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Lamotrigine

CAS No.
84057-84-1
Chemical Name:
Lamotrigine
Synonyms
LAMICTAL;LAMOTRIGIN;3,5-DIAMINO-6-(2,3-DICHLOROPHENYL)-1,2,4-TRIAZINE;6-(2,3-DICHLOROPHENYL)-1,2,4-TRIAZINE-3,5-DIAMINE;LTG;BW-430;BW-430C;GI 267119X;Lemotrigine;LAMOTRIGINE
CBNumber:
CB4166704
Molecular Formula:
C9H7Cl2N5
Molecular Weight:
256.09
MDL Number:
MFCD00865333
MOL File:
84057-84-1.mol
MSDS File:
SDS
Last updated:2024-11-19 20:33:22

Lamotrigine Properties

Melting point 177-181°C
Boiling point 503.1±60.0 °C(Predicted)
Density 1.572±0.06 g/cm3(Predicted)
Flash point 9℃
storage temp. 2-8°C
solubility DMSO: 20 mg/mL at 60 °C, soluble
form powder
pka 5.7(at 25℃)
color white
Merck 14,5353
BCS Class 2
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 N1C(C2=CC=CC(Cl)=C2Cl)=C(N)N=C(N)N=1
CAS DataBase Reference 84057-84-1(CAS DataBase Reference)
EWG's Food Scores 1
NCI Dictionary of Cancer Terms lamotrigine
FDA UNII U3H27498KS
NCI Drug Dictionary Lamictal
ATC code N03AX09

Pharmacokinetic data

Protein binding 55%
Excreted unchanged in urine <10%
Volume of distribution 0.92-1.22(L/kg)
Biological half-life 24-35 / Unchanged

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS06
Signal word  Danger
Hazard statements  H301
Precautionary statements  P264-P270-P301+P310-P405-P501
Hazard Codes  T,Xi,F
Risk Statements  25-36/37/38-39/23/24/25-23/24/25-11
Safety Statements  45-36-26-36/37-16
RIDADR  UN 2811 6.1/PG 3
WGK Germany  3
RTECS  XY5850700
HazardClass  6.1(b)
PackingGroup  III
HS Code  29336990
Hazardous Substances Data 84057-84-1(Hazardous Substances Data)
Toxicity LD50 in mice, rats (mg/kg): 250, >640 orally (Sawyer)
NFPA 704
0
2 0

Lamotrigine price More Price(56)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich L-019 Lamotrigine solution 1.0?mg/mL in methanol, ampule of 1?mL, certified reference material, Cerilliant? 84057-84-1 1mL $131 2024-03-01 Buy
Sigma-Aldrich 1356756 Lamotrigine United States Pharmacopeia (USP) Reference Standard 84057-84-1 150mg $816 2024-03-01 Buy
Sigma-Aldrich BP1097 Lamotrigine British Pharmacopoeia (BP) Reference Standard 84057-84-1 200MG $221 2023-06-20 Buy
TCI Chemical L0241 Lamotrigine >98.0%(HPLC)(T) 84057-84-1 1g $76 2024-03-01 Buy
TCI Chemical L0241 Lamotrigine >98.0%(HPLC)(T) 84057-84-1 5g $261 2024-03-01 Buy
Product number Packaging Price Buy
L-019 1mL $131 Buy
1356756 150mg $816 Buy
BP1097 200MG $221 Buy
L0241 1g $76 Buy
L0241 5g $261 Buy

Lamotrigine Chemical Properties,Uses,Production

Description

Lamotrigine, also known by the brand name Lamictal®, is a second-generation antiepileptic drug (AED) manufactured by GlaxoSmithKline 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.

Chemical Properties

It is a white to cream coloured powder that is soluble in isopropanol and somewhat soluble in water. It has a melting point of 216-218°C and readily dissolves in organic solvents like benzene, toluene, and hot ethanol.

Originator

Burroughs Wellcome (United Kingdom)

Uses

Lamotrigine is an anticonvulsant that works by Inhibits glutamate release, possibly through inhibition of Sodium, Potassium, and Calcium currents. Used in the treatment of bipolar depression, partial seizures in epilepsy, and generalized seizures of Lennox-Gastaut syndrome. Additionally, it is used for the maintenance treatment of bipolar I disorder and depression.

Definition

ChEBI: Lamotrigine is 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. It has a role as an anticonvulsant, an antimanic drug, an antidepressant, a non-narcotic analgesic, a calcium channel blocker, an excitatory amino acid antagonist, an EC 3.4.21.26 (prolyl oligopeptidase) inhibitor, an environmental contaminant, a xenobiotic and a geroprotector. It is a member of 1,2,4-triazines, a primary arylamine and a dichlorobenzene.

Preparation

The preparation method of Lamotrigine involves several steps. 2,3-dichlorobenzoic acid is chlorinated to 2,3-dichlorobenzoyl chloride, then reacted with cuprous cyanide, condensed with aminoguanidine, and finally cyclized under the action of potassium hydroxide Lamotrigine.
Two key methods for the synthesis of lamotrigine have been reported.
https://www.sciencedirect.com/topics/chemistry/lamotrigine
A novel process for the synthesis of lamotrigine and its intermediate
https://patents.google.com/patent/WO2007069265A1/en

brand name

Lamictal (Glax oSmithKline).

Therapeutic Function

Anticonvulsant

World Health Organization (WHO)

Lamotrigine is a relatively new antiepilepsy agent acting through stabilization of neuronal membranes and preventing liberation of neurotransmitters.

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.

General Description

Lamotrigine is an antiepileptic drug belonging in the phenyltriazine class. It is used in the treatment of both epilepsy and as a mood stabilizer in bipolar disorder. Lamotrigine is the first medication since lithium granted Food and Drug Administration (FDA) approval for the maintenance treatment of bipolar type I. It is approved for use in more than 30 countries.

Biological Activity

Anticonvulsant. Inhibits glutamate release, possibly through inhibition of Na + , K + and Ca 2+ currents.

Mechanism of action

Lamotrigine has been found effective against refractory partial seizures. Like phenytoin and CBZ, its main mechanism of action appears to be a blockade of sodium channels that is both voltage- and used-dependent. It also inhibits the high-threshold calcium channel, possibly through inhibition of presynaptic N-type calcium channels, and also blocks glutamate release. The most probable explanation for lamotrigine's efficacy is its ability to produce a blockade of sodium channel repetitive firing. In addition, lamotrigine appears to reduce glutaminergic excitatory transmission, although the mechanism for this action remains unclear.

Pharmacokinetics

Following oral administration, lamotrigine is absorbed rapidly and completely, exhibiting linear pharmacokinetics and modest protein binding (55%). Lamotrigine is metabolized predominantly by N-glucuronidation and subsequent urinary elimination of its major metabolite, the quaternary 2-N-glucuronide (80–90%), the minor 5-amino-N-glucuronide (8–10%), and unchanged drug (8–10%). Lamotrigine's usual elimination half-life of 24–35 hours is reduced to 13–15 hours in patients taking enzymeinducing AEDs. The presence of valproate increases the lamotrigine half-life substantially by inhibiting N-glucuronidation, necessitating a reduction in dose to avoid toxicity. Hepatic disease patients may demonstrate a reduced capacity to for lamotrigine glucuronidation, thus reducing its rate of clearance.

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.

Side effects

The usefulness of lamotrigine is limited by the increased incidence of serious rashes, particularly in children or patients taking valproate. This increase, however, may be attenuated by very slow dose escalation, because most rashes appear within the first 8 weeks of treatment. The drug should be discontinued if a rash appears at any time. Additionally, lamotrigine may be associated with development of myoclonus after 2 to 3 years of drug treatment. Additional common side effects associated with lamotrigine therapy include dizziness, diplopia, headache, ataxia, blurred vision, somnolence, and nausea.

Synthesis

The reaction of the Grignard compound of 2,3-dichloroiodobenzene with CO2 in diethyl ether gives 2,3-dichlorobenzoic acid, which is converted to the corresponding acyl chloride by refluxing with SOCl2. The reaction of 2,3-dichlorobenzoyl chloride with cuprous cyanide and KI in refluxing xylene yields 2,3-dichlorobenzoyl cyanide. Finally, this compound is cyclized with aminoguanidine in DMSO to yield lamotrigine .
Synthesis_84057-84-1

Metabolism

Lamotrigine is extensively metabolised in the liver by UDP-glucuronyl transferases and excreted almost entirely in urine, principally as an inactive glucuronide conjugate. It slightly induces its own metabolism. Only about 2% of lamotrigine-related material is excreted in faeces.

storage

Room temperature

References

https://my.clevelandclinic.org/health/drugs/20217-lamotrigine-tablets
https://pubchem.ncbi.nlm.nih.gov/compound/Lamotrigine
https://go.drugbank.com/drugs/DB00555
The_Renal_Drug_Handbook_The_Ultimate

Lamotrigine Preparation Products And Raw materials

Global( 634)Suppliers
Supplier Tel Email Country ProdList Advantage
Hebei Zhanyao Biotechnology Co. Ltd
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Hebei Mojin Biotechnology Co., Ltd
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View Lastest Price from Lamotrigine manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Lamotrigine pictures 2024-12-23 Lamotrigine
84057-84-1
US $980.00-750.00 / kg 1kg 99% 5000 HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Lamotrigine pictures 2024-12-13 Lamotrigine
84057-84-1
US $0.00-0.00 / Kg/Drum 1KG 98%-102%; USP 1000 KGS WUHAN FORTUNA CHEMICAL CO., LTD
Lamotrigine pictures 2024-12-12 Lamotrigine
84057-84-1
US $1.60-0.40 / g 10g 99% 300tons Hebei Dangtong Import and export Co LTD
  • Lamotrigine pictures
  • Lamotrigine
    84057-84-1
  • US $980.00-750.00 / kg
  • 99%
  • HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
  • Lamotrigine pictures
  • Lamotrigine
    84057-84-1
  • US $0.00-0.00 / Kg/Drum
  • 98%-102%; USP
  • WUHAN FORTUNA CHEMICAL CO., LTD
  • Lamotrigine pictures
  • Lamotrigine
    84057-84-1
  • US $1.60-0.40 / g
  • 99%
  • Hebei Dangtong Import and export Co LTD

Lamotrigine Spectrum

4-triazine-3,5-diamine,6-(2,3-dichlorophenyl)-2 BW-430C LAMOTRIGINE LAMOTRIGINE-13C1 GI 267119X Lemotrigine (2,3-Dichloro Phenyl)-1,2,4-triazine-3,5-diamine 6-(2,3-Dichlorophenyl)-1,2,4-triazine-3,5-diamine, LTG, BW-430C, Lamictal 1,2,4-Triazine-3,5-diamine, 6-(2,3-dichlorophenyl)- LAMOTRINGINE 6-(2,3-Dichlorophenyl)-1,2,4-triazine-3,5-diamine, GI 267119X LTG BW-430 Lamotrigine 6-(2,3-Dichlorophenyl)-1,2,4-triazine-3,5-diamine Lamotrigine (100 mg) LaMotrigine API LaMotrigine、3,5-DiaMino-6-(2,3- dichlorophenyl)-1,2,4-triazine Lamotrigine solution ORGANIC CHEMICAL, LAMOTRIGINE Lamotrigine (1356756) Lamotrigine 13CQ: What is Lamotrigine 13C Q: What is the CAS Number of Lamotrigine 13C Q: What is the storage condition of Lamotrigine 13C Q: What are the applications of Lamotrigine 13C Lamotrigine 13C D3Q: What is Lamotrigine 13C D3 Q: What is the CAS Number of Lamotrigine 13C D3 Q: What is the storage condition of Lamotrigine 13C D3 Q: What are the applications of Lamotrigine 13C D3 LamotrigineQ: What is Lamotrigine Q: What is the CAS Number of Lamotrigine Q: What is the storage condition of Lamotrigine Q: What are the applications of Lamotrigine Lamotrigine, ≥98% Lamotrigine (BW430C Lamictal XR Hot selling Lamotrigine Lamotrigine USP/EP/BP Lamotrigine CRS Lamotrigine for system suitability CRS Lamotrigine> Lamotrigine for peak identification CRS Lamotrigine, 98%, a novel anticonvulsant drug for inhibition of 5-HT Lamotrigine, 1000ppm LAMICTAL LAMOTRIGIN 3,5-DIAMINO-6-(2,3-DICHLOROPHENYL)-1,2,4-TRIAZINE 6-(2,3-DICHLOROPHENYL)-1,2,4-TRIAZINE-3,5-DIAMINE 2H3,13C]-Lamotrigine (S)-5-(2-Aminopropyl)-2-methoxy benzenesulfonamide hydrochloride LTG|||BW430C Lamotrigine USP/BP/EP Lamotrigine in methanol 84057-84-1 84507-84-1 74057-84-1 Glutamate receptor Amines Heterocycles Other APIs VANTIN Pharmaceutical intermediate APIs All Inhibitors Inhibitors Intermediates & Fine Chemicals Pharmaceuticals