Lamotrigine

Base Information

• Chemical Name: Lamotrigine
• CAS No.: 84057-84-1
• Molecular Formula: C9H7Cl2N5
• Molecular Weight: 256.094
• Hs Code.: 29336990
• European Community (EC) Number: 281-901-8,658-035-8
• NSC Number: 759171,746307
• UNII: U3H27498KS
• DSSTox Substance ID: DTXSID2023195
• Nikkaji Number: J25.814H
• Wikipedia: Lamotrigine
• Wikidata: Q410346
• NCI Thesaurus Code: C38703
• RXCUI: 28439
• Pharos Ligand ID: DTZ7PFA8CZ4J
• Metabolomics Workbench ID: 42891
• ChEMBL ID: CHEMBL741
• Mol file: 84057-84-1.mol

Synonyms:3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine;3,5-diamino-6-(2,3-dichlorophenyl)-as-triazine;BW 430C;BW-430C;BW430C;Crisomet;Labileno;Lamictal;Lamiktal;lamotrigine

Chemical Property of Lamotrigine

Chemical Property:

• Appearance/Colour: White to cream coloured powder
• Melting Point: 177-181 °C
• Boiling Point: 503.1 °C at 760 mmHg
• PKA: 5.7(at 25℃)
• Flash Point: 258.1 °C
• PSA: 90.71000
• Density: 1.572 g/cm³
• LogP: 3.17220
• Storage Temp.: 2-8°C
• Solubility.: DMSO: 20 mg/mL at 60 °C, soluble
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 255.0078506
• Heavy Atom Count: 16
• Complexity: 242

Purity/Quality:

99% ^*data from raw suppliers

Lamotrigine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xi
• Hazard Codes: T,Xi,F
• Statements: 25-36/37/38-39/23/24/25-23/24/25-11
• Safety Statements: 45-36-26-36/37-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Anticonvulsants
• Canonical SMILES: C1=CC(=C(C(=C1)Cl)Cl)C2=C(N=C(N=N2)N)N
• Recent ClinicalTrials: Bariatric Surgery and Pharmacokinetics of Lamotrigine
• Recent EU Clinical Trials: Treatment of Myotonia - Lamotrigine versus Namuscla
• Recent NIPH Clinical Trials: Open-label study on the efficacy of lamotrigine in patients with brain tumor, stroke or head injury, and comorbid depressive symptoms
• Description: Lamotrigine is a second- generation antiepileptic drug (AED) known by the proprietary brand name of Lamictal? (GlaxoSmithKline, Brentford) in the UK and USA. Lamotrigine is a new mazine, glutamate inhibitor anticonvulsant that significantly reduces the incidence of refractory partial seizures. The drug is reported to produce fewer CNS side effects than diazepam or sodium phenytoin. It is also indicated as add-on therapy for the treatment of generalized seizures not satisfactorily controlled by other anti-epileptics.
• Indications: Epilepsy: monotherapy and adjunctive therapy of focal and generalized seizures. Recommendations summarized from NICE (2012) Seizure types: first line (generalized tonic- clonic seizures, tonic/ atonic seizures, absence seizures, focal seizures), adjunctive (generalized tonicclonic seizures, absence seizures, focal seizures). Epilepsy types: first line (absence syndromes, juvenile myoclonic epilepsy, epilepsy with generalized tonic- clonic seizures only, idiopathic generalized epilepsy, benign epilepsy with centrotemporal spikes, Panayiotopoulos syndrome, late-onset childhood occipital epilepsy), adjunctive (absence syndromes, juvenile myoclonic epilepsy, epilepsy with generalized tonic- clonic seizures only, idiopathic generalized epilepsy, benign epilepsy with centrotemporal spikes, Panayiotopoulos syndrome, late- onset childhood occipital epilepsy, Lennox- Gastaut syndrome), contraindicated (Dravet syndrome) Psychiatry: prevention of depressive episodes associated with bipolar disorder (not indicated for manic phase)
• Uses: An anticonvulsant. Inhibits glutamate release, possible through inhibition of Sodium, Potassium and Calcium currents. Used in treatment of bipolar depression. antibacterial 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.
• Therapeutic Function: Anticonvulsant
• Biological Functions: Lamotrigine has a broad spectrum of action and is effective in generalized and partial epilepsies. Its primary mechanism of action appears to be blockage of voltagedependent sodium channels, although its effectiveness against absence seizures indicates that additional mechanisms may be active. Lamotrigine is almost completely absorbed from the gastrointestinal tract, and peak plasma levels are achieved in about 2 to 5 hours. The plasma half-life after a single dose is about 24 hours. Unlike most drugs, lamotrigine is metabolized primarily by glucuronidation. Therefore, it appears likely that lamotrigine will not induce or inhibit cytochrome P450 isozymes, in contrast to most AEDs. Severe skin rashes appear to be the major concern with lamotrigine use.The incidence of rash is greater in children than in adults.Other adverse effects are similar to those of drugs with the same mechanism of action, such as cerebellovestibular changes leading to dizziness, diplopia, ataxia, and blurred vision. Disseminated intravascular coagulation has been reported.
• Clinical Use: Lamotrigine is a 5-phenyl-1,2,4-triazine derivative indicated as monotherapy or as an adjunct for partial seizures in adults, as adjunct in patients with Lennox-Gastaut syndrome, and as adjunct for partial seizures in children 2 years of age and older. Lamotrigine may have additional benefit in combating myoclonic and typical absence seizures. It is approved for use in the maintenance treatment of bipolar disorder.
• Drug interactions: Potentially hazardous interactions with other drugs Antibacterials: concentration reduced by rifampicin. Antidepressants: antagonism of anticonvulsant effect; avoid with St John’s wort. Antiepileptics: concentration reduced by carbamazepine, phenobarbital and phenytoin, also possibility of increased concentration of active carbamazepine metabolite; concentration increased by valproate - reduce lamotrigine dose. Antimalarials: mefloquine antagonises anticonvulsant effect Antipsychotics: anticonvulsant effect antagonised. Oestrogens and progestogens: concentration of lamotrigine reduced and the dose may need to be increased by as much as 2-fold; may affect contraceptive effect. Orlistat: possibly increased risk of convulsions

Technology Process of Lamotrigine

There total 31 articles about Lamotrigine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine hydrochloride → lamotrigine (84057-84-1)

Guidance literature:

With sodium hydroxide; In water;

Reference yield: 97.0%

C9H7Cl2N5*H2O4S → lamotrigine (84057-84-1)

Guidance literature:

With sodium hydroxide; at 65 ℃; for 3h;

Reference yield: 90.0%

2-(2,3-dichlorophenyl)-2-(aminoguanidine)-acetonitrile → lamotrigine (84057-84-1)

Guidance literature:

In isopropyl alcohol;

upstream raw materials:

6-(2,3-dichloro-phenyl)-tetrazolo[1,5-b][1,2,4]triazin-7-ylamine

2,3-dichlorobenzoyl cyanide

2,3-dihlorophenylacetonitrile

2,3-dichlorotoluene

Downstream raw materials:

5-amino-6-(2,3-dichlorophenyl)-2,3-dihydro-3-imino-2-isopropyl-1,2,4-triazine

Refernces

• 1、 -. "Improved synthesis process for lamotrigine". . . Retrieved 2017/07/21.
• 2、 -. "AN IMPROVED PROCESS FOR THE PREPARATION OF LAMOTRIGINE". Page/Page column 3; 5. . Retrieved 2009/07/03.