Nortriptyline

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Nortriptyline
Nortriptyline.svg
Nortriptyline-from-4M48-ball-and-stick.png
Clinical data
Trade names Aventyl, others
Other namesDesitriptyline; ELF-101; E.L.F. 101; N-7048
AHFS/Drugs.com Monograph
MedlinePlus a682620
License data
Pregnancy
category
Routes of
administration 		By mouth
Drug class Tricyclic antidepressant (TCA)
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 32–79% [6]
Protein binding 92% [6]
Metabolism Liver
Metabolites 10-E-Hydroxynortriptyline
Elimination half-life 18–44 hours (mean 30 hours) [6]
Excretion Urine: 40% [6]
Feces: minor [6]
Identifiers
  • 3-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.000.717 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(c1c(cccc1)CC2)=C/CCNC)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/h2-5,7-11,20H,6,12-14H2,1H3 Yes check.svgY
  • Key:PHVGLTMQBUFIQQ-UHFFFAOYSA-N Yes check.svgY
   (verify)

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. [7] [8] 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. [8] Nortriptyline is not a preferred treatment for attention deficit hyperactivity disorder or smoking cessation. [8] It is taken by mouth. [8]

Contents

Common side effects include dry mouth, constipation, blurry vision, sleepiness, low blood pressure with standing, and weakness. [8] Serious side effects may include seizures, an increased risk of suicide in those less than 25 years of age, urinary retention, glaucoma, mania, and a number of heart issues. [8] Nortriptyline may cause problems if taken during pregnancy. [8] Use during breastfeeding appears to be relatively safe. [7] It is a tricyclic antidepressant (TCA) and is believed to work by altering levels of serotonin and norepinephrine. [8]

Nortriptyline was approved for medical use in the United States in 1964. [8] It is available as a generic medication. [7] In 2022, it was the 191st most commonly prescribed medication in the United States, with more than 2 million prescriptions. [9] [10]

Medical uses

Nortriptyline is used to treat depression. [11] A level between 50 and 150 ng/mL of nortriptyline in the blood generally corresponds with an antidepressant effect. [12]

It is also used off-label for the treatment of panic disorder, ADHD, irritable bowel syndrome, tobacco-cessation, migraine prophylaxis and chronic pain or neuralgia modification, particularly temporomandibular joint disorder. [13] [14] [15] [16]

Irritable bowel syndrome

Nortriptyline has also been used as an off-label treatment for irritable bowel syndrome (IBS). [17]

Contraindications

Nortriptyline should not be used in the acute recovery phase after myocardial infarction (heart attack). [5] Use of tricyclic antidepressants along with a monoamine oxidase inhibitor (MAOI), linezolid, or IV methylene blue are contraindicated as it can cause an increased risk of developing serotonin syndrome. [18]

Closer monitoring is required for those with a history of cardiovascular disease, [19] stroke, glaucoma, or seizures, as well as in persons with hyperthyroidism or receiving thyroid hormones.

Side effects

The most common side effects include dry mouth, sedation, constipation, increased appetite, blurred vision and tinnitus. [20] [21] An occasional side effect is a rapid or irregular heartbeat. Alcohol may exacerbate some of its side effects. [20]

Overdose

The symptoms and the treatment of an overdose are generally the same as for the other tricyclic antidepressants, including anticholinergic effects, serotonin syndrome and adverse cardiac effects. TCAs, particularly nortriptyline, have a relatively narrow therapeutic index, which increase the chance of an overdose (both accidental and intentional). Symptoms of overdose include: irregular heartbeat, seizures, coma, confusion, hallucination, widened pupils, drowsiness, agitation, fever, low body temperature, stiff muscles and vomiting. [11]

Interactions

Excessive consumption of alcohol in combination with nortriptyline therapy may have a potentiating effect, which may lead to the danger of increased suicidal attempts or overdosage, especially in patients with histories of emotional disturbances or suicidal ideation.

It may interact with the following drugs: [22]

Pharmacology

Nortriptyline is a strong norepinephrine reuptake inhibitor and a moderate serotonin reuptake inhibitor. Its pharmacologic profile is as the table shows with (inhibition or antagonism of all sites). [23] [24]

Pharmacodynamics

Nortriptyline [23]
SiteKi (nM)SpeciesRef
SERT Tooltip Serotonin transporter15–18Human [25] [26]
NET Tooltip Norepinephrine transporter1.8–4.4Human [25] [26]
DAT Tooltip Dopamine transporter1,140Human [25]
5-HT1A 294Human [27]
5-HT2A 5.0–41Human/rat [28] [27]
5-HT2C 8.5Rat [28]
5-HT3 1,400Rat [29]
5-HT6 148Rat [30]
α1 55Human [27]
α2 2,030Human [27]
β >10,000Rat [31]
D2 2,570Human [27]
H1 3.0–15Human [32] [27] [33]
H2 646Human [32]
H3 45,700Human [32]
H4 6,920Human [32]
mACh Tooltip Muscarinic acetylcholine receptor37Human [27]
   M1 40Human [34]
   M2 110Human [34]
   M3 50Human [34]
   M4 84Human [34]
   M5 97Human [34]
σ1 2,000Guinea pig [35]
Values are Ki (nM). The smaller the value, the more strongly the drug binds to the site.

Nortriptyline is an active metabolite of amitriptyline by demethylation in the liver. Chemically, it is a secondary amine dibenzocycloheptene and pharmacologically it is classed as a first-generation antidepressant. [36]

Nortriptyline may also have a sleep-improving effect due to antagonism of the H1 and 5-HT2A receptors. [37] In the short term, however, nortriptyline may disturb sleep due to its activating effect.

In one study, nortriptyline had the highest affinity for the dopamine transporter among the tricyclic antidepressants (KD = 1,140 nM) besides amineptine (a norepinephrine–dopamine reuptake inhibitor), although its affinity for this transporter was still 261- and 63-fold lower than for the norepinephrine and serotonin transporters (KD = 4.37 and 18 nM, respectively). [25]

Pharmacogenetics

Nortriptyline is metabolized in the liver by the hepatic enzyme CYP2D6, and genetic variations within the gene coding for this enzyme can affect its metabolism, leading to changes in the concentrations of the drug in the body. [38] Increased concentrations of nortriptyline may increase the risk for side effects, including anticholinergic and nervous system adverse effects, while decreased concentrations may reduce the drug's efficacy. [39] [40] [41]

Individuals can be categorized into different types of CYP2D6 metabolizers depending on which genetic variations they carry. These metabolizer types include poor, intermediate, extensive, and ultrarapid metabolizers. Most individuals (about 77–92%) are extensive metabolizers, [41] and have "normal" metabolism of nortriptyline. Poor and intermediate metabolizers have reduced metabolism of the drug as compared to extensive metabolizers; patients with these metabolizer types may have an increased probability of experiencing side effects. Ultrarapid metabolizers use nortriptyline much faster than extensive metabolizers; patients with this metabolizer type may have a greater chance of experiencing pharmacological failure. [39] [40] [41]

The Clinical Pharmacogenetics Implementation Consortium recommends avoiding nortriptyline in persons who are CYP2D6 ultrarapid or poor metabolizers, due to the risk of a lack of efficacy and side effects, respectively. A reduction in starting dose is recommended for patients who are CYP2D6 intermediate metabolizers. If use of nortriptyline is warranted, therapeutic drug monitoring is recommended to guide dose adjustments. [41] The Dutch Pharmacogenetics Working Group recommends reducing the dose of nortriptyline in CYP2D6 poor or intermediate metabolizers, and selecting an alternative drug or increasing the dose in ultrarapid metabolizers. [42]

Chemistry

Nortriptyline is a tricyclic compound, specifically a dibenzocycloheptadiene, and possesses three rings fused together with a side chain attached in its chemical structure. [43] Other dibenzocycloheptadiene tricyclic antidepressants include amitriptyline (N-methylnortriptyline), protriptyline, and butriptyline. [43] [44] Nortriptyline is a secondary amine tricyclic antidepressant, with its N-methylated parent amitriptyline being a tertiary amine. [45] [46] Other secondary amine tricyclic antidepressants include desipramine and protriptyline. [47] [48] The chemical name of nortriptyline is 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine and its free base form has a chemical formula of C19H21N1 with a molecular weight of 263.384 g/mol. [49] The drug is used commercially mostly as the hydrochloride salt; the free base form is used rarely. [49] [50] The CAS Registry Number of the free base is 72-69-5 and of the hydrochloride is 894-71-3. [49] [50] [51]

History

Nortriptyline was developed by Geigy. [52] It first appeared in the literature in 1962 and was patented the same year. [52] The drug was first introduced for the treatment of depression in 1963. [52] [53]

Society and culture

50 mg (left) and 25 mg generic nortriptyline HCl capsules made by Teva Pharmaceutical Industries. Nortriptyline HCL capsules - 50mg and 25mg.JPG
50 mg (left) and 25 mg generic nortriptyline HCl capsules made by Teva Pharmaceutical Industries.

Generic names

Nortriptyline is the generic name of the drug and its INN Tooltip International Nonproprietary Name, BAN Tooltip British Approved Name, and DCF Tooltip Dénomination Commune Française, while nortriptyline hydrochloride is its USAN Tooltip United States Adopted Name, USP Tooltip United States Pharmacopeia, BANM Tooltip British Approved Name, and JAN Tooltip Japanese Accepted Name. [49] [50] [54] [55] Its generic name in Spanish and Italian and its DCIT Tooltip Denominazione Comune Italiana are nortriptilina, in German is nortriptylin, and in Latin is nortriptylinum. [49] [50] [54] [55]

Brand names

Brand names of nortriptyline include Allegron, Aventyl, Noritren, Norpress, Nortrilen, Norventyl, Norzepine, Pamelor, and Sensival, among many others. [49] [50] [55]

Research

Although not approved by the US Food and Drug Administration (FDA) for neuropathic pain, randomized controlled trials have demonstrated the effectiveness of tricyclic antidepressants for the treatment of this condition in both depressed and non-depressed individuals. In 2010, an evidence-based guideline sponsored by the International Association for the Study of Pain recommended nortriptyline as a first-line medication for neuropathic pain. [56] However, in a 2015 Cochrane systematic review the authors did not recommend nortriptyline as a first-line agent for neuropathic pain. [57] [58]

It may be effective in the treatment of tobacco-cessation. [59] [60]

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">Bupropion</span> Medication mainly used for depression and smoking cessation

Bupropion, formerly called amfebutamone, and sold under the brand name Wellbutrin among others, is an atypical antidepressant primarily used to treat major depressive disorder, seasonal affective disorder and to support smoking cessation. It is also popular as an add-on medication in the cases of "incomplete response" to the first-line selective serotonin reuptake inhibitor (SSRI) antidepressant. Bupropion has several features that distinguish it from other antidepressants: it does not usually cause sexual dysfunction, it is not associated with weight gain and sleepiness, and it is more effective than SSRIs at improving symptoms of hypersomnia and fatigue. Bupropion, particularly the immediate release formulation, carries a higher risk of seizure than many other antidepressants, hence caution is recommended in patients with a history of seizure disorder. The medication is taken by mouth.

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

Venlafaxine, sold under the brand name Effexor/Efexor among others, is an antidepressant medication of the serotonin–norepinephrine reuptake inhibitor (SNRI) class. It is used to treat major depressive disorder, generalized anxiety disorder, panic disorder, and social anxiety disorder. Studies have shown that venlafaxine improves post-traumatic stress disorder (PTSD). It may also be used for chronic neuropathic pain. It is taken orally. It is also available as the salt venlafaxine besylate in an extended-release formulation.

<span class="mw-page-title-main">Duloxetine</span> Antidepressant medication used also for treatment of anxiety and chronic pain

Duloxetine, sold under the brand name Cymbalta among others, is a medication used to treat major depressive disorder, generalized anxiety disorder, obsessive-compulsive disorder, fibromyalgia, neuropathic pain and central sensitization. It is taken by mouth.

<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), and obsessive–compulsive disorder (OCD). 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">Atomoxetine</span> Medication used to treat ADHD

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

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

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<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">Viloxazine</span> Medication used to treat ADHD

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

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

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

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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">Protriptyline</span> Chemical compound

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<span class="mw-page-title-main">Desmetramadol</span> Opioid painkiller medication

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<span class="mw-page-title-main">Vortioxetine</span> Serotonin modulator antidepressant

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A monoamine reuptake inhibitor (MRI) is a drug that acts as a reuptake inhibitor of one or more of the three major monoamine neurotransmitters serotonin, norepinephrine, and dopamine by blocking the action of one or more of the respective monoamine transporters (MATs), which include the serotonin transporter (SERT), norepinephrine transporter (NET), and dopamine transporter (DAT). This in turn results in an increase in the synaptic concentrations of one or more of these neurotransmitters and therefore an increase in monoaminergic neurotransmission.

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