Fluoxetine

Overview

Description
A medication used to treat major depression, obsessive compulsive disorder, and panic disorders.
Description
A medication used to treat major depression, obsessive compulsive disorder, and panic disorders.
DrugBank ID
DB00472
Type
Small Molecule
US Approved
YES
Other Approved
YES
Clinical Trials
Phase 0
9
Phase 1
38
Phase 2
63
Phase 3
48
Phase 4
72
Therapeutic Categories
  • Antidepressive Agents Indicated for Depression
  • Selective Serotonin Reuptake Inhibitors
  • Serotonin Modulators
Mechanism of Action

Identification

Summary

Fluoxetine is a selective serotonin reuptake inhibitor used to treat major depressive disorder, bulimia, OCD, premenstrual dysphoric disorder, panic disorder, and bipolar I.

Brand Names
Prozac, Sarafem, Symbyax
Generic Name
Fluoxetine
DrugBank Accession Number
DB00472
Background

Fluoxetine is a 2nd generation antidepressant categorized as a selective serotonin reuptake inhibitor (SSRI).2 It gained FDA approval in 1987 and although it was initially intended for the treatment of depression, today it is commonly prescribed to manage depression in addition to various other pathologies.13

Type
Small Molecule
Groups
Approved, Vet approved
Structure
Weight
Average: 309.3261
Monoisotopic: 309.134048818
Chemical Formula
C17H18F3NO
Synonyms
  • (+-)-N-Methyl-3-phenyl-3-((alpha,alpha,alpha-trifluoro-P-tolyl)oxy)propylamine
  • (+-)-N-Methyl-gamma-(4-(trifluoromethyl)phenoxy)benzenepropanamine
  • Fluoxetin
  • Fluoxetina
  • Fluoxétine
  • Fluoxetine
  • Fluoxetinum
External IDs
  • Lilly 103472
  • Lilly 110 140

Pharmacology

Indication

Fluoxetine is indicated for both acute and maintenance treatment of major depressive disorder, obsessive compulsive disorder, and bulimia nervosa; however, it is only indicated for acute treatment of panic disorder independent of whether agoraphobia is present.12 Fluoxetine may also be used in combination with olanzapine to treat depression related to Bipolar I Disorder, and treatment resistant depression.12 Fluoxetine is additionally indicated for the treatment of female patients with premenstrual dysphoric disorder (PMDD).18

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofAlcohol dependence••• •••••
Management ofAnorexia nervosa••• •••••
Management ofBulimia nervosa•••••••••••••••••••• •• •••••• ••••••••
Treatment ofCataplexy••• •••••
Used in combination to manageDepressionRegimen in combination with: Olanzapine (DB00334)••••••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Fluoxetine blocks the serotonin reuptake transporter in the presynaptic terminal, which ultimately results in sustained levels of 5-hydroxytryptamine (5-HT) in certain brain areas.13 However, fluoxetine binds with relatively poor affinity to 5-HT, dopaminergic, adrenergic, cholinergic, muscarinic, and histamine receptors which explains why it has a far more desirable adverse effect profile compared to earlier developed classes of antidepressants such as tricyclic antidepressants.132

Mechanism of action

The monoaminergic hypothesis of depression emerged in 1965 and linked depression with dysfunction of neurotransmitters such as noradrenaline and serotonin.13 Indeed, low levels of serotonin have been observed in the cerebrospinal fluid of patients diagnosed with depression.3 As a result of this hypothesis, drugs that modulate levels of serotonin such as fluoxetine were developed.13

Fluoxetine is a selective serotonin reuptake inhibitor (SSRI) and as the name suggests, it exerts it's therapeutic effect by inhibiting the presynaptic reuptake of the neurotransmitter serotonin.2 As a result, levels of 5-hydroxytryptamine (5-HT) are increased in various parts of the brain.13 Further, fluoxetine has high affinity for 5-HT transporters, weak affinity for noradrenaline transporters and no affinity for dopamine transporters indicating that it is 5-HT selective.13

Fluoxetine interacts to a degree with the 5-HT2C receptor and it has been suggested that through this mechanism, it is able to increase noradrenaline and dopamine levels in the prefrontal cortex.13

TargetActionsOrganism
ASodium-dependent serotonin transporter
inhibitor
Humans
U5-hydroxytryptamine receptor 2C
antagonist
Humans
UNeuronal acetylcholine receptor subunit alpha-2
antagonist
Humans
UNeuronal acetylcholine receptor subunit alpha-3
antagonist
Humans
UNeuronal acetylcholine receptor subunit beta-4
antagonist
Humans
UCyclin-dependent kinases regulatory subunit 1Not AvailableHumans
UVoltage-gated inwardly rectifying potassium channel KCNH2
inhibitor
Humans
Absorption

The oral bioavailability of fluoxetine is <90% as a result of hepatic first pass metabolism.13

In a bioequivalence study, the Cmax of fluoxetine 20 mg for the established reference formulation was 11.754 ng/mL while the Cmax for the proposed generic formulation was 11.786 ng/ml.11

Fluoxetine is very lipophilic and highly plasma protein bound, allowing the drug and it's active metabolite, norfluoxetine, to be distributed to the brain.13

Volume of distribution

The volume of distribution of fluoxetine and it's metabolite varies between 20 to 42 L/kg.6

Protein binding

Approximately 94% of fluoxetine is plasma protein bound.2

Metabolism

Fluoxetine is metabolized to norfluoxetine by CYP1A2, CYP2B6, CYP2C9, CYP2C19, CYP2D6, CYP3A4, and CYP3A5 upon ingestion.138 Although all of the mentioned enzymes contribute to N-demethylation of fluoxetine, CYP2D6, CYP2C9 and CYP3A4 appear to be the major contributing enzymes for phase I metabolism.8 In addition, there is evidence to suggest that CYP2C19 and CYP3A4 mediate O-dealkylation of fluoxetine and norfluoxetine to produce para-trifluoromethylphenol which is subsequently metabolized to hippuric acid.910 Both fluoxetine and norfluoxetine undergo glucuronidation to facilitate excretion.13

Notably, both the parent drug and active metabolite inhibit CYP2D6 isozymes, and as a result patients who are being treated with fluoxetine are susceptible to drug interactions.1316

Hover over products below to view reaction partners

Route of elimination

Fluoxetine is primarily eliminated in the urine.15

Half-life

The half life of fluoxetine is significant with the elimination half-life of the parent drug averaging 1-3 days after acute administration, and 4-6 days after chronic administration.12 Further, the elimination half life of it's active metabolite, norfluoxetine, ranges from 4-16 days after both acute and chronic administration.12 The half-life of fluoxetine should be considered when switching patients from fluoxetine to another antidepressant since marked accumulation occurs after chronic use.12 Fluoxetine's long half-life may even be beneficial when discontinuing the drug since the risk of withdrawal is minimized.13

Clearance

The clearance value of fluoxetine in healthy patients is reported to be 9.6 ml/min/kg.7

Adverse Effects
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Toxicity

In a report that included 234 fluoxetine overdose cases, it was concluded that symptoms resulting from fluoxetine overdose were generally minor and short in duration.5 The most common overdose adverse effects included drowsiness, tremor, tachycardia, nausea and vomiting, and providing the patient with aggressive supportive care was the recommended intervention.45

Despite this evidence, more severe adverse effects have been linked to fluoxetine ingestion although most of these reports involved co-ingestion with other substances or drugs as well as other factors.4 For example, there is a case report that details a patient who ingested 1400 mg of fluoxetine in a suicide attempt and as a result, experienced a generalized seizure three hours later.4 In a separate case, a 14 year old patient ingested 1.2 g of fluoxetine and subsequently experienced tonic/clonic seizures, symptoms consistent with serotonin syndrome, and rhabdomyolysis, although the patient did not experience sustained renal injury.6

Pathways
PathwayCategory
Fluoxetine Metabolism PathwayDrug metabolism
Fluoxetine Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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
1,2-BenzodiazepineThe serum concentration of 1,2-Benzodiazepine can be increased when it is combined with Fluoxetine.
AbametapirThe serum concentration of Fluoxetine can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Fluoxetine can be increased when combined with Abatacept.
AbciximabThe risk or severity of hemorrhage can be increased when Fluoxetine is combined with Abciximab.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Fluoxetine.
Food Interactions
  • Avoid alcohol.
  • Take with or without food.

Products

Drug product information from 10+ global regions
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dosage, form, labeller, route of administration, and marketing period.
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Product Ingredients
IngredientUNIICASInChI Key
Fluoxetine hydrochlorideI9W7N6B1KJ56296-78-7GIYXAJPCNFJEHY-UHFFFAOYSA-N
Product Images
International/Other Brands
Adofen (Brainpharma) / Animex-On (Laboratorios) / Fluoxeren (Menarini) / Fontex (Lilly) / Ladose (Lilly)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act FluoxetineCapsule10 mgOralDr. Reddy's Laboratories Limited2000-05-312023-06-27Canada flag
Act FluoxetineCapsule20 mgOralDr. Reddy's Laboratories Limited2000-05-312023-06-27Canada flag
Act FluoxetineCapsule40 mgOralDr. Reddy's Laboratories LimitedNot applicableNot applicableCanada flag
Bci FluoxetineCapsule20 mgOralBaker Cummins IncNot applicableNot applicableCanada flag
FluoxetineCapsule20 mgOralAltamed Pharma2020-03-05Not applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Accel-fluoxetineCapsule10 mgOralAccel Pharma Inc2015-03-262018-03-29Canada flag
Accel-fluoxetineCapsule20 mgOralAccel Pharma Inc2015-03-262018-03-29Canada flag
Ach-fluoxetineCapsule10 mgOralAccord Healthcare, S.L.U.2012-10-10Not applicableCanada flag
Ach-fluoxetineCapsule20 mgOralAccord Healthcare, S.L.U.2012-05-01Not applicableCanada flag
Ag-fluoxetineCapsule20 mgOralAngita Pharma Inc.2019-03-15Not applicableCanada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
FLUXOPIN 12 MG/25 MG KAPSÜL ,30 KAPSÜLFluoxetine hydrochloride (25 mg) + Olanzapine (12 mg)CapsuleOralDeva Holding A.S.2020-08-142018-10-26Turkey flag
FLUXOPIN 12 MG/50 MG KAPSÜL ,30 KAPSÜLFluoxetine hydrochloride (50 mg) + Olanzapine (12 mg)CapsuleOralDeva Holding A.S.2020-08-142018-10-26Turkey flag
FLUXOPIN 3 MG/25 MG KAPSÜL ,30 KAPSÜLFluoxetine hydrochloride (25 mg) + Olanzapine (3 mg)CapsuleOralDeva Holding A.S.2020-08-142018-10-26Turkey flag
FLUXOPIN 6 MG/25 MG KAPSÜL ,30 KAPSÜLFluoxetine hydrochloride (25 mg) + Olanzapine (6 mg)CapsuleOralDeva Holding A.S.2020-08-142018-10-26Turkey flag
FLUXOPIN 6 MG/50 MG KAPSÜL ,30 KAPSÜLFluoxetine hydrochloride (50 mg) + Olanzapine (6 mg)CapsuleOralDeva Holding A.S.2020-08-142018-10-26Turkey flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
GaboxetineFluoxetine hydrochloride (10 mg/1) + Choline (125 mg/1)KitOralPhysician Therapeutics Llc2011-07-07Not applicableUS flag
Sentraflox AM-10Fluoxetine hydrochloride (10 mg/1) + Choline (250 mg/1)KitOralPhysician Therapeutics Llc2011-07-07Not applicableUS flag
SentroxatineFluoxetine hydrochloride (10 mg/1) + Choline (250 mg/1)KitOralPhysician Therapeutics Llc2011-02-17Not applicableUS flag

Categories

ATC Codes
N06CA03 — Fluoxetine and psycholepticsN06AB03 — Fluoxetine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Trifluoromethylbenzenes
Direct Parent
Trifluoromethylbenzenes
Alternative Parents
Phenoxy compounds / Phenol ethers / Aralkylamines / Alkyl aryl ethers / Dialkylamines / Organopnictogen compounds / Organofluorides / Hydrocarbon derivatives / Alkyl fluorides
Substituents
Alkyl aryl ether / Alkyl fluoride / Alkyl halide / Amine / Aralkylamine / Aromatic homomonocyclic compound / Ether / Hydrocarbon derivative / Organic nitrogen compound / Organic oxygen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
aromatic ether, secondary amino compound, (trifluoromethyl)benzenes (CHEBI:86990)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
01K63SUP8D
CAS number
54910-89-3
InChI Key
RTHCYVBBDHJXIQ-UHFFFAOYSA-N
InChI
InChI=1S/C17H18F3NO/c1-21-12-11-16(13-5-3-2-4-6-13)22-15-9-7-14(8-10-15)17(18,19)20/h2-10,16,21H,11-12H2,1H3
IUPAC Name
methyl({3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl})amine
SMILES
CNCCC(OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1

References

Synthesis Reference

Eduard Schwartz, Joseph Kaspi, Zinovi Itov, Gidon Pilarski, "Production of fluoxetine and new intermediates." U.S. Patent US5225585, issued October, 1990.

US5225585
General References
  1. Wong DT, Bymaster FP, Engleman EA: Prozac (fluoxetine, Lilly 110140), the first selective serotonin uptake inhibitor and an antidepressant drug: twenty years since its first publication. Life Sci. 1995;57(5):411-41. [Article]
  2. Sommi RW, Crismon ML, Bowden CL: Fluoxetine: a serotonin-specific, second-generation antidepressant. Pharmacotherapy. 1987 Jan-Feb;7(1):1-15. [Article]
  3. Sohel AJ, Molla M: Fluoxetine . [Article]
  4. Suchard JR: Fluoxetine overdose-induced seizure. West J Emerg Med. 2008 Aug;9(3):154-6. [Article]
  5. Borys DJ, Setzer SC, Ling LJ, Reisdorf JJ, Day LC, Krenzelok EP: Acute fluoxetine overdose: a report of 234 cases. Am J Emerg Med. 1992 Mar;10(2):115-20. [Article]
  6. Lee-Kelland R, Zehra S, Mappa P: Fluoxetine overdose in a teenager resulting in serotonin syndrome, seizure and delayed onset rhabdomyolysis. BMJ Case Rep. 2018 Oct 8;2018. pii: bcr-2018-225529. doi: 10.1136/bcr-2018-225529. [Article]
  7. Schenker S, Bergstrom RF, Wolen RL, Lemberger L: Fluoxetine disposition and elimination in cirrhosis. Clin Pharmacol Ther. 1988 Sep;44(3):353-9. doi: 10.1038/clpt.1988.161. [Article]
  8. Margolis JM, O'Donnell JP, Mankowski DC, Ekins S, Obach RS: (R)-, (S)-, and racemic fluoxetine N-demethylation by human cytochrome P450 enzymes. Drug Metab Dispos. 2000 Oct;28(10):1187-91. [Article]
  9. Liu ZQ, Zhu B, Tan YF, Tan ZR, Wang LS, Huang SL, Shu Y, Zhou HH: O-Dealkylation of fluoxetine in relation to CYP2C19 gene dose and involvement of CYP3A4 in human liver microsomes. J Pharmacol Exp Ther. 2002 Jan;300(1):105-11. doi: 10.1124/jpet.300.1.105. [Article]
  10. Crifasi JA, Le NX, Long C: Simultaneous identification and quantitation of fluoxetine and its metabolite, norfluoxetine, in biological samples by GC-MS. J Anal Toxicol. 1997 Oct;21(6):415-9. doi: 10.1093/jat/21.6.415. [Article]
  11. Shi S, Liu Y, Wu J, Li Z, Zhao Y, Zhong D, Zeng F: Comparative bioavailability and tolerability of a single 20-mg dose of two fluoxetine hydrochloride dispersible tablet formulations in fasting, healthy Chinese male volunteers: an open-label, randomized-sequence, two-period crossover study. Clin Ther. 2010 Oct;32(11):1977-86. doi: 10.1016/j.clinthera.2010.10.003. [Article]
  12. FDA Approved Drug Products: Prozac (fluoxetine) oral capsules [Link]
  13. Fluoxetine: A case history of its discovery and preclinical development [Link]
  14. The Distribution of Fluoxetine in Human Fluids and Tissues [Link]
  15. DailyMed - Fluoxetine [Link]
  16. Flockhart Table of Drug Interactions [Link]
  17. Health Canada Product Monograph: Fluoxetine oral capsules [Link]
  18. FDA Approved Drug Products: Sarafem (fluoxetine hydrochloride) tablets for oral use [Link]
  19. DailyMed Label: PROZAC (fluoxetine capsules) for oral use [Link]
Human Metabolome Database
HMDB0014615
KEGG Drug
D00823
PubChem Compound
3386
PubChem Substance
46507902
ChemSpider
3269
BindingDB
30130
RxNav
4493
ChEBI
86990
ChEMBL
CHEMBL41
Therapeutic Targets Database
DAP000186
PharmGKB
PA449673
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Fluoxetine
MSDS
Download (76.7 KB)

Clinical Trials

Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package
PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
Not AvailableActive Not RecruitingTreatmentEnuresis / Nocturnal Enuresis1somestatusstop reasonjust information to hide
Not AvailableCompletedNot AvailableAcute Kidney Injury (AKI) / Depression1somestatusstop reasonjust information to hide
Not AvailableCompletedNot AvailableHealthy Volunteers (HV)1somestatusstop reasonjust information to hide
Not AvailableCompletedNot AvailableMajor Depressive Disorder (MDD)2somestatusstop reasonjust information to hide
Not AvailableCompletedNot AvailableType 1 Diabetes Mellitus1somestatusstop reasonjust information to hide

Pharmacoeconomics

Manufacturers
  • Barr laboratories inc
  • Dr reddys laboratories ltd
  • Eli lilly and co
  • Mutual pharmacal co
  • Watson laboratories inc
  • Alembic ltd
  • Alphapharm party ltd
  • Aurobindo pharma ltd
  • Beijing double crane pharmaceutical co ltd
  • Carlsbad technology inc
  • Dr reddys laboratories inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Landela pharmaceutical
  • Mallinckrodt inc
  • Mylan pharmaceuticals inc
  • Par pharmaceutical inc
  • Pliva inc
  • Ranbaxy laboratories ltd
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Wockhardt ltd
  • Lilly research laboratories div eli lilly and co
  • Actavis mid atlantic llc
  • Aurobindo pharma usa inc
  • Hi tech pharmacal co inc
  • Lannett holdings inc
  • Novex pharma
  • Pharmaceutical assoc inc div beach products
  • Silarx pharmaceuticals inc
  • Wockhardt eu operations (swiss) ag
  • Warner chilcott inc
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Alphapharm Party Ltd.
  • Amerisource Health Services Corp.
  • Amneal Pharmaceuticals
  • Apotex Inc.
  • AQ Pharmaceuticals Inc.
  • A-S Medication Solutions LLC
  • Atlantic Biologicals Corporation
  • Aurobindo Pharma Ltd.
  • Barr Pharmaceuticals
  • Blenheim Pharmacal
  • Bryant Ranch Prepack
  • Cardinal Health
  • Caremark LLC
  • Carlsbad Technology Inc.
  • Comprehensive Consultant Services Inc.
  • Corepharma LLC
  • Coupler Enterprises Inc.
  • D.M. Graham Laboratories Inc.
  • DHHS Program Support Center Supply Service Center
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Doctor Reddys Laboratories Ltd.
  • DSM Corp.
  • Eli Lilly & Co.
  • Eon Labs
  • Golden State Medical Supply Inc.
  • H.J. Harkins Co. Inc.
  • Heartland Repack Services LLC
  • Innoviant Pharmacy Inc.
  • Ivax Pharmaceuticals
  • Kaiser Foundation Hospital
  • Keltman Pharmaceuticals Inc.
  • Lake Erie Medical and Surgical Supply
  • Legacy Pharmaceuticals Packaging LLC
  • Liberty Pharmaceuticals
  • Lilly Del Caribe Inc.
  • Major Pharmaceuticals
  • Mallinckrodt Inc.
  • Medvantx Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Northstar Rx LLC
  • Norwich Pharmaceuticals Inc.
  • Novex Pharma
  • Novopharm Ltd.
  • Nucare Pharmaceuticals Inc.
  • Ohm Laboratories Inc.
  • Palmetto Pharmaceuticals Inc.
  • Par Pharmaceuticals
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Association
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmedix
  • Pharmpak Inc.
  • Physician Partners Ltd.
  • Physicians Total Care Inc.
  • Pliva Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Promex Medical Inc.
  • Prx Pharmaceuticals
  • Ranbaxy Laboratories
  • Rebel Distributors Corp.
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Sandhills Packaging Inc.
  • Sandoz
  • Silarx Pharmaceuticals
  • Southwood Pharmaceuticals
  • Spectrum Pharmaceuticals
  • St Mary's Medical Park Pharmacy
  • Stat Rx Usa
  • Teva Pharmaceutical Industries Ltd.
  • Tya Pharmaceuticals
  • UDL Laboratories
  • Va Cmop Dallas
  • Vangard Labs Inc.
  • Warner Chilcott Co. Inc.
  • WC Pharmaceuticals
  • Wockhardt Ltd.
  • Xactdose Inc.
Dosage Forms
FormRouteStrength
CapsuleOral11542 MG
CapsuleOral22400 MG
TabletOral22.357 mg
CapsuleOral20.000 mg
TabletOral
Tablet, solubleOral
SolutionOral0.4 g
CapsuleOral22.400 mg
TabletOral22.400 mg
CapsuleOral20 mg
Tablet, solubleOral20 MG
Tablet, film coatedOral
SolutionOral
TabletOral10 MG
TabletOral40 MG
Tablet, film coatedOral20 MG
Tablet, film coatedOral40 MG
SyrupOral0.421 g
Capsule, coatedOral20 mg
Tablet, orally disintegratingOral20 MG
Tablet, coatedOral20 mg
CapsuleNot applicable20 mg/1
CapsuleOral20 mg/1
LiquidOral20 mg/5mL
Tablet, film coatedOral60 mg/1
CapsuleOral10 mg/1
CapsuleOral40 mg/1
Capsule, delayed releaseOral90 mg/1
Capsule, delayed release pelletsOral90 mg/1
For solutionOral20 mg/5mL
TabletOral10 mg/1
TabletOral20 mg/1
TabletOral22.36 MG
TabletOral60 mg/1
Tablet, coatedOral10 mg/1
Tablet, coatedOral20 mg/1
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral20 mg/1
CapsuleOral40 mg
TabletOral20.000 mg
CapsuleOral22.36 mg
Capsule, gelatin coatedOral20 mg
SyrupOral0.4 g
Tablet, film coatedOral60 mg
SolutionOral20 mg / 5 mL
CapsuleOral
CapsuleOral20.00 mg
CapsuleOral60 mg
CapsuleOral
CapsuleOral20.0000 mg
SolutionOral20 mg/5mL
Tablet, for suspensionOral20 MG
CapsuleOral22.360 mg
CapsuleOral10 mg
Capsule, coatedOral90 mg
LiquidOral20 mg / 5 mL
CapsuleOral11.2 MG
CapsuleOral22.4 MG
TabletOral15 mg/1
KitOral
CapsuleOral10 mg / cap
CapsuleOral20 mg / cap
TabletOral20.00 mg
SolutionOral448 mg
TabletOral20 mg
Prices
Unit descriptionCostUnit
PROzac 20 mg/5ml Solution 120ml Bottle266.51USD bottle
PROzac Weekly 1 Package = 4 capsule (90 mg) Disp Pack140.77USD disp
Sarafem 7 10 mg tablet Box61.08USD box
Sarafem 7 20 mg tablet Each Box Contains 7 tablet59.55USD box
Prozac weekly 90 mg capsule34.5USD capsule
PROzac 40 mg capsule13.89USD capsule
Fluoxetine hcl powder8.32USD g
Sarafem 10 mg tablet7.91USD tablet
Sarafem 15 mg tablet7.91USD tablet
Sarafem 20 mg tablet7.91USD tablet
PROzac 20 mg capsule6.95USD capsule
PROzac 10 mg capsule6.77USD capsule
FLUoxetine HCl 40 mg capsule5.54USD capsule
PROzac 10 mg tablet4.31USD tablet
Fluoxetine hcl 20 mg tablet4.26USD tablet
Rapiflux 20 mg tablet3.11USD tablet
FLUoxetine HCl 20 mg capsule2.77USD capsule
Fluoxetine hcl 10 mg tablet2.72USD tablet
FLUoxetine HCl 10 mg capsule2.7USD capsule
Fxt 40 40 mg Capsule2.3USD capsule
Prozac 10 mg Capsule2.02USD capsule
Prozac 20 mg Capsule2.02USD capsule
Apo-Fluoxetine 10 mg Capsule1.13USD capsule
Co Fluoxetine 10 mg Capsule1.13USD capsule
Mylan-Fluoxetine 10 mg Capsule1.13USD capsule
Novo-Fluoxetine 10 mg Capsule1.13USD capsule
Nu-Fluoxetine 10 mg Capsule1.13USD capsule
Phl-Fluoxetine 10 mg Capsule1.13USD capsule
Pms-Fluoxetine 10 mg Capsule1.13USD capsule
Ratio-Fluoxetine Hydrochloride 10 mg Capsule1.13USD capsule
Sandoz Fluoxetine 10 mg Capsule1.13USD capsule
Apo-Fluoxetine 20 mg Capsule1.06USD capsule
Co Fluoxetine 20 mg Capsule1.06USD capsule
Mylan-Fluoxetine 20 mg Capsule1.06USD capsule
Novo-Fluoxetine 20 mg Capsule1.06USD capsule
Nu-Fluoxetine 20 mg Capsule1.06USD capsule
Phl-Fluoxetine 20 mg Capsule1.06USD capsule
Pms-Fluoxetine 20 mg Capsule1.06USD capsule
Ratio-Fluoxetine Hydrochloride 20 mg Capsule1.06USD capsule
Sandoz Fluoxetine 20 mg Capsule1.06USD capsule
FLUoxetine HCl 20 mg/5ml Solution1.03USD ml
Apo-Fluoxetine 4 mg/ml Liquid0.61USD liquid
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US6960577No2005-11-012017-11-01US flag
US5910319Yes1999-06-082017-11-29US flag
US5985322Yes1999-11-162017-11-29US flag
USRE39030No2006-03-212017-05-29US flag
US5945416No1999-08-312017-03-24US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)193 - 197 °CMSDS
boiling point (°C)395.1°C at 760 mmHghttps://www.lookchem.com/Fluoxetine/
water solubilityinsolublehttps://www.lookchem.com/Fluoxetine/
logP4.05ADLARD,M ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0017 mg/mLALOGPS
logP4.09ALOGPS
logP4.17Chemaxon
logS-5.3ALOGPS
pKa (Strongest Basic)9.8Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area21.26 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity80.37 m3·mol-1Chemaxon
Polarizability30.33 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.983
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.5899
P-glycoprotein inhibitor IInhibitor0.8565
P-glycoprotein inhibitor IIInhibitor0.5459
Renal organic cation transporterInhibitor0.5633
CYP450 2C9 substrateNon-substrate0.7475
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateSubstrate0.5754
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorInhibitor0.8993
CYP450 3A4 inhibitorInhibitor0.7959
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7149
Ames testNon AMES toxic0.7105
CarcinogenicityNon-carcinogens0.8089
BiodegradationNot ready biodegradable0.9868
Rat acute toxicity2.6048 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.6058
hERG inhibition (predictor II)Inhibitor0.8467
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-MSsplash10-0006-9530000000-45c870b2463186b9230c
Mass Spectrum (Electron Ionization)MSsplash10-0006-9200000000-dcf68dbfd090c7fdfe11
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-01t9-0592000000-92a48c620c961fdb430f
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03di-0009000000-ed61090013f0dc5f5c5a
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0190000000-e9bcd2accdf5b7e40a88
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0590000000-04b1d4265cb156217f40
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0790000000-5c42b9a9a2cd0c4114aa
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0gb9-0960000000-88822d2fb3e7c0cdc0b3
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-6b560941c92823b7901c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0109000000-1531c1e1630dcb42b497
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-9000000000-53199cfe3b343ae81afd
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0109000000-0e790a7e6032e51bfeb3
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00kf-9800000000-64d39c4a4fcc7f8b6f47
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00kf-9700000000-e516356ce3eca65bece8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-6b560941c92823b7901c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0zgi-1390000000-84c6bc70aefcd3758f31
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0f7o-6940000000-a424e26ecc7465229968
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4m-0390000000-9b7253cd5718aa434e46
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4m-0290000000-d88f8004205c7223aa9f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-01t9-0592000000-92a48c620c961fdb430f
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0409000000-03f5678c6178e634f254
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014l-4900000000-2940e7bc3f6a559e61fc
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014l-5900000000-c904d50adb4d1ea90abd
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014l-5900000000-5cbc74ddfe414085c9bd
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0900000000-6b560941c92823b7901c
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0900000000-f5f65bd85fe3483260bb
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4j-0903000000-336450f4e92f0ad57203
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9303000000-befa4649ed515eb63a92
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9310000000-494ba11edaf63292ecb9
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-195ef0f5145ec1fd5c2f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ox-4941000000-bd7eb2985b2a3cac0137
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-ed37087a0d3c8eb00ebf
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]-177.5806429
predicted
DarkChem Lite v0.1.0
[M-H]-170.9421
predicted
DeepCCS 1.0 (2019)
[M+H]+178.3538429
predicted
DarkChem Lite v0.1.0
[M+H]+173.3001
predicted
DeepCCS 1.0 (2019)
[M+Na]+177.7759429
predicted
DarkChem Lite v0.1.0
[M+Na]+179.39323
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serotonin transporter that cotransports serotonin with one Na(+) ion in exchange for one K(+) ion and possibly one proton in an overall electroneutral transport cycle. Transports serotonin across the plasma membrane from the extracellular compartment to the cytosol thus limiting serotonin intercellular signaling (PubMed:10407194, PubMed:12869649, PubMed:21730057, PubMed:27049939, PubMed:27756841, PubMed:34851672). Essential for serotonin homeostasis in the central nervous system. In the developing somatosensory cortex, acts in glutamatergic neurons to control serotonin uptake and its trophic functions accounting for proper spatial organization of cortical neurons and elaboration of sensory circuits. In the mature cortex, acts primarily in brainstem raphe neurons to mediate serotonin uptake from the synaptic cleft back into the pre-synaptic terminal thus terminating serotonin signaling at the synapse (By similarity). Modulates mucosal serotonin levels in the gastrointestinal tract through uptake and clearance of serotonin in enterocytes. Required for enteric neurogenesis and gastrointestinal reflexes (By similarity). Regulates blood serotonin levels by ensuring rapid high affinity uptake of serotonin from plasma to platelets, where it is further stored in dense granules via vesicular monoamine transporters and then released upon stimulation (PubMed:17506858, PubMed:18317590). Mechanistically, the transport cycle starts with an outward-open conformation having Na1(+) and Cl(-) sites occupied. The binding of a second extracellular Na2(+) ion and serotonin substrate leads to structural changes to outward-occluded to inward-occluded to inward-open, where the Na2(+) ion and serotonin are released into the cytosol. Binding of intracellular K(+) ion induces conformational transitions to inward-occluded to outward-open and completes the cycle by releasing K(+) possibly together with a proton bound to Asp-98 into the extracellular compartment. Na1(+) and Cl(-) ions remain bound throughout the transport cycle (PubMed:10407194, PubMed:12869649, PubMed:21730057, PubMed:27049939, PubMed:27756841, PubMed:34851672). Additionally, displays serotonin-induced channel-like conductance for monovalent cations, mainly Na(+) ions. The channel activity is uncoupled from the transport cycle and may contribute to the membrane resting potential or excitability (By similarity)
Specific Function
actin filament binding
Gene Name
SLC6A4
Uniprot ID
P31645
Uniprot Name
Sodium-dependent serotonin transporter
Molecular Weight
70324.165 Da
References
  1. Iceta R, Mesonero JE, Alcalde AI: Effect of long-term fluoxetine treatment on the human serotonin transporter in Caco-2 cells. Life Sci. 2007 Mar 27;80(16):1517-24. Epub 2007 Jan 20. [Article]
  2. Mirza NR, Nielsen EO, Troelsen KB: Serotonin transporter density and anxiolytic-like effects of antidepressants in mice. Prog Neuropsychopharmacol Biol Psychiatry. 2007 May 9;31(4):858-66. Epub 2007 Jan 30. [Article]
  3. Sanders AC, Hussain AJ, Hen R, Zhuang X: Chronic blockade or constitutive deletion of the serotonin transporter reduces operant responding for food reward. Neuropsychopharmacology. 2007 Nov;32(11):2321-9. Epub 2007 Mar 14. [Article]
  4. Goren MZ, Kucukibrahimoglu E, Berkman K, Terzioglu B: Fluoxetine partly exerts its actions through GABA: a neurochemical evidence. Neurochem Res. 2007 Sep;32(9):1559-65. Epub 2007 May 8. [Article]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [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. Fluoxetine: A case history of its discovery and preclinical development [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin) (PubMed:12970106, PubMed:18703043, PubMed:19057895, PubMed:29398112, PubMed:7895773). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-iodophenyl-2-aminopropane (DOI) and lysergic acid diethylamide (LSD) (PubMed:19057895, PubMed:29398112). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of downstream effectors (PubMed:18703043, PubMed:29398112). HTR2C is coupled to G(q)/G(11) G alpha proteins and activates phospholipase C-beta, releasing diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) second messengers that modulate the activity of phosphatidylinositol 3-kinase and promote the release of Ca(2+) ions from intracellular stores, respectively (PubMed:18703043, PubMed:29398112). Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways (PubMed:29398112). Regulates neuronal activity via the activation of short transient receptor potential calcium channels in the brain, and thereby modulates the activation of pro-opiomelanocortin neurons and the release of CRH that then regulates the release of corticosterone (By similarity). Plays a role in the regulation of appetite and eating behavior, responses to anxiogenic stimuli and stress (By similarity). Plays a role in insulin sensitivity and glucose homeostasis (By similarity)
Specific Function
1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine binding
Gene Name
HTR2C
Uniprot ID
P28335
Uniprot Name
5-hydroxytryptamine receptor 2C
Molecular Weight
51804.645 Da
References
  1. Chanrion B, Mannoury la Cour C, Gavarini S, Seimandi M, Vincent L, Pujol JF, Bockaert J, Marin P, Millan MJ: Inverse agonist and neutral antagonist actions of antidepressants at recombinant and native 5-hydroxytryptamine2C receptors: differential modulation of cell surface expression and signal transduction. Mol Pharmacol. 2008 Mar;73(3):748-57. Epub 2007 Dec 14. [Article]
  2. Cryan JF, Lucki I: Antidepressant-like behavioral effects mediated by 5-Hydroxytryptamine(2C) receptors. J Pharmacol Exp Ther. 2000 Dec;295(3):1120-6. [Article]
  3. Ni YG, Miledi R: Blockage of 5HT2C serotonin receptors by fluoxetine (Prozac). Proc Natl Acad Sci U S A. 1997 Mar 4;94(5):2036-40. doi: 10.1073/pnas.94.5.2036. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane
Specific Function
acetylcholine receptor activity
Gene Name
CHRNA2
Uniprot ID
Q15822
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-2
Molecular Weight
59764.82 Da
References
  1. Garcia-Colunga J, Awad JN, Miledi R: Blockage of muscle and neuronal nicotinic acetylcholine receptors by fluoxetine (Prozac). Proc Natl Acad Sci U S A. 1997 Mar 4;94(5):2041-4. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane
Specific Function
acetylcholine binding
Gene Name
CHRNA3
Uniprot ID
P32297
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-3
Molecular Weight
57479.54 Da
References
  1. Garcia-Colunga J, Awad JN, Miledi R: Blockage of muscle and neuronal nicotinic acetylcholine receptors by fluoxetine (Prozac). Proc Natl Acad Sci U S A. 1997 Mar 4;94(5):2041-4. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane
Specific Function
acetylcholine receptor activity
Gene Name
CHRNB4
Uniprot ID
P30926
Uniprot Name
Neuronal acetylcholine receptor subunit beta-4
Molecular Weight
56378.985 Da
References
  1. Garcia-Colunga J, Awad JN, Miledi R: Blockage of muscle and neuronal nicotinic acetylcholine receptors by fluoxetine (Prozac). Proc Natl Acad Sci U S A. 1997 Mar 4;94(5):2041-4. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Binds to the catalytic subunit of the cyclin dependent kinases and is essential for their biological function
Specific Function
cyclin-dependent protein serine/threonine kinase activator activity
Gene Name
CKS1B
Uniprot ID
P61024
Uniprot Name
Cyclin-dependent kinases regulatory subunit 1
Molecular Weight
9660.14 Da
References
  1. Krishnan A, Hariharan R, Nair SA, Pillai MR: Fluoxetine mediates G0/G1 arrest by inducing functional inhibition of cyclin dependent kinase subunit (CKS)1. Biochem Pharmacol. 2008 May 15;75(10):1924-34. doi: 10.1016/j.bcp.2008.02.013. Epub 2008 Feb 17. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel (PubMed:10219239, PubMed:10753933, PubMed:10790218, PubMed:10837251, PubMed:11997281, PubMed:12063277, PubMed:18559421, PubMed:22314138, PubMed:22359612, PubMed:26363003, PubMed:27916661, PubMed:9230439, PubMed:9351446, PubMed:9765245). Channel properties are modulated by cAMP and subunit assembly (PubMed:10837251). Characterized by unusual gating kinetics by producing relatively small outward currents during membrane depolarization and large inward currents during subsequent repolarization which reflect a rapid inactivation during depolarization and quick recovery from inactivation but slow deactivation (closing) during repolarization (PubMed:10219239, PubMed:10753933, PubMed:10790218, PubMed:10837251, PubMed:11997281, PubMed:12063277, PubMed:18559421, PubMed:22314138, PubMed:22359612, PubMed:26363003, PubMed:27916661, PubMed:9230439, PubMed:9351446, PubMed:9765245). Channel properties are modulated by cAMP and subunit assembly (PubMed:10837251). Forms a stable complex with KCNE1 or KCNE2, and that this heteromultimerization regulates inward rectifier potassium channel activity (PubMed:10219239, PubMed:9230439)
Specific Function
delayed rectifier potassium channel activity
Gene Name
KCNH2
Uniprot ID
Q12809
Uniprot Name
Voltage-gated inwardly rectifying potassium channel KCNH2
Molecular Weight
126653.52 Da
References
  1. Chiu PJ, Marcoe KF, Bounds SE, Lin CH, Feng JJ, Lin A, Cheng FC, Crumb WJ, Mitchell R: Validation of a [3H]astemizole binding assay in HEK293 cells expressing HERG K+ channels. J Pharmacol Sci. 2004 Jul;95(3):311-9. [Article]
  2. Rajamani S, Eckhardt LL, Valdivia CR, Klemens CA, Gillman BM, Anderson CL, Holzem KM, Delisle BP, Anson BD, Makielski JC, January CT: Drug-induced long QT syndrome: hERG K+ channel block and disruption of protein trafficking by fluoxetine and norfluoxetine. Br J Pharmacol. 2006 Nov;149(5):481-9. doi: 10.1038/sj.bjp.0706892. Epub 2006 Sep 11. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
A cytochrome P450 monooxygenase involved in the metabolism of endocannabinoids and steroids (PubMed:12865317, PubMed:21289075). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the epoxidation of double bonds of arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:21289075). Hydroxylates steroid hormones, including testosterone at C-16 and estrogens at C-2 (PubMed:12865317, PubMed:21289075). Plays a role in the oxidative metabolism of xenobiotics, including plant lipids and drugs (PubMed:11695850, PubMed:22909231). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850)
Specific Function
anandamide 11,12 epoxidase activity
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Margolis JM, O'Donnell JP, Mankowski DC, Ekins S, Obach RS: (R)-, (S)-, and racemic fluoxetine N-demethylation by human cytochrome P450 enzymes. Drug Metab Dispos. 2000 Oct;28(10):1187-91. [Article]
  2. Ekins S, Iyer M, Krasowski MD, Kharasch ED: Molecular characterization of CYP2B6 substrates. Curr Drug Metab. 2008 Jun;9(5):363-73. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
A cytochrome P450 monooxygenase involved in the metabolism of steroid hormones and vitamins (PubMed:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). Exhibits high catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes 6beta-hydroxylation of the steroid hormones testosterone, progesterone, and androstenedione (PubMed:2732228). Catalyzes the oxidative conversion of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes all trans-retinoic acid (atRA) to 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Also involved in the oxidative metabolism of xenobiotics, including calcium channel blocking drug nifedipine and immunosuppressive drug cyclosporine (PubMed:2732228)
Specific Function
aromatase activity
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Margolis JM, O'Donnell JP, Mankowski DC, Ekins S, Obach RS: (R)-, (S)-, and racemic fluoxetine N-demethylation by human cytochrome P450 enzymes. Drug Metab Dispos. 2000 Oct;28(10):1187-91. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)
Specific Function
(R)-limonene 6-monooxygenase activity
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Margolis JM, O'Donnell JP, Mankowski DC, Ekins S, Obach RS: (R)-, (S)-, and racemic fluoxetine N-demethylation by human cytochrome P450 enzymes. Drug Metab Dispos. 2000 Oct;28(10):1187-91. [Article]
  2. Wang JF, Yan JY, Wei DQ, Chou KC: Binding of CYP2C9 with diverse drugs and its implications for metabolic mechanism. Med Chem. 2009 May;5(3):263-70. [Article]
  3. 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]
  4. Hemeryck A, De Vriendt C, Belpaire FM: Inhibition of CYP2C9 by selective serotonin reuptake inhibitors: in vitro studies with tolbutamide and (S)-warfarin using human liver microsomes. Eur J Clin Pharmacol. 1999 Feb;54(12):947-51. [Article]
  5. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
General Function
A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
Specific Function
anandamide 11,12 epoxidase activity
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Margolis JM, O'Donnell JP, Mankowski DC, Ekins S, Obach RS: (R)-, (S)-, and racemic fluoxetine N-demethylation by human cytochrome P450 enzymes. Drug Metab Dispos. 2000 Oct;28(10):1187-91. [Article]
  2. Flockhart Table of Drug Interactions [Link]
  3. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
Curator comments
Data in the literature are limited regarding this enzyme. One study found that fluoxetine was a CYP2B inducer in rats.
General 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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Specific Function
arachidonic acid epoxygenase activity
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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:11555828, PubMed:12865317). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2 (PubMed:11555828, PubMed:12865317). Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). May act as a major enzyme for all-trans retinoic acid biosynthesis in the liver. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). Primarily catalyzes stereoselective epoxidation of the last double bond of polyunsaturated fatty acids (PUFA), displaying a strong preference for the (R,S) stereoisomer (PubMed:19965576). Catalyzes bisallylic hydroxylation and omega-1 hydroxylation of PUFA (PubMed:9435160). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195). Plays a role in the oxidative metabolism of xenobiotics. Catalyzes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin (PubMed:14725854). Metabolizes caffeine via N3-demethylation (Probable)
Specific Function
aromatase activity
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58406.915 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. 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. English BA, Dortch M, Ereshefsky L, Jhee S: Clinically significant psychotropic drug-drug interactions in the primary care setting. Curr Psychiatry Rep. 2012 Aug;14(4):376-90. doi: 10.1007/s11920-012-0284-9. [Article]
  4. Margolis JM, O'Donnell JP, Mankowski DC, Ekins S, Obach RS: (R)-, (S)-, and racemic fluoxetine N-demethylation by human cytochrome P450 enzymes. Drug Metab Dispos. 2000 Oct;28(10):1187-91. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
Curator comments
The level of CYP3A4 enzyme inhibition caused by fluoxetine is not thought to be clinically significant, according to official prescribing information.
General Function
A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
Specific Function
1,8-cineole 2-exo-monooxygenase activity
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. 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]
  3. Margolis JM, O'Donnell JP, Mankowski DC, Ekins S, Obach RS: (R)-, (S)-, and racemic fluoxetine N-demethylation by human cytochrome P450 enzymes. Drug Metab Dispos. 2000 Oct;28(10):1187-91. [Article]
  4. Spina E, Avenoso A, Scordo MG, Ancione M, Madia A, Gatti G, Perucca E: Inhibition of risperidone metabolism by fluoxetine in patients with schizophrenia: a clinically relevant pharmacokinetic drug interaction. J Clin Psychopharmacol. 2002 Aug;22(4):419-23. doi: 10.1097/00004714-200208000-00014. [Article]
  5. 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]
  6. Fluoxetine FDA label [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
A cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position (PubMed:18577768). Catalyzes the epoxidation of double bonds of PUFA (PubMed:19965576, PubMed:20972997). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). 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 imipramine. Hydroxylates fenbendazole at the 4' position (PubMed:23959307)
Specific Function
(R)-limonene 6-monooxygenase activity
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55944.565 Da
References
  1. Harvey AT, Preskorn SH: Fluoxetine pharmacokinetics and effect on CYP2C19 in young and elderly volunteers. J Clin Psychopharmacol. 2001 Apr;21(2):161-6. [Article]
  2. Liu ZQ, Cheng ZN, Huang SL, Chen XP, Ou-Yang DS, Jiang CH, Zhou HH: Effect of the CYP2C19 oxidation polymorphism on fluoxetine metabolism in Chinese healthy subjects. Br J Clin Pharmacol. 2001 Jul;52(1):96-9. [Article]
  3. Margolis JM, O'Donnell JP, Mankowski DC, Ekins S, Obach RS: (R)-, (S)-, and racemic fluoxetine N-demethylation by human cytochrome P450 enzymes. Drug Metab Dispos. 2000 Oct;28(10):1187-91. [Article]
  4. Flockhart Table of Drug Interactions [Link]
  5. Drug Interactions & Labeling - FDA [Link]
  6. Fluoxetine Metabolism Pathway [Link]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
Specific Function
antioxidant activity
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Albumin
Molecular Weight
69365.94 Da
References
  1. FDA Approved Drug Products: Prozac (fluoxetine) oral capsules [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Functions as a transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in the body. Appears to function in modulating the activity of the immune system during the acute-phase reaction
Specific Function
Not Available
Gene Name
ORM1
Uniprot ID
P02763
Uniprot Name
Alpha-1-acid glycoprotein 1
Molecular Weight
23539.43 Da
References
  1. FDA Approved Drug Products: Prozac (fluoxetine) oral capsules [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
Specific Function
ABC-type xenobiotic transporter activity
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
ATP-dependent translocase ABCB1
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. O'Brien FE, Dinan TG, Griffin BT, Cryan JF: Interactions between antidepressants and P-glycoprotein at the blood-brain barrier: clinical significance of in vitro and in vivo findings. Br J Pharmacol. 2012 Jan;165(2):289-312. doi: 10.1111/j.1476-5381.2011.01557.x. [Article]
  3. Human P-glycoprotein differentially affects antidepressant drug transport: relevance to blood-brain barrier permeability [Link]

Drug created at June 13, 2005 13:24 / Updated at November 06, 2024 19:56