Amitriptyline

Amitriptyline
Clinical data
Pronunciation/ˌæmɪˈtrɪptɪliːn/[1]
Trade namesElavil, others
AHFS/Drugs.comMonograph
MedlinePlusa682388
License data
Pregnancy
category
Routes of
administration		Oral, intramuscular injection
Drug classTricyclic antidepressant (TCA)
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)[3]
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: ℞-only
Pharmacokinetic data
Bioavailability45%[4]-53%[5]
Protein binding96%[6]
MetabolismLiver (CYP2D6, CYP2C19, CYP3A4)[8][5][9]
Metabolitesnortriptyline, (E)-10-hydroxynortriptyline
Elimination half-life21 hours[4]
ExcretionUrine: 12–80% after 48 hours;[7] feces: not studied
Identifiers
IUPAC name
  • 3-(10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-ylidene)-N,N-dimethylpropan-1-amine
CAS Number
  • 50-48-6 Y
    549-18-8 (hydrochloride)
    17086-03-2 (embonate)
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 point197.5 °C (387.5 °F) [10]
SMILES
  • c3cc2c(/C(c1c(cccc1)CC2)=C\CCN(C)C)cc3
InChI
  • InChI=1S/C20H23N/c1-21(2)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20/h3-6,8-12H,7,13-15H2,1-2H3 Y
  • Key:KRMDCWKBEZIMAB-UHFFFAOYSA-N Y
  (verify)

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.[11] Due to the frequency and prominence of side effects, amitriptyline is generally considered a second-line therapy for these indications.[12][13][14][15]

The most common side effects are dry mouth, drowsiness, dizziness, constipation, and weight gain. Glaucoma, liver toxicity and abnormal heart rhythms are rare but serious side effects. Blood levels of amitriptyline vary significantly from one person to another,[16] and amitriptyline interacts with many other medications potentially aggravating its side effects.

Amitriptyline was discovered in the late 1950s by scientists at Merck and approved by the US Food and Drug Administration (FDA) in 1961.[17] It is on the World Health Organization's List of Essential Medicines.[18] It is available as a generic medication.[19] In 2022, it was the 87th most commonly prescribed medication in the United States, with more than 7 million prescriptions.[20][21]

  1. ^ "Amitriptyline". Oxford Dictionary. Archived from the original on 14 July 2014. Retrieved 6 January 2021 – via Lexico.com.
  2. ^ "Amitriptyline Use During Pregnancy". Drugs.com. 2 September 2020. Archived from the original on 9 November 2020. Retrieved 13 September 2020.
  3. ^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
  4. ^ a b Cite error: The named reference pmid3893842 was invoked but never defined (see the help page).
  5. ^ a b Cite error: The named reference pmid33438398 was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference TGA was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference pmid6667101 was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference pmid15554244 was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference pmid11583471 was invoked but never defined (see the help page).
  10. ^ Blessel KW, Rudy BC, Senkowski BZ (1974). "Amitriptyline Hydrochloride". Analytical Profiles of Drug Substances. 3: 127–148. doi:10.1016/S0099-5428(08)60066-0. ISBN 9780122608032.
  11. ^ "Amitriptyline Tablets BP 50mg – Summary of Product Characteristics (SPC)". electronic Medicines Compendium. Actavis UK Ltd. 24 March 2013. Archived from the original on 3 December 2013. Retrieved 1 December 2013.
  12. ^ Cite error: The named reference top100drugs was invoked but never defined (see the help page).
  13. ^ Cite error: The named reference pmid32040849 was invoked but never defined (see the help page).
  14. ^ Cite error: The named reference pmid27377815 was invoked but never defined (see the help page).
  15. ^ Cite error: The named reference pmid22529202 was invoked but never defined (see the help page).
  16. ^ Tfelt-Hansen P, Ågesen FN, Pavbro A, Tfelt-Hansen J (May 2017). "Pharmacokinetic Variability of Drugs Used for Prophylactic Treatment of Migraine". CNS Drugs. 31 (5): 389–403. doi:10.1007/s40263-017-0430-3. PMID 28405886. S2CID 23560743.
  17. ^ Fangmann P, Assion HJ, Juckel G, González CA, López-Muñoz F (February 2008). "Half a century of antidepressant drugs: on the clinical introduction of monoamine oxidase inhibitors, tricyclics, and tetracyclics. Part II: tricyclics and tetracyclics". Journal of Clinical Psychopharmacology. 28 (1): 1–4. doi:10.1097/jcp.0b013e3181627b60. PMID 18204333. S2CID 31018835.
  18. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  19. ^ "Amitriptyline Hydrochloride". Drugs.com. The American Society of Health-System Pharmacists. Archived from the original on 24 September 2014. Retrieved 25 September 2014.
  20. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  21. ^ "Amitriptyline Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Archived from the original on 30 April 2017. Retrieved 30 August 2024.
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