lamotrigine

Names

[ Name ]:
lamotrigine

[Synonym ]:
Lamictal
Lamotrigin
6-(2,3-Dichlorophenyl)-1,2,4-triazine-3,5-diamine
EINECS 281-901-8
6-(2,3-Dichlorophenyl)-3-imino-3,4-dihydro-1,2,4-triazin-5-amine
1,2,4-Triazin-5-amine, 6-(2,3-dichlorophenyl)-3,4-dihydro-3-imino-
Crisomet
Lamictal CD
HYDROXYMETHYL PROGESTERONE
6-O-TRITYL-1,2,3,4-TETRA-O-ACETYL-ALPHA-D-MANNOPYRANOSE
BW 430C
LAMOTRIGENE
LAMOTRIGINE API
MFCD00865333
LAMOTRIGINE / 6-(2,3-DICHLOROPHENYL)-1,2,4-TRIAZINE-3,5-DIAMINE
Lamictal XR
1,2,4-Triazine-3,5-diamine, 6-(2,3-dichlorophenyl)-
LAMOTRIGINE-13C3
LAMOTRIGINE (10 MG )
Lamotrigina
1,2,4-TRIAZINE-3,5-DIAMINE,6-(2,3-DICHLOROPHENYL)-
Labileno
Lamotriginum
Lamotrigine

Biological Activity

[Description]:

Lamotrigine(BW430C) is a novel anticonvulsant drug for inhibition of 5-HT and sodium channelTarget: Sodium ChannelLamotrigine stabilises presynaptic neuronal membranes by blockade of voltage-dependent sodium channels, thus preventing the release of excitatory neurotransmitters, particularly glutamate and aspartate [1]. In rat cerebral cortex tissue incubated with veratrine 10 mg/L, lamotrigine is twice as potent in inhibiting the release of glutamate and aspartate (ED 50 = 5.38 mg/L for each) than the release of GABA (ED50 = 11.2 mg/L), and is much less potent in inhibiting acetylcholine release (ED50 = 25.6 mg/L) when cortical slices is exposed to veratrine 75 mg/L. Basal glutamate release is unaffected [2]. Lamotrigine inhibits high-frequency sustained repetitive firing of sodium-dependent action potentials, indicating a direct effect on voltage-activated sodium channels [3]. Lamotrigine (Lamictal), a phenyltriazine derivative, is a well established anticonvulsant agent that has shown efficacy in the prevention of mood episodes in adult patients with bipolar I disorder. lamotrigine significantly delayed time to intervention for a depressive episode and showed limited efficacy in delaying time to intervention for a manic/hypomanic episode, compared with placebo. Lamotrigine is generally well tolerated [4].

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> Membrane Transporter/Ion Channel >> Sodium Channel

Research Areas >> Neurological Disease

[References]

[1]. Goa, K.L., S.R. Ross, and P. Chrisp, Lamotrigine. A review of its pharmacological properties and clinical efficacy in epilepsy. Drugs, 1993. 46(1): p. 152-76.

[2]. Leach, M.J., C.M. Marden, and A.A. Miller, Pharmacological studies on lamotrigine, a novel potential antiepileptic drug: II. Neurochemical studies on the mechanism of action. Epilepsia, 1986. 27(5): p. 490-7.

[3]. Cheung, H., D. Kamp, and E. Harris, An in vitro investigation of the action of lamotrigine on neuronal voltage-activated sodium channels. Epilepsy Res, 1992. 13(2): p. 107-12.

[4]. Goldsmith, D.R., et al., Lamotrigine: a review of its use in bipolar disorder. Drugs, 2003. 63(19): p. 2029-50.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
503.1±60.0 °C at 760 mmHg

[ Melting Point ]:
177-181°C

[ Molecular Formula ]:
C₉H₇Cl₂N₅

[ Molecular Weight ]:
256.091

[ Flash Point ]:
258.1±32.9 °C

[ Exact Mass ]:
255.007858

[ PSA ]:
90.71000

[ LogP ]:
-0.19

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.706

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
DMSO: 20 mg/mL at 60 °C, soluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XY5850700

CHEMICAL NAME :: 1,2,4-Triazine-3,5-diamine, 6-(2,3-dichlorophenyl)-

CAS REGISTRY NUMBER :: 84057-84-1

LAST UPDATED :: 199706

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C9-H7-Cl2-N5

MOLECULAR WEIGHT :: 256.11

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 19 mg/kg

TOXIC EFFECTS :: Behavioral - muscle contraction or spasticity Sense Organs and Special Senses (Eye) - effect, not otherwise specified Cardiac - EKG changes not diagnostic of specified effects

REFERENCE :: LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 342,1552,1993

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 2 mg/kg/30H-I

TOXIC EFFECTS :: Gastrointestinal - nausea or vomiting Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)

REFERENCE :: PEDIAU Pediatrics. (American Academy of Pediatrics, P.O. Box 1034, Evanston, IL 60204) V.1- 1948- Volume(issue)/page/year: 98,294,1996

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 205 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EPILAK Epilepsia (New York). (Raven Press, 1185 Ave. of the Americas, New York, NY 10036) Ser.1-3: 1909-55; Ser.4: V.1- 1959- Volume(issue)/page/year: 25,655,1984

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 245 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EPILAK Epilepsia (New York). (Raven Press, 1185 Ave. of the Americas, New York, NY 10036) Ser.1-3: 1909-55; Ser.4: V.1- 1959- Volume(issue)/page/year: 25,655,1984

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301

[ Precautionary Statements ]:
P301 + P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T: Toxic;

[ Risk Phrases ]:
R25

[ Safety Phrases ]:
S45

[ RIDADR ]:
UN 2811 6.1/PG 3

[ WGK Germany ]:
3

[ RTECS ]:
XY5850700

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
2933699090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933699090

[ Summary ]:
2933699090 other compounds containing an unfused triazine ring (whether or not hydrogenated) in the structure。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:20.0%

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Related Compounds

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