Details
Stereochemistry | ACHIRAL |
Molecular Formula | C19H21N |
Molecular Weight | 263.3767 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CNCCCC1C2=C(C=CC=C2)C=CC3=C1C=CC=C3
InChI
InChIKey=BWPIARFWQZKAIA-UHFFFAOYSA-N
InChI=1S/C19H21N/c1-20-14-6-11-19-17-9-4-2-7-15(17)12-13-16-8-3-5-10-18(16)19/h2-5,7-10,12-13,19-20H,6,11,14H2,1H3
DescriptionCurator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB00344 | https://www.drugs.com/pro/protriptyline.html | http://reference.medscape.com/drug/vivactil-protriptyline-342945 | https://www.ncbi.nlm.nih.gov/pubmed/26988801 | https://www.ncbi.nlm.nih.gov/pubmed/20804147
Curator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB00344 | https://www.drugs.com/pro/protriptyline.html | http://reference.medscape.com/drug/vivactil-protriptyline-342945 | https://www.ncbi.nlm.nih.gov/pubmed/26988801 | https://www.ncbi.nlm.nih.gov/pubmed/20804147
Protriptyline (trade name Vivactil) is a tricyclic antidepressant, indicated for the treatment of depression. Protriptyline acts by decreasing the reuptake of norepinephrine and to a lesser extent serotonin (5-HT) in the brain. Tricyclic antidepressants act to change the balance of naturally occurring chemicals in the brain that regulate the transmission of nerve impulses between cells. Protriptyline increases the concentration of norepinephrine and serotonin (both chemicals that stimulate nerve cells) and, to a lesser extent, blocks the action of another brain chemical, acetylcholine. The therapeutic effects of protriptyline, like other antidepressants, appear slowly. Maximum benefit is often not evident for at least two weeks after starting the drug. Protriptyline is used primarily to treat depression and to treat the combination of symptoms of anxiety and depression. Like most antidepressants of this chemical and pharmacological class, protriptyline has also been used in limited numbers of patients to treat panic disorder, obsessive-compulsive disorder, attention-deficit/hyperactivity disorder, enuresis, eating disorders such as bulimia nervosa, cocaine dependency, and the depressive phase of bipolar disorder (manic-depressive) disorder. It has also been used to support smoking cessation programs. Like all tricyclic antidepressants, protriptyline should be used cautiously and with close physician supervision. This is especially so in the elderly, or people who have benign prostatic hypertrophy (enlarged prostate gland), or urinary retention, or glaucoma, especially angle-closure glaucoma (the most severe form). Before starting treatment, people should discuss the relative risks and benefits of treatment with their doctors to help determine if protriptyline is the right antidepressant for them. A common problem with tricyclic antidepressants is sedation (drowsiness, lack of physical and mental alertness), but protriptyline is considered the least sedating agent among this class of agents. Its side effects are especially noticeable early in therapy. In most people, early tricyclic side-effects decrease or disappear entirely with time, but, until then, patients taking protriptyline should take care to assess which side-effects occur in them and should not perform hazardous activities requiring mental acuity or coordination. The side-effects are increased when protriptyline is taken with central nervous system depressants, such as alcoholic beverages, sleeping medications, other sedatives, or antihistamines, as well as with other antidepressants including SSRIs, SNRIs or monoamine oxidase Inhibitors.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26988801 |
2.8 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | VIVACTIL Approved UseProtriptyline Hydrochloride Tablets, USP are indicated for the treatment of symptoms of mental depression in patients who are under close medical supervision. Its activating properties make it particularly suitable for withdrawn and anergic patients. Launch Date-7.1452803E10 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
14.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/639433/ |
30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROTRIPTYLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1448 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/639433/ |
30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROTRIPTYLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
74.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/639433/ |
30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROTRIPTYLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
PubMed
Title | Date | PubMed |
---|---|---|
Iatrogenic epilepsy due to antidepressant drugs. | 1969 Oct 11 |
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Seven cases of somnambulism induced by drugs. | 1979 Jul |
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Hypomania and mania after withdrawal of tricyclic antidepressants. | 1981 Jan |
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Protriptyline and tinnitus. | 1981 Nov |
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Monoaminergic mechanisms and experimental cataplexy. | 1981 Oct |
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Pharmacologic reversal of hypotensive effect complicating antiarrhythmic therapy with bretylium. | 1982 Sep |
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Antiarrhythmic action of bethanidine. | 1984 Aug 1 |
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Antiarrhythmic and electrophysiologic actions of bethanidine sulfate in primary ventricular fibrillation or life-threatening ventricular tachycardia. | 1984 May 1 |
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Bethanechol chloride can reverse erectile and ejaculatory dysfunction induced by tricyclic antidepressants and mazindol: case report. | 1986 Apr |
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Haloperidol-induced catalepsy: a model for screening antidepressants effective in treatment of depression with Parkinson's disease. | 1997 Dec |
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Pharmacological profile of antidepressants and related compounds at human monoamine transporters. | 1997 Dec 11 |
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The neuropharmacology of upper airway motor control in the awake and asleep states: implications for obstructive sleep apnoea. | 2001 |
|
High-performance liquid chromatographic analysis for a non-chromophore-containing phosphatidyl inositol analog, 1-((1-O-octadecyl-2-O-methyl-sn-glycero)phospho)-1D-3-deoxy-myo-inositol, using indirect UV detection. | 2001 Apr 13 |
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Drug treatments for obstructive sleep apnoea. | 2002 |
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Effects of antidepressants in rats trained to discriminate centrally administered isoproterenol. | 2002 Aug |
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Painful ejaculation and urinary hesitancy in association with antidepressant therapy: relief with tamsulosin. | 2002 Aug |
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The effects of tricyclic antidepressants on breast cancer risk. | 2002 Jan 7 |
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The role of noradrenaline and selective noradrenaline reuptake inhibition in depression. | 2002 Oct |
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Diagnosis and treatment of sleep disorders: a brief review for clinicians. | 2003 Dec |
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Behavioral and pharmacologic therapy of obstructive sleep apnea. | 2003 Jun |
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Tricyclic antidepressants as long-acting local anesthetics. | 2003 May |
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Current use of selective serotonin reuptake inhibitors and risk of acute myocardial infarction. | 2004 |
|
Pharmacotherapies for obstructive sleep apnoea: where are we now? | 2004 |
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Intrathecal tri-cyclic antidepressants produce spinal anesthesia. | 2004 Nov |
|
Antidepressant medication use among First Nations peoples residing within British Columbia. | 2004 Nov 5 |
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Risk of fetal exposure to tricyclic antidepressants. | 2004 Oct |
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Hypersomnia. | 2005 |
|
The pharmacological management of depression. | 2005 |
|
Bupropion SR in adults with ADHD: a short-term, placebo-controlled trial. | 2005 Sep |
|
Use of antidepressant medications in relation to the incidence of breast cancer. | 2006 Apr 10 |
|
Obstructive sleep apnea - management update. | 2006 Sep |
|
Prophylaxis of migraine. | 2006 Sep |
|
Narcolepsy: treatment issues. | 2007 |
|
Solid-phase extraction and gas chromatographic- mass spectrometric determination of the veterinary drug xylazine in human blood. | 2007 Apr |
|
Tricyclic antidepressant pharmacology and therapeutic drug interactions updated. | 2007 Jul |
|
Prophylaxis of migraine: general principles and patient acceptance. | 2008 Dec |
|
Atomoxetine improves sleepiness and global severity of illness but not the respiratory disturbance index in mild to moderate obstructive sleep apnea with sleepiness. | 2008 Jul |
|
Obstructive sleep apnea syndrome: from phenotype to genetic basis. | 2009 Apr |
|
Accuracy of Veterans Affairs databases for diagnoses of chronic diseases. | 2009 Oct |
|
Drugs associated with more suicidal ideations are also associated with more suicide attempts. | 2009 Oct 2 |
|
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010 Dec |
|
Antidepressant drugs in oral fluid using liquid chromatography-tandem mass spectrometry. | 2010 Mar |
|
Tricyclic antidepressants and headaches: systematic review and meta-analysis. | 2010 Oct 20 |
|
First-in-class, dual-action, 3,5-disubstituted indole derivatives having human nitric oxide synthase (nNOS) and norepinephrine reuptake inhibitory (NERI) activity for the treatment of neuropathic pain. | 2012 Apr 12 |
|
A class of tricyclic compounds blocking malaria parasite oocyst development and transmission. | 2013 Jan |
Sample Use Guides
Usual Adult Dosage
Fifteen to 40 mg a day divided into 3 or 4 doses. If necessary, dosage may be increased to 60 mg a day. Dosages
above this amount are not recommended. Increases should be made in the morning dose.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20804147
The standard reaction mixture with calf thymus DNA contained (unless otherwise specified) 0.2 μM HRP, 13 μM per bp calf thymus DNA (∼10 ng/μL), 500 μM Protriptyline, and 500 μM H2O2 in Sorenson buffer (pH 7.0) containing 67 mM dibasic sodium phosphate and 67 mM monobasic potassium phosphate.
The standard reaction mixture with pBR322 plasmid contained 0.2 μM HRP, 3 ng/μL (∼5 μM per bp) plasmid, 500 μM Protriptyline, and 500 μMH2O2 in 67 mM Sorenson buffer (pH 7.0). The volume of the reaction mixtures prepared for the 15-well gels was 10 μL; the volume of the reactions prepared for 8-well gels was 20 μL. The components were added in the order listed. All reaction mixtures were incubated at 37 C for 1 h in a water bath.
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WHO-ATC |
N06AA11
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N0000175752
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NBK548310
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WHO-VATC |
QN06AA11
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NCI_THESAURUS |
C94727
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1663
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PROTRIPTYLINE
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7285
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4NDU154T12
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Protriptyline
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CHEMBL668
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m9280
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3391
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8886
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4976
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SUB10145MIG
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438-60-8
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8598
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DTXSID0023535
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DB00344
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8597
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4NDU154T12
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C61913
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207-119-9
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100000080857
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ACTIVE MOIETY
METABOLITE (PARENT)
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