Amitriptyline

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 from neuropathic pain to fibromyalgia to migraine and tension headaches.[4] Due to the frequency and prominence of side effects, amitriptyline is generally considered a second-line therapy for these indications.[5][6][7][8]

Amitriptyline
Clinical data
Pronunciation/ˌæmɪˈtrɪptɪliːn/[1]
Trade namesElavil, others
Other namesAmitryptyline; Amytriptyline; Amitryptiline; Amitriptiline; MK-230; N-750; Ro 4-1575
AHFS/Drugs.comMonograph
MedlinePlusa682388
License data
Pregnancy
category
Routes of
administration		By mouth, intramuscular injection
Drug classTricyclic antidepressant (TCA)
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability30–60%
Protein binding96%[3]
MetabolismLiver[3] (CYP2D6, CYP2C19)
Metabolitesnortriptyline
Elimination half-life10–50 hours[3]
ExcretionUrine[3]
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.038
Chemical and physical data
FormulaC20H23N
Molar mass277.411 g·mol−1
3D model (JSmol)
Melting point188 °C (370 °F)
  (verify)

The most common side effects are dry mouth, drowsiness, dizziness, constipation, and weight gain. Of note is sexual dysfunction, observed primarily in males. Glaucoma, liver toxicity and heart arrythmias are rare but serious side effects. Blood levels of amitriptyline vary significantly from one person to another,[9] and amitriptyline interacts with many medications potentially aggravating its side effects.

Amitriptyline was discovered in 1960[10] and approved by the US Food and Drug Administration (FDA) in 1961.[11] It is on the World Health Organization's List of Essential Medicines.[12] It is available as a generic medication.[3] In 2017, it was the 87th most commonly prescribed medication in the United States, with more than nine million prescriptions.[13][14]

Medical uses

Amitriptyline is indicated for the treatment of major depressive disorder and neuropathic pain and for the prevention of migraine and chronic tension headache. It can be used for the treatment of nocturnal enuresis in children older than 6 after other treatments failed.[4]

Depression

Amitriptyline is rarely used as a first-line antidepressant due to its higher toxicity in overdose and generally poorer tolerability.[15] It can be tried for depression as a second-line therapy, after the failure of other treatments.[5] For treatment-resistant adolescent depression[16] or for cancer-related depression[17] amitriptyline is no better than placebo. It is sometimes used for the treatment of depression in Parkinson's disease,[18] but supporting evidence for that is lacking.[19]

Pain

Amitriptyline alleviates painful diabetic neuropathy. It is recommended by a variety of guidelines as a first or second line treatment.[6] It is as effective for this indication as gabapentine or pregabalin but less well tolerated.[20]

Low doses of amitriptyline moderately improve sleep disturbances and reduce pain and fatigue associated with fibromyalgia.[21] It is recommended for fibromyalgia accompanied by depression by Association of the Scientific Medical Societies in Germany[21] and as a second-line option for fibromyalgia, with exercise being the first line option, by European League Against Rheumatism.[7] Combinations of amitriptyline and fluoxetine or melatonin may reduce fibromyalgia pain better than either medication alone.[22]

There is some (low-quality) evidence that amitriptyline may reduce pain in cancer patients. It is recommended only as a second line therapy for non-chemotherapy-induced neuropathic or mixed neuropathic pain, if opioids did not provide the desired effect.[23]

Moderate evidence exists in favor of amitriptyline use for atypical facial pain.[24] Amitriptyline is ineffective for HIV-associated neuropathy.[20]

Headache

Amitriptyline is probably effective for the prevention of periodic migraine in adults. Amitriptyline is similar in efficacy to venlafaxine and topiramate but carries a higher burden of adverse effects than topiramate. [8] For many patients, even very small doses of amitriptyline are helpful, which may allow to minimize the side effects.[25] Amitriptyline is not significantly different from placebo when used for the prevention of migraine in children.[26]

Amitriptyline may reduce the frequency and duration of chronic tension headache, but it is associated with worse adverse effects than mirtazapine. Overall, amitriptyline is recommended for tension headache prophylaxis, along with lifestyle advice, which should include avoidance of analgesia and caffeine.[27]

Other indications

Amitriptyline is effective for the treatment of irritable bowel syndrome; however, because of its side effects, it should be reserved for select patients for whom other agents do not work.[28] It is ineffective for abdominal pain in children with functional gastrointestinal disorders.[29]

Tricyclic antidepressants decrease the frequency, severity and duration of cyclic vomiting syndrome episodes. Amitriptyline, as the most commonly used of them, is recommended as a first line agent for its therapy.[30]

It may improve pain and urgency intensity associated with bladder pain syndrome and can be used in the management of this syndrome.[31][32] Amitriptyline can be used in the treatment of nocturnal enuresis in children. However, its effect is not sustained after the treatment ends. Alarm therapy gives better short- and long-term results.[33]

Contraindications and precautions

The known contraindications of amitriptyline are:[4]

  • History of myocardial infarction
  • History of arrhythmias, particularly any degree of heart block
  • Coronary artery insufficiency
  • Porphyria
  • Severe liver disease
  • Being under six years of age
  • Patients who are taking monoamine oxidase inhibitors (MAOIs) or have taken them within the last 14 days.

Amitriptyline should be used with caution in patients with epilepsy, impaired liver function, pheochromocytoma, urinary retention, prostate enlargement, hyperthyroidism, and pyloric stenosis.[4]

In patients with the rare condition of shallow anterior chamber of eyeball and narrow anterior chamber angle, amitriptyline may provoke attacks of acute glaucoma due to dilation of the pupil. It may aggravate psychosis, if used for depression with schizophrenia, or precipitate the switch to mania in those with bipolar disorder.[4]

CYP2D6 poor metabolizers should avoid amitriptyline due to increased side effects. If it is necessary to use it, half dose is recommended.[34] Amitriptyline can be used during pregnancy and lactation, in the cases when SSRI do not work.[35]

Side effects

The most frequent side effects, occurring in 20% or more of users, are dry mouth, drowsiness, dizziness, constipation, and weight gain (on average 1.8 kg[36]).[37] Other common side effects (in 10% or more) are vision problems (amblyopia, blurred vision), tachycardia, increased appetite, tremor, sexual dysfunction, fatigue/asthenia/feeling slowed down, and dyspepsia.[37]

Amitriptyline-associated sexual dysfunction seems to be mostly confined to males with depression and is expressed predominantly as erectile dysfunction and low libido disorder, with lesser frequency of ejaculatory and orgasmic problems. The rate of sexual dysfunction in males treated for indications other that depression and in females is not significantly different from placebo.[38]

Liver tests abnormalities occur in 10-12% of patients on amitriptyline, but are usually mild, asymptomatic and transient,[39] with consistently elevated alanine transaminase in 3% of all patients.[40][41] The increases of the enzymes above the 3-fold threshold of liver toxicity are uncommon, and cases of clinically apparent liver toxicity are rare;[39] nevertheless, amitriptyline is placed in the group of antidepressants with greater risks of hepatic toxicity.[40]

Amitriptyline prolongs QT interval.[42] This prolongation is relatively small at therapeutic doses[43] but becomes severe in overdose.[44]

Overdose
Main article: Tricyclic antidepressant overdose

The symptoms and the treatment of an overdose are largely the same as for the other TCAs, including the presentation of serotonin syndrome and adverse cardiac effects. The British National Formulary notes that amitriptyline can be particularly dangerous in overdose,[45] thus it and other TCAs are no longer recommended as first-line therapy for depression. The treatment of overdose is mostly supportive as no specific antidote for amitriptyline overdose is available. Activated charcoal may reduce absorption if given within 1–2 hours of ingestion. If the affected person is unconscious or has an impaired gag reflex, a nasogastric tube may be used to deliver the activated charcoal into the stomach. ECG monitoring for cardiac conduction abnormalities is essential and if one is found close monitoring of cardiac function is advised. Body temperature should be regulated with measures such as heating blankets if necessary. Cardiac monitoring is advised for at least five days after the overdose. Benzodiazepines are recommended for control of seizures. Dialysis is of no use due to the high degree of protein binding with amitriptyline.[46]

Interactions

Oral contraceptives may increase the blood level of amitriptyline by as high as 90%.[47] The prescribing information warns that the combination of amitriptyline with monoamine oxidase inhibitors may cause potentially lethal serotonin syndrome;[4] however, this has been disputed.[48] The prescribing information cautions that some patients may experience a large increase in amitriptyline concentration in the presence of topiramate.[49] However, other literature states that there is little or no interaction: in a pharmacokinetic study topiramate only increased the level of amitriptyline by 20% and nortriptyline by 33%.[50] Amitriptiline counteracts the antihypertensive action of guanethidine.[46][51] When given with amitriptyline, other anticholinergic agents may result in hyperpyrexia or paralytic ileus.[49] Co-administration of amitriptyline and disulfiram is not recommended due to the potential for the development of toxic delirium.[46][52] Amitriptyline causes an unusual type of interaction with the anticoagulant phenprocoumon during which great fluctuations of the prothrombin time have been observed.[53]

Since amitriptyline and its active metabolite nortriptyline are primarily metabolized by cytochromes CYP2D6 and CYP2C19 (see Amitriptyline#Pharmacology), the inhibitors of these enzymes are expected to exhibit pharmacokinetic interactions with amitriptyline. According to the prescribing information, the interaction with CYP2D6 inhibitors may increase the plasma level of amitriptyline.[4] However, the results in the other literature are inconsistent:[54] the co-administration of amitriptyline with a potent CYP2D6 inhibitor paroxetine does increase the plasma levels of amitriptyline two-fold and of the main active metabolite nortriptyline 1.5-fold,[55] but combination with less potent CYP2D6 inhibitors thioridazine or levomepromazine does not affect the levels of amitriptyline and increases nortriptyline by about 1.5-fold;[56] a moderate CYP2D6 inhibitor fluoxetine does not seem to have a significant effect on the levels of amitriptyline or nortriptyline.[57][58]

A potent inhibitor of CYP2C19 and other cytochromes fluvoxamine increases the level of amitriptyline two-fold while slightly decreasing the level of nortriptyline.[57] Similar changes occur with a moderate inhibitor of CYP2C19 and other cytochromes cimetidine: amitriptyline level increases by about 70%, while nortriptyline decreases by 50%.[59] CYP3A4 inhibitor ketoconazole elevates amitriptyline level by about a quarter.[60] On the other hand, cytochrome P450 inducers such as carbamazepine and St. John's wart decrease the levels of both amitriptyline and nortriptyline[56][61]

Pharmacology

Pharmacodynamics
See also: Pharmacology of antidepressants and Tricyclic antidepressant § Binding profiles
Amitriptyline (and metabolite)[62]
SiteAMINTISpeciesRef
SERT2.8–3615–279Human[63][64]
NET19–1021.8–21Human[63][64]
DAT3,2501,140Human[63]
5-HT1A450–1,800294Human[65][66]
5-HT1B840NDRat[67]
5-HT2A18–2341Human[65][66]
5-HT2B174NDHuman[68]
5-HT2C4-88.5Rat[69]
5-HT34301,400Rat[70]
5-HT665–141148Human/rat[71][72][73]
5-HT792.8–123NDRat[74]
α14.4–2455Human[64][65]
α2114–6902,030Human[64][65]
β>10,000>10,000Rat[75][76]
D189NDHuman[77]
D2196–1,4602,570Human[65][77]
D3206NDHuman[77]
D4NDNDNDND
D5170NDHuman[77]
H10.5–1.13.0–15Human[77][78][79]
H266646Human[78]
H375,90045,700Human[77][78]
H426,3006,920Human[78][80]
mACh9.637Human[65]
  M111.0–14.740Human[81][82]
  M211.8110Human[81]
  M312.8–3950Human[81][82]
  M47.284Human[81]
  M515.7–2497Human[81][82]
σ13002,000Guinea pig[83]
σ2NDNDNDND
hERG>3,000NDHuman[84]
Values are Ki (nM), unless otherwise noted. The smaller the value, the more strongly the drug binds to the site.

Amitriptyline is classified as a tricyclic antidepressant (TCA), with strong actions on the serotonin transporter (SERT) and moderate effects on the norepinephrine transporter (NET).[63][85] It has negligible influence on the dopamine transporter (DAT) and therefore does not affect dopamine reuptake, being nearly 1,000 times weaker on inhibition of the reuptake of this neurotransmitter than on serotonin.[63] It is metabolized to nortriptyline, a more potent and selective norepinephrine reuptake inhibitor, and this may serve to complement its effects on norepinephrine reuptake.[46]

Amitriptyline additionally acts as an antagonist or inverse agonist of the serotonin 5-HT2A, 5-HT2C, 5-HT3, 5-HT6, and 5-HT7 receptors, the α1-adrenergic receptor, the histamine H1 and H2 receptors,[86] and the muscarinic acetylcholine receptors, and as an agonist of the sigma σ1 receptor.[64][87][88][89] It has also been shown to be a relatively weak NMDA receptor antagonist via the dizocilpine (MK-801)/phencyclidine (PCP) site.[90] Amitriptyline inhibits sodium channels, L-type calcium channels, and Kv1.1, Kv7.2, and Kv7.3 voltage-gated potassium channels, and therefore acts as a sodium, calcium, and potassium channel blocker as well.[91][92]

Amitriptyline has been demonstrated to act as an agonist of the TrkA and TrkB receptors.[93] It promotes the heterodimerization of these proteins in the absence of NGF and has potent neurotrophic activity both in-vivo and in-vitro in mouse models.[93][94] These are the same receptors BDNF activates, an endogenous neurotrophin with powerful antidepressant effects, and as such this property may contribute significantly to its therapeutic efficacy against depression. Amitriptyline also acts as a functional inhibitor of acid sphingomyelinase,[95] and as a PARP1 inhibitor.[96]

Mechanism of action

Amitriptyline inhibits neuronal reuptake of serotonin and noradrenaline from the synapse in the central nervous system; this increases their availability in the synapse to cause neurotransmission on the post-synaptic neurone.[97] Amitriptyline is metabolised by cytochrome P450 enzymes in the liver to nortriptyline, which also acts as a noradrenaline reuptake inhibitor; this potentiates the antidepressant effects of amitriptyline.[98]

Pharmacokinetics

Amitriptyline is a highly lipophilic molecule having an octanol-water partition coefficient (pH 7.4) of 3.0,[99] while the log P of the free base was reported as 4.92.[100] Solubility in water is 9.71 mg/litre at 24 °C.[101]

Amitriptyline is readily absorbed from the gastrointestinal tract and is extensively metabolized on first pass through the liver.[46] It is metabolized mostly by CYP2D6, CYP3A4, and CYP2C19-mediated N-demethylation into nortriptyline,[46] which is another TCA in its own right.[102] It is 96% bound to plasma proteins; nortriptyline is 93–95% bound to plasma proteins.[46][103] It is mostly excreted in the urine (around 30–50%) as metabolites either free or as glucuronide and sulfate conjugates within 24 hours.[46] 2% of the unchanged drug is excreted in the urine.[97] Small amounts are also excreted in feces.[104] Amitriptyline has an elimination half life of 25 hours and its volume of distribution is 10–50L/kg.[98]

Therapeutic levels of amitriptyline range from 75 to 175 ng/mL (270–631 nM),[105] or 80–250 ng/mL of both amitriptyline and its metabolite nortriptyline.[106]

Pharmacogenetics

Since amitriptyline is primarily metabolized by CYP2D6 and CYP2C19, genetic variations within the genes coding for these enzymes can affect its metabolism, leading to changes in the concentrations of the drug in the body.[107] Increased concentrations of amitriptyline may increase the risk for side effects, including anticholinergic and nervous system adverse effects, while decreased concentrations may reduce the drug's efficacy.[108][109][110][111]

Individuals can be categorized into different types of CYP2D6 or CYP2C19 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,[34] and have "normal" metabolism of amitriptyline. 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 amitriptyline much faster than extensive metabolizers; patients with this metabolizer type may have a greater chance of experiencing pharmacological failure.[108][109][34][111]

The Clinical Pharmacogenetics Implementation Consortium recommends avoiding amitriptyline in patients who are CYP2D6 ultrarapid or poor metabolizers, due to the risk for a lack of efficacy and side effects, respectively. The consortium also recommends considering an alternative drug not metabolized by CYP2C19 in patients who are CYP2C19 ultrarapid metabolizers. A reduction in starting dose is recommended for patients who are CYP2D6 intermediate metabolizers and CYP2C19 poor metabolizers. If use of amitriptyline is warranted, therapeutic drug monitoring is recommended to guide dose adjustments.[34] The Dutch Pharmacogenetics Working Group also recommends selecting an alternative drug or monitoring plasma concentrations of amitriptyline in patients who are CYP2D6 poor or ultrarapid metabolizers, and selecting an alternative drug or reducing initial dose in patients who are CYP2D6 intermediate metabolizers.[112]

Chemistry

Amitriptyline is a tricyclic compound, specifically a dibenzocycloheptadiene, and possesses three rings fused together with a side chain attached in its chemical structure.[113] Other dibenzocycloheptadiene TCAs include nortriptyline (noramitriptyline, N-desmethylamitriptyline), protriptyline, and butriptyline.[113] Amitriptyline is a tertiary amine TCA, with its side chain-demethylated metabolite nortriptyline being a secondary amine.[114][115] Other tertiary amine TCAs include imipramine, clomipramine, dosulepin (dothiepin), doxepin, and trimipramine.[116][117] The chemical name of amitriptyline is 3-(10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-ylidene)-N,N-dimethylpropan-1-amine and its free base form has a chemical formula of C20H23N with a molecular weight of 277.403 g/mol.[118] The drug is used commercially mostly as the hydrochloride salt; the free base form is used rarely and the embonate (pamoate) salt is used for intramuscular administration.[118][119] The CAS Registry Number of the free base is 50-48-6, of the hydrochloride is 549-18-8, and of the embonate is 17086-03-2.[118][119]

History

Amitriptyline was first synthesized in 1960 and was introduced for medical use in United States in 1961 and in the United Kingdom in 1962, in both countries under the brand name Elavil.[120][121][122][123] It was the second TCA to be introduced, following the introduction of imipramine in 1957.[121][122]

Society and culture
Two boxes of amitriptyline (Endep) in 10 and 25 mg doses

English folk singer Nick Drake died from an overdose of Tryptizol in 1974.[124]

Generic names

Amitriptyline is the English and French generic name of the drug and its INN, BAN, and DCF, while amitriptyline hydrochloride is its USAN, USP, BANM, and JAN.[118][119][125][126] Its generic name in Spanish and Italian and its DCIT are amitriptilina, in German is Amitriptylin, and in Latin is amitriptylinum.[119][126] The embonate salt is known as amitriptyline embonate, which is its BANM, or as amitriptyline pamoate unofficially.[119]

Brand names

As of September 2018, amitriptyline was marketed under many brand names worldwide alone and as a combination drug with each of chlordiazepoxide, perphenazine, and medazepam.[127]

Brands include Adepril, ADT, Ambival, Amicon, Amilavil, Amilin, Amiline, Amineurin, Amiplin, Amirol, Amit, Amitin, Amitone, Amitrac, Amitrip, Amitriptilina, Amitriptilino, Amitriptilins, Amitriptine, Amitriptylin, Amitriptyline, Amitriptylinhydrochlorid, Amitriptylini, Amitriptylinum, Amitryp, Amotrip, Amyline, Amypres, Amytril, Amyzol, Anapsique, Arpidox, Deprelio, Elatrol, Elatrolet, Elavil, Endep, Fiorda, Laroxyl, Latilin, Levate, Maxitrip, Maxivalet, Mitryp, Modup, Normaln, Odep, Pinsaun, Polytanol, Protanol, Qualitriptine, Redomex, Saroten, Sarotex, Stelminal, Syneudon, Teperin, Trepiline, Triamyl, Trilin, Trip, Tripta, Triptiline, Triptizol, Triptric, Triptyl, Triptyline, Tripyline, Trynol, Tryptalgin, Tryptanol, Tryptin, Tryptizol, Tryptomer, and Vanatrip.[127]

Brands as of that date for the combination with chlordiazepoxide included Amicon Forte, Amitrac-CZ, Amypres-C, Antalin, Antalin Forte, Arpidox-CP, Axeptyl, Diapatol, Diaztric-A, Emotrip, Klotriptyl, Libotryp, Limbatril, Limbitrol, Limbitryl, Limbival, Limbritol, Maxitrip-CZ, Mitryp Forte, Morelin, Ristryl, and Sedans.[127]

Brands as of that date for the combination with perphenazine included Levazine, Minitran, Mutabase, Mutabon, Pertriptyl, Triavil, and Triptafen.[127]

Brands as of that date for the combination with medazepam included Nobritol.[127]

Research

Amitriptyline has been studied in several disorders:


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Further reading
  • "Amitriptyline". Drug Information Portal. U.S. National Library of Medicine.
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