Lamotrigine

Lamotrigine, sold under the brand name Lamictal among others, is a medication used to treat epilepsy and stabilize mood in bipolar disorder. For epilepsy, this includes focal seizures, tonic-clonic seizures, and seizures in Lennox-Gastaut syndrome. 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.

Lamotrigine
Clinical data
Pronunciation/ləˈmoʊtrɪˌdʒiːn/
Trade namesLamictal, others
Other namesBW-430C; BW430C; 3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine
AHFS/Drugs.comMonograph
MedlinePlusa695007
License data
Pregnancy
category
  • AU: D
Routes of
administration		Oral (by mouth)
Drug classPhenyltriazine
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: WARNINGRx-only
  • EU: Rx-only
Pharmacokinetic data
Bioavailability98%
Protein binding55%
MetabolismLiver (mostly UGT1A4-mediated)
Elimination half-life29 hours
ExcretionUrine (65%), feces (2%)
Identifiers
  • 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=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)

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

Lamotrigine was first marketed in Ireland in 1991, and approved for use in the United States in 1994. It is on the World Health Organization's List of Essential Medicines. In 2021, it was the 50th most commonly prescribed medication in the United States, with more than 13 million prescriptions.

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