라모트리진

라모트리진 · LAMOTRIGIN · LAMICTAL · 3,5-DIAMINO-6-(2,3-DICHLOROPHENYL)-1,2,4-TRIAZINE · 6-(2,3-DICHLOROPHENYL)-1,2,4-TRIAZINE-3,5-DIAMINE · LTG · TNFSF · BW-430

https://huagongshe.com/ko/chemical/3878

식별자 및 물리적 특성

CAS No.	84057-84-1
분자식	C9H7Cl2N5
평균 분자량	256.09 g/mol
단동위원소 질량	255.00785058 g/mol
SMILES	Nc1nnc(-c2cccc(Cl)c2Cl)c(N)n1
InChIKey	PYZRQGJRPPTADH-UHFFFAOYSA-N
PubChem CID	3878
ChEMBL	CHEMBL741
ChEBI	CHEBI:6367
EC No.	281-901-8
DTXSID	DTXSID2023195
현지명	라모트리진

화학 및 물리적 성질

XLogP	1.4
극성 표면적	90.7
수소 결합 공여자 수	2
수소 결합 수용자 수	5
회전 가능 결합 수	1
무거운 원자 수	16
형식 전하	0
복잡도	242
의약품	PharmaceuticalsPharmaceuticals -> AntiepilepticPharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Used in Switzerland
LogP(분배 계수)	log Kow = 2.571.6
Color/Form	White to pale cream-colored powder. Crystals from isopropanol
용해도	In water, 170 mg/L at 25 °CSolubility in 0.1M hydrochloric acid: 4.1 mg/mL at 25 °C4.88e-01 g/LDMSO: 60°C에서 20mg/mL, 용해성
Human Drugs	Breast FeedingLactationMilk, HumanAnticonvulsantsAntimanic AgentsAntidepressive AgentsFDA approved drugs -> Active ingredientPharmaceuticalsAntiseizure medicines
끓는 점	503.1±60.0503.1±60.0 °C(Predicted)
녹는점	177-181216-218 °C (uncorr)216 - 218 °C (uncorr.)177-181°C
Physical Description	Solid
Dissociation Constants	5.7pKa = 5.7
Collision Cross Section	150.6 Å² [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]149.56 Å² [M+H]+ [CCS Type: TW151.2 Å² [M+H]+ [CCS Type: TWMethod: Major Mix IMS/Tof Calibration Kit (Waters)]
밀도	1.572±0.06 g/cm3(Predicted)
인화점	9℃
저장 조건	2-8°C
pKa(산도 계수)	5.7(at 25℃)
물리적 상태	가루
색상	하얀색
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

화학적 성질

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.

안전 및 규제

GHS 분류	DangerH301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]P264, P270, P273, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 68 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
규제 정보	Lamotrigine: Does not have an individual approval but may be used under an appropriate group standard
FDA 요건	The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including lamotrigine, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
Toxic Combustion Products	Special hazards arising from the substance or mixture: Carbon oxides, nitrogen oxides (NOx), Hydrogen chloride gas
Hazard Classes and Categories	Acute Tox. 3 (100%)
소화 절차	Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
보관 조건	Conditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place. Recommended storage temperature: 2 - 8 degC Keep in a dry place.
정리 방법	ACCIDENTAL RELEASE MEASURES. Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains.Methods and materials for containment and cleaning up Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.
처리 방법	SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.

용도

개요

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.

역사

The development of lamotrigine began in the early 1980s, accidentally discovered by a group of chemists at the Wellcome Research Laboratory while searching for novel antifolate compounds. Initially synthesized as an antifolate analog, subsequent animal model screening revealed its significant anticonvulsant activity, demonstrating its potential as an antiepileptic drug. In 1980, the Wellcome Foundation filed the first synthetic method and related patent applications for lamotrigine (e.g., European Patent EP 0021121), mentioning researchers such as M. G. Baxter. During clinical development, the efficacy of lamotrigine (trade name: lamotrigine tablets) was confirmed, and it was first launched in Ireland in 1991. Subsequently, it was approved by the U.S. Food and Drug Administration (FDA) for the treatment of epilepsy in 1994. In subsequent studies, the clinical applications of lamotrigine have continued to expand, particularly its efficacy as a mood stabilizer. Researchers such as Richard H. Weissler have advanced the application of lamotrigine in the treatment of bipolar disorder, especially in the maintenance treatment of bipolar depression, through clinical observation and research.

용도

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.

일반 설명

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.

제조 및 합성 방법

제조 방법

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 intermediatehttps://patents.google.com/patent/WO2007069265A1/en