1.0 2009-07-05 03:30:53 UTC 2026-05-14 16:42:05 UTC T3D2570 Lamotrigine SmallMolecule 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. Drug Food Toxin Synthetic Toxin Organic Compound Organochloride Amine Drug Food Toxin Anticonvulsant Antimanic Agent Analgesic Antidepressant Calcium Channel Blocker Excitatory Amino Acid Antagonist Metabolite Synthetic Compound Antidepressive Agent Human Neurotoxin 3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine Convulsan Crisomet Dafex Daksol Danoptin Dezepil Elmendos Epilepax Epimil Epiral Epitec Epitrigine GW 273293 Labileno Lambipol Lamect Lameptil Lameptil S Lametec Lamez Lamictal Lamictal CD Lamictal XR Lamictin Lamotrigina Lamotriginum Lamotrix Larig Medotrigin Mogine Trimolep Trogine Xebarin C9H7Cl2N5 256.091 255.007850663 6-(2,3-dichlorophenyl)-1,2,4-triazine-3,5-diamine lamotrigine 84057-84-1 NC1=NC(N)=C(N=N1)C1=C(Cl)C(Cl)=CC=C1 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) PYZRQGJRPPTADH-UHFFFAOYSA-N Organic compounds Benzenoids Benzene and substituted derivatives Halobenzenes Dichlorobenzenes 1,2,4-triazines Aminotriazines Aryl chlorides Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives Imidolactams Organochlorides Organopnictogen compounds Primary amines 1,2,4-triazine 1,2-dichlorobenzene Amine Aminotriazine Aromatic heteromonocyclic compound Aryl chloride Aryl halide Azacycle Heteroaromatic compound Hydrocarbon derivative Imidolactam Organic nitrogen compound Organochloride Organohalogen compound Organoheterocyclic compound Organonitrogen compound Organopnictogen compound Primary amine Triazine Aromatic heteromonocyclic compounds 1,2,4-triazines dichlorobenzene primary arylamine Detected and Not Quantified Exogenous Cytoplasm Extracellular Membrane Lamotrigine Action Pathway SMP0126274 Lamotrigine Drug Metabolism Action Pathway SMP0143004 Solid White to pale cream-colored powder. Crystals from isopropanol (T66). melting_point 216-218°C (uncorr) solubility 4.88e-01 g/L logp 2.5 logp 1.87 ALOGPS logs -2.72 ALOGPS solubility 4.88e-01 g/l ALOGPS logp 1.93 ChemAxon pka_strongest_acidic 14.98 ChemAxon pka_strongest_basic 5.87 ChemAxon iupac 6-(2,3-dichlorophenyl)-1,2,4-triazine-3,5-diamine ChemAxon average_mass 256.091 ChemAxon mono_mass 255.007850663 ChemAxon smiles NC1=NC(N)=C(N=N1)C1=C(Cl)C(Cl)=CC=C1 ChemAxon formula C9H7Cl2N5 ChemAxon 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) ChemAxon inchikey PYZRQGJRPPTADH-UHFFFAOYSA-N ChemAxon polar_surface_area 90.71 ChemAxon refractivity 66.62 ChemAxon polarizability 23.1 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Inhalation (A308); dermal (A308); ingestion (A308). One proposed mechanism of action of Lamotrigine, the relevance of which remains to be established in humans, involves an effect on sodium channels. <i>in vitro</i> 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. Lamotrigine is metabolized predominantly by glucuronic acid conjugation. The major metabolite is an inactive 2-N-glucuronide conjugate. Exretion occur in the urine and the feces with unchanged lamotrigine (10%), the 2-N-glucuronide (76%), a 5-N-glucuronide (10%), a 2-N-methyl metabolite (0.14%), and other unidentified minor metabolites (4%). (A308) Half Life: 25 +/- 10 hours (healthy individuals); 42.9 hours (chronic renal failure) LD50: 250 (mg/kg) (mice) LD50: 250 (mg/kg) (rat) LD50> 640 (mg/kg) (oral, rat) (Sawyer) LD50> 640 (mg/kg) (oral, mice) (Sawyer) No indication of carcinogenicity to humans (not listed by IARC). 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. Off-label uses include the treatment of peripheral neuropathy, trigeminal neuralgia, cluster headaches, migraines, and reducing neuropathic pain. (A308, L1155) #<HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f3bbf9e9560> Symptoms of overdose include decreased level of consciousness, coma, delayed heartbeat, increased seizures, lack of coordination, and rolling eyeballs. 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. (A308) DB00555 HMDB14695 3878 CHEMBL741 3741 6367 Lamotrigine Lamotrigine 18048412 15115640 12716240 11888243 14667954 19579915 O'Neil MJ (ed) (2001). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th ed. Whitehouse Station, NJ: Merck and Co., Inc. Wikipedia. Lamotrigine. Last Updated 25 July 2009.: http://en.wikipedia.org/wiki/Lamotrigine Drugs.com: http://www.drugs.com/cons/Lamotrigine.html BE0002081 One proposed mechanism of action of Lamotrigine, the relevance of which remains to be established in humans, involves an effect on sodium channels. <i>in vitro</i> 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). IC50 10 uM BindingDB 50031299 IC50 >100 uM BindingDB 50031299 BE0000197 One proposed mechanism of action of Lamotrigine, the relevance of which remains to be established in humans, involves an effect on sodium channels. <i>in vitro</i> 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). IC50 62 uM BindingDB 50031299 BE0000141 One proposed mechanism of action of Lamotrigine, the relevance of which remains to be established in humans, involves an effect on sodium channels. <i>in vitro</i> 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). BE0002082 One proposed mechanism of action of Lamotrigine, the relevance of which remains to be established in humans, involves an effect on sodium channels. <i>in vitro</i> 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). BE0002083 One proposed mechanism of action of Lamotrigine, the relevance of which remains to be established in humans, involves an effect on sodium channels. <i>in vitro</i> 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). Inhibitory 17 uM BindingDB 50031299 BE0002084 One proposed mechanism of action of Lamotrigine, the relevance of which remains to be established in humans, involves an effect on sodium channels. <i>in vitro</i> 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). BE0001143 One proposed mechanism of action of Lamotrigine, the relevance of which remains to be established in humans, involves an effect on sodium channels. <i>in vitro</i> 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). BE0000330 One proposed mechanism of action of Lamotrigine, the relevance of which remains to be established in humans, involves an effect on sodium channels. <i>in vitro</i> 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). BE0000090 IC50 229.08677 uM BindingDB 50031299 BE0000177 IC50 96 uM BindingDB 50031299 BE0004901 BE0000192 BE0000311 BE0004902 BE0000013 BE0000924 BE0000501 BE0000289 BE0000172 BE0000020 BE0000145 BE0000756 BE0003596 BE0003599 BE0000795 BE0002344 BE0003592 BE0002345 BE0000471 BE0000523 BE0000381 BE0002346 BE0000478 BE0003595 BE0000764 BE0003593 BE0003594 BE0003597 BE0000442 BE0000632 BE0004661 BE0000451 BE0000640