Details
Stereochemistry | ACHIRAL |
Molecular Formula | C21H24F3N3S |
Molecular Weight | 407.4974 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1CCN(CCCN2c3ccccc3Sc4ccc(cc42)C(F)(F)F)CC1
InChI
InChIKey=ZEWQUBUPAILYHI-UHFFFAOYSA-N
InChI=1S/C21H24F3N3S/c1-25-11-13-26(14-12-25)9-4-10-27-17-5-2-3-6-19(17)28-20-8-7-16(15-18(20)27)21(22,23)24/h2-3,5-8,15H,4,9-14H2,1H3
DescriptionCurator's Comment:: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB00831 | https://www.drugs.com/cdi/trifluoperazine.html | https://clinicaltrials.gov/ct2/show/NCT02600741 | http://reference.medscape.com/drug/trifluoperazine-342991
Curator's Comment:: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB00831 | https://www.drugs.com/cdi/trifluoperazine.html | https://clinicaltrials.gov/ct2/show/NCT02600741 | http://reference.medscape.com/drug/trifluoperazine-342991
Trifluoperazine (Eskazinyl, Eskazine, Jatroneural, Modalina, Stelazine, Terfluzine, Trifluoperaz, Triftazin) is a typical antipsychotic of the phenothiazine chemical class used for the short-term treatment of certain types of anxiety. Trifluoperazine blocks postsynaptic mesolimbic dopaminergic D1 and D2 receptors in the brain; depresses the release of hypothalamic and hypophyseal hormones and is believed to depress the reticular activating system thus affecting basal metabolism, body temperature, wakefulness, vasomotor tone, and emesis. The primary application of trifluoperazine is for schizophrenia. Other official indications may vary country by country, but generally, it is also indicated for use in agitation and patients with behavioral problems, severe nausea, and vomiting as well as severe anxiety. Trials have shown a moderate benefit of this drug in patients with borderline personality disorder. A 2004 meta-analysis of the studies on trifluoperazine found that it is more likely than placebo to cause extrapyramidal side effects such as akathisia, dystonia, and Parkinsonism. It is also more likely to cause somnolence and anticholinergic side effects such as red-eye and xerostomia (dry mouth).
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26372073 |
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Target ID: CHEMBL2056 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26372073 |
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Target ID: CHEMBL234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26372073 |
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Target ID: CHEMBL219 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26372073 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | STELAZINE Approved UseFor the management of schizophrenia. Trifluoperazine HCl is effective for the short-term treatment of generalized non-psychotic anxiety. However, trifluoperazine HCl is not the first drug to be used in therapy for most patients with non-psychotic anxiety because certain risks associated with its use are not shared by common alternative treatments (i.e., benzodiazepines). When used in the treatment of non-psychotic anxiety, trifluoperazine HCl should not be administered at doses of more than 6 mg per day or for longer than 12 weeks because the use of trifluoperazine HCl at higher doses or for longer intervals may cause persistent tardive dyskinesia that may prove irreversible (see WARNINGS ). The effectiveness of trifluoperazine HCl as a treatment for non-psychotic anxiety was established in a four-week clinical multicenter study of outpatients with generalized anxiety disorder (DSM-III). This evidence does not predict that trifluoperazine HCl will be useful in patients with other non-psychotic conditions in which anxiety, or signs that mimic anxiety, are found (i.e., physical illness, organic mental conditions, agitated depression, character pathologies, etc.). Trifluoperazine HCl has not been shown effective in the management of behavioral complications in patients with mental retardation. Launch Date-3.38083185E11 |
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Primary | STELAZINE Approved UseFor the management of schizophrenia. Trifluoperazine HCl is effective for the short-term treatment of generalized non-psychotic anxiety. However, trifluoperazine HCl is not the first drug to be used in therapy for most patients with non-psychotic anxiety because certain risks associated with its use are not shared by common alternative treatments (i.e., benzodiazepines). When used in the treatment of non-psychotic anxiety, trifluoperazine HCl should not be administered at doses of more than 6 mg per day or for longer than 12 weeks because the use of trifluoperazine HCl at higher doses or for longer intervals may cause persistent tardive dyskinesia that may prove irreversible (see WARNINGS ). The effectiveness of trifluoperazine HCl as a treatment for non-psychotic anxiety was established in a four-week clinical multicenter study of outpatients with generalized anxiety disorder (DSM-III). This evidence does not predict that trifluoperazine HCl will be useful in patients with other non-psychotic conditions in which anxiety, or signs that mimic anxiety, are found (i.e., physical illness, organic mental conditions, agitated depression, character pathologies, etc.). Trifluoperazine HCl has not been shown effective in the management of behavioral complications in patients with mental retardation. Launch Date-3.38083185E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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1.053 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3137618 |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRIFLUOPERAZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10.144 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3137618 |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRIFLUOPERAZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
12.9 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3137618 |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRIFLUOPERAZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
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Page: abstract |
no | |||
Page: abstract |
no | |||
Page: abstract |
no | |||
Page: abstract |
no | |||
Page: abstract |
no | |||
Page: abstract |
no | |||
Page: abstract |
no | |||
Page: abstract |
no | |||
Page: abstract |
no | |||
Page: abstract |
no | |||
Page: 230.0 |
yes [IC50 17.6 uM] | |||
Page: abstract |
yes [IC50 8 uM] | |||
Page: abstract |
yes | |||
Page: abstract |
yes | |||
Page: abstract |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 607.0 |
likely | |||
Page: 60.0 |
yes | |||
Page: 3.0 |
yes | |||
Page: 24.0 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 1369.0 |
PubMed
Title | Date | PubMed |
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The antinicotinic effects of drugs with clinically useful sedative-antianxiety properties. | 1975 |
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Deanol in the treatment of tardive dyskinesia. | 1975 Aug |
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Drug-induced dystonia. | 1975 May |
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Low urinary dopamine and prediction of phenothiazine-induced Parkinsonism: a preliminary report. | 1976 Jun |
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Drug-induced torsade de pointes. | 1985 Nov-Dec |
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The effects of chronic treatment and withdrawal of CNS depressants on aggressive behavior. | 1989 Dec |
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Organic amnestic disorder: a long-term sequel after neuroleptic malignant syndrome. | 1991 Feb 15 |
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Biochemical properties of a minimal functional domain with ATP-binding activity of the NTPase/helicase of hepatitis C virus. | 1999 Dec |
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Neuroleptic malignant syndrome after venlafaxine. | 2000 Jan 22 |
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A new potent calmodulin antagonist with arylalkylamine structure: crystallographic, spectroscopic and functional studies. | 2000 Mar 31 |
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Calmodulin antagonists inhibit T-type Ca(2+) currents in mouse spermatogenic cells and the zona pellucida-induced sperm acrosome reaction. | 2001 Aug 1 |
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Voltage dependence of the [Ca2+](i) oscillations system, in the Mg2+ -stimulated oocyte of the prawn Palaemon serratus. | 2001 Feb |
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Use of trifluoroperazine isolates a [(3)H]Ifenprodil binding site in rat brain membranes with the pharmacology of the voltage-independent ifenprodil site on N-methyl-D-aspartate receptors containing NR2B subunits. | 2001 Jan |
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Activity of phenothiazines against antibiotic-resistant Mycobacterium tuberculosis: a review supporting further studies that may elucidate the potential use of thioridazine as anti-tuberculosis therapy. | 2001 May |
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Calcium involvement in the luminescence control of three ophiuroid species (Echinodermata). | 2002 Feb |
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Atypical antipsychotics: mechanism of action. | 2002 Feb |
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Characterization of PMCA isoforms and their contribution to transcellular Ca2+ flux in MDCK cells. | 2003 Jan |
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New agents active against Mycobacterium avium complex selected by molecular topology: a virtual screening method. | 2004 Jan |
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Discovering modes of action for therapeutic compounds using a genome-wide screen of yeast heterozygotes. | 2004 Jan 9 |
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"Wages of fear": transient threefold decrease in intracellular ATP level imposes apoptosis. | 2004 Jul 23 |
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Quaternary ammonium-linked glucuronidation of tamoxifen by human liver microsomes and UDP-glucuronosyltransferase 1A4. | 2004 Jun 1 |
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Anticataleptic effect of energostim during single treatment with trifluoperazine. | 2004 Mar |
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Search of chemical scaffolds for novel antituberculosis agents. | 2005 Apr |
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Delirium and extrapyramidal symptoms due to a lithium-olanzapine combination therapy: a case report. | 2005 Aug |
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Altered inducible nitric oxide synthase expression and nitric oxide production in the bladder of cats with feline interstitial cystitis. | 2005 Feb |
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Characterization of afloqualone N-glucuronidation: species differences and identification of human UDP-glucuronosyltransferase isoform(s). | 2005 Jan |
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Overview and emerging trends. | 2005 Oct |
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Steady-state kinetics and inhibitory action of antitubercular phenothiazines on mycobacterium tuberculosis type-II NADH-menaquinone oxidoreductase (NDH-2). | 2006 Apr 28 |
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Hydrogen peroxide inhibits IL-12 p40 induction in macrophages by inhibiting c-rel translocation to the nucleus through activation of calmodulin protein. | 2006 Feb 15 |
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Consideration of use of phenothiazines in particular trifluorperazine for epidermal growth factor receptor associated cancers. | 2007 |
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In silico prediction of pregnane X receptor activators by machine learning approaches. | 2007 Jan |
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Unusual case reports: Tardive oculogyric crisis (tardive syndromes). | 2007 Jul |
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Activity and post antifungal effect of chlorpromazine and trifluopherazine against Aspergillus, Scedosporium and zygomycetes. | 2007 Jul |
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Inflammation-related genes up-regulated in schizophrenia brains. | 2007 Sep 6 |
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Clozapine-induced tardive dystonia (blepharospasm). | 2007 Winter |
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Pleiotropic effects of cadmium in mesangial cells. | 2009 Aug 1 |
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Spectroscopic and electrochemical analysis of psychotropic drugs. | 2009 Jan |
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Finding my faith. | 2009 Jan |
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Structure of the inhibitor W7 bound to the regulatory domain of cardiac troponin C. | 2009 Jun 23 |
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In vivo reorganization of the actin cytoskeleton in leaves of Nicotiana tabacum L. transformed with plastin-GFP. Correlation with light-activated chloroplast responses. | 2009 May 29 |
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Mechanism of catch force: tethering of thick and thin filaments by twitchin. | 2010 |
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Lithium, trifluperazine and idiopathic leucopenia: Author and reviewer perspectives on how to write a good case report. | 2010 Apr |
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Acute akathisia with quetiapine: A case report and review of literature. | 2010 Dec |
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Identification of human Ether-à-go-go related gene modulators by three screening platforms in an academic drug-discovery setting. | 2010 Dec |
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Research on antidepressants in India. | 2010 Jan |
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Changes in clinical trials methodology over time: a systematic review of six decades of research in psychopharmacology. | 2010 Mar 3 |
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Inhibitory effect of chlorpromazine on RANKL-induced osteoclastogenesis in mouse bone marrow cells. | 2011 |
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Comparison of the effect of non-antifungal and antifungal agents on Candida isolates from the gastrointestinal tract. | 2012 Jan |
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Regorafenib impairs mitochondrial functions, activates AMP-activated protein kinase, induces autophagy, and causes rat hepatocyte necrosis. | 2015 Jan 2 |
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In vitro selective inhibition of human UDP-glucuronosyltransferase (UGT) 1A4 by finasteride, and prediction of in vivo drug-drug interactions. | 2015 Jan 22 |
Patents
Sample Use Guides
Initial: 2-5 mg PO q12hr
Maintenance Dose: 15-20 mg/day
Not to exceed 40mg/day
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6861140
Log-phase suspension cultures of P388/S and P388/R cells were treated with ADR (Adriamycin) (0.01 to 5.0 mkg/ml) in the presence and absence of 4 mkM TFP (Trifluoperazine ) for 24 hr at 37C. Cell counts in control and treated cultures were then determined by trypan blue dye exclusion in a hemacytometer.
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000007544
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NDF-RT |
N0000175746
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NCI_THESAURUS |
C29710
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WHO-VATC |
QN05AB06
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NDF-RT |
N0000007544
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NDF-RT |
N0000007544
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NCI_THESAURUS |
C740
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WHO-ATC |
N05AB06
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LIVERTOX |
998
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Code System | Code | Type | Description | ||
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3195
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PRIMARY | |||
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M11116
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PRIMARY | Merck Index | ||
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DB00831
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PRIMARY | |||
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Trifluoperazine
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PRIMARY | |||
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117-89-5
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PRIMARY | |||
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CHEMBL422
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PRIMARY | |||
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117-89-5
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PRIMARY | |||
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204-219-4
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PRIMARY | |||
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214
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PRIMARY | |||
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D014268
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PRIMARY | |||
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C62084
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718
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SUB11288MIG
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214IZI85K3
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5566
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PRIMARY | |||
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10800
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PRIMARY | RxNorm | ||
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TRIFLUOPERAZINE
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PRIMARY | |||
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2740
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PRIMARY |
ACTIVE MOIETY