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Nortriptyline information


Nortriptyline
Skeletal formula of nortriptyline
Ball-and-stick model of the nortriptyline molecule
Clinical data
Trade namesAventyl, others
Other namesDesitriptyline; ELF-101; E.L.F. 101; N-7048
AHFS/Drugs.comMonograph
MedlinePlusa682620
License data
  • US DailyMed: Nortriptyline
Pregnancy
category
  • AU: C[1]
Routes of
administration
By mouth
Drug classTricyclic antidepressant (TCA)
ATC code
  • N06AA10 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)[2]
  • CA: ℞-only[3]
  • US: ℞-only
Pharmacokinetic data
Bioavailability32–79%[4]
Protein binding92%[4]
MetabolismLiver
Metabolites10-E-Hydroxynortriptyline
Elimination half-life18–44 hours (mean 30 hours)[4]
ExcretionUrine: 40%[4]
Feces: minor[4]
Identifiers
IUPAC name
  • 3-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine
CAS Number
  • 72-69-5 checkY
  • 894-71-3
PubChem CID
  • 4543
IUPHAR/BPS
  • 2404
DrugBank
  • DB00540 checkY
ChemSpider
  • 4384 checkY
UNII
  • BL03SY4LXB
KEGG
  • D08288 checkY
ChEBI
  • CHEBI:7640 checkY
ChEMBL
  • ChEMBL445 checkY
CompTox Dashboard (EPA)
  • DTXSID9023384 Edit this at Wikidata
ECHA InfoCard100.000.717 Edit this at Wikidata
Chemical and physical data
FormulaC19H21N
Molar mass263.384 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • c3cc2c(/C(c1c(cccc1)CC2)=C/CCNC)cc3
InChI
  • 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 checkY
  • Key:PHVGLTMQBUFIQQ-UHFFFAOYSA-N checkY
  (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.[5][6] 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.[6] Nortriptyline is a less preferred treatment for ADHD and stopping smoking.[6] It is taken by mouth.[6]

Common side effects include dry mouth, constipation, blurry vision, sleepiness, low blood pressure with standing, and weakness.[6] 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.[6] Nortriptyline may cause problems if taken during pregnancy.[6] Use during breastfeeding appears to be relatively safe.[5] It is a tricyclic antidepressant (TCA) and is believed to work by altering levels of serotonin and norepinephrine.[6][a]

Nortriptyline was approved for medical use in the United States in 1964.[6] It is available as a generic medication.[5] In 2021, it was the 139th most commonly prescribed medication in the United States, with more than 4 million prescriptions.[7][8]

  1. ^ "Nortriptyline Use During Pregnancy". Drugs.com. 22 June 2020. Retrieved 10 October 2020.
  2. ^ 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.
  3. ^ "Product monograph brand safety updates". Health Canada. February 2024. Retrieved 24 March 2024.
  4. ^ a b c d e Lemke TL, Williams DA (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 588–. ISBN 978-1-60913-345-0.
  5. ^ a b c British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 374. ISBN 9780857113382.
  6. ^ a b c d e f g h i "Nortriptyline Hydrochloride Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 22 March 2019.
  7. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  8. ^ "Nortriptyline - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.


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