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Lamotrigine information


Lamotrigine
Clinical data
Pronunciation/ləˈmtrɪˌn/
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
  • US DailyMed: Lamotrigine
Pregnancy
category
  • AU: D[2]
Routes of
administration
Oral (by mouth)
Drug classPhenyltriazine
ATC code
  • N03AX09 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)[4]
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: WARNING[3]Rx-only[5][6]
  • EU: Rx-only[7]
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
  • 84057-84-1 checkY
PubChem CID
  • 3878
IUPHAR/BPS
  • 2622
DrugBank
  • DB00555 ☒N
ChemSpider
  • 3741 checkY
UNII
  • U3H27498KS
KEGG
  • D00354 checkY
ChEBI
  • CHEBI:6367 ☒N
ChEMBL
  • ChEMBL741 checkY
CompTox Dashboard (EPA)
  • DTXSID2023195 Edit this at Wikidata
ECHA InfoCard100.074.432 Edit this at Wikidata
Chemical and physical data
FormulaC9H7Cl2N5
Molar mass256.09 g·mol−1
3D model (JSmol)
  • Interactive image
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) checkY
  • Key:PYZRQGJRPPTADH-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Lamotrigine, sold under the brand name Lamictal among others, is a medication used to treat epilepsy and stabilize mood in bipolar disorder.[5][8] For epilepsy, this includes focal seizures, tonic-clonic seizures, and seizures in Lennox-Gastaut syndrome.[8] In bipolar disorder, lamotrigine has not been shown to reliably treat acute depression for all groups except in 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.[9]

Common side effects include nausea, sleepiness, headache, vomiting, trouble with coordination, and rash.[8] 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.[8] Lamotrigine is a phenyltriazine,[5] making it chemically different from other anticonvulsants.[8] 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.[8][10][11]

Lamotrigine was first marketed in Ireland in 1991,[12] and approved for use in the United States in 1994.[8][13] It is on the World Health Organization's List of Essential Medicines.[14] In 2021, it was the 50th most commonly prescribed medication in the United States, with more than 13 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. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  4. ^ 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.
  5. ^ a b c Cite error: The named reference Lamictal FDA label was invoked but never defined (see the help page).
  6. ^ "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.
  7. ^ "Lamictal". European Medicines Agency. 17 September 2018. Archived from the original on 27 August 2022. Retrieved 27 August 2022.
  8. ^ 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.
  9. ^ "Lamotrigine: Its Role in Bipolar Disorder". PsychiatricTimes. 26 November 2019. Archived from the original on 26 January 2021. Retrieved 1 September 2020.
  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 (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  15. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  16. ^ "Lamotrigine - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

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Lamotrigine

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there is evidence for using gabapentin, lamotrigine, oxcarbazepine or topiramate as monotherapy. Lamotrigine can be included in the options for children...

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Absence seizure

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are of equal efficacy controlling absences in around 75% of patients. Lamotrigine monotherapy is less effective, controlling absences in around 50% of...

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Phenyltriazines

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group. These molecules are pharmacologically important. As an example, lamotrigine is a phenyltriazine derivative used as an anticonvulsant drug and has...

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the strong enzyme-inducing ASMs. Clobazam, eslicarbazepine, felbamate, lamotrigine, rufinamide and topiramate are examples of weak enzyme-inducing ASMs...

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Mood stabilizer

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when taken as a free acid. Liver function and CBC should be monitored. Lamotrigine (aka Lamictal) – FDA approved for bipolar disorder maintenance therapy...

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Hallucinogen persisting perception disorder

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therapy with lamotrigine, these complex visual disturbances receded almost completely. There are also many anecdotal reports on lamotrigine alleviating...

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Visual snow syndrome

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studies, lamotrigine as a treatment for visual snow syndrome only showed efficiacy in 20% of patients, and in one study, patients using lamotrigine even reported...

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Leukopenia

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bipolar disorder) and migraine.[citation needed] The anticonvulsant drug, lamotrigine, has been associated with a decrease in white blood cell count. The FDA...

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Persistent aura without infarction

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medications have been tried as treatment, notably acetazolamide, valproate, lamotrigine, topiramate, and furosemide. Chen, WT; Fuh, JL; Lu, SR; Wang, SJ (September...

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Bipolar II disorder

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evidence that lamotrigine decreases the risk of relapse in rapid-cycling BP-II. It is more effective in BP-II than BP-I, suggesting that lamotrigine is more...

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Cocaine

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Bipolar disorder

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or valproate. Lamotrigine has some efficacy in treating depression, and this benefit is greatest in more severe depression. Lamotrigine may have a similar...

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Trigeminal neuralgia

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drug withdrawal in as many as 23% of patients. Other options include lamotrigine, baclofen, gabapentin, amitriptyline and pimozide. Opioids are not usually...

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Depersonalization

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avenue of treatment, with medications such as clomipramine, fluoxetine, lamotrigine, and opioid antagonists being commonly prescribed. However, it is important...

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Ginseng

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has been reported with imatinib, resulting in hepatotoxicity, and with lamotrigine. The common ginsengs (P. ginseng and P. quinquefolia) are generally considered...

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Toxic epidermal necrolysis

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organ failure. The most common cause is certain medications such as lamotrigine, carbamazepine, allopurinol, sulfonamide antibiotics, and nevirapine...

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Combined hormonal contraception

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anti-epileptic drug lamotrigine for 6 weeks, it was revealed that the contraceptive effectiveness could be lowered, despite lamotrigine not being an enzyme...

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Ketamine

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Psychotomimetic effects limit the acceptance of ketamine; however, lamotrigine and nimodipine decrease psychotomimetic effects and can be counteracted...

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MDMA

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Fourphit Metaphit Naluzotan Tapentadol Tenocyclidine Antagonists: AHD1 AZ66 Lamotrigine Naloxone SM-21 UMB-100 UMB-101 UMB-103 UMB-116 YZ-011 YZ-069 YZ-185 Allosteric...

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Gabapentin

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Topiramate

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of the very few anticonvulsants [see: levetiracetam, carbamazepine, lamotrigine] that do not induce apoptosis in young animals at doses needed to produce...

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Taro Pharmaceuticals

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and Drug Administration (FDA) announced a voluntary recall of 100  mg Lamotrigine (Generic for Lamictal) tablets manufactured by Taro Pharmaceuticals USA...

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Glucuronidation

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Disease states Fulminant hepatitis, cirrhosis ↓ Zidovudine, oxazepam, lamotrigine Hypothyroidism ↓ Oxazepam, paracetamol HIV ↓ Paracetamol Tobacco smoking...

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Methamphetamine

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Peripheral neuropathy

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medications (gabapentin, pregabalin, oxcarbazepine zonisamide levetiracetam, lamotrigine, topiramate, clonazepam, phenytoin, lacosamide, sodium valproate and...

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Epilepsy

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may have fewer side effects. In the United Kingdom, carbamazepine or lamotrigine are recommended as first-line treatment for focal seizures, with levetiracetam...

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