Lamictal

Lamotrigine

Clinical data
Pronunciation	/ləˈmoʊtrᵻˌdʒiːn/
Trade names	Originally Lamictal, many brands worldwide
AHFS/Drugs.com	Monograph
MedlinePlus	a695007
License data	US FDA: Lamotrigine
Pregnancy category	AU: D US: C (Risk not ruled out)
Routes of administration	Oral
ATC code	N03AX09 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	98%
Protein binding	55%
Metabolism	Hepatic (mostly UGT1A4-mediated)
Biological half-life	29 hours
Excretion	Urine (65%), faeces (2%)
Identifiers
IUPAC name 6-(2,3-dichlorophenyl)-1,2,4-triazine-3,5-diamine
CAS Number	84057-84-1 Y
PubChem CID	3878
IUPHAR/BPS	2622
DrugBank	DB00555 N
ChemSpider	3741 Y
UNII	U3H27498KS
KEGG	D00354 Y
ChEBI	CHEBI:6367 N
ChEMBL	CHEMBL741 Y
ECHA InfoCard	100.074.432
Chemical and physical data
Formula	C9H7Cl2N5
Molar mass	256.091 g/mol
3D model (Jmol)	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) Y Key:PYZRQGJRPPTADH-UHFFFAOYSA-N Y
NY (what is this?)

Lamotrigine, originally marketed as Lamictal and available under many brands worldwide, is an anticonvulsant drug used in the treatment of epilepsy and bipolar disorder. It is also used off-label as an adjunct in treating clinical depression. For epilepsy, it is used to treat focal seizures, primary and secondary tonic-clonic seizures, and seizures associated with Lennox-Gastaut syndrome. Like many other anticonvulsant medications, lamotrigine also seems to act as an effective mood stabilizer, and has been the first US Food and Drug Administration (FDA)-approved drug for this purpose since lithium, a drug approved almost 30 years earlier. It is approved for the maintenance treatment of bipolar type II.

Lamotrigine is a synthetic phenyltriazine with anti-epileptic and analgesic properties. Lamotrigine enhances the action of gamma-aminobutyric acid (GABA), an inhibitory neurotransmitter, which may result in a reduction of pain-related transmission of signals along nerve fibers. This agent may also inhibit voltage-gated sodium channels, suppress glutamate release, and inhibit serotonin reuptake. It is generally accepted to be a member of the sodium channel blocking class of antiepileptic drugs, but it could have additional actions since it has a broader spectrum of action than other sodium channel antiepileptic drugs such as phenytoin and carbamazepine and is effective in the treatment of the depressed phase of bipolar disorder, whereas other sodium channel blocking antiepileptic drugs are not, possibly on account of its sigma receptor activity. In addition, lamotrigine shares few side-effects with other, unrelated anticonvulsants known to inhibit sodium channels, which further emphasises its unique properties. Lamotrigine is inactivated by glucuronidation in the liver.