CHEBI:6367 - lamotrigine

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ChEBI Name lamotrigine
ChEBI ID CHEBI:6367
Definition A member of the class of 1,2,4-triazines in which the triazene skeleton is substituted by amino groups at positions 3 and 5, and by a 2,3-dichlorophenyl group at position 6.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C9H7Cl2N5
Net Charge 0
Average Mass 256.09100
Monoisotopic Mass 255.008
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)
InChIKey PYZRQGJRPPTADH-UHFFFAOYSA-N
SMILES Nc1nnc(c(N)n1)-c1cccc(Cl)c1Cl
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
Any EC 3.4.21.* (serine endopeptidase) inhibitor that interferes with the action of prolyl oligopeptidase (EC 3.4.21.26).
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
calcium channel blocker
One of a class of drugs that acts by selective inhibition of calcium influx through cell membranes or on the release and binding of calcium in intracellular pools.
excitatory amino acid antagonist
Any substance which inhibits the action of receptors for excitatory amino acids.
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
Application(s): anticonvulsant
A drug used to prevent seizures or reduce their severity.
antimanic drug
Antimanic drugs are agents used to treat bipolar disorders or mania associated with other affective disorders.
antidepressant
Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing lamotrigine (CHEBI:6367) has role anticonvulsant (CHEBI:35623)
lamotrigine (CHEBI:6367) has role antidepressant (CHEBI:35469)
lamotrigine (CHEBI:6367) has role antimanic drug (CHEBI:35477)
lamotrigine (CHEBI:6367) has role calcium channel blocker (CHEBI:38215)
lamotrigine (CHEBI:6367) has role EC 3.4.21.26 (prolyl oligopeptidase) inhibitor (CHEBI:76779)
lamotrigine (CHEBI:6367) has role environmental contaminant (CHEBI:78298)
lamotrigine (CHEBI:6367) has role excitatory amino acid antagonist (CHEBI:60798)
lamotrigine (CHEBI:6367) has role non-narcotic analgesic (CHEBI:35481)
lamotrigine (CHEBI:6367) has role xenobiotic (CHEBI:35703)
lamotrigine (CHEBI:6367) is a 1,2,4-triazines (CHEBI:39410)
lamotrigine (CHEBI:6367) is a dichlorobenzene (CHEBI:23697)
lamotrigine (CHEBI:6367) is a primary arylamine (CHEBI:50471)
IUPAC Name
6-(2,3-dichlorophenyl)-1,2,4-triazine-3,5-diamine
INNs Sources
lamotrigina ChemIDplus
lamotrigine ChemIDplus
lamotriginum ChemIDplus
Synonym Source
3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine ChemIDplus
Brand Name Source
Lamictal KEGG DRUG
Manual Xrefs Databases
1540 DrugCentral
D00354 KEGG DRUG
DB00555 DrugBank
HMDB0014695 HMDB
Lamotrigine Wikipedia
LSM-4104 LINCS
View more database links
Registry Numbers Types Sources
7589268 Reaxys Registry Number Reaxys
84057-84-1 CAS Registry Number KEGG DRUG
84057-84-1 CAS Registry Number NIST Chemistry WebBook
84057-84-1 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
20825390 PubMed citation Europe PMC
21242744 PubMed citation Europe PMC
Last Modified
22 February 2017
General Comments
2011-02-04 An anticonvulsant, lamotrigine is used in the treatment of epilepsy, bipolar disorder, and to relieve some of the symptoms of post-traumatic stress disorder. There is evidence that it is also of use in the treatment of neuropathic pain.
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag