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Lamotrigine

CAS No.84057-84-1
Chemical Name:Lamotrigine
CBNumber:CB4166704
Molecular Formula:C9H7Cl2N5
Formula Weight:256.09
MOL File:84057-84-1.mol

Lamotrigine Property

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
UNSPSC Code 41116107
NACRES NA.77

Safety

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordDanger
Hazard statements H301
Precautionary statements P264-P270-P301+P310-P405-P501

Lamotrigine Price More Price(8)

Brand: Sigma-Aldrich(India)
Product number: PHR1392
Product name : Lamotrigine
Purity: Pharmaceutical Secondary Standard; Certified Reference Material
Packaging: 1G
Price: ₹10381.18
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: L3791
Product name : Lamotrigine
Purity: ≥98%, powder
Packaging: 10MG
Price: ₹12719.38
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Brand: Sigma-Aldrich(India)
Product number: L3791
Product name : Lamotrigine
Purity: ≥98%, powder
Packaging: 50MG
Price: ₹50769.25
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: L-019
Product name : Lamotrigine solution
Purity: 1.0?mg/mL in methanol, ampule of 1?mL, certified reference material, Cerilliant?
Packaging: 1ML
Price: ₹11943.4
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Brand: TCI Chemicals (India)
Product number: L0241
Product name : Lamotrigine
Purity:
Packaging: 1G
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Lamotrigine Chemical Properties,Usage,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 .
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
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