Identification

Name
Lamotrigine
Accession Number
DB00555  (APRD00570)
Type
Small Molecule
Groups
Approved, Investigational
Description

Lamotrigine is an anticonvulsant drug used in the treatment of epilepsy and bipolar disorder. For epilepsy it is used to treat partial seizures, primary and secondary tonic-clonic seizures, and seizures associated with Lennox-Gastaut syndrome. Lamotrigine also acts as a mood stabilizer. It is the first medication since lithium granted Food and Drug Administration (FDA) approval for the maintenance treatment of bipolar type I. Chemically unrelated to other anticonvulsants, lamotrigine has relatively few side-effects and does not require blood monitoring. The exact way lamotrigine works is unknown. [Wikipedia]

Structure
Thumb
Synonyms
  • 3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine
  • Lamotrigina
  • Lamotrigine
  • Lamotriginum
External IDs
BW 430 C / BW 430C / BW-430C / GW 273293
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
LamictalTablet100 mg/1OralGlaxosmithkline Inc1995-01-17Not applicableUs00173 0642 55 nlmimage10 c518e287
LamictalTablet150 mg/1OralLake Erie Medical &Surgical Supply Dba Quality Care Products Llc2012-02-292017-11-07Us
LamictalTablet100 mg/1OralPd Rx Pharmaceuticals, Inc.1995-01-17Not applicableUs
LamictalTablet2 mgOralGlaxosmithkline Inc2001-09-13Not applicableCanada
LamictalTablet150 mg/1OralRebel Distributors1995-01-17Not applicableUs00173 0643 60 nlmimage10 f118f8a7
LamictalTablet100 mgOralGlaxosmithkline Inc1995-12-31Not applicableCanada
LamictalTablet100 mg/1OralLake Erie Medical &Surgical Supply Dba Quality Care Products Llc2012-02-292017-11-07Us
LamictalTablet200 mg/1OralGlaxosmithkline Inc1995-01-18Not applicableUs00173 0644 60 nlmimage10 b218d956
LamictalTablet100 mg/1OralPhysicians Total Care, Inc.2008-05-09Not applicableUs
LamictalKitGlaxosmithkline Inc2003-09-29Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-lamotrigineTablet100 mgOralApotex Corporation2002-03-18Not applicableCanada
Apo-lamotrigineTablet150 mgOralApotex Corporation2002-03-18Not applicableCanada
Apo-lamotrigineTablet25 mgOralApotex Corporation2002-03-18Not applicableCanada
Auro-lamotrigineTablet100 mgOralAuro Pharma Inc2012-06-13Not applicableCanada
Auro-lamotrigineTablet25 mgOralAuro Pharma Inc2012-06-13Not applicableCanada
Auro-lamotrigineTablet150 mgOralAuro Pharma Inc2012-06-13Not applicableCanada
Dom-lamotrigineTablet25 mgOralDominion PharmacalNot applicableNot applicableCanada
Dom-lamotrigineTablet150 mgOralDominion PharmacalNot applicableNot applicableCanada
Dom-lamotrigineTablet100 mgOralDominion PharmacalNot applicableNot applicableCanada
LamotrigineTablet200 mg/1OralUpsher Smith Laboratories2009-01-272017-11-09Us
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
LamotrigineTablet25 mg/1OralAlembic Pharmaceuticals Limited2013-01-01Not applicableUs
LamotrigineTablet150 mg/1OralAlembic Pharmaceuticals Limited2013-01-01Not applicableUs
LamotrigineTablet100 mg/1OralAlembic Pharmaceuticals Limited2013-01-01Not applicableUs
LamotrigineTablet200 mg/1OralAlembic Pharmaceuticals Limited2013-01-01Not applicableUs
International/Other Brands
Convulsan (Actavis) / Crisomet (Juste) / Dafex (Phoenix) / Daksol (Pharmavita) / Danoptin (Pliva) / Dezepil (Rafarm) / Elmendos (GlaxoSmithKline) / Epilepax (Ivax) / Epimil (Ivax) / Epiral (Zentiva) / Epitec (Cipla Medpro) / Epitrigine (Actavis) / Labileno (GlaxoSmithKline) / Lambipol (GlaxoSmithKline) / Lamect (PharmaSwiss) / Lameptil (Sandoz) / Lameptil S (Sandoz) / Lametec (Vitalchem) / Lamez (Intas) / Lamictal / Lamictal CD (GlaxoSmithKline) / Lamictin (GlaxoSmithKline) / Lamotrix (Glenmark) / Larig (Rowex) / Medotrigin (Medochemie) / Mogine (Douglas) / Trimolep (Psicofarma) / Trogine (Ranbaxy) / Xebarin (Dr Reddys)
Categories
UNII
U3H27498KS
CAS number
84057-84-1
Weight
Average: 256.091
Monoisotopic: 255.007850663
Chemical Formula
C9H7Cl2N5
InChI Key
PYZRQGJRPPTADH-UHFFFAOYSA-N
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)
IUPAC Name
6-(2,3-dichlorophenyl)-1,2,4-triazine-3,5-diamine
SMILES
NC1=NC(N)=C(N=N1)C1=C(Cl)C(Cl)=CC=C1

Pharmacology

Indication

For the adjunctive treatment of partial seizures in epilepsy and generalized seizures of Lennox-Gastaut syndrome. Also for the maintenance treatment of bipolar I disorder and depression.

Structured Indications
Pharmacodynamics

Lamotrigine, an antiepileptic drug (AED) of the phenyltriazine class, is chemically unrelated to existing antiepileptic drugs. Lamotrigine is also used in the treatment of depression and bipolar disorder. Lamotrigine is thought to exert its anticonvulsant effect by stabilizing presynaptic neuronal membranes. Lamotrigine inhibits sodium currents by selectively binding to the inactivated state of the sodium channel and subsequently suppresses the release of the excilatory amino acid, glutamate.

Mechanism of action

One proposed mechanism of action of Lamotrigine, the relevance of which remains to be established in humans, involves an effect on sodium channels. in vitro pharmacological studies suggest that lamotrigine inhibits voltage-sensitive sodium channels and/or calcium channels, thereby stabilizing neuronal membranes and consequently modulating presynaptic transmitter release of excitatory amino acids (e.g., glutamate and aspartate). Studies on lamotrigine show binding to sodium channels similar to local anesthetics.

TargetActionsOrganism
USodium channel protein type 2 subunit alpha
inhibitor
Human
Absorption

98%

Volume of distribution
  • 0.9 to 1.3 L/kg
Protein binding

55%

Metabolism

Hepatic

Route of elimination
Not Available
Half life

25 +/- 10 hours (healthy individuals); 42.9 hours (chronic renal failure)

Clearance
  • Apparent plasma cl=0.44 mL/min/kg [healthy volunteers taking single-dose LAMICTAL]
  • Apparent plasma cl=0.58 mL/min/kg [healthy volunteers taking multiple-dose LAMICTAL]
  • Apparent plasma cl=0.30 mL/min/kg [healthy volunteers taking valproate and single-dose LAMICTAL]
  • Apparent plasma cl=0.18 mL/min/kg [healthy volunteers taking valproate and multiple-dose LAMICTAL]
  • Apparent plasma cl=1.1 mL/min/kg [Patients with epilepsy taking carbamazepine, phenytoin, phenobarbital, or primidone plus valproate and single-dose LAMICTAL]
  • Apparent plasma cl=1.12 mL/min/kg [Patients with epilepsy taking carbamazepine, phenytoin, phenobarbital, or primidone plus valproate and multiple-dose LAMICTAL]
Toxicity

LD50=250 (mg/kg) (in rat, mice); LD50>640 orally (mg/kg) (in rat, mice) (Sawyer). Symptoms of overdose include decreased level of consciousness, coma, delayed heartbeat, increased seizures, lack of coordination, and rolling eyeballs.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
2-HYDROXY-1,4-NAPHTHOQUINONEThe risk or severity of adverse effects can be increased when 2-HYDROXY-1,4-NAPHTHOQUINONE is combined with Lamotrigine.Experimental
2-mercaptobenzothiazoleThe risk or severity of adverse effects can be increased when 2-mercaptobenzothiazole is combined with Lamotrigine.Vet Approved
AlfuzosinAlfuzosin may increase the hypotensive activities of Lamotrigine.Approved, Investigational
AmobarbitalThe serum concentration of Lamotrigine can be decreased when it is combined with Amobarbital.Approved, Illicit
AmorolfineThe risk or severity of adverse effects can be increased when Amorolfine is combined with Lamotrigine.Approved, Investigational
Amphotericin BThe risk or severity of adverse effects can be increased when Amphotericin B is combined with Lamotrigine.Approved, Investigational
AnidulafunginThe risk or severity of adverse effects can be increased when Anidulafungin is combined with Lamotrigine.Approved, Investigational
ArotinololThe risk or severity of hypotension, conduction block, and bradycardia can be increased when Arotinolol is combined with Lamotrigine.Investigational
ArtemetherThe risk or severity of adverse effects can be increased when Artemether is combined with Lamotrigine.Approved
AtazanavirThe serum concentration of Lamotrigine can be decreased when it is combined with Atazanavir.Approved, Investigational
AtorvastatinThe risk or severity of adverse effects can be increased when Lamotrigine is combined with Atorvastatin.Approved
AtosibanThe risk or severity of adverse effects can be increased when Lamotrigine is combined with Atosiban.Approved, Investigational
Bafilomycin A1The risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Lamotrigine.Experimental
BarbexacloneThe serum concentration of Lamotrigine can be decreased when it is combined with Barbexaclone.Experimental
BarbitalThe serum concentration of Lamotrigine can be decreased when it is combined with Barbital.Illicit
Benzoic AcidThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Lamotrigine.Approved
BifonazoleThe risk or severity of adverse effects can be increased when Bifonazole is combined with Lamotrigine.Approved, Investigational
Brefeldin AThe risk or severity of adverse effects can be increased when Brefeldin A is combined with Lamotrigine.Experimental
BucindololBucindolol may increase the hypotensive activities of Lamotrigine.Investigational
BunazosinBunazosin may increase the hypotensive activities of Lamotrigine.Investigational
ButenafineThe risk or severity of adverse effects can be increased when Butenafine is combined with Lamotrigine.Approved
ButoconazoleThe risk or severity of adverse effects can be increased when Butoconazole is combined with Lamotrigine.Approved
Calcium AcetateThe therapeutic efficacy of Lamotrigine can be decreased when used in combination with Calcium Acetate.Approved
Calcium CarbonateThe therapeutic efficacy of Lamotrigine can be decreased when used in combination with Calcium Carbonate.Approved
Calcium ChlorideThe therapeutic efficacy of Lamotrigine can be decreased when used in combination with Calcium Chloride.Approved
Calcium CitrateThe therapeutic efficacy of Lamotrigine can be decreased when used in combination with Calcium Citrate.Approved
Calcium glubionateThe therapeutic efficacy of Lamotrigine can be decreased when used in combination with Calcium glubionate.Approved
Calcium GluceptateThe therapeutic efficacy of Lamotrigine can be decreased when used in combination with Calcium Gluceptate.Approved
Calcium gluconateThe therapeutic efficacy of Lamotrigine can be decreased when used in combination with Calcium gluconate.Approved, Vet Approved
Calcium lactateThe therapeutic efficacy of Lamotrigine can be decreased when used in combination with Calcium lactate.Approved, Experimental, Investigational, Vet Approved
Calcium lactate gluconateThe therapeutic efficacy of Lamotrigine can be decreased when used in combination with Calcium lactate gluconate.Experimental
Calcium levulinateThe therapeutic efficacy of Lamotrigine can be decreased when used in combination with Calcium laevulate.Experimental
Calcium pangamateThe therapeutic efficacy of Lamotrigine can be decreased when used in combination with Calcium pangamate.Experimental
Calcium PhosphateThe therapeutic efficacy of Lamotrigine can be decreased when used in combination with Calcium Phosphate.Approved
CandicidinThe risk or severity of adverse effects can be increased when Candicidin is combined with Lamotrigine.Withdrawn
Capric acidThe risk or severity of adverse effects can be increased when Capric acid is combined with Lamotrigine.Experimental
CarbamazepineThe risk or severity of adverse effects can be increased when Lamotrigine is combined with Carbamazepine.Approved, Investigational
CarbomycinThe metabolism of Lamotrigine can be decreased when combined with Carbomycin.Vet Approved
CarvedilolCarvedilol may increase the hypotensive activities of Lamotrigine.Approved, Investigational
CaseinThe therapeutic efficacy of Lamotrigine can be decreased when used in combination with Casein.Approved
CaspofunginThe risk or severity of adverse effects can be increased when Caspofungin is combined with Lamotrigine.Approved
CerivastatinThe risk or severity of adverse effects can be increased when Lamotrigine is combined with Cerivastatin.Withdrawn
CeruleninThe risk or severity of adverse effects can be increased when Cerulenin is combined with Lamotrigine.Approved
ChlorotrianiseneThe serum concentration of Lamotrigine can be decreased when it is combined with Chlorotrianisene.Investigational, Withdrawn
ChloroxineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Lamotrigine.Approved
CiclopiroxThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Lamotrigine.Approved, Investigational
CimetidineThe serum concentration of Lamotrigine can be increased when it is combined with Cimetidine.Approved
ClarithromycinThe metabolism of Lamotrigine can be decreased when combined with Clarithromycin.Approved
ClopidogrelThe therapeutic efficacy of Clopidogrel can be decreased when used in combination with Lamotrigine.Approved
ClotrimazoleThe risk or severity of adverse effects can be increased when Clotrimazole is combined with Lamotrigine.Approved, Vet Approved
Conjugated estrogensThe serum concentration of Lamotrigine can be decreased when it is combined with Conjugated estrogens.Approved
CordycepinThe risk or severity of adverse effects can be increased when Cordycepin is combined with Lamotrigine.Investigational
CyclosporineThe risk or severity of adverse effects can be increased when Cyclosporine is combined with Lamotrigine.Approved, Investigational, Vet Approved
DapoxetineDapoxetine may increase the orthostatic hypotensive activities of Lamotrigine.Investigational
DesmopressinThe risk or severity of adverse effects can be increased when Lamotrigine is combined with Desmopressin.Approved
DesogestrelThe serum concentration of Desogestrel can be decreased when it is combined with Lamotrigine.Approved
DichloropheneThe risk or severity of adverse effects can be increased when Dichlorophene is combined with Lamotrigine.Vet Approved
DienestrolThe serum concentration of Lamotrigine can be decreased when it is combined with Dienestrol.Approved, Investigational
DienogestThe serum concentration of Dienogest can be decreased when it is combined with Lamotrigine.Approved
DiethylstilbestrolThe serum concentration of Lamotrigine can be decreased when it is combined with Diethylstilbestrol.Approved, Investigational
DofetilideThe serum concentration of Dofetilide can be increased when it is combined with Lamotrigine.Approved
DoxazosinDoxazosin may increase the hypotensive activities of Lamotrigine.Approved
DoxofyllineThe serum concentration of Doxofylline can be decreased when it is combined with Lamotrigine.Approved, Investigational
DrospirenoneThe serum concentration of Drospirenone can be decreased when it is combined with Lamotrigine.Approved
EconazoleThe risk or severity of adverse effects can be increased when Econazole is combined with Lamotrigine.Approved
EfavirenzThe serum concentration of Lamotrigine can be decreased when it is combined with Efavirenz.Approved, Investigational
EfinaconazoleThe risk or severity of adverse effects can be increased when Efinaconazole is combined with Lamotrigine.Approved
ErythromycinThe metabolism of Lamotrigine can be decreased when combined with Erythromycin.Approved, Vet Approved
EstradiolThe serum concentration of Lamotrigine can be decreased when it is combined with Estradiol.Approved, Investigational, Vet Approved
EstramustineThe serum concentration of Lamotrigine can be decreased when it is combined with Estramustine.Approved
Estrogens, esterifiedThe serum concentration of Lamotrigine can be decreased when it is combined with Estrogens, esterified.Approved
Estrone sulfateThe serum concentration of Lamotrigine can be decreased when it is combined with Estrone sulfate.Approved
Ethinyl EstradiolThe serum concentration of Lamotrigine can be decreased when it is combined with Ethinyl Estradiol.Approved
Ethynodiol diacetateThe serum concentration of Ethynodiol diacetate can be decreased when it is combined with Lamotrigine.Approved
EtonogestrelThe serum concentration of Etonogestrel can be decreased when it is combined with Lamotrigine.Approved, Investigational
EzogabineThe serum concentration of Lamotrigine can be decreased when it is combined with Ezogabine.Approved
FenticonazoleThe risk or severity of adverse effects can be increased when Fenticonazole is combined with Lamotrigine.Experimental
FluconazoleThe serum concentration of Lamotrigine can be increased when it is combined with Fluconazole.Approved
FlucytosineThe risk or severity of adverse effects can be increased when Flucytosine is combined with Lamotrigine.Approved
FlutrimazoleThe risk or severity of adverse effects can be increased when Flutrimazole is combined with Lamotrigine.Experimental
FluvastatinThe risk or severity of adverse effects can be increased when Lamotrigine is combined with Fluvastatin.Approved
FosphenytoinThe serum concentration of Lamotrigine can be decreased when it is combined with Fosphenytoin.Approved
GestodeneThe serum concentration of Gestodene can be decreased when it is combined with Lamotrigine.Approved, Investigational
GlyphosateThe risk or severity of adverse effects can be increased when Glyphosate is combined with Lamotrigine.Experimental
GriseofulvinThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Lamotrigine.Approved, Vet Approved
HachimycinThe risk or severity of adverse effects can be increased when Hachimycin is combined with Lamotrigine.Experimental
HaloproginThe risk or severity of adverse effects can be increased when Haloprogin is combined with Lamotrigine.Approved, Withdrawn
HexestrolThe serum concentration of Lamotrigine can be decreased when it is combined with Hexestrol.Withdrawn
HexetidineThe risk or severity of adverse effects can be increased when Hexetidine is combined with Lamotrigine.Approved, Investigational
HexobarbitalThe serum concentration of Lamotrigine can be decreased when it is combined with Hexobarbital.Approved
IndoraminIndoramin may increase the hypotensive activities of Lamotrigine.Withdrawn
IsoconazoleThe risk or severity of adverse effects can be increased when Isoconazole is combined with Lamotrigine.Approved
ItraconazoleThe risk or severity of adverse effects can be increased when Itraconazole is combined with Lamotrigine.Approved, Investigational
JosamycinThe metabolism of Lamotrigine can be decreased when combined with Josamycin.Approved, Investigational
KetoconazoleThe risk or severity of adverse effects can be increased when Ketoconazole is combined with Lamotrigine.Approved, Investigational
KitasamycinThe metabolism of Lamotrigine can be decreased when combined with Kitasamycin.Experimental
LabetalolLabetalol may increase the hypotensive activities of Lamotrigine.Approved
LevonorgestrelThe serum concentration of Levonorgestrel can be decreased when it is combined with Lamotrigine.Approved, Investigational
LovastatinThe risk or severity of adverse effects can be increased when Lamotrigine is combined with Lovastatin.Approved, Investigational
LumacaftorThe serum concentration of Lamotrigine can be decreased when it is combined with Lumacaftor.Approved
LynestrenolThe serum concentration of Lynestrenol can be decreased when it is combined with Lamotrigine.Investigational
Medroxyprogesterone acetateThe serum concentration of Medroxyprogesterone acetate can be decreased when it is combined with Lamotrigine.Approved, Investigational
MefloquineThe therapeutic efficacy of Lamotrigine can be decreased when used in combination with Mefloquine.Approved
MepartricinThe risk or severity of adverse effects can be increased when Mepartricin is combined with Lamotrigine.Experimental
MestranolThe serum concentration of Lamotrigine can be decreased when it is combined with Mestranol.Approved
MetforminThe serum concentration of Metformin can be increased when it is combined with Lamotrigine.Approved
MethallenestrilThe serum concentration of Lamotrigine can be decreased when it is combined with Methallenestril.Experimental
MethohexitalThe serum concentration of Lamotrigine can be decreased when it is combined with Methohexital.Approved
MethylphenobarbitalThe serum concentration of Lamotrigine can be decreased when it is combined with Methylphenobarbital.Approved
MevastatinThe risk or severity of adverse effects can be increased when Mevastatin is combined with Lamotrigine.Experimental
MianserinThe therapeutic efficacy of Lamotrigine can be decreased when used in combination with Mianserin.Approved, Investigational
MicafunginThe risk or severity of adverse effects can be increased when Micafungin is combined with Lamotrigine.Approved, Investigational
MiconazoleThe risk or severity of adverse effects can be increased when Miconazole is combined with Lamotrigine.Approved, Investigational, Vet Approved
MiltefosineThe risk or severity of adverse effects can be increased when Miltefosine is combined with Lamotrigine.Approved
MonensinThe risk or severity of adverse effects can be increased when Monensin is combined with Lamotrigine.Vet Approved
MyxothiazolThe risk or severity of adverse effects can be increased when Myxothiazol is combined with Lamotrigine.Experimental
NafcillinThe metabolism of Lamotrigine can be increased when combined with Nafcillin.Approved
NaftifineThe risk or severity of adverse effects can be increased when Naftifine is combined with Lamotrigine.Approved
NatamycinThe risk or severity of adverse effects can be increased when Natamycin is combined with Lamotrigine.Approved
NifuratelThe risk or severity of adverse effects can be increased when Nifuratel is combined with Lamotrigine.Experimental
Nikkomycin ZThe risk or severity of adverse effects can be increased when Nikkomycin Z is combined with Lamotrigine.Investigational
NitroprussideLamotrigine may increase the hypotensive activities of Nitroprusside.Approved
NitroxolineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Lamotrigine.Approved
NorelgestrominThe serum concentration of Norelgestromin can be decreased when it is combined with Lamotrigine.Approved
NorgestimateThe serum concentration of Norgestimate can be decreased when it is combined with Lamotrigine.Approved
NorgestrelThe serum concentration of Norgestrel can be decreased when it is combined with Lamotrigine.Approved
NystatinThe risk or severity of adverse effects can be increased when Nystatin is combined with Lamotrigine.Approved, Vet Approved
OlanzapineLamotrigine may increase the sedative activities of Olanzapine.Approved, Investigational
OleandomycinThe metabolism of Lamotrigine can be decreased when combined with Oleandomycin.Vet Approved
OmoconazoleThe risk or severity of adverse effects can be increased when Omoconazole is combined with Lamotrigine.Experimental
OrlistatThe serum concentration of Lamotrigine can be decreased when it is combined with Orlistat.Approved, Investigational
OxiconazoleThe risk or severity of adverse effects can be increased when Oxiconazole is combined with Lamotrigine.Approved
PafuramidineThe risk or severity of adverse effects can be increased when Pafuramidine is combined with Lamotrigine.Investigational
PentamidineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Lamotrigine.Approved
PentobarbitalThe serum concentration of Lamotrigine can be decreased when it is combined with Pentobarbital.Approved, Vet Approved
PhenobarbitalThe serum concentration of Lamotrigine can be decreased when it is combined with Phenobarbital.Approved
PhenytoinThe serum concentration of Lamotrigine can be decreased when it is combined with Phenytoin.Approved, Vet Approved
PitavastatinThe risk or severity of adverse effects can be increased when Lamotrigine is combined with Pitavastatin.Approved
PosaconazoleThe risk or severity of adverse effects can be increased when Posaconazole is combined with Lamotrigine.Approved, Investigational, Vet Approved
PravastatinThe risk or severity of adverse effects can be increased when Lamotrigine is combined with Pravastatin.Approved
PrazosinPrazosin may increase the hypotensive activities of Lamotrigine.Approved
PregabalinThe therapeutic efficacy of Lamotrigine can be decreased when used in combination with Pregabalin.Approved, Illicit, Investigational
PrimidoneThe serum concentration of Lamotrigine can be decreased when it is combined with Primidone.Approved, Vet Approved
ProcainamideThe serum concentration of Procainamide can be increased when it is combined with Lamotrigine.Approved
PyrrolnitrinThe risk or severity of adverse effects can be increased when Pyrrolnitrin is combined with Lamotrigine.Experimental
RadicicolThe risk or severity of adverse effects can be increased when Radicicol is combined with Lamotrigine.Experimental
RanolazineThe serum concentration of Lamotrigine can be increased when it is combined with Ranolazine.Approved, Investigational
RifabutinThe serum concentration of Lamotrigine can be decreased when it is combined with Rifabutin.Approved
RifampicinThe metabolism of Lamotrigine can be increased when combined with Rifampicin.Approved
RifapentineThe serum concentration of Lamotrigine can be decreased when it is combined with Rifapentine.Approved
RifaximinThe serum concentration of Lamotrigine can be decreased when it is combined with Rifaximin.Approved, Investigational
RitonavirThe serum concentration of Lamotrigine can be decreased when it is combined with Ritonavir.Approved, Investigational
RosuvastatinThe risk or severity of adverse effects can be increased when Lamotrigine is combined with Rosuvastatin.Approved
Salicylhydroxamic AcidThe risk or severity of adverse effects can be increased when Salicylhydroxamic Acid is combined with Lamotrigine.Experimental
Salicylic acidThe risk or severity of adverse effects can be increased when Salicylic acid is combined with Lamotrigine.Approved, Vet Approved
SecobarbitalThe serum concentration of Lamotrigine can be decreased when it is combined with Secobarbital.Approved, Vet Approved
SertaconazoleThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Lamotrigine.Approved
SilodosinSilodosin may increase the hypotensive activities of Lamotrigine.Approved
SimvastatinThe risk or severity of adverse effects can be increased when Lamotrigine is combined with Simvastatin.Approved
SinefunginThe risk or severity of adverse effects can be increased when Sinefungin is combined with Lamotrigine.Experimental
SirolimusThe risk or severity of adverse effects can be increased when Sirolimus is combined with Lamotrigine.Approved, Investigational
SolithromycinThe metabolism of Lamotrigine can be decreased when combined with Solithromycin.Investigational
SulconazoleThe risk or severity of adverse effects can be increased when Sulconazole is combined with Lamotrigine.Approved
Synthetic Conjugated Estrogens, AThe serum concentration of Lamotrigine can be decreased when it is combined with Synthetic Conjugated Estrogens, A.Approved
TamsulosinTamsulosin may increase the hypotensive activities of Lamotrigine.Approved, Investigational
TavaboroleThe risk or severity of adverse effects can be increased when Tavaborole is combined with Lamotrigine.Approved
TelithromycinThe metabolism of Lamotrigine can be decreased when combined with Telithromycin.Approved
TerazosinTerazosin may increase the hypotensive activities of Lamotrigine.Approved
TerbinafineThe risk or severity of adverse effects can be increased when Terbinafine is combined with Lamotrigine.Approved, Investigational, Vet Approved
TerconazoleThe risk or severity of adverse effects can be increased when Terconazole is combined with Lamotrigine.Approved
ThiamylalThe serum concentration of Lamotrigine can be decreased when it is combined with Thiamylal.Approved, Vet Approved
ThiopentalThe serum concentration of Lamotrigine can be decreased when it is combined with Thiopental.Approved, Vet Approved
ThymolThe risk or severity of adverse effects can be increased when Thymol is combined with Lamotrigine.Approved
TioconazoleThe risk or severity of adverse effects can be increased when Tioconazole is combined with Lamotrigine.Approved
TolciclateThe risk or severity of adverse effects can be increased when Tolciclate is combined with Lamotrigine.Experimental
TolnaftateThe risk or severity of adverse effects can be increased when Tolnaftate is combined with Lamotrigine.Approved, Vet Approved
TrimazosinTrimazosin may increase the hypotensive activities of Lamotrigine.Experimental
TrimetrexateThe risk or severity of adverse effects can be increased when Trimetrexate is combined with Lamotrigine.Approved, Investigational
TylosinThe metabolism of Lamotrigine can be decreased when combined with Tylosin.Vet Approved
UbidecarenoneThe risk or severity of adverse effects can be increased when Lamotrigine is combined with Ubidecarenone.Approved, Investigational, Nutraceutical
UrapidilUrapidil may increase the hypotensive activities of Lamotrigine.Investigational
Valproic AcidThe risk or severity of adverse effects can be increased when Valproic Acid is combined with Lamotrigine.Approved, Investigational
VemurafenibThe serum concentration of Lamotrigine can be increased when it is combined with Vemurafenib.Approved
VoriconazoleThe risk or severity of adverse effects can be increased when Voriconazole is combined with Lamotrigine.Approved, Investigational
Food Interactions
  • Take without regard to meals.

References

Synthesis Reference

Grahame Roy Lee, "Process for the preparation of lamotrigine." U.S. Patent US5925755, issued January, 1981.

US5925755
General References
  1. Backonja M: Neuromodulating drugs for the symptomatic treatment of neuropathic pain. Curr Pain Headache Rep. 2004 Jun;8(3):212-6. [PubMed:15115640]
  2. Barbosa L, Berk M, Vorster M: A double-blind, randomized, placebo-controlled trial of augmentation with lamotrigine or placebo in patients concomitantly treated with fluoxetine for resistant major depressive episodes. J Clin Psychiatry. 2003 Apr;64(4):403-7. [PubMed:12716240]
  3. Jensen TS: Anticonvulsants in neuropathic pain: rationale and clinical evidence. Eur J Pain. 2002;6 Suppl A:61-8. [PubMed:11888243]
  4. Pappagallo M: Newer antiepileptic drugs: possible uses in the treatment of neuropathic pain and migraine. Clin Ther. 2003 Oct;25(10):2506-38. [PubMed:14667954]
  5. Tehrani SP, Daryaafzoon M, Bakhtiarian A, Ejtemaeemehr S, Sahraei H: The effects of lamotrigine on the acquisition and expression of morphine-induced place preference in mice. Pak J Biol Sci. 2009 Jan 1;12(1):33-9. [PubMed:19579915]
External Links
Human Metabolome Database
HMDB0014695
KEGG Drug
D00354
PubChem Compound
3878
PubChem Substance
46505408
ChemSpider
3741
BindingDB
50031299
ChEBI
6367
ChEMBL
CHEMBL741
Therapeutic Targets Database
DAP000039
PharmGKB
PA450164
IUPHAR
2622
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Lamotrigine
ATC Codes
N03AX09 — Lamotrigine
AHFS Codes
  • 28:12.92 — Miscellaneous Anticonvulsants
FDA label
Download (3.15 MB)
MSDS
Download (28.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingBasic SciencePsychiatric Disorder NOS1
1CompletedNot AvailableHealthy Volunteers8
1CompletedTreatmentBipolar Disorder (BD)1
1CompletedTreatmentBipolar Disorder (BD) / Epilepsies1
1CompletedTreatmentEpilepsies6
1CompletedTreatmentEpilepsies / Seizure, Absence1
1CompletedTreatmentFasting State1
1CompletedTreatmentFed1
1CompletedTreatmentHealthy Volunteers8
1CompletedTreatmentHealthy Volunteers / Psychiatric Disorder NOS2
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
1RecruitingTreatmentBipolar Affective Disorders / Bipolar Disorder (BD)1
1TerminatedTreatmentBipolar Disorder (BD) / Healthy Volunteers1
1, 2CompletedDiagnosticBipolar Disorder (BD) / Depression, Bipolar / Epilepsies / Seizures1
1, 2RecruitingTreatmentBrain Injury1
2CompletedTreatmentAnxiety Disorders / Moods Disorders / Psychotic Disorder NOS1
2CompletedTreatmentBipolar Disorder (BD)1
2CompletedTreatmentBipolar II Disorder, Most Recent Episode Major Depressive1
2CompletedTreatmentCocaine-Related Disorders1
2CompletedTreatmentDermatillomania / Neurotic Excoriation / Pathologic Skin Picking / Psychogenic Excoriation1
2CompletedTreatmentEpilepsies2
2CompletedTreatmentMixed Mania Bipolar Disorder1
2CompletedTreatmentNeurotic Disorders / Obsessive-Compulsive Disorder (OCD)1
2CompletedTreatmentSecondary Progressive Multiple Sclerosis (SPMS)1
2TerminatedTreatmentBipolar 1 Disorder1
2Unknown StatusTreatmentRelapsing Remitting Multiple Sclerosis (RRMS)1
2WithdrawnTreatmentOpioid-Related Disorders1
2, 3CompletedTreatmentTrigeminal Neuralgia (TN)1
2, 3RecruitingTreatmentAddictions1
2, 3RecruitingTreatmentNeurofibromatosis Type 11
3Active Not RecruitingTreatmentAdverse Effects / Epilepsy, Localization Related1
3CompletedNot AvailableSeizures1
3CompletedDiagnosticBipolar Disorder (BD)1
3CompletedSupportive CareNeurotoxicity / Pain / Unspecified Adult Solid Tumor, Protocol Specific1
3CompletedTreatmentBinge Eating Disorder (BED) / BMI >30 kg/m21
3CompletedTreatmentBipolar Disorder (BD)7
3CompletedTreatmentBipolar Disorder (BD) / Depression, Bipolar2
3CompletedTreatmentChildhood Absence Epilepsy / Epilepsies / Petit Mal Epilepsy / Seizures1
3CompletedTreatmentDepression1
3CompletedTreatmentDepression, Bipolar1
3CompletedTreatmentDystrophia Myotonica Type 1 / Myotonia Congenita / Paralysis, Hyperkalemic Periodic / Paramyotonia Congenita / Potassium-Aggravated Myotonia1
3CompletedTreatmentEpilepsies6
3CompletedTreatmentEpilepsy, Localization Related2
3CompletedTreatmentMenière's Disease / Ménière's Vertigo / Vertigo, Aural / Vertigo, Intermittent1
3CompletedTreatmentMoods Disorders1
3CompletedTreatmentSchizophrenic Disorders2
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
3TerminatedTreatmentBipolar Disorder (BD)1
3TerminatedTreatmentEpilepsies1
3WithdrawnTreatmentAlcohol Dependence / Post Traumatic Stress Disorder (PTSD)1
4Active Not RecruitingTreatmentBipolar Disorder (BD) / Depression / Depression, Bipolar / Lamotrigine / Melancholic Depression1
4CompletedNot AvailableHippocampal Atrophy Due to Corticosteroid / Hypomania Due to Corticosteroid Use / Memory Impairment Due to Corticosteroid Use1
4CompletedBasic ScienceEpilepsies1
4CompletedBasic ScienceHealthy Volunteers1
4CompletedHealth Services ResearchMemory Disturbances1
4CompletedOtherHealthy Volunteers1
4CompletedPreventionBipolar Disorder (BD)1
4CompletedTreatmentBipolar Disorder (BD)7
4CompletedTreatmentBipolar Disorder (BD) / Dependence, Cocaine1
4CompletedTreatmentBipolar Disorder (BD) / Depression1
4CompletedTreatmentBipolar Disorder (BD) / Mania1
4CompletedTreatmentBipolar I Disorder / Bipolar II Disorder1
4CompletedTreatmentBorderline Personality Disorder (BPD)1
4CompletedTreatmentBronchial Asthma1
4CompletedTreatmentEpilepsies5
4CompletedTreatmentEpilepsy, Localization Related2
4CompletedTreatmentEpilepsy, Tonic-Clonic1
4CompletedTreatmentMajor Depressive Disorder (MDD)1
4Enrolling by InvitationTreatmentEpilepsies1
4Not Yet RecruitingBasic ScienceBariatric Surgery Candidate1
4Not Yet RecruitingBasic ScienceEpilepsies1
4RecruitingNot AvailableEpilepsies1
4RecruitingTreatmentBipolar Disorder (BD)1
4RecruitingTreatmentEpilepsies1
4TerminatedTreatmentMajor Depressive Disorder (MDD)1
4Unknown StatusTreatmentAlcohol Dependence / Bipolar Disorder (BD) / Depression / Mania / Psychosis1
4Unknown StatusTreatmentEpilepsies1
Not AvailableCompletedNot AvailableBipolar Disorder (BD)3
Not AvailableCompletedNot AvailableEpilepsies4
Not AvailableCompletedBasic ScienceDepression, Bipolar1
Not AvailableCompletedPreventionBipolar Disorder (BD) / Depression / Psychotic Disorder NOS / Schizophrenic Disorders1
Not AvailableCompletedTreatmentBipolar Disorder (BD)1
Not AvailableCompletedTreatmentFacial Neuropathy1
Not AvailableCompletedTreatmentTrigeminal Neuralgia (TN)1
Not AvailableCompletedTreatmentUnipolar Depression1
Not AvailableEnrolling by InvitationNot AvailableBipolar Disorder (BD)1
Not AvailableRecruitingNot AvailableBipolar Disorder (BD)1
Not AvailableRecruitingNot AvailableDepression / Suicidal Ideation1
Not AvailableRecruitingNot AvailableEpilepsies1
Not AvailableRecruitingBasic ScienceBipolar Disorder (BD) / Depression, Bipolar / Unipolar Depression1
Not AvailableTerminatedTreatmentAdolescent Depression1
Not AvailableUnknown StatusTreatmentAdults With Tonic Clonic Seizures and/or Partial Seizures1
Not AvailableUnknown StatusTreatmentEpilepsies1

Pharmacoeconomics

Manufacturers
  • Glaxosmithkline
  • Aurobindo pharma ltd
  • Dr reddys laboratories ltd
  • Glenmark generics ltd
  • Mylan pharmaceuticals inc
  • Sandoz inc
  • Taro pharmaceutical industries ltd
  • Teva pharmaceuticals usa inc
  • Watson laboratories inc
  • Zydus pharmaceuticals usa inc
  • Smithkline beecham corp
  • Smithkline beecham corp dba glaxosmithkline
  • Apotex inc
  • Cadista pharmaceuticals inc
  • Lupin ltd
  • Matrix laboratories ltd
  • Roxane laboratories inc
  • Torrent pharmaceuticals ltd
  • Upsher smith laboratories inc
  • Wockhardt ltd
Packagers
Dosage forms
FormRouteStrength
TabletOral100 mg
TabletOral150 mg/1
TabletOral150 mg
TabletOral2 mg
TabletOral25 mg
TabletOral5 mg
Tablet, chewableOral2 mg/1
TabletOral200 mg
Tablet, orally disintegratingOral100 mg/1
Tablet, orally disintegratingOral200 mg/1
Tablet, orally disintegratingOral25 mg/1
Tablet, orally disintegratingOral50 mg/1
Tablet, film coated, extended releaseOral100 mg/1
Tablet, film coated, extended releaseOral200 mg/1
Tablet, film coated, extended releaseOral25 mg/1
Tablet, film coated, extended releaseOral250 mg/1
Tablet, film coated, extended releaseOral300 mg/1
Tablet, film coated, extended releaseOral50 mg/1
Kit
TabletOral100 mg/1
TabletOral200 mg/1
TabletOral25 mg/1
TabletOral250 mg/1
TabletOral50 mg/1
Tablet, chewableOral25 mg/1
Tablet, chewableOral5 mg/1
Tablet, extended releaseOral100 mg/1
Tablet, extended releaseOral200 mg/1
Tablet, extended releaseOral25 mg/1
Tablet, extended releaseOral300 mg/1
Tablet, extended releaseOral50 mg/1
Tablet, for suspensionOral25 mg/1
Tablet, for suspensionOral5 mg/1
TabletOral300 mg/1
Prices
Unit descriptionCostUnit
LaMICtal Starter 98 25 (84)-100(14)mg Kit Box556.69USD box
LaMICtal XR 200 mg 24 Hour tablet12.11USD tablet
Lamictal xr 200 mg tablet11.65USD tablet
LaMICtal XR 100 mg 24 Hour tablet11.36USD tablet
Lamictal xr 100 mg tablet10.92USD tablet
Lamictal xr 50 mg tablet10.2USD tablet
Lamictal 200 mg tablet7.44USD tablet
Lamictal odt start kt (orange)7.28USD tablet
Lamictal xr start kit (orange)7.28USD tablet
Lamictal odt 200 mg tablet6.95USD tablet
Lamictal odt 100 mg tablet5.82USD tablet
Lamotrigine 200 mg tablet5.78USD tablet
LaMICtal 25 mg Chew Tabs5.63USD tab
Lamictal odt 50 mg tablet5.46USD tablet
Lamictal tab start kit (green)5.46USD tablet
Lamictal 150 mg tablet5.38USD tablet
Lamictal odt 25 mg tablet5.1USD tablet
Lamictal xr 25 mg tablet5.1USD tablet
Lamictal 100 mg tablet4.72USD tablet
Lamotrigine tablet starter kit4.24USD tablet
Lamotrigine 150 mg tablet3.98USD tablet
Lamictal 25 mg tablet3.78USD tablet
Lamotrigine 100 mg tablet3.52USD tablet
LamoTRIgine 25 mg Chew Tabs3.33USD tab
LamoTRIgine 5 mg Chew Tabs3.18USD tab
Lamotrigine 25 mg tablet2.9USD tablet
Apo-Lamotrigine 150 mg Tablet1.31USD tablet
Mylan-Lamotrigine 150 mg Tablet1.31USD tablet
Novo-Lamotrigine 150 mg Tablet1.31USD tablet
Pms-Lamotrigine 150 mg Tablet1.31USD tablet
Ratio-Lamotrigine 150 mg Tablet1.31USD tablet
Apo-Lamotrigine 100 mg Tablet0.88USD tablet
Mylan-Lamotrigine 100 mg Tablet0.88USD tablet
Novo-Lamotrigine 100 mg Tablet0.88USD tablet
Pms-Lamotrigine 100 mg Tablet0.88USD tablet
Ratio-Lamotrigine 100 mg Tablet0.88USD tablet
Apo-Lamotrigine 25 mg Tablet0.22USD tablet
Mylan-Lamotrigine 25 mg Tablet0.22USD tablet
Novo-Lamotrigine 25 mg Tablet0.22USD tablet
Pms-Lamotrigine 25 mg Tablet0.22USD tablet
Ratio-Lamotrigine 25 mg Tablet0.22USD tablet
Lamictal 5 mg Chewable Tablet0.18USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5698226No1995-07-292012-07-29Us
CA2277722No2001-03-272012-01-29Canada
US9144547No2003-09-222023-09-22Us
US8637512No2008-06-142028-06-14Us
US8840925No2008-07-022028-07-02Us
US7919115No2009-01-042029-01-04Us
US9339504No2008-07-022028-07-02Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)216-218 °C (uncorr)Not Available
logP2.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.488 mg/mLALOGPS
logP1.87ALOGPS
logP1.93ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)14.98ChemAxon
pKa (Strongest Basic)5.87ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area90.71 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity66.62 m3·mol-1ChemAxon
Polarizability23.1 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9382
Caco-2 permeable+0.8867
P-glycoprotein substrateNon-substrate0.7155
P-glycoprotein inhibitor INon-inhibitor0.911
P-glycoprotein inhibitor IINon-inhibitor0.9604
Renal organic cation transporterNon-inhibitor0.8176
CYP450 2C9 substrateNon-substrate0.9162
CYP450 2D6 substrateNon-substrate0.9055
CYP450 3A4 substrateNon-substrate0.6862
CYP450 1A2 substrateNon-inhibitor0.611
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.7007
CYP450 2C19 inhibitorNon-inhibitor0.8594
CYP450 3A4 inhibitorNon-inhibitor0.7678
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5515
Ames testNon AMES toxic0.8202
CarcinogenicityNon-carcinogens0.7895
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7556 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9168
hERG inhibition (predictor II)Non-inhibitor0.8735
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0090000000-0ca7be847ef73a25032b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0c09-0890000000-f7244245bf6816d03dc7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0090000000-97d10d3ad5d45edcaeba
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0090000000-b2dbf89c13423bc1b59f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0090000000-d26cb5886894916aa1d8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0590000000-528845465e0a140f6b60
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0930000000-9a68c83a3573a48cf6c2
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0kmi-0900000000-bb97e1aecda1747cbf29
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0090000000-97d10d3ad5d45edcaeba
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0090000000-97d10d3ad5d45edcaeba
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0090000000-1e756e80b9a7d4b0dd18
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0490000000-a29a09ef58e19c7e62e1
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0940000000-85279d67921a0106c4e2
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0kmi-0900000000-eba38744d927d1c39a74
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0ab9-0790000000-036c53ed1835e3d33348
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-0290000000-26664a56093e292ec551
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-0190000000-33187897c9fb0b0a178f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-2940000000-1a4f3a098b426ac4febb

Taxonomy

Description
This compound belongs to the class of organic compounds known as dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Halobenzenes
Direct Parent
Dichlorobenzenes
Alternative Parents
Aminotriazines / Imidolactams / Aryl chlorides / 1,2,4-triazines / Heteroaromatic compounds / Azacyclic compounds / Primary amines / Organopnictogen compounds / Organochlorides / Hydrocarbon derivatives
Substituents
1,2-dichlorobenzene / Aminotriazine / Aryl chloride / Aryl halide / Triazine / Imidolactam / 1,2,4-triazine / Heteroaromatic compound / Organoheterocyclic compound / Azacycle
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
dichlorobenzene, primary arylamine, 1,2,4-triazines (CHEBI:6367)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Voltage-gated sodium channel activity
Specific Function
Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a...
Gene Name
SCN2A
Uniprot ID
Q99250
Uniprot Name
Sodium channel protein type 2 subunit alpha
Molecular Weight
227972.64 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Lipkind GM, Fozzard HA: Molecular modeling of local anesthetic drug binding by voltage-gated sodium channels. Mol Pharmacol. 2005 Dec;68(6):1611-22. Epub 2005 Sep 20. [PubMed:16174788]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Protein homodimerization activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A4
Uniprot ID
P22310
Uniprot Name
UDP-glucuronosyltransferase 1-4
Molecular Weight
60024.535 Da
References
  1. Argikar UA, Senekeo-Effenberger K, Larson EE, Tukey RH, Remmel RP: Studies on induction of lamotrigine metabolism in transgenic UGT1 mice. Xenobiotica. 2009 Nov;39(11):826-35. doi: 10.3109/00498250903188985. [PubMed:19845433]
  2. Chen H, Yang K, Choi S, Fischer JH, Jeong H: Up-regulation of UDP-glucuronosyltransferase (UGT) 1A4 by 17beta-estradiol: a potential mechanism of increased lamotrigine elimination in pregnancy. Drug Metab Dispos. 2009 Sep;37(9):1841-7. doi: 10.1124/dmd.109.026609. Epub 2009 Jun 22. [PubMed:19546240]
  3. Argikar UA, Remmel RP: Variation in glucuronidation of lamotrigine in human liver microsomes. Xenobiotica. 2009 May;39(5):355-63. doi: 10.1080/00498250902745082. [PubMed:19387891]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative reg...
Gene Name
UGT1A3
Uniprot ID
P35503
Uniprot Name
UDP-glucuronosyltransferase 1-3
Molecular Weight
60337.835 Da
References
  1. Argikar UA, Remmel RP: Variation in glucuronidation of lamotrigine in human liver microsomes. Xenobiotica. 2009 May;39(5):355-63. doi: 10.1080/00498250902745082. [PubMed:19387891]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Luna-Tortos C, Fedrowitz M, Loscher W: Several major antiepileptic drugs are substrates for human P-glycoprotein. Neuropharmacology. 2008 Dec;55(8):1364-75. doi: 10.1016/j.neuropharm.2008.08.032. Epub 2008 Sep 11. [PubMed:18824002]

Drug created on June 13, 2005 07:24 / Updated on January 19, 2018 10:49