Identification

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Name
Fluoxetine
Accession Number
DB00472  (APRD00530)
Type
Small Molecule
Groups
Approved, Vet approved
Description

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

Structure
Thumb
Synonyms
  • (+-)-N-Methyl-3-phenyl-3-((alpha,alpha,alpha-trifluoro-P-tolyl)oxy)propylamine
  • (+-)-N-Methyl-gamma-(4-(trifluoromethyl)phenoxy)benzenepropanamine
  • Fluoxetin
  • Fluoxetina
  • Fluoxetine
  • Fluoxétine
  • Fluoxetinum
External IDs
Lilly 103472 / Lilly 110 140
Product Ingredients
IngredientUNIICASInChI Key
Fluoxetine hydrochlorideI9W7N6B1KJ56296-78-7GIYXAJPCNFJEHY-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act FluoxetineCapsuleOralDr Reddys Laboratories Inc2000-05-31Not applicableCanada
Act FluoxetineCapsuleOralDr Reddys Laboratories IncNot applicableNot applicableCanada
Act FluoxetineCapsuleOralDr Reddys Laboratories Inc2000-05-31Not applicableCanada
Bci FluoxetineCapsuleOralBaker Cummins IncNot applicableNot applicableCanada
FluoxetineCapsule20 mgOralMeliapharm Inc2010-06-112014-06-25Canada
FluoxetineCapsule10 mgOralSivem Pharmaceuticals Ulc2011-10-14Not applicableCanada
FluoxetineCapsule10 mgOralAltamed PharmaNot applicableNot applicableCanada
FluoxetineCapsule20 mgOralSanis Health Inc2009-10-22Not applicableCanada
FluoxetineCapsule10 mgOralMeliapharm Inc2010-06-112014-06-25Canada
FluoxetineCapsule20 mg/1OralTeva2007-01-092007-01-26Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Accel-fluoxetineCapsuleOralAccel Pharma Inc2015-03-262018-03-29Canada
Accel-fluoxetineCapsuleOralAccel Pharma Inc2015-03-262018-03-29Canada
Ach-fluoxetineCapsuleOralAccord Healthcare Inc2012-10-10Not applicableCanada
Ach-fluoxetineCapsuleOralAccord Healthcare Inc2012-05-01Not applicableCanada
Ag-fluoxetineCapsuleOralAngita Pharma Inc.2019-03-15Not applicableCanada
Ag-fluoxetineCapsuleOralAngita Pharma Inc.2019-03-15Not applicableCanada
Apo-fluoxetineCapsuleOralApotex Corporation1996-12-31Not applicableCanada
Apo-fluoxetineSolutionOralApotex Corporation1997-06-16Not applicableCanada
Apo-fluoxetineCapsuleOralApotex Corporation1996-12-31Not applicableCanada
Auro-fluoxetineCapsuleOralAuro Pharma Inc2012-07-24Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Olanzapine and FluoxetineFluoxetine hydrochloride (50 mg/1) + Olanzapine (6 mg/1)CapsuleOralAvKARE, Inc.2014-01-21Not applicableUs00093 5505 56 nlmimage10 f426fa17
Olanzapine and FluoxetineFluoxetine hydrochloride (25 mg/1) + Olanzapine (6 mg/1)CapsuleOralPar Pharmaceutical, Inc.2012-11-26Not applicableUs
Olanzapine and FluoxetineFluoxetine hydrochloride (50 mg/1) + Olanzapine (6 mg/1)CapsuleOralTeva2012-06-19Not applicableUs0093 550520180913 8702 o1l3y5
Olanzapine and FluoxetineFluoxetine hydrochloride (50 mg/1) + Olanzapine (6 mg/1)CapsuleOralSandoz2012-11-30Not applicableUs
Olanzapine and FluoxetineFluoxetine hydrochloride (25 mg/1) + Olanzapine (6 mg/1)CapsuleOralAvKARE, Inc.2014-01-21Not applicableUs00093 5504 56 nlmimage10 292714e8
Olanzapine and FluoxetineFluoxetine hydrochloride (25 mg/1) + Olanzapine (3 mg/1)CapsuleOralPar Pharmaceutical, Inc.2012-11-26Not applicableUs49884 0277 11 nlmimage10 c53be2ef
Olanzapine and FluoxetineFluoxetine hydrochloride (25 mg/1) + Olanzapine (6 mg/1)CapsuleOralTeva2012-06-19Not applicableUs0093 550420180913 8702 1mep0h9
Olanzapine and FluoxetineFluoxetine hydrochloride (25 mg/1) + Olanzapine (6 mg/1)CapsuleOralSandoz2012-11-30Not applicableUs
Olanzapine and FluoxetineFluoxetine hydrochloride (25 mg/1) + Olanzapine (3 mg/1)CapsuleOralAvKARE, Inc.2014-01-21Not applicableUs
Olanzapine and FluoxetineFluoxetine hydrochloride (25 mg/1) + Olanzapine (3 mg/1)CapsuleOralTeva2013-04-10Not applicableUs00093 5503 56 nlmimage10 a8365432
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
GaboxetineFluoxetine hydrochloride (10 mg/1) + Choline (125 mg/1)KitOralPhysician Therapeutics Llc2011-07-07Not applicableUs
Sentraflox AM-10Fluoxetine hydrochloride (10 mg/1) + Choline (250 mg/1)KitOralPhysician Therapeutics Llc2011-07-07Not applicableUs
SentroxatineFluoxetine hydrochloride (10 mg/1) + Choline (250 mg/1)KitOralPhysician Therapeutics Llc2011-02-17Not applicableUs
International/Other Brands
Adofen (Brainpharma) / Animex-On (Laboratorios) / Fluoxeren (Menarini) / Fontex (Lilly) / Ladose (Lilly)
Categories
UNII
01K63SUP8D
CAS number
54910-89-3
Weight
Average: 309.3261
Monoisotopic: 309.134048818
Chemical Formula
C17H18F3NO
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

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

Associated Conditions
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
UPotassium voltage-gated channel subfamily H member 2
inhibitor
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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

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

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

Affected organisms
  • Humans and other mammals
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
(R)-warfarinThe serum concentration of (R)-warfarin can be increased when it is combined with Fluoxetine.
(S)-WarfarinThe serum concentration of (S)-Warfarin can be increased when it is combined with Fluoxetine.
1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidineThe metabolism of Fluoxetine can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine.
1,10-PhenanthrolineThe therapeutic efficacy of Fluoxetine can be decreased when used in combination with 1,10-Phenanthroline.
2,4-thiazolidinedioneThe risk or severity of hypoglycemia can be increased when Fluoxetine is combined with 2,4-thiazolidinedione.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when Fluoxetine is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with Fluoxetine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Fluoxetine.
3,5-DiiodotyrosineThe therapeutic efficacy of 3,5-Diiodotyrosine can be decreased when used in combination with Fluoxetine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when Fluoxetine is combined with 4-Bromo-2,5-dimethoxyamphetamine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Avoid alcohol.
  • Take with food to reduce irritation and nausea.

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. [PubMed:7623609]
  2. Sommi RW, Crismon ML, Bowden CL: Fluoxetine: a serotonin-specific, second-generation antidepressant. Pharmacotherapy. 1987 Jan-Feb;7(1):1-15. [PubMed:3554156]
  3. Sohel AJ, Molla M: Fluoxetine . [PubMed:29083803]
  4. Suchard JR: Fluoxetine overdose-induced seizure. West J Emerg Med. 2008 Aug;9(3):154-6. [PubMed:19561732]
  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. [PubMed:1586402]
  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. [PubMed:30301727]
  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. [PubMed:3262026]
  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. [PubMed:10997938]
  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. [PubMed:11752104]
  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. [PubMed:9323519]
  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. [PubMed:21095492]
  12. Prozac FDA Label [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]
External Links
Human Metabolome Database
HMDB0014615
KEGG Drug
D00823
PubChem Compound
3386
PubChem Substance
46507902
ChemSpider
3269
BindingDB
30130
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
ATC Codes
N06CA03 — Fluoxetine and psycholepticsN06AB03 — Fluoxetine
AHFS Codes
  • 28:16.04.20 — Selective-serotonin Reuptake Inhibitors
MSDS
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Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingOtherType 1 Insulin-Dependent Diabetes Mellitus1
0RecruitingPreventionDepression / Stroke Hemorrhagic1
0RecruitingTreatmentHypoglycemia Associated Autonomic Failure / Type 1 Insulin-Dependent Diabetes Mellitus1
0WithdrawnPreventionCognitive Dysfunctions1
1CompletedNot AvailableHealthy Volunteers5
1CompletedBasic ScienceHealthy Volunteers1
1CompletedTreatmentCancer, Advanced / Obese experiencing rapid weight loss1
1CompletedTreatmentDepression3
1CompletedTreatmentHealthy Volunteers4
1CompletedTreatmentMajor Depressive Disorder (MDD)2
1, 2CompletedHealth Services ResearchAdolescent Depression2
1, 2CompletedTreatmentDepressive Disorder NOS / Depressive Disorder Not Otherwise Specified / Dysthymic Disorder / Major Depressive Disorder (MDD)1
1, 2CompletedTreatmentHypochondriasis1
1, 2RecruitingTreatmentSyndrome X1
2Active Not RecruitingTreatmentMotor Function / Strokes1
2Active Not RecruitingTreatmentPulmonary Arterial Hypertension (PAH)1
2Active Not RecruitingTreatmentSecondary Progressive Multiple Sclerosis (SPMS)1
2CompletedPreventionEpilepsies / Sudden unexplained death in epilepsy1
2CompletedSupportive CareMultiple System Atrophy (MSA)1
2CompletedTreatmentAlcohol Dependence / Depression1
2CompletedTreatmentAnxiety Disorders / Depression / Lung Cancers / Tiredness1
2CompletedTreatmentAutistic Disorder1
2CompletedTreatmentBack Pain / Sciatica1
2CompletedTreatmentCannabis Abuse / Major Depressive Disorder (MDD)1
2CompletedTreatmentCocaine-Related Disorders1
2CompletedTreatmentDepression1
2CompletedTreatmentDepression / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentDomestic Violence1
2CompletedTreatmentFibromyalgia / Human Growth Hormone Deficiency1
2CompletedTreatmentIntermittent Explosive Disorder1
2CompletedTreatmentMajor Depressive Disorder (MDD)2
2CompletedTreatmentMajor Depressive Disorder (MDD) / Unipolar Depression1
2CompletedTreatmentMenopausal and Postmenopausal Disorders / Moderate Depression1
2CompletedTreatmentMotor Impairments / Stroke, Ischemic1
2CompletedTreatmentPulmonary Arterial Hypertension (PAH)1
2CompletedTreatmentSevere Mood Dysregulation1
2Not Yet RecruitingTreatmentStroke, Acute / Stroke, Ischemic1
2RecruitingTreatmentBrain Diseases / Brain Infarction / Central Nervous System Diseases / Cerebral Infarctions / Cerebrovascular Accidents / Cerebrovascular Diseases / Ischemia, Brain / Nervous System Diseases / Strokes / Vascular Diseases1
2RecruitingTreatmentStroke, Acute / Visual Field Loss1
2SuspendedTreatmentOverweight and Obesity1
2TerminatedTreatmentMajor Depressive Disorder (MDD)1
2TerminatedTreatmentObsessive Compulsive Disorder (OCD)1
2WithdrawnTreatmentAutism, Early Infantile1
2WithdrawnTreatmentSevere Stroke With Affected Arm Motor Function1
2, 3CompletedTreatmentDepression1
2, 3CompletedTreatmentDepression / Suicide, Attempted1
2, 3CompletedTreatmentNon-erosive Reflux Disease (NERD)1
3Active Not RecruitingTreatmentClinical High Risk / Personality Disorders / Psychotic Disorder NOS1
3CompletedTreatmentAnxiety Disorders1
3CompletedTreatmentAutistic Disorder1
3CompletedTreatmentDepression1
3CompletedTreatmentDepression / Depressive Disorders / Major Depressive Disorder (MDD) / Moods Disorders / Psychiatric Disorder NOS1
3CompletedTreatmentDepression / Major Depressive Disorder (MDD)1
3CompletedTreatmentDepression / Major Depressive Disorder (MDD) / Nicotine Dependence1
3CompletedTreatmentDepression / Smoking1
3CompletedTreatmentEpilepsies / Ictal/Post-ictal Hypoxemia1
3CompletedTreatmentFibromyalgia / Juvenile Primary Fibromyalgia Syndrome (JPFS)1
3CompletedTreatmentMajor Depressive Disorder (MDD)11
3CompletedTreatmentObsessive Compulsive Disorder (OCD)1
3CompletedTreatmentPost Traumatic Stress Disorder (PTSD)1
3CompletedTreatmentSocial Phobia1
3CompletedTreatmentTreatment Resistant Depression (TRD)1
3RecruitingTreatmentMajor Depressive Disorder (MDD)3
3RecruitingTreatmentPremenstrual Syndrome3
3RecruitingTreatmentStrokes1
3TerminatedSupportive CareIntracerebral Hemorrhage / Motor Impairments1
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
3TerminatedTreatmentAutistic Disorder1
3TerminatedTreatmentBipolar Disorder (BD) / Depression1
3TerminatedTreatmentTreatment Resistant Depression (TRD)1
4CompletedBasic ScienceMajor Depressive Disorder (MDD)1
4CompletedDiagnosticMajor Depressive Disorder (MDD)1
4CompletedHealth Services ResearchHealthy Volunteers1
4CompletedHealth Services ResearchObsessive Compulsive Disorder (OCD)1
4CompletedOtherHealthy Controls / Major Depressive Disorder (MDD)1
4CompletedTreatmentAlcohol Dependence / Depression1
4CompletedTreatmentAlcohol-Related Disorders / Marijuana Abuse / Substance-Related Disorders1
4CompletedTreatmentAnorexia Nervosa (AN) / Eating Disorders1
4CompletedTreatmentAnxiety Disorders / Moods Disorders / Schizophrenic Disorders1
4CompletedTreatmentBipolar Disorder (BD)3
4CompletedTreatmentBipolar Disorder (BD) / Depression1
4CompletedTreatmentBody Dysmorphic Disorders1
4CompletedTreatmentBorderline Personality Disorder (BPD)1
4CompletedTreatmentDepression1
4CompletedTreatmentDepression, Bipolar2
4CompletedTreatmentDepression / Menopause1
4CompletedTreatmentDepression / Sleep Initiation and Maintenance Disorders1
4CompletedTreatmentFibromyalgia1
4CompletedTreatmentMajor Depressive Disorder (MDD)6
4CompletedTreatmentObsessive Compulsive Disorder (OCD)2
4CompletedTreatmentPremenstrual Dysphoric Disorder / Premenstrual Syndrome1
4CompletedTreatmentPsychotic Disorder NOS1
4Not Yet RecruitingTreatmentMajor Depressive Disorder (MDD)1
4RecruitingNot AvailableDepressive Disorders / Lactation1
4RecruitingBasic ScienceBipolar Disorder (BD)1
4RecruitingDiagnosticFragile X Syndrome (FXS) / Velocardiofacial Syndrome / Williams Syndrome1
4RecruitingOtherAttenuated Psychosis Syndrome1
4RecruitingTreatmentAnxiety Disorders / Obsessive Compulsive Disorder (OCD) / Psychiatric Disorder NOS1
4RecruitingTreatmentBulimia Nervosa (BN)1
4RecruitingTreatmentDepression / Hemodialysis-Induced Symptom1
4RecruitingTreatmentDepressive Disorders1
4RecruitingTreatmentStrokes1
4TerminatedPreventionDepression2
4TerminatedTreatmentBipolar Disorder (BD)1
4TerminatedTreatmentDepression1
4TerminatedTreatmentDepression / Relapsing Remitting Multiple Sclerosis (RRMS)1
4TerminatedTreatmentEnd Stage Renal Disease (ESRD) / Major Depressive Disorder (MDD)1
4TerminatedTreatmentPediatric Bipolar Disorder / Pediatric OCD1
4Unknown StatusTreatmentAlcohol Dependence / Depression / Suicidal Behaviour1
4Unknown StatusTreatmentAntidepressive Agents / Fluoxetine / Major Depressive Disorder (MDD) / Pharmacogenetics / Venlafaxine1
4Unknown StatusTreatmentBorderline Personality Disorder (BPD) / Suicide1
4Unknown StatusTreatmentMajor Depressive Disorder (MDD)3
4Unknown StatusTreatmentPosttraumatic Stress Disorder, Combat-related1
4WithdrawnTreatmentDepression1
Not AvailableActive Not RecruitingNot AvailableAnxiety Disorders / Generalized Anxiety Disorder (GAD) / Obsessive Compulsive Disorder (OCD) / Panic Disorders / Post Traumatic Stress Disorder (PTSD) / Social Anxiety Disorder (SAD)1
Not AvailableActive Not RecruitingNot AvailableMajor Depressive Disorder (MDD)1
Not AvailableActive Not RecruitingDiagnosticGeneralized Anxiety Disorder (GAD) / Separation Anxiety Disorder / Social Phobia1
Not AvailableActive Not RecruitingTreatmentDepression1
Not AvailableCompletedNot AvailableAcute Kidney Injury (AKI) / Depression1
Not AvailableCompletedNot AvailableHealthy Volunteers2
Not AvailableCompletedNot AvailableType 1 Insulin-Dependent Diabetes Mellitus1
Not AvailableCompletedBasic ScienceAnorexia Nervosa (AN)1
Not AvailableCompletedBasic ScienceDrug Drug Interaction (DDI) / Healthy Volunteers1
Not AvailableCompletedBasic ScienceMajor Depressive Disorder (MDD)2
Not AvailableCompletedOtherDepression1
Not AvailableCompletedPreventionBipolar Disorder (BD) / Depression / Psychotic Disorder NOS / Schizophrenic Disorders1
Not AvailableCompletedPreventionCardiovascular Disease (CVD) / Heart Diseases1
Not AvailableCompletedPreventionDepression1
Not AvailableCompletedSupportive CareIctal Hypoventilation / Uncontrolled Partial Epilepsy1
Not AvailableCompletedTreatmentAutism, Early Infantile1
Not AvailableCompletedTreatmentAutistic Disorder1
Not AvailableCompletedTreatmentBulimia Nervosa (BN)1
Not AvailableCompletedTreatmentCancer, Advanced1
Not AvailableCompletedTreatmentCocaine-Related Disorders / Opioid-Related Disorders1
Not AvailableCompletedTreatmentDepersonalization Disorder1
Not AvailableCompletedTreatmentDepression3
Not AvailableCompletedTreatmentDepression / Major Depressive Disorder (MDD)1
Not AvailableCompletedTreatmentDepression / Strokes1
Not AvailableCompletedTreatmentEating Disorders1
Not AvailableCompletedTreatmentGeneralized Anxiety Disorder (GAD)1
Not AvailableCompletedTreatmentMajor Depressive Disorder (MDD)3
Not AvailableCompletedTreatmentObsessive Compulsive Disorder (OCD)1
Not AvailableCompletedTreatmentPremenstrual Syndrome1
Not AvailableEnrolling by InvitationNot AvailableBipolar Disorder (BD)1
Not AvailableEnrolling by InvitationTreatmentMenopausal Hot Flushes / Quality of Life1
Not AvailableNot Yet RecruitingHealth Services ResearchPosttraumatic Stress Disorders / Traumas / Unipolar Depression1
Not AvailableNot Yet RecruitingTreatmentObsessive Compulsive Disorder (OCD)1
Not AvailableRecruitingNot AvailableObesity, Morbid1
Not AvailableRecruitingOtherObsessive Compulsive Disorder (OCD)1
Not AvailableRecruitingTreatmentAlcohol-Related Disorders / Brain Injury / Depression / Disease, Chronic / Mild Cognitive Impairment (MCI) / Pain NOS / Posttraumatic Stress Disorders / Quality of Life / Substance-Related Disorders / Suicidal Thoughts / Wounds and Injuries1
Not AvailableRecruitingTreatmentFeeding and Eating Disorders1
Not AvailableRecruitingTreatmentObsessive Compulsive Disorder (OCD)1
Not AvailableRecruitingTreatmentPost-stroke Depression1
Not AvailableTerminatedTreatmentAdolescent Depression1
Not AvailableTerminatedTreatmentCerebral Infarctions1
Not AvailableTerminatedTreatmentMajor Depressive Disorder (MDD)1
Not AvailableUnknown StatusTreatmentDepression1
Not AvailableUnknown StatusTreatmentMajor Depressive Disorder (MDD)1
Not AvailableUnknown StatusTreatmentTreatment Resistant Depression (TRD)1
Not AvailableWithdrawnNot AvailableDepression1
Not AvailableWithdrawnTreatmentPsychotic Disorder NOS1
Not AvailableWithdrawnTreatmentStrokes1

Pharmacoeconomics

Manufacturers
  • Barr laboratories inc
  • Dr reddys laboratories ltd
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  • WC Pharmaceuticals
  • Wockhardt Ltd.
  • Xactdose Inc.
Dosage forms
FormRouteStrength
CapsuleNot applicable20 mg/1
CapsuleOral10 mg
CapsuleOral20 mg/1
CapsuleOral20 mg
LiquidOral20 mg/5mL
TabletOral60 mg/1
Tablet, film coatedOral60 mg/1
CapsuleOral10 mg/1
CapsuleOral40 mg/1
Capsule, delayed releaseOral90 mg/1
Capsule, delayed release pelletsOral90 mg/1
TabletOral10 mg/1
TabletOral20 mg/1
Tablet, coatedOral10 mg/1
Tablet, coatedOral20 mg/1
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral20 mg/1
CapsuleOral
SolutionOral
CapsuleOral
SolutionOral20 mg/5mL
LiquidOral
TabletOral15 mg/1
KitOral
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)
US6960577No2005-11-012017-11-01Us
US5910319Yes1999-06-082017-11-29Us
US5985322Yes1999-11-162017-11-29Us
USRE39030No2006-03-212017-05-29Us
US5945416No1999-08-312017-03-24Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

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-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0006-9200000000-dcf68dbfd090c7fdfe11
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
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

Taxonomy

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
Trifluoromethylbenzene / Phenoxy compound / Phenol ether / Alkyl aryl ether / Aralkylamine / Secondary aliphatic amine / Ether / Secondary amine / Organic oxygen compound / Organooxygen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
aromatic ether, secondary amino compound, (trifluoromethyl)benzenes (CHEBI:86990)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serotonin:sodium symporter activity
Specific Function
Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into t...
Gene Name
SLC6A4
Uniprot ID
P31645
Uniprot Name
Sodium-dependent serotonin transporter
Molecular Weight
70324.165 Da
References
  1. 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. [PubMed:17289086]
  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. [PubMed:17335951]
  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. [PubMed:17356573]
  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. [PubMed:17486443]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  6. Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821]
  7. Fluoxetine: A case history of its discovery and preclinical development [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-...
Gene Name
HTR2C
Uniprot ID
P28335
Uniprot Name
5-hydroxytryptamine receptor 2C
Molecular Weight
51820.705 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. [PubMed:18083778]
  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. [PubMed:11082448]
  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. [PubMed:9050900]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Drug binding
Specific 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.
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. [PubMed:9050901]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Ligand-gated ion channel activity
Specific 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.
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. [PubMed:9050901]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Ligand-gated ion channel activity
Specific 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.
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. [PubMed:9050901]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Cyclin-dependent protein serine/threonine kinase regulator activity
Specific Function
Binds to the catalytic subunit of the cyclin dependent kinases and is essential for their biological function.
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. [PubMed:18371935]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarization
Specific Function
Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the ...
Gene Name
KCNH2
Uniprot ID
Q12809
Uniprot Name
Potassium voltage-gated channel subfamily H member 2
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. [PubMed:15272206]
  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. [PubMed:16967046]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Harvey AT, Preskorn SH: Fluoxetine pharmacokinetics and effect on CYP2C19 in young and elderly volunteers. J Clin Psychopharmacol. 2001 Apr;21(2):161-6. [PubMed:11270912]
  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. [PubMed:11453896]
  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. [PubMed:10997938]
  4. Flockhart Table of Drug Interactions [Link]
  5. Drug Interactions & Labeling - FDA [Link]
  6. Fluoxetine Metabolism Pathway [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. 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. [PubMed:10997938]
  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
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. 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. [PubMed:10997938]
  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. [PubMed:19442216]
  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. [PubMed:9384467]
  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. [PubMed:10192756]
  5. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Not Available
Gene Name
CYP2B
Uniprot ID
Q14097
Uniprot Name
CYP2B protein
Molecular Weight
43147.81 Da
References
  1. Haduch A, Wojcikowski J, Daniel WA: Effect of selected antidepressant drugs on cytochrome P450 2B (CYP2B) in rat liver. An in vitro and in vivo study. Pharmacol Rep. 2008 Nov-Dec;60(6):957-65. [PubMed:19211989]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Micallef J, Fakra E, Blin O: [Use of antidepressant drugs in schizophrenic patients with depression]. Encephale. 2006 Mar-Apr;32(2 Pt 1):263-9. [PubMed:16910628]
  2. 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. [PubMed:9384467]
  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. [PubMed:22707017]
  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. [PubMed:10997938]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Substrate
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Micallef J, Fakra E, Blin O: [Use of antidepressant drugs in schizophrenic patients with depression]. Encephale. 2006 Mar-Apr;32(2 Pt 1):263-9. [PubMed:16910628]
  2. DeVane CL, Donovan JL, Liston HL, Markowitz JS, Cheng KT, Risch SC, Willard L: Comparative CYP3A4 inhibitory effects of venlafaxine, fluoxetine, sertraline, and nefazodone in healthy volunteers. J Clin Psychopharmacol. 2004 Feb;24(1):4-10. [PubMed:14709940]
  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. [PubMed:10997938]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. 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. [PubMed:10997938]
  2. Ekins S, Iyer M, Krasowski MD, Kharasch ED: Molecular characterization of CYP2B6 substrates. Curr Drug Metab. 2008 Jun;9(5):363-73. [PubMed:18537573]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
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. [PubMed:10997938]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Prozac FDA Label [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Not Available
Specific Function
Functions as 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...
Gene Name
ORM1
Uniprot ID
P02763
Uniprot Name
Alpha-1-acid glycoprotein 1
Molecular Weight
23511.38 Da
References
  1. Prozac FDA Label [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Weiss J, Dormann SM, Martin-Facklam M, Kerpen CJ, Ketabi-Kiyanvash N, Haefeli WE: Inhibition of P-glycoprotein by newer antidepressants. J Pharmacol Exp Ther. 2003 Apr;305(1):197-204. [PubMed:12649369]
  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. [PubMed:21718296]
  3. Human P-glycoprotein differentially affects antidepressant drug transport: relevance to blood-brain barrier permeability [Link]

Drug created on June 13, 2005 07:24 / Updated on October 13, 2019 23:23