Lamotrigine (CED0002128)

Record Information

Version

1.0

Creation Date

2009-07-05 03:30:53 UTC

Update Date

2026-05-14 16:42:05 UTC

SynCED ID

CED0002128

Secondary Accession Numbers

CHEM002096
T3D2570

Identification

Common Name

Lamotrigine

Class

Small Molecule

Description

Lamotrigine is an exogenous organic compound with the formula C9H7Cl2N5 and an average molecular weight of 256.09 g/mol. It exists as a solid at room temperature. Lamotrigine belongs to the halobenzenes, a subclass of benzene and substituted derivatives within the organic compounds. This compound is utilized as an anticonvulsant, antimanic drug, and antidepressant. Biologically, it functions as a non-narcotic analgesic, calcium channel blocker, and excitatory amino acid antagonist, and it acts as an inhibitor of prolyl oligopeptidase (EC 3.4.21.26). Lamotrigine has 43 recorded protein targets, including sodium channel protein type 5 subunit alpha (SCN5A), type 1 subunit alpha (SCN1A), type 2 subunit alpha (SCN2A), and type 3 subunit alpha (SCN3A). It also acts as an inducer, blocker, or inhibitor of the voltage-gated inwardly rectifying potassium channel KCNH2, as well as sodium channel protein type 10 subunit alpha (SCN10A), type 7 subunit alpha (SCN7A), and type 11 subunit alpha (SCN11A). One proposed mechanism of action involves the inhibition of voltage-sensitive sodium channels, which may stabilize neuronal membranes and modulate the presynaptic transmitter release of excitatory amino acids such as aspartate and glutamate, though the relevance of this in humans remains to be established. Lamotrigine is found in 13 recorded sources, including antiepileptics, drinking water, food preservation, various electrical and electronic equipment (such as radio transmission systems, magnets, and electric hearing aids), and household consumer products (including tobacco smoke filters and cigar cigarettes). The recorded exposure route for this compound is oral.

Contaminant Type

Amine
Analgesic
Anticonvulsant
Antidepressant
Antidepressive Agent
Antimanic Agent
Calcium Channel Blocker
Drug
Excitatory Amino Acid Antagonist
Food Toxin
Human Neurotoxin
Metabolite
Organic Compound
Organochloride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine	ChEBI
Lamictal	ChEBI
Lamotrigina	ChEBI
Lamotriginum	ChEBI
GW 273293	HMDB
Labileno	HMDB
3,5-Diamino-6-(2,3-dichlorophenyl)-as-triazine	HMDB
BW-430C	HMDB
Crisomet	HMDB
Lamiktal	HMDB
BW 430C	HMDB

Chemical Formula

C₉H₇Cl₂N₅

Average Molecular Mass

256.091 g/mol

Monoisotopic Mass

255.008 g/mol

CAS Registry Number

84057-84-1

IUPAC Name

6-(2,3-dichlorophenyl)-1,2,4-triazine-3,5-diamine

Traditional Name

lamotrigine

SMILES

NC1=NC(N)=C(N=N1)C1=C(Cl)C(Cl)=CC=C1

InChI Identifier

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)

InChI Key

PYZRQGJRPPTADH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes 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

Substituents

1,2-dichlorobenzene
Aminotriazine
Aryl chloride
Aryl halide
Triazine
Imidolactam
1,2,4-triazine
Heteroaromatic compound
Organoheterocyclic compound
Azacycle
Amine
Primary amine
Organonitrogen compound
Organochloride
Organohalogen compound
Organopnictogen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dichlorobenzene (CHEBI:6367 )
primary arylamine (CHEBI:6367 )
1,2,4-triazines (CHEBI:6367 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Biological Roles

Chemical Roles

EC 3.4.21.26 (prolyl oligopeptidase) inhibitor ?

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

White to pale cream-colored powder. Crystals from isopropanol (9).

Experimental Properties

Property	Value
Melting Point	216-218°C (uncorr)
Boiling Point	Not Available
Solubility	4.88e-01 g/L

Predicted Properties

Property	Value	Source
Water Solubility	0.49 g/L	ALOGPS
logP	1.87	ALOGPS
logP	1.93	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	14.98	ChemAxon
pKa (Strongest Basic)	5.87	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	90.71 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	66.62 m³·mol⁻¹	ChemAxon
Polarizability	23.1 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0a4i-1890000000-760d1195ef5ceae75026	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-2940000000-1a4f3a098b426ac4febb	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0090000000-0ca7be847ef73a25032b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0c09-0890000000-f7244245bf6816d03dc7	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0090000000-97d10d3ad5d45edcaeba	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0090000000-b2dbf89c13423bc1b59f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0090000000-d26cb5886894916aa1d8	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0590000000-528845465e0a140f6b60	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0930000000-9a68c83a3573a48cf6c2	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0kmi-0900000000-bb97e1aecda1747cbf29	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0090000000-97d10d3ad5d45edcaeba	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0090000000-97d10d3ad5d45edcaeba	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0090000000-1e756e80b9a7d4b0dd18	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0490000000-a29a09ef58e19c7e62e1	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0940000000-85279d67921a0106c4e2	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0kmi-0900000000-eba38744d927d1c39a74	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0ab9-0790000000-036c53ed1835e3d33348	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0290000000-26664a56093e292ec551	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0190000000-33187897c9fb0b0a178f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-2940000000-1a4f3a098b426ac4febb	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0930000000-9a68c83a3573a48cf6c2	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0c00-0930000000-c74544f7cc2b154abc50	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0490000000-7e0691bbc63bbcbcb960	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0ab9-1910000000-63c7876312597f683101	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0c09-0890000000-f7244245bf6816d03dc7	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0090000000-4921c6fa708f6f3208b5	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0090000000-045d503a22a8fff17f1e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0090000000-ad5887f59c598bd4412f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0kmi-0900000000-eba38744d927d1c39a74	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-1590000000-3258d431fd85f1099698	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0ab9-1910000000-5beb5962e63deb734d80	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0ab9-0790000000-036c53ed1835e3d33348	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0090000000-d658d5f76013dc5acf49	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0c00-0930000000-b468512722b2bc0ceef4	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0290000000-98ff8239bf913ebb8a12	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0090000000-97d10d3ad5d45edcaeba	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0kmi-0900000000-bb97e1aecda1747cbf29	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0090000000-b2dbf89c13423bc1b59f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0490000000-ace1928aff206a3d35d9	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0900000000-89f039730d1e06819f5a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-0970000000-96d9f9e44a05a48ae86a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0940000000-85279d67921a0106c4e2	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0090000000-172e28dbdb6a16d367a2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0090000000-4283661a0ad9c11f2e42	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0090000000-7f7abcbaad5c89ee8109	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01w0-2490000000-3dbf5856c09bbcdde184	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0090000000-55f38f4a1708215a2509	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ug0-0090000000-067db3f005caf26c9b9a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9010000000-87e51d16bdb0c8facd59	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0090000000-3da178c8ab5db2a879a7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0uec-5290000000-d8719b88accd25aff9e1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-9600000000-481d2d2a7a57d3259aa7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0090000000-d9300440a7002c2e4869	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0090000000-d9300440a7002c2e4869	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a59-0900000000-ba20bffdd6f1d48d2e8d	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
250.0	mice	LD50	Not Available	experimental	Not Available	Not Available
250.0	rat	LD50	Not Available	experimental	Not Available	Not Available
255.0 Log mg/kg [140:450]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

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.

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Minimum Risk Level

Not Available

Symptoms

Symptoms of overdose include decreased level of consciousness, coma, delayed heartbeat, increased seizures, lack of coordination, and rolling eyeballs.

Treatment

There are no specific antidotes for lamotrigine. Following a suspected overdose, hospitalization of the patient is advised. General supportive care is indicated, including frequent monitoring of vital signs and close observation of the patient. If indicated, emesis should be induced or gastric lavage should be performed; usual precautions should be taken to protect the airway. (1)

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000010	Insecticides?Insecticides are synthetic chemicals designed to control or eliminate insect pests that threaten crops and other agricultural products.	Agriculture & land management	Not Available
CEDs000115	Drinking water?Drinking water can be a medium for synthetic chemical contamination, often originating from various industrial processes and agricultural practices.	Drinking water & water supply	Not Available
CEDs000371	Antiepileptics?Antiepileptics are a class of synthetic drugs used primarily to manage seizure disorders.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000511	Conductors Or Conductive Bodies Characterised By The Conductive Materials?Conductors, or conductive bodies, are materials that allow the flow of electrical current, typically made from metals such as copper, aluminum, or silver.	Electrical & Electronic Equipment	Not Available
CEDs000516	Electric Hearing Aids?Electric hearing aids are small electronic devices designed to amplify sound for individuals with hearing loss.	Electrical & Electronic Equipment	Not Available
CEDs000518	Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.	Electrical & Electronic Equipment	Not Available
CEDs000527	Magnets?Magnets, commonly used in various electrical and electronic applications, can be a source of synthetic chemical contamination due to the materials used in their production.	Electrical & Electronic Equipment	Not Available
CEDs000530	Radio Transmission Systems?Radio transmission systems utilize a variety of synthetic chemicals in their manufacturing and maintenance processes.	Electrical & Electronic Equipment	Not Available
CEDs000531	Relays?Relays are electromechanical switches used to control circuits and manage electrical loads.	Electrical & Electronic Equipment	Not Available
CEDs000545	Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.	Food, food processing & cookware	Not Available
CEDs000556	Cigar Cigarettes?Cigar cigarettes are a source of synthetic chemical contamination due to the combustion of various tobacco blends and additives.	Household cleaning & consumer products	Not Available
CEDs000559	Non Electric Simulated Smoking Devices?Non-electric simulated smoking devices, often designed to mimic the experience of smoking without combustion, can be sources of synthetic chemical contamination due to the materials and chemicals used in their construction and operation.	Household cleaning & consumer products	Not Available
CEDs000560	Other Smoking Requisites?Other smoking requisites, including items such as lighters, matches, and rolling papers, can introduce synthetic chemical contamination through various components and additives.	Household cleaning & consumer products	Not Available
CEDs000569	Tobacco Smoke Filters?Tobacco smoke filters are designed to reduce the inhalation of harmful substances in cigarette smoke, including tar and other particulate matter.	Household cleaning & consumer products	Not Available
CEDs000580	Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.	Industrial manufacturing & chemical processing	Not Available
CEDs000600	Herbicides And Algicides?Herbicides and algicides are synthetic chemicals primarily used to control unwanted plants and algae in various environments.	Agriculture & land management	Not Available
CEDs000606	Plant Growth Regulators?Plant Growth Regulators (PGRs) are synthetic chemicals designed to influence the growth and development of plants.	Agriculture & land management	Not Available
CEDs000609	Aftershave?Aftershave is a grooming product typically used to soothe and protect the skin following shaving.	Personal care & cosmetics	Not Available
CEDs000611	Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.	Personal care & cosmetics	Not Available
CEDs000615	Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.	Personal care & cosmetics	Not Available
CEDs000618	Lip Makeup Products?Lip makeup products, such as lipsticks, lip glosses, and lip liners, often contain a variety of synthetic chemicals, including pigments, preservatives, and emollients.	Personal care & cosmetics	Not Available
CEDs000632	Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.	Textiles, leather & furnishings	Not Available
CEDs000642	Footwear?Footwear production often involves the use of various synthetic chemicals, such as adhesives, dyes, and treatments, which can contribute to environmental contamination.	Textiles, leather & furnishings	Not Available
CEDs000671	Airplanes And Helicopters?Airplanes and helicopters are significant sources of synthetic chemical contamination primarily through the use of aviation fuels, lubricants, and de-icing agents.	Aviation & Aerospace	Not Available
CEDs000685	Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.	Building & Construction	Not Available
CEDs000693	Silica Glass?Silica glass, primarily composed of silicon dioxide (SiO2), is widely used in various applications, including windows, glass facades, and insulation materials.	Building & Construction	Not Available
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	Not Available
CEDs000735	Explosives?Explosives are chemical compounds or mixtures designed to undergo rapid decomposition, releasing energy in the form of gas and heat.	Defense & military infrastructure	Not Available
CEDs000738	Cooling Circuit Water?Cooling circuit water is utilized in various industrial processes to absorb and dissipate heat generated during operations.	Industrial manufacturing & chemical processing	Not Available
CEDs000739	Inks?Inks are complex mixtures composed of pigments or dyes, solvents, resins, and additives used primarily for printing and writing applications.	Paper, pulp & fiber products	Not Available
CEDs000741	Pigment Pastes?Pigment pastes are concentrated dispersions of pigments used to impart color and properties to materials.	Paper, pulp & fiber products	Not Available
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	Not Available

Pathways

2 pathwaysPathway Source: PathBank

Lamotrigine Action Pathway

Lamotrigine Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Sodium channel protein type 2 subunit alpha	Q99250	Humans	Predicted (SEA)	Prediction Confidence Score 0.376 Applicability Domain 1.0 Statistical Significance 0.0032 Supporting Reference Compounds 63 E-value 24.8339
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q9R0C9	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.323 Applicability Domain 1.0 Statistical Significance 0.0136 Supporting Reference Compounds 207 E-value 106.031
Click to view 3D structure	Multidrug and toxin extrusion protein 1	Q8K0H1	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.283 Applicability Domain 0.283 Low confidence Statistical Significance 6.90e-04 Supporting Reference Compounds 1 E-value 5.3716
Click to view 3D structure	Biotin carboxylase	P37798	Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM14847 / LMG 12228 / 1C / PRS 101 / PAO1)	Predicted (SEA)	Prediction Confidence Score 0.282 Applicability Domain 0.348 Statistical Significance 1.60e-04 Supporting Reference Compounds 3 E-value 1.24559
Click to view 3D structure	Tyrosine-protein phosphatase non-receptor type 11	P35235	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.279 Applicability Domain 0.279 Low confidence Statistical Significance 0.0011 Supporting Reference Compounds 1 E-value 8.56341
Click to view 3D structure	Fibroblast growth factor receptor 1	P11362	Humans	Predicted (SEA)	Prediction Confidence Score 0.276 Applicability Domain 0.348 Statistical Significance 0.1932 Supporting Reference Compounds 1010 E-value 1504.12
Click to view 3D structure	Proto-oncogene tyrosine-protein kinase Src	P12931	Humans	Predicted (SEA)	Prediction Confidence Score 0.276 Applicability Domain 0.348 Statistical Significance 0.2028 Supporting Reference Compounds 1158 E-value 1578.86
Click to view 3D structure	Proto-oncogene tyrosine-protein kinase Src	P00523	Gallus gallus	Predicted (SEA)	Prediction Confidence Score 0.268 Applicability Domain 0.348 Statistical Significance 0.0245 Supporting Reference Compounds 64 E-value 190.419
Click to view 3D structure	Epidermal growth factor receptor	P00533	Humans	Predicted (SEA)	Prediction Confidence Score 0.262 Applicability Domain 0.283 Low confidence Statistical Significance 0.3106 Supporting Reference Compounds 1301 E-value 2418.31
Click to view 3D structure	Receptor-type tyrosine-protein kinase FLT3	P36888	Humans	Predicted (SEA)	Prediction Confidence Score 0.261 Applicability Domain 0.325 Statistical Significance 0.32 Supporting Reference Compounds 1274 E-value 2491.18
Click to view 3D structure	Dihydrofolate reductase	P00374	Humans	Predicted (SEA)	Prediction Confidence Score 0.258 Applicability Domain 0.286 Low confidence Statistical Significance 0.0157 Supporting Reference Compounds 156 E-value 122.145
Click to view 3D structure	Dihydrofolate reductase	P0ABQ4	Escherichia coli (strain K12)	Predicted (SEA)	Prediction Confidence Score 0.258 Applicability Domain 0.286 Low confidence Statistical Significance 0.01 Supporting Reference Compounds 92 E-value 77.6935
Click to view 3D structure	Tyrosine-protein phosphatase non-receptor type 11	Q06124	Humans	Predicted (SEA)	Prediction Confidence Score 0.256 Applicability Domain 0.279 Low confidence Statistical Significance 0.0263 Supporting Reference Compounds 109 E-value 204.977
Click to view 3D structure	Dihydrofolate reductase	Q920D2	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.254 Applicability Domain 0.286 Low confidence Statistical Significance 0.0107 Supporting Reference Compounds 82 E-value 83.0651
Click to view 3D structure	Dihydrofolate reductase	P16184	Pneumocystis carinii	Predicted (SEA)	Prediction Confidence Score 0.25 Applicability Domain 0.286 Low confidence Statistical Significance 0.01 Supporting Reference Compounds 62 E-value 77.6935
Click to view 3D structure	Protein phosphatase 1 regulatory subunit 15A	O75807	Humans	Predicted (SEA)	Prediction Confidence Score 0.25 Applicability Domain 0.25 Low confidence Statistical Significance 6.50e-04 Supporting Reference Compounds 1 E-value 5.0602
Click to view 3D structure	Protein phosphatase 1 regulatory subunit 15B	Q5SWA1	Humans	Predicted (SEA)	Prediction Confidence Score 0.25 Applicability Domain 0.25 Low confidence Statistical Significance 6.50e-04 Supporting Reference Compounds 1 E-value 5.0602
Click to view 3D structure	Bifunctional dihydrofolate reductase-thymidylate synthase	Q07422	Toxoplasma gondii	Predicted (SEA)	Prediction Confidence Score 0.25 Applicability Domain 0.283 Low confidence Statistical Significance 0.0151 Supporting Reference Compounds 89 E-value 117.397
Click to view 3D structure	5-hydroxytryptamine receptor 7	P34969	Humans	Predicted (SEA)	Prediction Confidence Score 0.248 Applicability Domain 0.255 Low confidence Statistical Significance 0.2009 Supporting Reference Compounds 565 E-value 1564.15
Click to view 3D structure	Serine/threonine-protein kinase PLK3	Q9H4B4	Humans	Predicted (SEA)	Prediction Confidence Score 0.245 Applicability Domain 0.325 Statistical Significance 0.293 Supporting Reference Compounds 561 E-value 2280.83
Click to view 3D structure	Tyrosine-protein kinase JAK2	O60674	Humans	Predicted (SEA)	Prediction Confidence Score 0.245 Applicability Domain 0.295 Low confidence Statistical Significance 0.4301 Supporting Reference Compounds 1022 E-value 3348.14
Click to view 3D structure	Serine/threonine-protein kinase pim-1	P11309	Humans	Predicted (SEA)	Prediction Confidence Score 0.244 Applicability Domain 0.265 Low confidence Statistical Significance 0.4207 Supporting Reference Compounds 967 E-value 3274.81
Click to view 3D structure	Glycogen synthase kinase-3	P51136	Dictyostelium discoideum	Predicted (SEA)	Prediction Confidence Score 0.242 Applicability Domain 0.242 Low confidence Statistical Significance 0.0017 Supporting Reference Compounds 1 E-value 12.923
Click to view 3D structure	Aurora kinase B	Q96GD4	Humans	Predicted (SEA)	Prediction Confidence Score 0.242 Applicability Domain 0.265 Low confidence Statistical Significance 0.4465 Supporting Reference Compounds 1017 E-value 3476.28
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	Prediction Confidence Score 0.24 Applicability Domain 0.279 Low confidence Statistical Significance 0.6596 Supporting Reference Compounds 1498 E-value 5134.93
Click to view 3D structure	Sodium channel protein type 2 subunit alpha	Q99250	Humans	Known	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, thereby stabilizing neuronal membranes and consequently modulating presynaptic transmitter release of excitatory amino acids (e.g., glutamate and aspartate).
Click to view 3D structure	Sodium channel protein type 5 subunit alpha	Q14524	Humans	Known	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, thereby stabilizing neuronal membranes and consequently modulating presynaptic transmitter release of excitatory amino acids (e.g., glutamate and aspartate).
Click to view 3D structure	Sodium channel protein type 1 subunit alpha	P35498	Humans	Known	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, thereby stabilizing neuronal membranes and consequently modulating presynaptic transmitter release of excitatory amino acids (e.g., glutamate and aspartate).
Click to view 3D structure	Sodium channel protein type 3 subunit alpha	Q9NY46	Humans	Known	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, thereby stabilizing neuronal membranes and consequently modulating presynaptic transmitter release of excitatory amino acids (e.g., glutamate and aspartate).
Click to view 3D structure	Sodium channel protein type 4 subunit alpha	P35499	Humans	Known	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, thereby stabilizing neuronal membranes and consequently modulating presynaptic transmitter release of excitatory amino acids (e.g., glutamate and aspartate).
Click to view 3D structure	Sodium channel protein type 8 subunit alpha	Q9UQD0	Humans	Known	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, thereby stabilizing neuronal membranes and consequently modulating presynaptic transmitter release of excitatory amino acids (e.g., glutamate and aspartate).
Click to view 3D structure	Sodium channel protein type 9 subunit alpha	Q15858	Humans	Known	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, thereby stabilizing neuronal membranes and consequently modulating presynaptic transmitter release of excitatory amino acids (e.g., glutamate and aspartate).
Click to view 3D structure	Dihydrofolate reductase	P00374	Humans	Known	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, thereby stabilizing neuronal membranes and consequently modulating presynaptic transmitter release of excitatory amino acids (e.g., glutamate and aspartate).
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Known	Not Available
Click to view 3D structure	Sodium channel protein type 10 subunit alpha	Q9Y5Y9	Humans	Known	Not Available

Concentrations

Status	Value	Unit	Sample Location	Reference
Detected and Quantified	120	ng/L	Bioggio,Lugano	24417318
Detected and Quantified	140	ng/L	Bussigny-prés-Lausanne	24417318
Detected and Quantified	400	ng/L	Hallau,Klettgau	24417318
Detected and Quantified	170	ng/L	Thal,Altenrhein	24417318
Detected and Quantified	450	ng/L	Uetendorf,Thun	24417318
Detected and Quantified	280	ng/L	Vernier,Aïre	24417318
Detected and Quantified	760	ng/L	Winterthur	24417318
Detected and Quantified	390	ng/L	Werdhölzli,Zürich	24417318
Detected and Quantified	630	ng/L	Schönau,Zug	24417318
Detected and Quantified	410	ng/L	Affoltern,Zwillikon	24417318

External Links

DrugBank ID

DB00555

HMDB ID

HMDB0014695

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

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

MSDS

Link

General References

Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M: DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6. Epub 2007 Nov 29. [PubMed: 18048412]
Backonja M: Neuromodulating drugs for the symptomatic treatment of neuropathic pain. Curr Pain Headache Rep. 2004 Jun;8(3):212-6. [PubMed: 15115640]
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]
Jensen TS: Anticonvulsants in neuropathic pain: rationale and clinical evidence. Eur J Pain. 2002;6 Suppl A:61-8. [PubMed: 11888243]
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]
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]
Wikipedia. Lamotrigine. Last Updated 25 July 2009. - http://en.wikipedia.org/wiki/Lamotrigine
Drugs.com - http://www.drugs.com/cons/Lamotrigine.html
O'Neil MJ (ed) (2001). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th ed. Whitehouse Station, NJ: Merck and Co., Inc.

Lamotrigine (CED0002128)

Structure for CHEM002096: Lamotrigine

Structure