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84057-84-1 molecular structure
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6-(2,3-dichlorophenyl)-1,2,4-triazine-3,5-diamine

ChemBase ID: 437
Molecular Formular: C9H7Cl2N5
Molecular Mass: 256.09138
Monoisotopic Mass: 255.00785061
SMILES and InChIs

SMILES:
Clc1c(c2nnc(nc2N)N)cccc1Cl
Canonical SMILES:
Nc1nnc(c(n1)N)c1cccc(c1Cl)Cl
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

Cite this record

CBID:437 http://www.chembase.cn/molecule-437.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
6-(2,3-dichlorophenyl)-1,2,4-triazine-3,5-diamine
IUPAC Traditional name
lamotrigine
6-(2,3-dichlorophenyl)-1,2,4-triazine-3,5-diamine
Brand Name
Lamictal
Lamictal CD
Lamictin
Lamictal XR
Synonyms
Lamotrigina [Spanish]
Lamotriginum [Latin]
GW 273293
lamotrigine
Lamotrigine
3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine
BW 430C
LTG
Lamictal
Lamictal XR
Lamotrigin
6-(2,3-dichlorophenyl)-1,2,4-triazine-3,5-diamine
6-(2,3-Dichlorophenyl)-1,2,4-triazine-3,5-diamine
GI 267119X
Lamotrigine
Lamictin
CAS Number
84057-84-1
EC Number
281-901-8
MDL Number
MFCD00865333
PubChem SID
24278792
160963900
46505408
PubChem CID
3878

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 14.979241  H Acceptors
H Donor LogD (pH = 5.5) 1.4001383 
LogD (pH = 7.4) 1.9137787  Log P 1.9265221 
Molar Refractivity 66.6197 cm3 Polarizability 24.699194 Å3
Polar Surface Area 90.71 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.87  LOG S -2.72 
Solubility (Water) 4.88e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
DMSO: soluble20 mg/mL at 60 °C expand Show data source
Ethanol expand Show data source
H2O: insoluble expand Show data source
Methanol expand Show data source
Apperance
white powder expand Show data source
White to Cream Coloured Solid expand Show data source
Melting Point
216-218°C expand Show data source
Hydrophobicity(logP)
2.5 expand Show data source
2.534 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
RTECS
XY5850700 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
3 expand Show data source
Risk Statements
25 expand Show data source
Safety Statements
45 expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H301 expand Show data source
GHS Precautionary statements
P301 + P310 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges expand Show data source
RID/ADR
UN 2811 6.1/PG 3 expand Show data source
Storage Temperature
2-8°C expand Show data source
Target
Sodium Channel expand Show data source
Gene Information
human ... SCN5A(6331)rat ... Scn2a1(24766), Scnn1a(25122) expand Show data source
Mechanism of Action
Inhibits release of excitatory amino acids via blockage of neuronal voltage-dependent sodium channels expand Show data source
Purity
≥98% expand Show data source
95% expand Show data source
95+% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Application(s)
Anticonvulsant expand Show data source
Used in the treatment of epilepsy and bipolar disorder expand Show data source
Empirical Formula (Hill Notation)
C9H7Cl2N5 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00555 external link
Item Information
Drug Groups approved; investigational
Description Lamotrigine is an anticonvulsant drug used in the treatment of epilepsy and bipolar disorder. For epilepsy it is used to treat partial seizures, primary and secondary tonic-clonic seizures, and seizures associated with Lennox-Gastaut syndrome. Lamotrigine also acts as a mood stabilizer. It is the first medication since lithium granted Food and Drug Administration (FDA) approval for the maintenance treatment of bipolar type I. Chemically unrelated to other anticonvulsants, lamotrigine has relatively few side-effects and does not require blood monitoring. The exact way lamotrigine works is unknown. [Wikipedia]
Indication 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.
Pharmacology Lamotrigine, an antiepileptic drug (AED) of the phenyltriazine class, is chemically unrelated to existing antiepileptic drugs. Lamotrigine is also used in the treatment of depression and bipolar disorder. Lamotrigine is thought to exert its anticonvulsant effect by stabilizing presynaptic neuronal membranes. Lamotrigine inhibits sodium currents by selectively binding to the inactivated state of the sodium channel and subsequently suppresses the release of the excilatory amino acid, glutamate.
Toxicity LD50=250 (mg/kg) (in rat, mice); LD50>640 orally (mg/kg) (in rat, mice) (Sawyer). Symptoms of overdose include decreased level of consciousness, coma, delayed heartbeat, increased seizures, lack of coordination, and rolling eyeballs.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Absorption 98%
Half Life 25 +/- 10 hours (healthy individuals); 42.9 hours (chronic renal failure)
Protein Binding 55%
Distribution * 0.9 to 1.3 L/kg
Clearance * Apparent plasma cl=0.44 mL/min/kg [healthy volunteers taking single-dose LAMICTAL]
* Apparent plasma cl=0.58 mL/min/kg [healthy volunteers taking multiple-dose LAMICTAL]
* Apparent plasma cl=0.30 mL/min/kg [healthy volunteers taking valproate and single-dose LAMICTAL]
* Apparent plasma cl=0.18 mL/min/kg [healthy volunteers taking valproate and multiple-dose LAMICTAL]
* Apparent plasma cl=1.1 mL/min/kg [Patients with epilepsy taking carbamazepine, phenytoin, phenobarbital, or primidone plus valproate and single-dose LAMICTAL]
* Apparent plasma cl=1.12 mL/min/kg [Patients with epilepsy taking carbamazepine, phenytoin, phenobarbital, or primidone plus valproate and multiple-dose LAMICTAL]
References
Backonja M: Neuromodulating drugs for the symptomatic treatment of neuropathic pain. Curr Pain Headache Rep. 2004 Jun;8(3):212-6. [Pubmed]
Barbosa L, Berk M, Vorster M: A double-blind, randomized, placebo-controlled trial of augmentation with lamotrigine or placebo in patients concomitantly treated with fluoxetine for resistant major depressive episodes. J Clin Psychiatry. 2003 Apr;64(4):403-7. [Pubmed]
Jensen TS: Anticonvulsants in neuropathic pain: rationale and clinical evidence. Eur J Pain. 2002;6 Suppl A:61-8. [Pubmed]
Pappagallo M: Newer antiepileptic drugs: possible uses in the treatment of neuropathic pain and migraine. Clin Ther. 2003 Oct;25(10):2506-38. [Pubmed]
Tehrani SP, Daryaafzoon M, Bakhtiarian A, Ejtemaeemehr S, Sahraei H: The effects of lamotrigine on the acquisition and expression of morphine-induced place preference in mice. Pak J Biol Sci. 2009 Jan 1;12(1):33-9. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Sigma Aldrich - L3791 external link
Biochem/physiol Actions
Anticonvulsant.
Packaging
10, 50 mg in glass bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. L3791.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Toronto Research Chemicals - L173250 external link
An anticonvulsant. Inhibits glutamate release, possible through inhibition of Sodium, Potassium and Calcium currents. Used in treatment of bipolar depression.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Backonja M: Neuromodulating drugs for the symptomatic treatment of neuropathic pain. Curr Pain Headache Rep. 2004 Jun;8(3):212-6. Pubmed
  • • Barbosa L, Berk M, Vorster M: A double-blind, randomized, placebo-controlled trial of augmentation with lamotrigine or placebo in patients concomitantly treated with fluoxetine for resistant major depressive episodes. J Clin Psychiatry. 2003 Apr;64(4):403-7. Pubmed
  • • Jensen TS: Anticonvulsants in neuropathic pain: rationale and clinical evidence. Eur J Pain. 2002;6 Suppl A:61-8. Pubmed
  • • Pappagallo M: Newer antiepileptic drugs: possible uses in the treatment of neuropathic pain and migraine. Clin Ther. 2003 Oct;25(10):2506-38. Pubmed
  • • Tehrani SP, Daryaafzoon M, Bakhtiarian A, Ejtemaeemehr S, Sahraei H: The effects of lamotrigine on the acquisition and expression of morphine-induced place preference in mice. Pak J Biol Sci. 2009 Jan 1;12(1):33-9. Pubmed
  • • Miller, A.A., et al.: Epilepsia, 27, 483 (1986)
  • • Grunze, et al.: Neuropsychobiology, 38, 131 (1986)
  • • Calabrese, J.R., et al.: J. Clin. Psychiatry, 60, 79 (1986)
  • • Eur. Pat., 1982, Wellcome, 21 121; CA, 98, 89397d, (synth, pharmacol)
  • • Eur. Pat., 1985, Wellcome, 142 306; CA, 103, 142021, (synth, pharmacol)
  • • Miller, A.A. et al., Curr. Probl. Epilepsy, 1986, 4, 165, (rev)
  • • Cohen, A.F. et al., Clin. Pharmacol. Ther. (St. Louis), 1987, 42, 535, (metab)
  • • Janes, R.W. et al., Acta Cryst. C, 1989, 45, 129, (cryst struct)
  • • Antiepileptic Drugs, (Eds. Levy, R.H., et al), 4th edn., Raven Press, 1995, 300
  • • Fitton, A. et al., Drugs, 1995, 50, (rev, pharmacol)
  • • Burstein, A.H. et al., Pharmacotherapy (Carlisle, Mass.), 1995, 15, 129, (rev)
  • • Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 375
  • • Wang, S.-J. et al., Synapse (N.Y.), 1996, 24, 248, (pharmacol)
  • • Bartoli, A. et al., Ther. Drug Monit., 1997, 19, 100, (hplc)
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PATENTS

PATENTS

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