 mg Capsule 1.01USD capsule Ratio-Sertraline 50 mg Capsule 1.01USD capsule Sandoz Sertraline 50 mg Capsule 1.01USD capsule Sertraline 50 mg Capsule 1.01USD capsule Zoloft 25 mg Capsule 0.91USD capsule Apo-Sertraline 25 mg Capsule 0.51USD capsule Co Sertraline 25 mg Capsule 0.51USD capsule Mylan-Sertraline 25 mg Capsule 0.51USD capsule Novo-Sertraline 25 mg Capsule 0.51USD capsule Phl-Sertraline 25 mg Capsule 0.51USD capsule Pms-Sertraline 25 mg Capsule 0.51USD capsule Ratio-Sertraline 25 mg Capsule 0.51USD capsule Sandoz Sertraline 25 mg Capsule 0.51USD capsule Sertraline 25 mg Capsule 0.51USD capsule DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US4962128 No 1990-10-09 2009-11-02 US CA2029065 No 1994-11-08 2010-10-31 Canada US6727283 Yes 2004-04-27 2020-04-11 US US7067555 Yes 2006-06-27 2020-04-11 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 245-246 https://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 solubility 3.8mg/mL http://www.inchem.org/documents/pims/pharm/pim177.htm logP 5.51 http://foodb.ca/compounds/FDB023583 logS -6.3 http://www.t3db.ca/toxins/T3D2985 pKa 9.16 https://www.ncbi.nlm.nih.gov/pubmed/16848750 - Predicted Properties
Property Value Source Water Solubility 0.000145 mg/mL ALOGPS logP 5.06 ALOGPS logP 5.15 Chemaxon logS -6.3 ALOGPS pKa (Strongest Basic) 9.56 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 12.03 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 85.74 m3·mol-1 Chemaxon Polarizability 32.44 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9713 Caco-2 permeable + 0.6995 P-glycoprotein substrate Non-substrate 0.5858 P-glycoprotein inhibitor I Inhibitor 0.7333 P-glycoprotein inhibitor II Non-inhibitor 0.8319 Renal organic cation transporter Non-inhibitor 0.6726 CYP450 2C9 substrate Non-substrate 0.71 CYP450 2D6 substrate Substrate 0.8918 CYP450 3A4 substrate Substrate 0.6304 CYP450 1A2 substrate Inhibitor 0.7909 CYP450 2C9 inhibitor Non-inhibitor 0.9307 CYP450 2D6 inhibitor Non-inhibitor 0.6469 CYP450 2C19 inhibitor Inhibitor 0.6839 CYP450 3A4 inhibitor Non-inhibitor 0.5442 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6633 Ames test AMES toxic 0.5353 Carcinogenicity Non-carcinogens 0.8499 Biodegradation Not ready biodegradable 0.9522 Rat acute toxicity 2.5020 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9151 hERG inhibition (predictor II) Inhibitor 0.7185
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 166.5034035 predictedDarkChem Lite v0.1.0 [M-H]- 168.69624 predictedDeepCCS 1.0 (2019) [M+H]+ 167.5262035 predictedDarkChem Lite v0.1.0 [M+H]+ 171.05423 predictedDeepCCS 1.0 (2019) [M+Na]+ 166.8793035 predictedDarkChem Lite v0.1.0 [M+Na]+ 177.47963 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- InhibitorBinderDownregulator
- 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
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- InhibitorBinder
- 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
- 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]
- Ghanizadeh A: Sertraline-associated hair loss. J Drugs Dermatol. 2008 Jul;7(7):693-4. [Article]
- Lemke MR: [Antidepressant effects of dopamine agonists. Experimental and clinical findings]. Nervenarzt. 2007 Jan;78(1):31-8. [Article]
- 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]
- Goodnick PJ, Goldstein BJ: Selective serotonin reuptake inhibitors in affective disorders--I. Basic pharmacology. J Psychopharmacol. 1998;12(3 Suppl B):S5-20. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- InhibitorBinder
- General Function
- Steroid binding
- Specific Function
- Receptor for progesterone.
Components:
Name | UniProt ID |
---|---|
Membrane-associated progesterone receptor component 1 | O00264 |
Sigma non-opioid intracellular receptor 1 | Q99720 |
References
- 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]
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- InhibitorDownregulator
- 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
- 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]
- 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]
- 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
- 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]
- 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]
- 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
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- Baumann P: Pharmacokinetic-pharmacodynamic relationship of the selective serotonin reuptake inhibitors. Clin Pharmacokinet. 1996 Dec;31(6):444-69. [Article]
- 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]
- 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]
- 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]
- Flockhart Table of Drug Interactions [Link]
- FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- 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]
- 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]
- 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]
- Catterson ML, Preskorn SH: Pharmacokinetics of selective serotonin reuptake inhibitors: clinical relevance. Pharmacol Toxicol. 1996 Apr;78(4):203-8. [Article]
- 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]
- Zoloft, PDR [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- 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]
- 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]
- 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]
- 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]
- Flockhart Table of Drug Interactions [Link]
- Zoloft, PDR [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- 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]
- 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]
- 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]
- 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]
- 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]
- FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
- 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
- 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]
- 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
- 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]
- 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
- 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]
- 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
- Sertraline pathway [Link]
Carriers
- 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
- 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
- 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
- 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]
- 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