Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C19H21N.ClH |
| Molecular Weight | 299.838 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CNCCCC1C2=CC=CC=C2C=CC3=CC=CC=C13
InChI
InChIKey=OGQDIIKRQRZXJH-UHFFFAOYSA-N
InChI=1S/C19H21N.ClH/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;1H
| Molecular Formula | C19H21N |
| Molecular Weight | 263.3767 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 Date1967 |
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 |
|---|---|---|
| A class of tricyclic compounds blocking malaria parasite oocyst development and transmission. | 2013-01 |
|
| 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. | 2012-04-12 |
|
| Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010-12 |
|
| Tricyclic antidepressants and headaches: systematic review and meta-analysis. | 2010-10-20 |
|
| In vitro studies of DNA damage caused by tricyclic antidepressants: a role of peroxidase in the side effects of the drugs. | 2010-09-20 |
|
| Niemann-Pick disease type C. | 2010-06-03 |
|
| Antidepressant drugs in oral fluid using liquid chromatography-tandem mass spectrometry. | 2010-03 |
|
| A cell protection screen reveals potent inhibitors of multiple stages of the hepatitis C virus life cycle. | 2010-02-23 |
|
| Trimipraminium maleate. | 2010-01-16 |
|
| Research on antidepressants in India. | 2010-01 |
|
| The geriatric population and psychiatric medication. | 2010-01 |
|
| Drugs associated with more suicidal ideations are also associated with more suicide attempts. | 2009-10-02 |
|
| Accuracy of Veterans Affairs databases for diagnoses of chronic diseases. | 2009-10 |
|
| Pharmacological approaches to the treatment of obstructive sleep apnoea. | 2009-05 |
|
| Association of changes in norepinephrine and serotonin transporter expression with the long-term behavioral effects of antidepressant drugs. | 2009-05 |
|
| Obstructive sleep apnea syndrome: from phenotype to genetic basis. | 2009-04 |
|
| Depression following thrombotic cardiovascular events in elderly medicare beneficiaries: risk of morbidity and mortality. | 2009 |
|
| Prophylaxis of migraine: general principles and patient acceptance. | 2008-12 |
|
| cis-4-(Piperazin-1-yl)-5,6,7a,8,9,10,11,11a-octahydrobenzofuro[2,3-h]quinazolin-2-amine (A-987306), a new histamine H4R antagonist that blocks pain responses against carrageenan-induced hyperalgesia. | 2008-11-27 |
|
| A novel method for the determination of guanfacine in urine by gas chromatography-mass spectrometry. | 2008-10 |
|
| Psychiatric disorders and traumatic brain injury. | 2008-08 |
|
| Determination of tricyclic antidepressants in human plasma using pipette tip solid-phase extraction and gas chromatography-mass spectrometry. | 2008-07 |
|
| Atomoxetine improves sleepiness and global severity of illness but not the respiratory disturbance index in mild to moderate obstructive sleep apnea with sleepiness. | 2008-07 |
|
| Narcolepsy: current treatment options and future approaches. | 2008-06 |
|
| Protriptyline block of the human ether-à-go-go-related gene (HERG) K+ channel. | 2008-01-30 |
|
| Toward achieving optimal response: understanding and managing antidepressant side effects. | 2008 |
|
| Tricyclic antidepressant pharmacology and therapeutic drug interactions updated. | 2007-07 |
|
| Solid-phase extraction and gas chromatographic- mass spectrometric determination of the veterinary drug xylazine in human blood. | 2007-04 |
|
| Narcolepsy: treatment issues. | 2007 |
|
| Tricyclic antidepressant poisoning: an evidence-based consensus guideline for out-of-hospital management. | 2007 |
|
| Obstructive sleep apnea - management update. | 2006-09 |
|
| Prophylaxis of migraine. | 2006-09 |
|
| Bupropion SR in adults with ADHD: a short-term, placebo-controlled trial. | 2005-09 |
|
| Enhancing central noradrenergic function in depression: is there still a place for a new antidepressant? | 2005-03 |
|
| Diagnosis and treatment of sleep disorders: a brief review for clinicians. | 2003-12 |
|
| The clinical pharmacology of depressive states. | 2002-03 |
|
| Pharmacological profile of antidepressants and related compounds at human monoamine transporters. | 1997-12-11 |
|
| Haloperidol-induced catalepsy: a model for screening antidepressants effective in treatment of depression with Parkinson's disease. | 1997-12 |
|
| Bethanechol chloride can reverse erectile and ejaculatory dysfunction induced by tricyclic antidepressants and mazindol: case report. | 1986-04 |
|
| Antiarrhythmic action of bethanidine. | 1984-08-01 |
|
| Antiarrhythmic and electrophysiologic actions of bethanidine sulfate in primary ventricular fibrillation or life-threatening ventricular tachycardia. | 1984-05-01 |
|
| Pharmacologic reversal of hypotensive effect complicating antiarrhythmic therapy with bretylium. | 1982-09 |
|
| Protriptyline and tinnitus. | 1981-11 |
|
| Monoaminergic mechanisms and experimental cataplexy. | 1981-10 |
|
| Hypomania and mania after withdrawal of tricyclic antidepressants. | 1981-01 |
|
| Electrophysiologic studies of perphenazine and protriptyline in a patient with psychotropic drug-induced ventricular fibrillation. | 1979-08 |
|
| Seven cases of somnambulism induced by drugs. | 1979-07 |
|
| Hypertensive episodes after adding methylphenidate (Ritalin) to tricyclic antidepressants. (Report of three cases and review of clinical advantages). | 1972-07-01 |
|
| Tricyclic antidepressants and monoamine oxidase inhibitors. | 1971-06 |
|
| Iatrogenic epilepsy due to antidepressant drugs. | 1969-10-11 |
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.
| Substance Class |
Chemical
Created
by
admin
on
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Mon Mar 31 17:46:45 GMT 2025
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| Record UNII |
44665V00O8
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| Record Status |
Validated (UNII)
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C94727
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100000085117
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C47695
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203199
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