Protriptyline

Last updated
Protriptyline
Protriptyline.svg
Clinical data
Trade names Vivactyl, others
Other namesAmimethyline; Protriptyline hydrochloride; MK-240
AHFS/Drugs.com Monograph
MedlinePlus a604025
Routes of
administration 		Oral
ATC code
Legal status
Legal status
  • BR: Class C1 (Other controlled substances) [1]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability 77–93% [2]
Protein binding 92% [2]
Metabolism Hepatic
Elimination half-life 54–92 hours
Excretion Urine: 50% [2]
Feces: minor [2]
Identifiers
  • 3-(5H-dibenzo[a,d][7]annulen-5-yl)-N-methylpropan-1-amine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.006.474 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C19H21N
Molar mass 263.384 g·mol−1
3D model (JSmol)
  • c3cc2c(\C=C/c1c(cccc1)C2CCCNC)cc3
  • 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 Yes check.svgY
  • Key:BWPIARFWQZKAIA-UHFFFAOYSA-N Yes check.svgY
   (verify)

Protriptyline, sold under the brand name Vivactil among others, is a tricyclic antidepressant (TCA), specifically a secondary amine, indicated for the treatment of depression and attention-deficit hyperactivity disorder (ADHD). Uniquely among most of the TCAs, protriptyline tends to be energizing instead of sedating, and is sometimes used for narcolepsy to achieve a wakefulness-promoting effect.

Contents

TCAs including protriptyline are also used to reduce the incidence of recurring headaches such as migraine, and for other types of chronic pain.

Medical uses

Protriptyline is used primarily to treat depression and to treat the combination of symptoms of anxiety and depression. [3] 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. [4]

Protriptyline is available as 5 mg and 10 mg tablets. [5] Doses range from 15 to 40 mg per day and can be taken in one daily dose or divided into up to four doses daily. [5] Some people with severe depression may require up to 60 mg per day. [5]

In adolescents and people over age 60, therapy should be initiated at a dose of 5 mg three times a day and increased under supervision of a physician as needed. [5] Patients over age 60 who are taking daily doses of 20 mg or more should be closely monitored for side effects such as rapid heart rate and urinary retention. [5]

Like all TCAs, protriptyline should be used cautiously and with close physician supervision. This is especially so for persons with glaucoma, especially angle-closure glaucoma (the most severe form) or urinary retention, for men with benign prostatic hypertrophy (enlarged prostate gland), and for the elderly. 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. [6]

Contraindications

Protriptyline may increase heart rate and stress on the heart. [7] It may be dangerous for people with cardiovascular disease, especially those who have recently had a heart attack, to take this drug or other antidepressants in the same pharmacological class. [7] In rare cases in which patients with cardiovascular disease must take protriptyline, they should be monitored closely for cardiac rhythm disturbances and signs of cardiac stress or damage. [7]

When protriptyline is used to treat the depressive component of schizophrenia, psychotic symptoms may be aggravated. Likewise, in manic-depressive psychosis, depressed patients may experience a shift toward the manic phase if they are treated with an antidepressant drug. Paranoid delusions, with or without associated hostility, may be exaggerated. [5] In any of these circumstances, it may be advisable to reduce the dose of protriptyline or to use an antipsychotic drug concurrently. [5]

Side effects

Protriptyline shares side effects common to all TCAs. [3] The most frequent of these are dry mouth, constipation, urinary retention, increased heart rate, sedation, irritability, decreased coordination, anxiety, blood disorders, confusion, decreased libido, dizziness, flushing, headache, impotence, insomnia, low blood pressure, nightmares, rapid or irregular heartbeat, rash, seizures, sensitivity to sunlight, stomach and intestinal problems. [5] Other more complicated side effects include; chest pain or heavy feeling, pain spreading to the arm or shoulder, nausea, sweating, general ill feeling; sudden numbness or weakness, especially on one side of the body; sudden headache, confusion, problems with vision, speech, or balance; hallucinations, or seizure (convulsions); easy bruising or bleeding, unusual weakness; restless muscle movements in your eyes, tongue, jaw, or neck; urinating less than usual or not at all; extreme thirst with headache, nausea, vomiting, and weakness; or feeling light-headed or fainting. [5]

Dry mouth, if severe to the point of causing difficulty speaking or swallowing, may be managed by dosage reduction or temporary discontinuation of the drug. [3] Patients may also chew sugarless gum or suck on sugarless candy in order to increase the flow of saliva. Some artificial saliva products may give temporary relief. [3] Men with prostate enlargement who take protriptyline may be especially likely to have problems with urinary retention. [5] Symptoms include having difficulty starting a urine flow and more difficulty than usual passing urine. [5] In most cases, urinary retention is managed with dose reduction or by switching to another type of antidepressant. [5] In extreme cases, patients may require treatment with bethanechol, a drug that reverses this particular side effect. [5]

A common problem with TCAs is sedation (drowsiness, lack of physical and mental alertness), but protriptyline is considered the least sedating agent among this class of agents. [6] Its side effects are especially noticeable early in therapy. [6] In most people, early TCA 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. [8] Protriptyline may increase the possibility of having seizures. [8]

Withdrawal

Though not indicative of addiction, abrupt cessation of treatment after prolonged therapy may produce nausea, headache, and malaise. [7]

List of side effects

Overdose

Deaths may occur from overdose with this class of drugs. [8] Multiple drug ingestion (including alcohol) is common in deliberate TCA overdose. [8] As management of overdose is complex and changing, it is recommended that the physician contact a poison control center for current information on treatment. [3] Signs and symptoms of toxicity develop rapidly after TCA overdose, therefore, hospital monitoring is required as soon as possible. [8]

Critical manifestations of overdose include: cardiac dysrhythmias, severe hypotension, convulsions, and CNS depression, including coma. [5] Changes in the electrocardiogram, particularly in QRS axis or width, are clinically significant indicators of TCA toxicity. [5] Other signs of overdose may include: confusion, disturbed concentration, transient visual hallucinations, dilated pupils, agitation, hyperactive reflexes, stupor, drowsiness, muscle rigidity, vomiting, hypothermia, hyperpyrexia. [5]

Interactions

The side effects of protriptyline are increased when it 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. [8] It may be dangerous to take protriptyline in combination with these substances. [8]

Pharmacology

Pharmacodynamics

Protriptyline [10]
SiteKi (nM)SpeciesRef
SERT Tooltip Serotonin transporter19.6Human [11]
NET Tooltip Norepinephrine transporter1.41Human [11]
DAT Tooltip Dopamine transporter2,100Human [11]
5-HT1A 3,800Human [12]
5-HT2A 70Human [12]
5-HT2C NDNDND
α1 130Human [13]
α2 6,600Human [13]
β >10,000Monkey/rat [14]
D2 2,300Human [13]
H1 7.2–25Human [15] [13]
H2 398Human [15]
H3 >100,000Human [15]
H4 15,100Human [15]
mACh Tooltip Muscarinic acetylcholine receptor25Human [13] [16]
Values are Ki (nM). The smaller the value, the more strongly the drug binds to the site.

Protriptyline acts by decreasing the reuptake of norepinephrine and to a lesser extent serotonin (5-HT) in the brain. [7] Its affinity for the human norepinephrine transporter (NET) is 1.41 nM, 19.6 nM for the serotonin transporter and 2,100 nM for the dopamine transporter. [17] TCAs 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. [7] 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. [7]

Protriptyline is a TCA. [5] It was thought that TCAs work by inhibiting the reuptake of the neurotransmitters norepinephrine and serotonin by neurons. [5] However, this response occurs immediately, yet mood does not lift for around two weeks. [5] It is now thought that changes occur in receptor sensitivity in the cerebral cortex and hippocampus. [5] The hippocampus is part of the limbic system, a part of the brain involved in emotions. TCAs are also known as effective analgesics for different types of pain, especially neuropathic or neuralgic pain. [5] A precise mechanism for their analgesic action is unknown, but it is thought that they modulate anti-pain opioid systems in the central nervous system via an indirect serotonergic route. TCAs are also effective in migraine prophylaxis, but not in abortion of acute migraine attack. [5] The mechanism of their anti-migraine action is also thought to be serotonergic, similar to psilocybin. [5]

Pharmacokinetics

Metabolic studies indicate that protriptyline is well absorbed from the gastrointestinal tract and is rapidly sequestered in tissues. [3] Relatively low plasma levels are found after administration, and only a small amount of unchanged drug is excreted in the urine of dogs and rabbits. [3] Preliminary studies indicate that demethylation of the secondary amine moiety occurs to a significant extent, and that metabolic transformation takes place in the liver. [3] It penetrates the brain rapidly in mice and rats, and moreover that which is present in the brain is almost all unchanged drug. [3] Studies on the disposition of radioactive protriptyline in human test subjects showed significant plasma levels within 2 hours, peaking at 8 to 12 hours, then declining gradually. [3]

Urinary excretion studies in the same subjects showed significant amounts of radioactivity in 2 hours. [3] The rate of excretion was slow. [3] Cumulative urinary excretion during 16 days accounted for approximately 50% of the drug. The fecal route of excretion did not seem to be important. [3]

Protriptyline has uniquely low dosing among TCAs, likely due to its exceptionally long terminal half-life. [18] It is used in dosages of 15 to 40 mg/day, whereas most other TCAs are used at dosages of 75 to 300 mg/day. [18] The maximum dose is 60 mg/day. [18] Therapeutic levels of protriptyline are typically in the range of 70 to 250 ng/mL (266-950 nmol/L), which is similar to that of other TCAs [19] [20] [21]

Chemistry

Protriptyline is a tricyclic compound, specifically a dibenzocycloheptadiene, and possesses three rings fused together with a side chain attached in its chemical structure. [22] Other dibenzocycloheptadiene TCAs include amitriptyline, nortriptyline, and butriptyline. [22] [23] Protriptyline is a secondary amine TCA, with its N-methylated analog N–methylprotriptyline being a tertiary amine, and a structural isomer of amitriptyline. [24] [25] The tertiary amine analog of protriptyline, N–methylprotriptyline, has not been marketed. Other secondary amine TCAs include desipramine and nortriptyline. [26] [27] The chemical name of protriptyline is 3-(5H-dibenzo[a,d][7]annulen-5-yl)-N-methylpropan-1-amine and its free base form has a chemical formula of C19H21N1 with a molecular weight of 263.377 g/mol. [28] The drug is used commercially mostly as the hydrochloride salt; the free base form is not used. [28] [29] The CAS Registry Number of the free base is 438-60-8 and of the hydrochloride is 1225-55-4. [28] [29]

History

Protriptyline was developed by Merck. [30] It was patented in 1962 and first appeared in the literature in 1964. [30] The drug was first introduced for the treatment of depression in 1966. [30] [31]

Society and culture

Generic names

Protriptyline is the English and French generic name of the drug and its INN Tooltip International Nonproprietary Name, BAN Tooltip British Approved Name, and DCF Tooltip Dénomination Commune Française, while protriptyline hydrochloride is its USAN Tooltip United States Adopted Name, USP Tooltip United States Pharmacopeia, and BANM Tooltip British Approved Name. [28] [29] [32] [33] Its generic name in Spanish and Italian and its DCIT Tooltip Denominazione Comune Italiana are protriptylina, in German is protriptylin, and in Latin is protriptylinum. [29] [33]

Brand names

Protriptyline is or has been marketed throughout the world under a variety of brand names including Anelun, Concordin, Maximed, Triptil, and Vivactil. [28] [29]

Availability

The sale of protriptyline was discontinued in the United Kingdom, Australia, and Ireland in 2000. [34] It remains available worldwide only in the United States as of 2024. [33] [35]

See also

Related Research Articles

<span class="mw-page-title-main">Tricyclic antidepressant</span> Class of medications

Tricyclic antidepressants (TCAs) are a class of medications that are used primarily as antidepressants. TCAs were discovered in the early 1950s and were marketed later in the decade. They are named after their chemical structure, which contains three rings of atoms. Tetracyclic antidepressants (TeCAs), which contain four rings of atoms, are a closely related group of antidepressant compounds.

<span class="mw-page-title-main">Maprotiline</span> Antidepressant

Maprotiline, sold under the brand name Ludiomil among others, is a tetracyclic antidepressant (TeCA) that is used in the treatment of depression. It may alternatively be classified as a tricyclic antidepressant (TCA), specifically a secondary amine. In terms of its chemistry and pharmacology, maprotiline is closely related to such-other secondary-amine TCAs as nortriptyline and protriptyline and has similar effects to them, albeit with more distinct anxiolytic effects. Additionally, whereas protriptyline tends to be somewhat more stimulating and in any case is distinctly more-or-less non-sedating, mild degrees of sedation may be experienced with maprotiline.

<span class="mw-page-title-main">Amitriptyline</span> Tricyclic antidepressant

Amitriptyline, sold under the brand name Elavil among others, is a tricyclic antidepressant primarily used to treat major depressive disorder, and a variety of pain syndromes such as neuropathic pain, fibromyalgia, migraine and tension headaches. Due to the frequency and prominence of side effects, amitriptyline is generally considered a second-line therapy for these indications.

<span class="mw-page-title-main">Serotonin–norepinephrine reuptake inhibitor</span> Class of antidepressant medication

Serotonin–norepinephrine reuptake inhibitors (SNRIs) are a class of antidepressant medications used to treat major depressive disorder (MDD), anxiety disorders, social phobia, chronic neuropathic pain, fibromyalgia syndrome (FMS), and menopausal symptoms. Off-label uses include treatments for attention-deficit hyperactivity disorder (ADHD), obsessive–compulsive disorder (OCD), and migraine prevention. SNRIs are monoamine reuptake inhibitors; specifically, they inhibit the reuptake of serotonin and norepinephrine. These neurotransmitters are thought to play an important role in mood regulation. SNRIs can be contrasted with the selective serotonin reuptake inhibitors (SSRIs) and norepinephrine reuptake inhibitors (NRIs), which act upon single neurotransmitters.

<span class="mw-page-title-main">Imipramine</span> Antidepressant

Imipramine, sold under the brand name Tofranil, among others, is a tricyclic antidepressant (TCA) mainly used in the treatment of depression. It is also effective in treating anxiety and panic disorder. Imipramine is taken by mouth.

<span class="mw-page-title-main">Desipramine</span> Antidepressant

Desipramine, sold under the brand name Norpramin among others, is a tricyclic antidepressant (TCA) used in the treatment of depression. It acts as a relatively selective norepinephrine reuptake inhibitor, though it does also have other activities such as weak serotonin reuptake inhibitory, α1-blocking, antihistamine, and anticholinergic effects. The drug is not considered a first-line treatment for depression since the introduction of selective serotonin reuptake inhibitor (SSRI) antidepressants, which have fewer side effects and are safer in overdose.

<span class="mw-page-title-main">Clomipramine</span> Antidepressant

Clomipramine, sold under the brand name Anafranil among others, is a tricyclic antidepressant (TCA). It is used in the treatment of various conditions, most notably obsessive–compulsive disorder but also many other disorders, including hyperacusis, panic disorder, major depressive disorder, trichotillomania, body dysmorphic disorder and chronic pain. It has also been notably used to treat premature ejaculation and the cataplexy associated with narcolepsy.

<span class="mw-page-title-main">Nortriptyline</span> Antidepressant medication

Nortriptyline, sold under the brand name Aventyl, among others, is a tricyclic antidepressant. This medicine is also sometimes used for neuropathic pain, attention deficit hyperactivity disorder (ADHD), smoking cessation and anxiety. As with many antidepressants, its use for young people with depression and other psychiatric disorders may be limited due to increased suicidality in the 18–24 population initiating treatment. Nortriptyline is a less preferred treatment for ADHD and stopping smoking. It is taken by mouth.

<span class="mw-page-title-main">Doxepin</span> Medication to treat depressive disorder, anxiety disorders, chronic hives, and trouble sleeping

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<span class="mw-page-title-main">Trimipramine</span> Antidepressant

Trimipramine, sold under the brand name Surmontil among others, is a tricyclic antidepressant (TCA) which is used to treat depression. It has also been used for its sedative, anxiolytic, and weak antipsychotic effects in the treatment of insomnia, anxiety disorders, and psychosis, respectively. The drug is described as an atypical or "second-generation" TCA because, unlike other TCAs, it seems to be a fairly weak monoamine reuptake inhibitor. Similarly to other TCAs, however, trimipramine does have antihistamine, antiserotonergic, antiadrenergic, antidopaminergic, and anticholinergic activities.

<span class="mw-page-title-main">Trazodone</span> Antidepressant medication

Trazodone, sold under many brand names, is an antidepressant medication, used to treat major depressive disorder, anxiety disorders, and insomnia. It is a phenylpiperazine compound of the serotonin antagonist and reuptake inhibitor (SARI) class. The medication is taken orally.

<span class="mw-page-title-main">Chlorprothixene</span> Typical antipsychotic medication

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<span class="mw-page-title-main">Dosulepin</span> Antidepressant

Dosulepin, also known as dothiepin and sold under the brand name Prothiaden among others, is a tricyclic antidepressant (TCA) which is used in the treatment of depression. Dosulepin was once the most frequently prescribed antidepressant in the United Kingdom, but it is no longer widely used due to its relatively high toxicity in overdose without therapeutic advantages over other TCAs. It acts as a serotonin–norepinephrine reuptake inhibitor (SNRI) and also has other activities including antihistamine, antiadrenergic, antiserotonergic, anticholinergic, and sodium channel-blocking effects.

<span class="mw-page-title-main">Dibenzepin</span> Chemical compound

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<span class="mw-page-title-main">Desvenlafaxine</span> Medication used to treat major depressive disorder

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<span class="mw-page-title-main">Butriptyline</span> Atypical tricyclic antidepressant medication

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<span class="mw-page-title-main">Lofepramine</span> Chemical compound

Lofepramine, sold under the brand names Gamanil, Lomont, and Tymelyt among others, is a tricyclic antidepressant (TCA) which is used to treat depression. The TCAs are so named as they share the common property of having three rings in their chemical structure. Like most TCAs lofepramine is believed to work in relieving depression by increasing concentrations of the neurotransmitters norepinephrine and serotonin in the synapse, by inhibiting their reuptake. It is usually considered a third-generation TCA, as unlike the first- and second-generation TCAs it is relatively safe in overdose and has milder and less frequent side effects.

<span class="mw-page-title-main">Iprindole</span> Atypical tricyclic antidepressant

Iprindole, sold under the brand names Prondol, Galatur, and Tertran, is an atypical tricyclic antidepressant (TCA) that has been used in the United Kingdom and Ireland for the treatment of depression but appears to no longer be marketed. It was developed by Wyeth and was marketed in 1967. The drug has been described by some as the first "second-generation" antidepressant to be introduced. However, it was very little-used compared to other TCAs, with the number of prescriptions dispensed only in the thousands.

<span class="mw-page-title-main">Opipramol</span> Drug used to treat depressive and anxiety disorders

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Selective norepinephrine reuptake inhibitors (sNRIs) are a class of drugs that have been marketed as antidepressants and are used for various mental disorders, mainly depression and attention-deficit hyperactivity disorder (ADHD). The norepinephrine transporter (NET) serves as the fundamental mechanism for the inactivation of noradrenergic signaling because of the NET termination in the reuptake of norepinephrine (NE). The selectivity and mechanism of action for the NRI drugs remain mostly unresolved and, to date, only a limited number of NRI-selective inhibitors are available. The first commercially available selective NRI was the drug reboxetine (Edronax), developed as a first-line therapy for major depressive disorder. Atomoxetine (Strattera) is another potent and selective NRI which is also effective and well tolerated for the treatment of ADHD in adults; it may also be a new treatment option for adults with ADHD, particularly for those patients at risk of substance abuse.

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