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enzymes (3)transporters (1) Show 4 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:42 UTC

HMDB ID

HMDB0014695

Secondary Accession Numbers

HMDB14695

Metabolite Identification

Common Name

Lamotrigine

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 ]

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

555
  Mrv0541 02231214462D          

 16 17  0  0  0  0            999 V2000
    4.9509    0.9529    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    2.6029    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.2846    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.1096    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    0.1279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -1.1096    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.3472    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  2 13  1  0  0  0  0
  3  6  2  0  0  0  0
  3  9  1  0  0  0  0
  4 12  1  0  0  0  0
  4 16  2  0  0  0  0
  5 12  1  0  0  0  0
  6 16  1  0  0  0  0
  7 16  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  8 11  1  0  0  0  0
  9 12  2  0  0  0  0
 10 13  1  0  0  0  0
 11 14  2  0  0  0  0
 13 15  2  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014695

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=NC(N)=C(N=N1)C1=C(Cl)C(Cl)=CC=C1

> <INCHI_IDENTIFIER>
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)

> <INCHI_KEY>
PYZRQGJRPPTADH-UHFFFAOYSA-N

> <FORMULA>
C9H7Cl2N5

> <MOLECULAR_WEIGHT>
256.091

> <EXACT_MASS>
255.007850663

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
23.10429797036266

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-(2,3-dichlorophenyl)-1,2,4-triazine-3,5-diamine

> <ALOGPS_LOGP>
1.87

> <JCHEM_LOGP>
1.9265221886666666

> <ALOGPS_LOGS>
-2.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.21539181005468

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.97924095981977

> <JCHEM_PKA_STRONGEST_BASIC>
5.874296269611684

> <JCHEM_POLAR_SURFACE_AREA>
90.71

> <JCHEM_REFRACTIVITY>
66.61970000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.88e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lamotrigine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 555                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       9.242   1.779   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0       9.242   4.859   0.000  0.00  0.00          Cl+0
HETATM    3  N   UNK     0       7.908  -0.531   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       5.241  -2.071   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       3.907   0.239   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       7.908  -2.071   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       6.574  -4.381   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       6.574   1.779   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.574   0.239   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.908   2.549   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.241   2.549   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.241  -0.531   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.908   4.089   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.241   4.089   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.574   4.859   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.574  -2.841   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2   13                                                            
CONECT    3    6    9                                                       
CONECT    4   12   16                                                       
CONECT    5   12                                                            
CONECT    6    3   16                                                       
CONECT    7   16                                                            
CONECT    8    9   10   11                                                  
CONECT    9    3    8   12                                                  
CONECT   10    1    8   13                                                  
CONECT   11    8   14                                                       
CONECT   12    4    5    9                                                  
CONECT   13    2   10   15                                                  
CONECT   14   11   15                                                       
CONECT   15   13   14                                                       
CONECT   16    4    6    7                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine	ChEBI
Lamictal	ChEBI
Lamotrigina	ChEBI
Lamotriginum	ChEBI
GW 273293	HMDB
Labileno	HMDB
3,5-Diamino-6-(2,3-dichlorophenyl)-as-triazine	HMDB
BW-430C	HMDB
Crisomet	HMDB
Lamiktal	HMDB
BW 430C	HMDB

Chemical Formula

C₉H₇Cl₂N₅

Average Molecular Weight

256.091

Monoisotopic Molecular Weight

255.007850663

IUPAC Name

6-(2,3-dichlorophenyl)-1,2,4-triazine-3,5-diamine

Traditional Name

lamotrigine

CAS Registry Number

84057-84-1

SMILES

NC1=NC(N)=C(N=N1)C1=C(Cl)C(Cl)=CC=C1

InChI Identifier

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)

InChI Key

PYZRQGJRPPTADH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Halobenzenes

Direct Parent

Dichlorobenzenes

Alternative Parents

Substituents

1,2-dichlorobenzene
Aminotriazine
Aryl chloride
Aryl halide
Triazine
Imidolactam
1,2,4-triazine
Heteroaromatic compound
Organoheterocyclic compound
Azacycle
Amine
Primary amine
Organonitrogen compound
Organochloride
Organohalogen compound
Organopnictogen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dichlorobenzene (CHEBI:6367 )
primary arylamine (CHEBI:6367 )
1,2,4-triazines (CHEBI:6367 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014695)

Process

Not Available

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	216 - 218 °C (uncorr.)	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.49 g/L	Not Available
LogP	2.5	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	151.2	30932474
[M+H]+	Not Available	150.554	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000852

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.49 g/L	ALOGPS
logP	1.87	ALOGPS
logP	1.93	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	14.98	ChemAxon
pKa (Strongest Basic)	5.87	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	90.71 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	66.62 m³·mol⁻¹	ChemAxon
Polarizability	23.1 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	156.549	30932474
DeepCCS	[M-H]-	154.191	30932474
DeepCCS	[M-2H]-	187.078	30932474
DeepCCS	[M+Na]+	162.642	30932474
AllCCS	[M+H]+	152.6	32859911
AllCCS	[M+H-H2O]+	148.7	32859911
AllCCS	[M+NH4]+	156.2	32859911
AllCCS	[M+Na]+	157.3	32859911
AllCCS	[M-H]-	148.5	32859911
AllCCS	[M+Na-2H]-	148.5	32859911
AllCCS	[M+HCOO]-	148.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.84 minutes	32390414
Predicted by Siyang on May 30, 2022	10.3777 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.48 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	143.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	574.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	333.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	83.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	204.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	86.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	320.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	315.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	779.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	691.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	69.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	714.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	204.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	249.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	631.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	410.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	136.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lamotrigine	NC1=NC(N)=C(N=N1)C1=C(Cl)C(Cl)=CC=C1	3572.9	Standard polar	33892256
Lamotrigine	NC1=NC(N)=C(N=N1)C1=C(Cl)C(Cl)=CC=C1	2243.5	Standard non polar	33892256
Lamotrigine	NC1=NC(N)=C(N=N1)C1=C(Cl)C(Cl)=CC=C1	2564.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lamotrigine,1TMS,isomer #1	C[Si](C)(C)NC1=NN=C(C2=CC=CC(Cl)=C2Cl)C(N)=N1	2462.9	Semi standard non polar	33892256
Lamotrigine,1TMS,isomer #1	C[Si](C)(C)NC1=NN=C(C2=CC=CC(Cl)=C2Cl)C(N)=N1	2262.0	Standard non polar	33892256
Lamotrigine,1TMS,isomer #1	C[Si](C)(C)NC1=NN=C(C2=CC=CC(Cl)=C2Cl)C(N)=N1	4041.4	Standard polar	33892256
Lamotrigine,1TMS,isomer #2	C[Si](C)(C)NC1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl	2458.3	Semi standard non polar	33892256
Lamotrigine,1TMS,isomer #2	C[Si](C)(C)NC1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl	2222.7	Standard non polar	33892256
Lamotrigine,1TMS,isomer #2	C[Si](C)(C)NC1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl	3959.3	Standard polar	33892256
Lamotrigine,2TMS,isomer #1	C[Si](C)(C)NC1=NN=C(C2=CC=CC(Cl)=C2Cl)C(N[Si](C)(C)C)=N1	2391.7	Semi standard non polar	33892256
Lamotrigine,2TMS,isomer #1	C[Si](C)(C)NC1=NN=C(C2=CC=CC(Cl)=C2Cl)C(N[Si](C)(C)C)=N1	2316.5	Standard non polar	33892256
Lamotrigine,2TMS,isomer #1	C[Si](C)(C)NC1=NN=C(C2=CC=CC(Cl)=C2Cl)C(N[Si](C)(C)C)=N1	3713.7	Standard polar	33892256
Lamotrigine,2TMS,isomer #2	C[Si](C)(C)N(C1=NN=C(C2=CC=CC(Cl)=C2Cl)C(N)=N1)[Si](C)(C)C	2351.2	Semi standard non polar	33892256
Lamotrigine,2TMS,isomer #2	C[Si](C)(C)N(C1=NN=C(C2=CC=CC(Cl)=C2Cl)C(N)=N1)[Si](C)(C)C	2458.5	Standard non polar	33892256
Lamotrigine,2TMS,isomer #2	C[Si](C)(C)N(C1=NN=C(C2=CC=CC(Cl)=C2Cl)C(N)=N1)[Si](C)(C)C	3713.1	Standard polar	33892256
Lamotrigine,2TMS,isomer #3	C[Si](C)(C)N(C1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl)[Si](C)(C)C	2305.8	Semi standard non polar	33892256
Lamotrigine,2TMS,isomer #3	C[Si](C)(C)N(C1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl)[Si](C)(C)C	2424.0	Standard non polar	33892256
Lamotrigine,2TMS,isomer #3	C[Si](C)(C)N(C1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl)[Si](C)(C)C	3716.6	Standard polar	33892256
Lamotrigine,3TMS,isomer #1	C[Si](C)(C)NC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=NN=C1C1=CC=CC(Cl)=C1Cl	2384.6	Semi standard non polar	33892256
Lamotrigine,3TMS,isomer #1	C[Si](C)(C)NC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=NN=C1C1=CC=CC(Cl)=C1Cl	2483.4	Standard non polar	33892256
Lamotrigine,3TMS,isomer #1	C[Si](C)(C)NC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=NN=C1C1=CC=CC(Cl)=C1Cl	3218.9	Standard polar	33892256
Lamotrigine,3TMS,isomer #2	C[Si](C)(C)NC1=NN=C(C2=CC=CC(Cl)=C2Cl)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	2379.4	Semi standard non polar	33892256
Lamotrigine,3TMS,isomer #2	C[Si](C)(C)NC1=NN=C(C2=CC=CC(Cl)=C2Cl)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	2470.2	Standard non polar	33892256
Lamotrigine,3TMS,isomer #2	C[Si](C)(C)NC1=NN=C(C2=CC=CC(Cl)=C2Cl)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	3337.3	Standard polar	33892256
Lamotrigine,4TMS,isomer #1	C[Si](C)(C)N(C1=NN=C(C2=CC=CC(Cl)=C2Cl)C(N([Si](C)(C)C)[Si](C)(C)C)=N1)[Si](C)(C)C	2465.6	Semi standard non polar	33892256
Lamotrigine,4TMS,isomer #1	C[Si](C)(C)N(C1=NN=C(C2=CC=CC(Cl)=C2Cl)C(N([Si](C)(C)C)[Si](C)(C)C)=N1)[Si](C)(C)C	2612.1	Standard non polar	33892256
Lamotrigine,4TMS,isomer #1	C[Si](C)(C)N(C1=NN=C(C2=CC=CC(Cl)=C2Cl)C(N([Si](C)(C)C)[Si](C)(C)C)=N1)[Si](C)(C)C	2884.0	Standard polar	33892256
Lamotrigine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NN=C(C2=CC=CC(Cl)=C2Cl)C(N)=N1	2623.0	Semi standard non polar	33892256
Lamotrigine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NN=C(C2=CC=CC(Cl)=C2Cl)C(N)=N1	2489.6	Standard non polar	33892256
Lamotrigine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NN=C(C2=CC=CC(Cl)=C2Cl)C(N)=N1	4014.2	Standard polar	33892256
Lamotrigine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl	2590.2	Semi standard non polar	33892256
Lamotrigine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl	2447.4	Standard non polar	33892256
Lamotrigine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl	3960.8	Standard polar	33892256
Lamotrigine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NN=C(C2=CC=CC(Cl)=C2Cl)C(N[Si](C)(C)C(C)(C)C)=N1	2755.0	Semi standard non polar	33892256
Lamotrigine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NN=C(C2=CC=CC(Cl)=C2Cl)C(N[Si](C)(C)C(C)(C)C)=N1	2801.1	Standard non polar	33892256
Lamotrigine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NN=C(C2=CC=CC(Cl)=C2Cl)C(N[Si](C)(C)C(C)(C)C)=N1	3665.0	Standard polar	33892256
Lamotrigine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=NN=C(C2=CC=CC(Cl)=C2Cl)C(N)=N1)[Si](C)(C)C(C)(C)C	2753.9	Semi standard non polar	33892256
Lamotrigine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=NN=C(C2=CC=CC(Cl)=C2Cl)C(N)=N1)[Si](C)(C)C(C)(C)C	2826.4	Standard non polar	33892256
Lamotrigine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=NN=C(C2=CC=CC(Cl)=C2Cl)C(N)=N1)[Si](C)(C)C(C)(C)C	3610.6	Standard polar	33892256
Lamotrigine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl)[Si](C)(C)C(C)(C)C	2704.2	Semi standard non polar	33892256
Lamotrigine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl)[Si](C)(C)C(C)(C)C	2806.4	Standard non polar	33892256
Lamotrigine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl)[Si](C)(C)C(C)(C)C	3651.1	Standard polar	33892256
Lamotrigine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NN=C1C1=CC=CC(Cl)=C1Cl	2952.7	Semi standard non polar	33892256
Lamotrigine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NN=C1C1=CC=CC(Cl)=C1Cl	3079.2	Standard non polar	33892256
Lamotrigine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NN=C1C1=CC=CC(Cl)=C1Cl	3316.3	Standard polar	33892256
Lamotrigine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NN=C(C2=CC=CC(Cl)=C2Cl)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	2940.6	Semi standard non polar	33892256
Lamotrigine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NN=C(C2=CC=CC(Cl)=C2Cl)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	3080.2	Standard non polar	33892256
Lamotrigine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NN=C(C2=CC=CC(Cl)=C2Cl)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	3406.8	Standard polar	33892256
Lamotrigine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NN=C(C2=CC=CC(Cl)=C2Cl)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1)[Si](C)(C)C(C)(C)C	3164.1	Semi standard non polar	33892256
Lamotrigine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NN=C(C2=CC=CC(Cl)=C2Cl)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1)[Si](C)(C)C(C)(C)C	3334.6	Standard non polar	33892256
Lamotrigine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NN=C(C2=CC=CC(Cl)=C2Cl)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1)[Si](C)(C)C(C)(C)C	3142.4	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00555	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00555	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00555

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3741

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lamotrigine

METLIN ID

Not Available

PubChem Compound

3878

PDB ID

Not Available

ChEBI ID

6367

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Jensen TS: Anticonvulsants in neuropathic pain: rationale and clinical evidence. Eur J Pain. 2002;6 Suppl A:61-8. [PubMed:11888243 ]
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:12716240 ]
Pappagallo M: Newer antiepileptic drugs: possible uses in the treatment of neuropathic pain and migraine. Clin Ther. 2003 Oct;25(10):2506-38. [PubMed:14667954 ]
Backonja M: Neuromodulating drugs for the symptomatic treatment of neuropathic pain. Curr Pain Headache Rep. 2004 Jun;8(3):212-6. [PubMed:15115640 ]
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:19579915 ]

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:: UGT1A4
Uniprot ID:: P22310
Molecular weight:: 60024.535

References

Argikar UA, Senekeo-Effenberger K, Larson EE, Tukey RH, Remmel RP: Studies on induction of lamotrigine metabolism in transgenic UGT1 mice. Xenobiotica. 2009 Nov;39(11):826-35. doi: 10.3109/00498250903188985. [PubMed:19845433 ]
Chen H, Yang K, Choi S, Fischer JH, Jeong H: Up-regulation of UDP-glucuronosyltransferase (UGT) 1A4 by 17beta-estradiol: a potential mechanism of increased lamotrigine elimination in pregnancy. Drug Metab Dispos. 2009 Sep;37(9):1841-7. doi: 10.1124/dmd.109.026609. Epub 2009 Jun 22. [PubMed:19546240 ]
Argikar UA, Remmel RP: Variation in glucuronidation of lamotrigine in human liver microsomes. Xenobiotica. 2009 May;39(5):355-63. doi: 10.1080/00498250902745082. [PubMed:19387891 ]

Enzyme Details

2. UDP-glucuronosyltransferase 1-3

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:: UGT1A3
Uniprot ID:: P35503
Molecular weight:: 60337.835

References

Argikar UA, Remmel RP: Variation in glucuronidation of lamotrigine in human liver microsomes. Xenobiotica. 2009 May;39(5):355-63. doi: 10.1080/00498250902745082. [PubMed:19387891 ]

Enzyme Details

3. Sodium channel protein type 2 subunit alpha

General function:: Involved in ion channel activity
Specific function:: Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient
Gene Name:: SCN2A
Uniprot ID:: Q99250
Molecular weight:: 227972.6

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Lipkind GM, Fozzard HA: Molecular modeling of local anesthetic drug binding by voltage-gated sodium channels. Mol Pharmacol. 2005 Dec;68(6):1611-22. Epub 2005 Sep 20. [PubMed:16174788 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Luna-Tortos C, Fedrowitz M, Loscher W: Several major antiepileptic drugs are substrates for human P-glycoprotein. Neuropharmacology. 2008 Dec;55(8):1364-75. doi: 10.1016/j.neuropharm.2008.08.032. Epub 2008 Sep 11. [PubMed:18824002 ]

Showing metabocard for Lamotrigine (HMDB0014695)

MOL for HMDB0014695 (Lamotrigine)

3D MOL for HMDB0014695 (Lamotrigine)

3D SDF for HMDB0014695 (Lamotrigine)

3D-SDF for HMDB0014695 (Lamotrigine)

PDB for HMDB0014695 (Lamotrigine)

3D PDB for HMDB0014695 (Lamotrigine)

SMILES for HMDB0014695 (Lamotrigine)

INCHI for HMDB0014695 (Lamotrigine)

Structure for HMDB0014695 (Lamotrigine)

3D Structure for HMDB0014695 (Lamotrigine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

References

References

References

Transporters

References