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Identification
NameSertraline
Accession NumberDB01104  (APRD00175)
Typesmall molecule
Groupsapproved
Description

Sertraline hydrochloride belongs to a class of antidepressant agents known as selective serotonin-reuptake inhibitors (SSRIs). Despite distinct structural differences between compounds in this class, SSRIs possess similar pharmacological activity. As with other antidepressant agents, several weeks of therapy may be required before a clinical effect is seen. SSRIs are potent inhibitors of neuronal serotonin reuptake. They have little to no effect on norepinephrine or dopamine reuptake and do not antagonize α- or β-adrenergic, dopamine D2 or histamine H1 receptors. During acute use, SSRIs block serotonin reuptake and increase serotonin stimulation of somatodendritic 5-HT1A and terminal autoreceptors. Chronic use leads to desensitization of somatodendritic 5-HT1A and terminal autoreceptors. The overall clinical effect of increased mood and decreased anxiety is thought to be due to adaptive changes in neuronal function that leads to enhanced serotonergic neurotransmission. Side effects include dry mouth, nausea, dizziness, drowsiness, sexual dysfunction and headache (see Toxicity section below for a more detailed listing of side effects). Compared to other agents in this class, sertraline may cause greater diarrheal and male sexual dysfunction effects. Side effects generally occur within the first two weeks of therapy and are usually less severe and frequent than those observed with tricyclic antidepressants. Sertraline may be used to treat major depressive disorder, obsessive-compulsive disorder (OCD), panic disorder, post-traumatic stress disorder (PTSD), premenstrual dysphoric disorder (PMDD) and social anxiety disorder (social phobia).

Structure
Thumb
Synonyms
SynonymLanguageCode
(+)-SertralineNot AvailableNot Available
(1S-cis)-1,2,3,4-Tetrahydro-4-(3,4-dichlorophenyl)-N-methyl-1-naphthalenamineNot AvailableNot Available
(1S,4S)-SertralineNot AvailableNot Available
cis-(+)-SertralineNot AvailableNot Available
CP 51974Not AvailableNot Available
SertralinaSpanishNot Available
SertralineNot AvailableNot Available
SertralinumLatinNot Available
Salts
Name/CAS Structure Properties
Sertraline Hydrochloride
Thumb
  • InChI Key: BLFQGGGGFNSJKA-XHXSRVRCSA-N
  • Monoisotopic Mass: 341.050482702
  • Average Mass: 342.691
DBSALT000808
Brand names
NameCompany
Apo-SertralineApotex
LustralNot Available
ZoloftPfizer
Brand mixturesNot Available
Categories
CAS number79617-96-2
WeightAverage: 306.23
Monoisotopic: 305.073804963
Chemical FormulaC17H17Cl2N
InChI KeyVGKDLMBJGBXTGI-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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassTetralins
SubclassTametralines
Direct parentTametralines
Alternative parentsDichlorobenzenes; Aryl Chlorides; Polyamines; Dialkylamines; Organochlorides
Substituents1,2-dichlorobenzene; chlorobenzene; benzene; aryl chloride; aryl halide; secondary amine; polyamine; secondary aliphatic amine; organohalogen; organonitrogen compound; amine; organochloride
Classification descriptionThis compound belongs to the 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.
Pharmacology
IndicationFor the management of major depressive disorder, posttraumatic stress disorder, obsessive-compulsive disorder, panic disorder with or without agoraphobia, premenstrual dysphoric disorder, social phobia, premature ejaculation, and vascular headaches.
PharmacodynamicsSertraline, an antidepressant drug similar to citalopram, fluoxetine, and paroxetine, is of the selective serotonin reuptake inhibitor (SSRI) type. Sertraline has one active metabolite and, like the other SSRIs, have less sedative, anticholinergic, and cardiovascular effects than the tricyclic antidepressant drugs because it does not have clinically important anticholinergic, antihistamine, or adrenergic blocking activity.
Mechanism of actionThe exact mechanism of action sertraline is not fully known, but the drug appears to selectively inhibit the reuptake of serotonin at the presynaptic membrane. This results in an increased synaptic concentration of serotonin in the CNS, which leads to numerous functional changes associated with enhanced serotonergic neurotransmission. It is suggested that these modifications are responsible for the antidepressant action observed during long term administration of antidepressants. It has also been hypothesized that obsessive-compulsive disorder is caused by the dysregulation of serotonin, as it is treated by sertraline, and the drug corrects this imbalance.
AbsorptionThe effects of food on the bioavailability of the sertraline tablet and oral concentrate were studied in subjects administered a single dose with and without food. For the tablet, AUC was slightly increased when drug was administered with food but the Cmax was 25% greater, while the time to reach peak plasma concentration (Tmax) decreased from 8 hours post-dosing to 5.5 hours. For the oral concentrate, Tmax was slightly prolonged from 5.9 hours to 7.0 hours with food.
Volume of distributionNot Available
Protein binding98% bound to serum proteins, principally to albumin and α1-acid glycoprotein
Metabolism

Extensively metabolized in the liver. Sertraline metabolism involves N-demethylation, N-hydroxylation, oxidative deamination, and glucuronidation of sertraline carbamic acid. Sertraline undergoes N-demethylation primarily catalyzed by cytochrome P450 (CYP) 2B6, with CYP2C19, CYP3A4 and CYP2D6 contributing to a lesser extent. Deamination occurs via CYP3A4 and CYP2C19. In vitro studies have shown that monoamine oxidase A and B may also catalyze sertraline deamination. Sertraline N-carbamoyl glucuronidation has also been observed in human liver microsomes.

SubstrateEnzymesProduct
Sertraline
norsertralineDetails
Route of eliminationSertraline is extensively metabolized and excretion of unchanged drug in urine is a minor route of elimination.
Half lifeThe elimination half-life of sertraline is approximately 25-26 hours. The elimination half-life of desmethylsertraline is approximately 62-104 hours.
ClearanceNot Available
ToxicitySymptoms of toxicity include alopecia, decreased libido, diarrhea, ejaculation disorder, fatigue, insomnia, somnolence and serotonin syndrome. The most frequently observed side effects include: GI effects such as nausea, diarrhea or loose stools, dyspepsia, and dry mouth; nervous system effects such as somnolence, dizziness, insomnia, and tremor; sexual dysfunction in males (principally ejaculatory delay); and sweating.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrate Non-inhibitor 0.9307
CYP450 2D6 substrate Non-inhibitor 0.6469
CYP450 2C19 substrate Inhibitor 0.6839
CYP450 3A4 substrate 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
Pharmacoeconomics
Manufacturers
  • Aurobindo pharma ltd
  • Ranbaxy laboratories ltd
  • Roxane laboratories inc
  • Pfizer pharmaceuticals inc
  • Actavis elizabeth llc
  • Actavis totowa llc
  • Apotex inc
  • Austarpharma llc
  • Dr reddys laboratories ltd
  • Genpharm inc
  • Hikma pharmaceuticals
  • Invagen pharmaceuticals inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Lupin ltd
  • Matrix laboratories ltd
  • Mutual pharmaceutical co inc
  • Mylan pharmaceuticals inc
  • Pliva hrvatska doo
  • Sandoz inc
  • Sun pharmaceutical industries ltd
  • Teva pharmaceuticals usa inc
  • Torrent pharmaceuticals ltd
  • Watson laboratories inc
  • Wockhardt ltd
  • Zydus pharmaceuticals usa inc
Packagers
Dosage forms
FormRouteStrength
CapsuleOral100 mg
CapsuleOral25 mg
CapsuleOral50 mg
Solution, concentrateOral20 mg/ml
Tablet, film coatedOral100 mg
Tablet, film coatedOral150 mg
Tablet, film coatedOral200 mg
Tablet, film coatedOral25 mg
Tablet, film coatedOral50 mg
Prices
Unit descriptionCostUnit
Sertraline hcl powder480.0USDg
Zoloft 20 mg/ml Concentrate 60ml Bottle94.75USDbottle
Sertraline HCl 20 mg/ml Concentrate 60ml Bottle66.85USDbottle
Zoloft 50 mg tablet4.02USDtablet
Zoloft 100 mg tablet3.94USDtablet
Zoloft 25 mg tablet3.94USDtablet
Sertraline hcl 100 mg tablet2.77USDtablet
Sertraline hcl 25 mg tablet2.77USDtablet
Sertraline hcl 50 mg tablet2.77USDtablet
Zoloft 100 mg Capsule1.9USDcapsule
Zoloft 50 mg Capsule1.81USDcapsule
Apo-Sertraline 100 mg Capsule1.06USDcapsule
Co Sertraline 100 mg Capsule1.06USDcapsule
Mylan-Sertraline 100 mg Capsule1.06USDcapsule
Novo-Sertraline 100 mg Capsule1.06USDcapsule
Phl-Sertraline 100 mg Capsule1.06USDcapsule
Pms-Sertraline 100 mg Capsule1.06USDcapsule
Ratio-Sertraline 100 mg Capsule1.06USDcapsule
Sandoz Sertraline 100 mg Capsule1.06USDcapsule
Sertraline 100 mg Capsule1.06USDcapsule
Apo-Sertraline 50 mg Capsule1.01USDcapsule
Co Sertraline 50 mg Capsule1.01USDcapsule
Mylan-Sertraline 50 mg Capsule1.01USDcapsule
Novo-Sertraline 50 mg Capsule1.01USDcapsule
Phl-Sertraline 50 mg Capsule1.01USDcapsule
Pms-Sertraline 50 mg Capsule1.01USDcapsule
Ratio-Sertraline 50 mg Capsule1.01USDcapsule
Sandoz Sertraline 50 mg Capsule1.01USDcapsule
Sertraline 50 mg Capsule1.01USDcapsule
Zoloft 25 mg Capsule0.91USDcapsule
Apo-Sertraline 25 mg Capsule0.51USDcapsule
Co Sertraline 25 mg Capsule0.51USDcapsule
Mylan-Sertraline 25 mg Capsule0.51USDcapsule
Novo-Sertraline 25 mg Capsule0.51USDcapsule
Phl-Sertraline 25 mg Capsule0.51USDcapsule
Pms-Sertraline 25 mg Capsule0.51USDcapsule
Ratio-Sertraline 25 mg Capsule0.51USDcapsule
Sandoz Sertraline 25 mg Capsule0.51USDcapsule
Sertraline 25 mg Capsule0.51USDcapsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States70675552000-05-102020-05-10
United States49621281992-11-022009-11-02
Canada20290651994-11-082010-10-31
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point243-245 °CNot Available
water solubility3.5mg/LNot Available
logP5.1Not Available
Predicted Properties
PropertyValueSource
water solubility1.45e-04 g/lALOGPS
logP5.06ALOGPS
logP5.15ChemAxon
logS-6.3ALOGPS
pKa (strongest basic)9.85ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count1ChemAxon
polar surface area12.03ChemAxon
rotatable bond count2ChemAxon
refractivity85.74ChemAxon
polarizability32.44ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveNoChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

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

US4839104
General Reference
  1. Couzin J: The brains behind blockbusters. Science. 2005 Jul 29;309(5735):728. Pubmed
  2. Fabre LF, Abuzzahab FS, Amin M, Claghorn JL, Mendels J, Petrie WM, Dube S, Small JG: Sertraline safety and efficacy in major depression: a double-blind fixed-dose comparison with placebo. Biol Psychiatry. 1995 Nov 1;38(9):592-602. Pubmed
  3. Kronig MH, Apter J, Asnis G, Bystritsky A, Curtis G, Ferguson J, Landbloom R, Munjack D, Riesenberg R, Robinson D, Roy-Byrne P, Phillips K, Du Pont IJ: Placebo-controlled, multicenter study of sertraline treatment for obsessive-compulsive disorder. J Clin Psychopharmacol. 1999 Apr;19(2):172-6. Pubmed
  4. Brady K, Pearlstein T, Asnis GM, Baker D, Rothbaum B, Sikes CR, Farfel GM: Efficacy and safety of sertraline treatment of posttraumatic stress disorder: a randomized controlled trial. JAMA. 2000 Apr 12;283(14):1837-44. Pubmed
  5. Yonkers KA, Halbreich U, Freeman E, Brown C, Endicott J, Frank E, Parry B, Pearlstein T, Severino S, Stout A, Stone A, Harrison W: Symptomatic improvement of premenstrual dysphoric disorder with sertraline treatment. A randomized controlled trial. Sertraline Premenstrual Dysphoric Collaborative Study Group. JAMA. 1997 Sep 24;278(12):983-8. Pubmed
  6. Shelton RC: The role of sertraline in the management of depression. Clin Ther. 1994 Sep-Oct;16(5):768-82; discussion 767. Pubmed
  7. Murdoch D, McTavish D: Sertraline. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in depression and obsessive-compulsive disorder. Drugs. 1992 Oct;44(4):604-24. Pubmed
External Links
ResourceLink
KEGG DrugD02360
KEGG CompoundC07246
PubChem Compound68617
PubChem Substance46505341
ChemSpider61881
ChEBI9123
ChEMBLCHEMBL809
Therapeutic Targets DatabaseDAP000051
PharmGKBPA451333
Drug Product Database2245749
RxListhttp://www.rxlist.com/cgi/generic/sertral.htm
Drugs.comhttp://www.drugs.com/sertraline.html
WikipediaSertraline
ATC CodesN06AB06
AHFS Codes
  • 28:16.04.20
PDB EntriesNot Available
FDA labelshow(98.7 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AlmotriptanIncreased risk of CNS adverse effects
CarbamazepineSertraline increases the effect of carbamazepine
CarvedilolThe SSRI, sertraline, may increase the bradycardic effect of the beta-blocker, carvedilol.
CilostazolSertraline increases the effect of cilostazol
ClarithromycinPossible serotoninergic syndrome with this combination
ClozapineThe antidepressant increases the effect of clozapine
DesvenlafaxineIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
DonepezilPossible antagonism of action
EletriptanIncreased risk of CNS adverse effects
ErythromycinPossible serotoninergic syndrome with this combination
FosphenytoinSertraline increases the effect of hydantoin
FrovatriptanIncreased risk of CNS adverse effects
GalantaminePossible antagonism of action
Ginkgo bilobaAdditive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
IsocarboxazidPossible severe adverse reaction with this combination
KetoprofenConcomitant therapy may result in additive antiplatelet effects and increase the risk of bleeding. Monitor for increased risk of bleeding during concomitant therapy.
LinezolidCombination associated with possible serotoninergic syndrome
MetoprololThe SSRI increases the effect of the beta-blocker
MoclobemidePossible severe adverse reaction with this combination
NaratriptanIncreased risk of CNS adverse effects
OxycodoneIncreased risk of serotonin syndrome
PhenelzinePossible severe adverse reaction with this combination
PhenytoinSertraline increases the effect of hydantoin
PimozideThe SSRI, sertraline, increases the effect and toxicity of pimozide.
PropafenoneFluoxetine increases the effect and toxicity of propafenone
PropranololThe SSRI, sertraline, may increase the bradycardic effect of the beta-blocker, propranolol.
RasagilinePossible severe adverse reaction with this combination
TamoxifenSertraline may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
TamsulosinSertraline, a CYP3A4/2D6 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4/2D6 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Sertraline is initiated, discontinued, or dose changed.
TerbinafineTerbinafine may reduce the metabolism and clearance of Sertraline. Consider alternate therapy or monitor for therapeutic/adverse effects of Sertraline if Terbinafine is initiated, discontinued or dose changed.
Tiaprofenic acidAdditive antiplatelet effects increase the risk of bleeding. Consider alternate therapy or monitor for increased bleeding.
TipranavirTipranavir increases the concentration of Sertraline. The Sertraline dose may require an adjustment.
TolmetinIncreased antiplatelet effects may enhance the risk of bleeding. Alternate therapy may be considered or monitor for inreased bleeding during concomitant therapy.
TolterodineSertraline may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity.
TramadolTramadol increases the risk of serotonin syndrome and seizures. Sertraline may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance. Sertraline may decrease the effect of Tramadol by decreasing active metabolite production.
TranylcypromineIncreased risk of serotonin syndrome. Concomitant therapy should be avoided. A significant washout period, dependent on the half-lives of the agents, should be employed between therapies.
TrazodoneIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
TreprostinilThe prostacyclin analogue, Treprostinil, increases the risk of bleeding when combined with the antiplatelet agent, Sertraline. Monitor for increased bleeding during concomitant thearpy.
TrimipramineThe SSRI, Sertraline, may decrease the metabolism and clearance of Trimipramine. Increased risk of serotonin syndrome. Monitor for changes in Trimipramine efficacy and toxicity if Sertraline is initiated, discontinued or dose changed.
TriprolidineThe CNS depressants, Triprolidine and Sertraline, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
VenlafaxineIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
ZolmitriptanUse of two serotonin modulators, such as zolmitriptan and sertraline, increases the risk of serotonin syndrome. Consider alternate therapy or monitor for serotonin syndrome during concomitant therapy.
Food Interactions
  • Avoid alcohol.
  • Avoid St.John's Wort.
  • Avoid taking with grapefruit juice.
  • Take with food.

Targets

1. Sodium-dependent serotonin transporter

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Sodium-dependent serotonin transporter P31645 Details

References:

  1. Benmansour S, Cecchi M, Morilak DA, Gerhardt GA, Javors MA, Gould GG, Frazer A: Effects of chronic antidepressant treatments on serotonin transporter function, density, and mRNA level. J Neurosci. 1999 Dec 1;19(23):10494-501. Pubmed
  2. Benmansour S, Owens WA, Cecchi M, Morilak DA, Frazer A: Serotonin clearance in vivo is altered to a greater extent by antidepressant-induced downregulation of the serotonin transporter than by acute blockade of this transporter. J Neurosci. 2002 Aug 1;22(15):6766-72. Pubmed
  3. Borkowska A, Pilaczynska E, Araszkiewicz A, Rybakowski J: [The effect of sertraline on cognitive functions in patients with obsessive-compulsive disorder] Psychiatr Pol. 2002 Nov-Dec;36(6 Suppl):289-95. Pubmed
  4. Durham LK, Webb SM, Milos PM, Clary CM, Seymour AB: The serotonin transporter polymorphism, 5HTTLPR, is associated with a faster response time to sertraline in an elderly population with major depressive disorder. Psychopharmacology (Berl). 2004 Aug;174(4):525-9. Epub 2003 Sep 4. Pubmed
  5. Chen F, Larsen MB, Neubauer HA, Sanchez C, Plenge P, Wiborg O: Characterization of an allosteric citalopram-binding site at the serotonin transporter. J Neurochem. 2005 Jan;92(1):21-8. Pubmed
  6. Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. Pubmed
  7. David DJ, Bourin M, Hascoet M, Colombel MC, Baker GB, Jolliet P: Comparison of antidepressant activity in 4- and 40-week-old male mice in the forced swimming test: involvement of 5-HT1A and 5-HT1B receptors in old mice. Psychopharmacology (Berl). 2001 Feb;153(4):443-9. Pubmed
  8. Rogoz Z, Skuza G: Mechanism of synergistic action following co-treatment with pramipexole and fluoxetine or sertraline in the forced swimming test in rats. Pharmacol Rep. 2006 Jul-Aug;58(4):493-500. Pubmed
  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. Epub 2008 Aug 27. Pubmed
  10. Iehle C, Delos S, Filhol O, Martin PM: Baculovirus-directed expression of human prostatic steroid 5 alpha-reductase 1 in an active form. J Steroid Biochem Mol Biol. 1993 Aug;46(2):177-82. Pubmed

2. Sodium-dependent dopamine transporter

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Sodium-dependent dopamine transporter Q01959 Details

References:

  1. Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. Pubmed
  2. Ghanizadeh A: Sertraline-associated hair loss. J Drugs Dermatol. 2008 Jul;7(7):693-4. Pubmed
  3. Lemke MR: [Antidepressant effects of dopamine agonists. Experimental and clinical findings] Nervenarzt. 2007 Jan;78(1):31-8. Pubmed
  4. Nemeroff CB, Owens MJ: Pharmacologic differences among the SSRIs: focus on monoamine transporters and the HPA axis. CNS Spectr. 2004 Jun;9(6 Suppl 4):23-31. Pubmed
  5. Goodnick PJ, Goldstein BJ: Selective serotonin reuptake inhibitors in affective disorders—I. Basic pharmacology. J Psychopharmacol. 1998;12(3 Suppl B):S5-20. Pubmed

Enzymes

1. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Micallef J, Fakra E, Blin O: [Use of antidepressant drugs in schizophrenic patients with depression] Encephale. 2006 Mar-Apr;32(2 Pt 1):263-9. Pubmed
  2. Rojdmark S, von Bahr C: [Metabolic interaction between psychopharmaceuticals. Probable cause of exacerbation of hypothyroidism according to a case report] Lakartidningen. 2002 Jun 20;99(25):2854-6. Pubmed
  3. DeVane CL, Donovan JL, Liston HL, Markowitz JS, Cheng KT, Risch SC, Willard L: Comparative CYP3A4 inhibitory effects of venlafaxine, fluoxetine, sertraline, and nefazodone in healthy volunteers. J Clin Psychopharmacol. 2004 Feb;24(1):4-10. Pubmed
  4. Obach RS, Cox LM, Tremaine LM: Sertraline is metabolized by multiple cytochrome P450 enzymes, monoamine oxidases, and glucuronyl transferases in human: an in vitro study. Drug Metab Dispos. 2005 Feb;33(2):262-70. Epub 2004 Nov 16. Pubmed
  5. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

References:

  1. Baumann P: Pharmacokinetic-pharmacodynamic relationship of the selective serotonin reuptake inhibitors. Clin Pharmacokinet. 1996 Dec;31(6):444-69. Pubmed
  2. Micallef J, Fakra E, Blin O: [Use of antidepressant drugs in schizophrenic patients with depression] Encephale. 2006 Mar-Apr;32(2 Pt 1):263-9. Pubmed
  3. Rojdmark S, von Bahr C: [Metabolic interaction between psychopharmaceuticals. Probable cause of exacerbation of hypothyroidism according to a case report] Lakartidningen. 2002 Jun 20;99(25):2854-6. Pubmed
  4. Obach RS, Cox LM, Tremaine LM: Sertraline is metabolized by multiple cytochrome P450 enzymes, monoamine oxidases, and glucuronyl transferases in human: an in vitro study. Drug Metab Dispos. 2005 Feb;33(2):262-70. Epub 2004 Nov 16. Pubmed
  5. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  6. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 2C19

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C19 P33261 Details

References:

  1. Micallef J, Fakra E, Blin O: [Use of antidepressant drugs in schizophrenic patients with depression] Encephale. 2006 Mar-Apr;32(2 Pt 1):263-9. Pubmed
  2. Rojdmark S, von Bahr C: [Metabolic interaction between psychopharmaceuticals. Probable cause of exacerbation of hypothyroidism according to a case report] Lakartidningen. 2002 Jun 20;99(25):2854-6. Pubmed
  3. Obach RS, Cox LM, Tremaine LM: Sertraline is metabolized by multiple cytochrome P450 enzymes, monoamine oxidases, and glucuronyl transferases in human: an in vitro study. Drug Metab Dispos. 2005 Feb;33(2):262-70. Epub 2004 Nov 16. Pubmed
  4. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

4. Cytochrome P450 2C9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

References:

  1. Obach RS, Cox LM, Tremaine LM: Sertraline is metabolized by multiple cytochrome P450 enzymes, monoamine oxidases, and glucuronyl transferases in human: an in vitro study. Drug Metab Dispos. 2005 Feb;33(2):262-70. Epub 2004 Nov 16. Pubmed
  2. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed
  3. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  4. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

5. Cytochrome P450 2B6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2B6 P20813 Details

References:

  1. Obach RS, Cox LM, Tremaine LM: Sertraline is metabolized by multiple cytochrome P450 enzymes, monoamine oxidases, and glucuronyl transferases in human: an in vitro study. Drug Metab Dispos. 2005 Feb;33(2):262-70. Epub 2004 Nov 16. Pubmed
  2. Walsky RL, Astuccio AV, Obach RS: Evaluation of 227 drugs for in vitro inhibition of cytochrome P450 2B6. J Clin Pharmacol. 2006 Dec;46(12):1426-38. Pubmed
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

6. Cytochrome P450 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

References:

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

7. Amine oxidase [flavin-containing] B

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Amine oxidase [flavin-containing] B P27338 Details

References:

  1. Obach RS, Cox LM, Tremaine LM: Sertraline is metabolized by multiple cytochrome P450 enzymes, monoamine oxidases, and glucuronyl transferases in human: an in vitro study. Drug Metab Dispos. 2005 Feb;33(2):262-70. Epub 2004 Nov 16. Pubmed

8. Amine oxidase [flavin-containing] A

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Amine oxidase [flavin-containing] A P21397 Details

References:

  1. Obach RS, Cox LM, Tremaine LM: Sertraline is metabolized by multiple cytochrome P450 enzymes, monoamine oxidases, and glucuronyl transferases in human: an in vitro study. Drug Metab Dispos. 2005 Feb;33(2):262-70. Epub 2004 Nov 16. Pubmed

9. CYP2B protein

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
CYP2B protein Q14097 Details

References:

  1. Haduch A, Wojcikowski J, Daniel WA: Effect of selected antidepressant drugs on cytochrome P450 2B (CYP2B) in rat liver. An in vitro and in vivo study. Pharmacol Rep. 2008 Nov-Dec;60(6):957-65. Pubmed

Transporters

1. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

References:

  1. Weiss J, Dormann SM, Martin-Facklam M, Kerpen CJ, Ketabi-Kiyanvash N, Haefeli WE: Inhibition of P-glycoprotein by newer antidepressants. J Pharmacol Exp Ther. 2003 Apr;305(1):197-204. Pubmed

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