Lamotrigine

Lamotrigine
Clinical data
Pronunciation/ləˈmoʊtrɪˌdʒiːn/ lə-MOH-trih-jeen
Trade namesLamictal, others[1]
Other namesBW-430C; BW430C; 3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine
AHFS/Drugs.comMonograph
MedlinePlusa695007
License data
Pregnancy
category
Routes of
administration		Oral (by mouth)
Drug classPhenyltriazine
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability98%
Protein binding55%
MetabolismLiver (mostly UGT1A4-mediated)
Elimination half-life29 hours
ExcretionUrine (65%), feces (2%)
Identifiers
IUPAC name
  • 6-(2,3-dichlorophenyl)-1,2,4-triazine-3,5-diamine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.074.432
Chemical and physical data
FormulaC9H7Cl2N5
Molar mass256.09 g·mol−1
3D model (JSmol)
SMILES
  • NC1=NC(N)=NN=C1C2=CC=CC(Cl)=C2Cl
InChI
  • InChI=1S/C9H7Cl2N5/c10-5-3-1-2-4(6(5)11)7-8(12)14-9(13)16-15-7/h1-3H,(H4,12,13,14,16) Y
  • Key:PYZRQGJRPPTADH-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Lamotrigine (/ləˈmoʊtrɪˌdʒiːn/ luh-MOH-trih-jeen), sold under the brand name Lamictal among others, is a medication used to treat epilepsy and stabilize mood in bipolar disorder.[4][7] For epilepsy, this includes focal seizures, tonic-clonic seizures, and seizures in Lennox-Gastaut syndrome.[7] In bipolar disorder, lamotrigine has not been shown to reliably treat acute depression in any groups except for the severely depressed; but for patients with bipolar disorder who are not currently symptomatic, it appears to reduce the risk of future episodes of depression.[8] Lamotrigine is also used off label for unipolar depression (major depressive disorder) and depersonalization-derealization disorder.[9]

Common side effects include nausea, sleepiness, headache, vomiting, trouble with coordination, and rash.[7] Serious side effects include excessive breakdown of red blood cells, increased risk of suicide, severe skin reaction (Stevens–Johnson syndrome), and allergic reactions, which can be fatal.[7] Lamotrigine is a phenyltriazine,[4] making it chemically different from other anticonvulsants.[7] Its mechanism of action is not clear, but it appears to inhibit release of excitatory neurotransmitters via voltage-sensitive sodium channels and voltage-gated calcium channels in neurons.[7][10][11]

Lamotrigine was first marketed in Ireland in 1991,[12] and approved for use in the United States in 1994.[7][13] It is on the World Health Organization's List of Essential Medicines.[14] In 2022, it was the most commonly prescribed mood stabilizer and 58th most commonly prescribed medication in the United States, with more than 11 million prescriptions.[15][16]

  1. ^ Cite error: The named reference brands was invoked but never defined (see the help page).
  2. ^ "Lamotrigine Use During Pregnancy". Drugs.com. 8 October 2019. Archived from the original on 25 January 2021. Retrieved 24 March 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 c Cite error: The named reference Lamictal FDA label was invoked but never defined (see the help page).
  5. ^ "Lamictal XR- lamotrigine tablet, film coated, extended release Lamictal XR- lamotrigine kit". DailyMed. 13 April 2022. Archived from the original on 27 August 2022. Retrieved 27 August 2022.
  6. ^ "Lamictal". European Medicines Agency. 17 September 2018. Archived from the original on 27 August 2022. Retrieved 27 August 2022.
  7. ^ a b c d e f g "Lamotrigine". The American Society of Health-System Pharmacists. Archived from the original on 10 December 2017. Retrieved 8 December 2017.
  8. ^ "Lamotrigine: Its Role in Bipolar Disorder". PsychiatricTimes. 26 November 2019. Archived from the original on 26 January 2021. Retrieved 1 September 2020.
  9. ^ Wang S, Zheng S, Zhang FX, Ma R, Feng S, Song M, et al. (2024). "The Treatment of Depersonalization-Derealization Disorder: A Systematic Review". Journal of Trauma & Dissociation. 25 (1): 6–29. doi:10.1080/15299732.2023.2231920. PMID 37431255.
  10. ^ "Lamotrigine". PubChem Open Chemistry Database. US: National Institutes of Health. Archived from the original on 6 September 2016. Retrieved 13 December 2016.
  11. ^ Goldsmith DR, Wagstaff AJ, Ibbotson T, Perry CM (1 October 2003). "Lamotrigine: a review of its use in bipolar disorder". Drugs. 63 (19): 2029–2050. doi:10.2165/00003495-200363190-00009. PMID 12962521. Archived from the original on 27 August 2022. Retrieved 15 January 2022.
  12. ^ Cite error: The named reference pmid 18001843 was invoked but never defined (see the help page).
  13. ^ Shorvon SD, Perucca E, Engel J (2015). The Treatment of Epilepsy (4th ed.). John Wiley & Sons, Incorporated. p. 1321. ISBN 9781118936993. Archived from the original on 2 August 2021. Retrieved 31 August 2020.
  14. ^ 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.
  15. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  16. ^ "Lamotrigine Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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