Identification

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

Fluoxetine hydrochloride is the first agent of the class of antidepressants known as selective serotonin-reuptake inhibitors (SSRIs). Fluoxetine is a racemic mixture of the R- and S- enantiomers and are of equivalent pharmacologic activity. Despite distinct structural differences between compounds in this class, SSRIs possess similar pharmacological activity. As with other antidepressant agents, several weeks of therapy may be required before a clinical effect is seen. SSRIs are potent inhibitors of neuronal serotonin reuptake. They have little to no effect on norepinephrine or dopamine reuptake and do not antagonize α- or β-adrenergic, dopamine D2 or histamine H1 receptors. During acute use, SSRIs block serotonin reuptake and increase serotonin stimulation of somatodendritic 5-HT1A and terminal autoreceptors. Chronic use leads to desensitization of somatodendritic 5-HT1A and terminal autoreceptors. The overall clinical effect of increased mood and decreased anxiety is thought to be due to adaptive changes in neuronal function that leads to enhanced serotonergic neurotransmission. Side effects include dry mouth, nausea, dizziness, drowsiness, sexual dysfunction and headache. Side effects generally occur within the first two weeks of therapy and are usually less severe and frequent than those observed with tricyclic antidepressants. Fluoxetine may be used to treat major depressive disorder (MDD), moderate to severe bulimia nervosa, obsessive-compulsive disorder (OCD), premenstrual dysphoric disorder (PMDD), panic disorder with or without agoraphobia, and in combination with olanzapine for treatment-resistant or bipolar I depression. Fluoxetine is the most anorexic and stimulating SSRI.

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
  • 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 FluoxetineCapsule10 mgOralDr Reddy's Laboratories2000-05-31Not applicableCanada
Act FluoxetineCapsule40 mgOralDr Reddy's LaboratoriesNot applicableNot applicableCanada
Act FluoxetineCapsule20 mgOralDr Reddy's Laboratories2000-05-31Not applicableCanada
Bci FluoxetineCapsule20 mgOralBaker Cummins IncNot applicableNot applicableCanada
FluoxetineCapsule10 mgOralSivem Pharmaceuticals Ulc2011-10-14Not applicableCanada
FluoxetineCapsule10 mg/1OralBARR LABORATORIES, INC.2006-10-102006-10-10Us
FluoxetineCapsule20 mgOralMeliapharm Inc2010-06-112014-06-25Canada
FluoxetineCapsule20 mg/1OralTeva2007-01-092007-01-26Us
FluoxetineCapsule20 mgOralSanis Health Inc2009-10-22Not applicableCanada
FluoxetineCapsule20 mgOralSivem Pharmaceuticals Ulc2011-10-14Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Accel-fluoxetineCapsule10 mgOralAccel Pharma Inc2015-03-26Not applicableCanada
Accel-fluoxetineCapsule20 mgOralAccel Pharma Inc2015-03-26Not applicableCanada
Ach-fluoxetineCapsule20 mgOralAccord Healthcare Limited2012-05-01Not applicableCanada
Ach-fluoxetineCapsule10 mgOralAccord Healthcare Limited2012-10-10Not applicableCanada
Apo-fluoxetineCapsule10 mgOralApotex Corporation1996-12-31Not applicableCanada
Apo-fluoxetineSolution20 mgOralApotex Corporation1997-06-16Not applicableCanada
Apo-fluoxetineCapsule20 mgOralApotex Corporation1996-12-31Not applicableCanada
Auro-fluoxetineCapsule10 mgOralAuro Pharma Inc2012-07-24Not applicableCanada
Auro-fluoxetineCapsule20 mgOralAuro Pharma Inc2012-07-24Not applicableCanada
Ava-fluoxetineCapsule20 mgOralAvanstra Inc2011-11-282014-08-21Canada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
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 (12 mg/1)CapsuleOralSandoz2012-11-30Not applicableUs
Olanzapine and FluoxetineFluoxetine hydrochloride (25 mg/1) + Olanzapine (3 mg/1)CapsuleOralSandoz2012-11-30Not applicableUs
Olanzapine and FluoxetineFluoxetine hydrochloride (25 mg/1) + Olanzapine (12 mg/1)CapsuleOralPar Pharmaceutical2012-11-26Not applicableUs
Olanzapine and FluoxetineFluoxetine hydrochloride (25 mg/1) + Olanzapine (6 mg/1)CapsuleOralPar Pharmaceutical2012-11-26Not applicableUs
Olanzapine and FluoxetineFluoxetine hydrochloride (25 mg/1) + Olanzapine (12 mg/1)CapsuleOralAv Kare, Inc.2014-01-21Not applicableUs00093 5506 56 nlmimage10 1e270f18
Olanzapine and FluoxetineFluoxetine hydrochloride (25 mg/1) + Olanzapine (3 mg/1)CapsuleOralAv Kare, Inc.2014-01-21Not applicableUs
Olanzapine and FluoxetineFluoxetine hydrochloride (25 mg/1) + Olanzapine (12 mg/1)CapsuleOralTeva2012-06-19Not applicableUs0093 550620180913 8702 1lzk1pa
Olanzapine and FluoxetineFluoxetine hydrochloride (25 mg/1) + Olanzapine (3 mg/1)CapsuleOralTeva2013-04-10Not applicableUs00093 5503 56 nlmimage10 a8365432
Olanzapine and FluoxetineFluoxetine hydrochloride (50 mg/1) + Olanzapine (6 mg/1)CapsuleOralSandoz2012-11-30Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
GaboxetineFluoxetine hydrochloride (10 mg/1) + Choline (125 mg/1)KitPhysician Therapeutics Llc2011-07-07Not applicableUs
Sentraflox AM-10Fluoxetine hydrochloride (10 mg/1) + Choline (250 mg/1)KitPhysician Therapeutics Llc2011-07-07Not applicableUs
SentroxatineFluoxetine hydrochloride (10 mg/1) + Choline (250 mg/1)KitPhysician Therapeutics Llc2011-02-17Not applicableUs
International/Other Brands
Adofen (Brainpharma) / Animex-On (Laboratorios) / Fluoxeren (Menarini) / Fontex (Lilly) / Ladose (Lilly) / Prozac
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

Labeled indication include: major depressive disorder (MDD), moderate to severe bulimia nervosa, obsessive-compulsive disorder (OCD), premenstrual dysphoric disorder (PMDD), panic disorder with or without agoraphobia, and combination treatment with olanzapine for treatment-resistant or bipolar I depression. Unlabeled indications include: selective mutism, mild dementia-associated agitation in nonpsychotic patients, post-traumatic stress disorder (PTSD), social anxiety disorder, chronic neuropathic pain, fibromyalgia, and Raynaud's phenomenon.

Associated Conditions
Pharmacodynamics

Fluoxetine, an antidepressant agent belonging to the selective serotonin reuptake inhibitors (SSRIs), is used to treat depression, bulimia nervosa, premenstrual dysphoric disorder, panic disorder and post-traumatic stress. According to the amines hypothesis, a functional decrease in the activity of amines, such as serotonin and norepinephrine, would result in depression; a functional increase of the activity of these amines would result in mood elevation. Fluoxetine's effects are thought to be associated with the inhibition of 5HT receptor, which leads to an increase of serotonin level. Antagonism of muscarinic, histaminergic, and α1–adrenergic receptors has been hypothesized to be associated with various anticholinergic, sedative, and cardiovascular effects of classical tricyclic antidepressant (TCA) drugs. Fluoxetine binds to these and other membrane receptors from brain tissue much less potently in vitro than do the tricyclic drugs.

Mechanism of action

Metabolized to norfluoxetine, fluoxetine is a selective serotonin-reuptake inhibitor (SSRI), it blocks the reuptake of serotonin at the serotonin reuptake pump of the neuronal membrane, enhancing the actions of serotonin on 5HT1A autoreceptors. SSRIs bind with significantly less affinity to histamine, acetylcholine, and norepinephrine receptors than tricyclic antidepressant drugs.

TargetActionsOrganism
ASodium-dependent serotonin transporter
inhibitor
Human
UPotassium voltage-gated channel subfamily H member 2
inhibitor
Human
U5-hydroxytryptamine receptor 2C
antagonist
Human
UCyclin-dependent kinases regulatory subunit 1Not AvailableHuman
UNeuronal acetylcholine receptor subunit alpha-2
antagonist
Human
UNeuronal acetylcholine receptor subunit alpha-3
antagonist
Human
UNeuronal acetylcholine receptor subunit beta-4
antagonist
Human
Absorption

Well absorbed from the GI tract following oral administration. Oral bioavailability is estimated to be at least 60-80%. Peak plasma concentrations occur within 6-8 hours following a single oral administration of a 40 mg dose. The oral solution and delayed-release capsule are bioequivalent. Food does not affect the systemic bioavailability of fluoxetine but it delays the absorption by 1-2 hours (not clinically significant). Prozac Weekly capsules, a delayed–release formulation, contain enteric–coated pellets that resist dissolution until reaching a segment of the gastrointestinal tract where the pH exceeds 5.5. The enteric coating delays the onset of absorption of fluoxetine 1 to 2 hours relative to the immediate–release formulations.

Volume of distribution
  • 20-45 L/kg
Protein binding

94.5% bound to human serum proteins, including albumin and alpha-1-glycoprotein.

Metabolism

Limited data from animal studies suggest that fluoxetine may undergo first-pass metabolism may occur via the liver and/or lungs. Fluoxetine appears to be extensively metabolized, likely in the liver, to norfluoxetine and other metabolites. Norfluoxetine, the principal active metabolite, is formed via N-demethylation of fluoxetine. Norfluoxetine appears to be comparable pharmacologic potency as fluoxetine. Fluoxetine and norfluoxetine both undergo phase II glucuronidation reactions in the liver. It is also thought that fluoxetine and norfluoxetine undergo O-dealkylation to form p-trifluoromethylphenol, which is then subsequently metabolized to hippuric acid.

Route of elimination

The primary route of elimination appears to be hepatic metabolism to inactive metabolites excreted by the kidney. The S-enantiomer is eliminated more slowly and is the predominant enantiomer present at steady state.

Half life

1-3 days [acute administration]; 4-6 days [chronic administration]; 4-16 days [norfluoxetine, acute and chronic administration].

Clearance
Not Available
Toxicity

Symptoms of overdose include agitation, restlessness, hypomania, and other signs of CNS excitation. LD50=284mg/kg (orally in mice). The most frequent side effects include: nervous system effects such as anxiety, nervousness, insomnia, drowsiness, fatigue or asthenia, tremor, and dizziness or lightheadedness; GI effects such as anorexia, nausea, and diarrhea; vasodilation; dry mouth; abnormal vision; decreased libido; abnormal ejaculation; rash; and sweating. Withdrawal symptoms include flu-like symptoms, insomnia, nausea, imbalance, sensory changes and hyperactivity.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Fluoxetine Action PathwayDrug action
Fluoxetine Metabolism PathwayDrug metabolism
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Fluoxetine.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Fluoxetine.
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-isobutyl-1-methyl-7H-xanthineThe serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with Fluoxetine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Fluoxetine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Fluoxetine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Fluoxetine.
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. Wong DT, Horng JS, Bymaster FP, Hauser KL, Molloy BB: A selective inhibitor of serotonin uptake: Lilly 110140, 3-(p-trifluoromethylphenoxy)-N-methyl-3-phenylpropylamine. Life Sci. 1974 Aug 1;15(3):471-9. [PubMed:4549929]
  3. Carlsson A, Wong DT: Correction: a note on the discovery of selective serotonin reuptake inhibitors. Life Sci. 1997;61(12):1203. [PubMed:9315511]
  4. Gerber PE, Lynd LD: Selective serotonin-reuptake inhibitor-induced movement disorders. Ann Pharmacother. 1998 Jun;32(6):692-8. [PubMed:9640489]
  5. Caley CF: Extrapyramidal reactions and the selective serotonin-reuptake inhibitors. Ann Pharmacother. 1997 Dec;31(12):1481-9. [PubMed:9416386]
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
IUPHAR
203
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
FDA label
Download (194 KB)
MSDS
Download (76.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingOtherDiabetes, Diabetes Mellitus Type 11
0RecruitingTreatmentDiabetes, Diabetes Mellitus Type 1 / Hypoglycemia Associated Autonomic Failure1
0WithdrawnPreventionCognitive Dysfunctions1
1CompletedNot AvailableHealthy Volunteers4
1CompletedTreatmentCancer, Advanced / Obese experiencing rapid weight loss1
1CompletedTreatmentDepression2
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentMajor Depressive Disorder (MDD)2
1, 2CompletedHealth Services ResearchAdolescent Depression2
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
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)1
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 RecruitingTreatmentBrain Diseases / Brain Infarction / Central Nervous System Diseases / Cerebral Infarctions / Cerebrovascular Accidents / Cerebrovascular Disorders / Ischemia, Brain / Nervous System Diseases / Strokes / Vascular Diseases1
2Not Yet RecruitingTreatmentStroke, Acute / Stroke, Ischemic1
2RecruitingPreventionEpilepsies / Sudden unexplained death in epilepsy1
2RecruitingTreatmentStroke, Acute / Visual Field Loss1
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
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)9
3CompletedTreatmentPost Traumatic Stress Disorder (PTSD)1
3CompletedTreatmentSocial Phobia1
3CompletedTreatmentTreatment Resistant Depression (TRD)1
3RecruitingTreatmentClinical High Risk / Personality Disorders / Psychotic Disorder NOS1
3RecruitingTreatmentMajor Depressive Disorder (MDD)5
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)4
4CompletedTreatmentBipolar Disorder (BD) / Depression1
4CompletedTreatmentBody Dysmorphic Disorders1
4CompletedTreatmentBorderline Personality Disorder (BPD)1
4CompletedTreatmentDepression1
4CompletedTreatmentDepression, Bipolar2
4CompletedTreatmentDepression / Menopause1
4CompletedTreatmentDepression / Sleep Initiation and Maintenance Disorders1
4CompletedTreatmentDepressive Disorder NOS / Dysthymic Disorder / Major Depressive Disorder (MDD)1
4CompletedTreatmentMajor Depressive Disorder (MDD)6
4CompletedTreatmentObsessive Compulsive Disorder (OCD)2
4CompletedTreatmentPremenstrual Dysphoric Disorder / Premenstrual Syndrome1
4CompletedTreatmentPsychotic Disorder NOS1
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
4TerminatedPreventionDepression1
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 AvailableDiabetes, Diabetes Mellitus Type 11
Not AvailableCompletedNot AvailableHealthy Volunteers2
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 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 InvitationTreatmentGeneralized Anxiety Disorder (GAD)1
Not AvailableEnrolling by InvitationTreatmentMenopausal Hot Flushes / Quality of Life1
Not AvailableNot Yet RecruitingHealth Services ResearchUnipolar Depression1
Not AvailableNot Yet RecruitingTreatmentObsessive Compulsive Disorder (OCD)1
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 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
  • 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
CapsuleOral20 mg/1
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
CapsuleOral40 mg
SolutionOral20 mg
CapsuleOral
CapsuleOral60 mg
CapsuleOral20 mg
SolutionOral20 mg/5mL
CapsuleOral10 mg
LiquidOral20 mg
TabletOral15 mg/1
Kit
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)
US6960577No1997-11-012017-11-01Us
US5910319Yes1997-11-292017-11-29Us
US5985322Yes1997-11-292017-11-29Us
USRE39030No1997-05-292017-05-29Us
US5945416No1997-03-242017-03-24Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)179-182 °CNot Available
water solubility50 mg/mL at 25 °CNot Available
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
Human
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. Richman A, Heinrichs SC: Seizure prophylaxis in an animal model of epilepsy by dietary fluoxetine supplementation. Epilepsy Res. 2007 Apr;74(1):19-27. Epub 2007 Jan 9. [PubMed:17215106]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  7. 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]
Kind
Protein
Organism
Human
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]
Kind
Protein
Organism
Human
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]
Kind
Protein
Organism
Human
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
Human
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
Human
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
Human
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]

Enzymes

Kind
Protein
Organism
Human
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. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. 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]
  4. 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]
  5. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
  6. Drug Interactions & Labeling - FDA [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Urichuk L, Prior TI, Dursun S, Baker G: Metabolism of atypical antipsychotics: involvement of cytochrome p450 enzymes and relevance for drug-drug interactions. Curr Drug Metab. 2008 Jun;9(5):410-8. [PubMed:18537577]
  2. Baumann P: Pharmacokinetic-pharmacodynamic relationship of the selective serotonin reuptake inhibitors. Clin Pharmacokinet. 1996 Dec;31(6):444-69. [PubMed:8968657]
  3. 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]
  4. Rasmussen BB, Brosen K: Is therapeutic drug monitoring a case for optimizing clinical outcome and avoiding interactions of the selective serotonin reuptake inhibitors? Ther Drug Monit. 2000 Apr;22(2):143-54. [PubMed:10774624]
  5. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  6. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  7. 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]
  8. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
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. 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. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  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. 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]
  5. Woods DJ, Coulter DM, Pillans P: Interaction of phenytoin and fluoxetine. N Z Med J. 1994 Jan 26;107(970):19. [PubMed:8295752]
  6. Jalil P: Toxic reaction following the combined administration of fluoxetine and phenytoin: two case reports. J Neurol Neurosurg Psychiatry. 1992 May;55(5):412-3. [PubMed:1602320]
  7. 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. [PubMed:9384467]
  8. 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]
  9. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
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
Human
Pharmacological action
Unknown
Actions
Substrate
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  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. [PubMed:9384467]
  4. 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]
  5. 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
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Micallef J, Fakra E, Blin O: [Use of antidepressant drugs in schizophrenic patients with depression]. Encephale. 2006 Mar-Apr;32(2 Pt 1):263-9. [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. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  4. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  5. 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
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. 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
Human
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
Human
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
Kind
Protein
Organism
Human
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

Transporters

Kind
Protein
Organism
Human
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]

Drug created on June 13, 2005 07:24 / Updated on November 13, 2018 07:48