Details of the Drug

General Information of Drug (ID: DM8SXYG)

Drug Name

Lamotrigine

Synonyms

Crisomet; Labileno; Lamictal; Lamictin; Lamiktal; Lamitor; Lamotrigina; Lamotriginum; Desitin Brand of Lamotrigine; Faes Brand of Lamotrigine; Glaxo Wellcome Brand of Lamotrigine; GlaxoSmithKline Brand of Lamotrigine; Juste Brand of Lamotrigine; Lamictal Cd; Lamictal ODT; Lamictal XR; Lamotrigina [Spanish]; Lamotriginum [Latin]; BW 430C; GI 267119X; GW 273293; L 3791; BW-430C; EUR-1048; Lamictal (TN); Lamictin (TN); Lamotrigine [USAN:INN:BAN]; Lamotrigine (JAN/USAN/INN); 3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine; 3,5-Diamino-6-(2,3-dichlorophenyl)-as-triazine; 3,5-diamino-6-(2,3-dichlorophenyl)-as-triazine; 6-(2,3-Dichlorophenyl)-1,2,4-triazine-3,5-diamine; 6-(2,3-Dichlorophenyl)-1,2,4-triazine-3,5-diyldiamine; 6-(2,3-dichlorophenyl)-1,2,4-triazine-3,5-diamine

Indication

Disease Entry	ICD 11	Status	REF
Bipolar disorder	6A60	Approved	[1]
Epilepsy	8A60-8A68	Approved	[1]

Therapeutic Class

Anticonvulsants

Affected Organisms

Humans and other mammals

ATC Code

N03AX09: Lamotrigine

N03AX: Other antiepileptics

N03A: ANTIEPILEPTICS

N03: ANTIEPILEPTICS

N: NERVOUS SYSTEM

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

256.089

Logarithm of the Partition Coefficient (xlogp)

1.4

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [2]
Bioavailability: 97.6% of drug becomes completely available to its intended biological destination(s) [3]
Clearance: The clearance of drug is 0.18-1.21 mL/min/kg [4]
Elimination: Following oral administration of 240 mg radiolabelled lamotrigine, about 94% of total drug and its metabolites administered is recovered in the urine and 2% is recovered in the feces [5]
Half-life: The concentration or amount of drug in body reduced by one-half in 14 - 59 hours [6]
Metabolism: The drug is metabolized via the glucuronidated, forming 2-N-glucuronide conjugate [5]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 27.89137 micromolar/kg/day [7]
Vd: The volume of distribution (Vd) of drug is 0.9-1.3 L/kg [4]
Water Solubility: The ability of drug to dissolve in water is measured as 0.17 mg/mL [2]

Chemical Identifiers

Formula: C9H7Cl2N5
IUPAC Name: 6-(2,3-dichlorophenyl)-1,2,4-triazine-3,5-diamine
Canonical SMILES: C1=CC(=C(C(=C1)Cl)Cl)C2=C(N=C(N=N2)N)N
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

Cross-matching ID

PubChem CID: 3878
ChEBI ID: CHEMBL6367
CAS Number: 84057-84-1
UNII: U3H27498KS
DrugBank ID: DB00555
TTD ID: D03FLC
VARIDT ID: DR00056
INTEDE ID: DR0913
ACDINA ID: D00348

Drug-Molecule Activity Atlas (DMA)^NEW

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Drug Pharmacogenomic Perturbation (DPP)^NEW

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Drug ADMET Endpoint Profile (DAE)^NEW

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Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Voltage-gated sodium channel alpha Nav1.9 (SCN11A)	TTN9VTF	SCNBA_HUMAN	Blocker	[8]

Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Organic cation transporter 1 (SLC22A1)	DTT79CX	S22A1_HUMAN	Substrate	[9]
P-glycoprotein 1 (ABCB1)	DTUGYRD	MDR1_HUMAN	Substrate	[10]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
UDP-glucuronosyltransferase 1A1 (UGT1A1)	DEYGVN4	UD11_HUMAN	Substrate	[11]
UDP-glucuronosyltransferase 1A3 (UGT1A3)	DEF2WXN	UD13_HUMAN	Substrate	[12]
UDP-glucuronosyltransferase 1A4 (UGT1A4)	DELOY3P	UD14_HUMAN	Substrate	[13]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2 (HSD3B2)	OT02MSKN	3BHS2_HUMAN	Gene/Protein Processing	[14]
Adrenocorticotropic hormone receptor (MC2R)	OT6V19Y9	ACTHR_HUMAN	Drug Response	[15]
ATP-dependent translocase ABCB1 (ABCB1)	OTEJROBO	MDR1_HUMAN	Gene/Protein Processing	[16]
D(2) dopamine receptor (DRD2)	OTBLXKEG	DRD2_HUMAN	Drug Response	[15]
POU domain, class 5, transcription factor 1 (POU5F1)	OTDHHN7O	PO5F1_HUMAN	Gene/Protein Processing	[17]
Protein lin-28 homolog A (LIN28A)	OTJJBRCQ	LN28A_HUMAN	Gene/Protein Processing	[17]
Sodium channel protein type 2 subunit alpha (SCN2A)	OTUSYE4Z	SCN2A_HUMAN	Gene/Protein Processing	[18]
Steroidogenic acute regulatory protein, mitochondrial (STAR)	OTFEZ5AI	STAR_HUMAN	Gene/Protein Processing	[17]
UDP-glucuronosyltransferase 1A3	OTUEOER3	UD13_HUMAN	Biotransformations	[19]
UDP-glucuronosyltransferase 1A4	OT4PU620	UD14_HUMAN	Biotransformations	[19]

Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Lamotrigine (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Levomilnacipran	DMV26S8	Moderate	Antagonize the effect of Lamotrigine when combined with Levomilnacipran.	Chronic pain [MG30]	[20]
Olopatadine	DMKMWQG	Moderate	Additive CNS depression effects by the combination of Lamotrigine and Olopatadine.	Conjunctiva disorder [9A60]	[21]
Ethanol	DMDRQZU	Moderate	Additive CNS depression effects by the combination of Lamotrigine and Ethanol.	Cystitis [GC00]	[21]
Sertraline	DM0FB1J	Moderate	Antagonize the effect of Lamotrigine when combined with Sertraline.	Depression [6A70-6A7Z]	[20]
Vilazodone	DM4LECQ	Moderate	Antagonize the effect of Lamotrigine when combined with Vilazodone.	Depression [6A70-6A7Z]	[20]
Paroxetine	DM5PVQE	Moderate	Antagonize the effect of Lamotrigine when combined with Paroxetine.	Depression [6A70-6A7Z]	[20]
Vortioxetine	DM6F1PU	Moderate	Antagonize the effect of Lamotrigine when combined with Vortioxetine.	Depression [6A70-6A7Z]	[20]
Milnacipran	DMBFE74	Moderate	Antagonize the effect of Lamotrigine when combined with Milnacipran.	Depression [6A70-6A7Z]	[20]
Escitalopram	DMFK9HG	Moderate	Antagonize the effect of Lamotrigine when combined with Escitalopram.	Depression [6A70-6A7Z]	[20]
Desvenlafaxine	DMHD4PE	Moderate	Antagonize the effect of Lamotrigine when combined with Desvenlafaxine.	Depression [6A70-6A7Z]	[20]
Esketamine	DMVU687	Moderate	Additive CNS depression effects by the combination of Lamotrigine and Esketamine.	Depression [6A70-6A7Z]	[22]
Primidone	DM0WX6I	Moderate	Increased metabolism of Lamotrigine caused by Primidone mediated induction of UGT.	Epilepsy/seizure [8A61-8A6Z]	[23]
Fosphenytoin	DMOX3LB	Moderate	Increased metabolism of Lamotrigine caused by Fosphenytoin mediated induction of UGT.	Epilepsy/seizure [8A61-8A6Z]	[23]
Phenobarbital	DMXZOCG	Moderate	Increased metabolism of Lamotrigine caused by Phenobarbital mediated induction of UGT.	Epilepsy/seizure [8A61-8A6Z]	[23]
Carbamazepine	DMZOLBI	Moderate	Increased metabolism of Lamotrigine caused by Carbamazepine mediated induction of UGT.	Epilepsy/seizure [8A61-8A6Z]	[23]
Rifampin	DMA8J1G	Moderate	Increased metabolism of Lamotrigine caused by Rifampin mediated induction of UGT.	HIV-infected patients with tuberculosis [1B10-1B14]	[24]
Lopinavir	DMITQS0	Moderate	Increased metabolism of Lamotrigine caused by Lopinavir mediated induction of UGT.	Human immunodeficiency virus disease [1C60-1C62]	[22]
Atazanavir	DMSYRBX	Moderate	Decreased metabolism of Lamotrigine caused by Atazanavir mediated inhibition of UGT.	Human immunodeficiency virus disease [1C60-1C62]	[22]
Porfimer Sodium	DM7ZWNY	Moderate	Increased risk of photosensitivity reactions by the combination of Lamotrigine and Porfimer Sodium.	Lung cancer [2C25]	[25]
Chloroquine	DMSI5CB	Moderate	Antagonize the effect of Lamotrigine when combined with Chloroquine.	Malaria [1F40-1F45]	[22]
Hydroxychloroquine	DMSIVND	Moderate	Antagonize the effect of Lamotrigine when combined with Hydroxychloroquine.	Malaria [1F40-1F45]	[22]
Allopregnanolone	DMNLHAC	Moderate	Additive CNS depression effects by the combination of Lamotrigine and Allopregnanolone.	Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z]	[26]
Lasmiditan	DMXLVDT	Moderate	Additive CNS depression effects by the combination of Lamotrigine and Lasmiditan.	Migraine [8A80]	[27]
Flibanserin	DM70DTN	Moderate	Additive CNS depression effects by the combination of Lamotrigine and Flibanserin.	Mood disorder [6A60-6E23]	[28]
Thalidomide	DM70BU5	Moderate	Additive CNS depression effects by the combination of Lamotrigine and Thalidomide.	Multiple myeloma [2A83]	[29]
Orlistat	DMRJSP8	Moderate	Altered absorption of Lamotrigine caused by Orlistat.	Obesity [5B80-5B81]	[30]
Apraclonidine	DMO4PVE	Moderate	Additive CNS depression effects by the combination of Lamotrigine and Apraclonidine.	Optic nerve disorder [9C40]	[31]
Dextropropoxyphene	DM23HCX	Major	Additive CNS depression effects by the combination of Lamotrigine and Dextropropoxyphene.	Pain [MG30-MG3Z]	[32]
Buprenorphine	DMPRI8G	Major	Additive CNS depression effects by the combination of Lamotrigine and Buprenorphine.	Pain [MG30-MG3Z]	[33]
Tizanidine	DMR2IQ4	Moderate	Additive CNS depression effects by the combination of Lamotrigine and Tizanidine.	Tonus and reflex abnormality [MB47]	[34]


⏷ Show the Full List of 30 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Acesulfame	E00341	36573	Flavoring agent
Allura red AC dye	E00338	33258	Colorant
Aspartame	E00402	134601	Flavoring agent
Calcium carbonate	E00198	10112	Binding agent; Buffering agent; Diluent; Opacifying agent
Caprylic acid	E00017	379	Emulsifying agent; Flavoring agent; Surfactant
Diethyl phthalate	E00135	6781	Plasticizing agent; Solvent
FD&C blue no. 1	E00263	19700	Colorant
FD&C blue no. 2	E00446	2723854	Colorant
Glyceryl monostearate	E00310	24699	Emollient; Emulsifying agent; Emulsion stabilizing agent; Solubilizing agent; Surfactant; Viscosity-controlling agent
Mannitol	E00103	6251	Diluent; Flavoring agent; Lyophilization aid; Plasticizing agent; Tonicity agent
Quinoline yellow WS	E00309	24671	Colorant
Saccharin sodium dihydrate	E00577	46942257	Flavoring agent
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Sodium stearyl fumarate	E00545	23665634	lubricant
Stearic acid	E00079	5281	Emulsifying agent; Solubilizing agent; Viscosity-controlling agent; lubricant
Sucralose	E00370	71485	Flavoring agent
Sunset yellow FCF	E00255	17730	Colorant
Tricaprin	E00366	69310	Emollient
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Carmellose sodium	E00625	Not Available	Disintegrant
Crospovidone	E00626	Not Available	Disintegrant
Eisenoxyd	E00585	56841934	Colorant
Ferric hydroxide oxide yellow	E00539	23320441	Colorant
Ferrosoferric oxide	E00231	14789	Colorant
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium aluminum silicate	E00462	3084116	Adsorbent; Binding agent; Disintegrant; Suspending agent; Viscosity-controlling agent
Magnesium carbonate	E00205	11029	Adsorbent; Diluent
Magnesium stearate	E00208	11177	lubricant
Polyethylene glycol 400	E00653	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polysorbate 80	E00665	Not Available	Dispersing agent; Emollient; Emulsifying agent; Plasticizing agent; Solubilizing agent; Surfactant; Suspending agent
Povidone	E00667	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Sodium chloride	E00077	5234	Diluent; Tonicity agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Triacetin	E00080	5541	Humectant; Plasticizing agent; Solvent
Triethyl citrate	E00128	6506	Plasticizing agent; Solvent
Vinylpyrrolidone	E00668	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent


⏷ Show the Full List of 38 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Lamotrigine 250 mg tablet	250 mg	24 HR Extended Release Oral Tablet	Oral
Lamotrigine 100 mg tablet	100 mg	Disintegrating Oral Tablet	Oral
Lamotrigine 200 mg tablet	200 mg	Disintegrating Oral Tablet	Oral
Lamotrigine 25 mg tablet	25 mg	Disintegrating Oral Tablet	Oral
Lamotrigine 50 mg tablet	50 mg	Disintegrating Oral Tablet	Oral
Lamotrigine 100 mg tablet	100 mg	24 HR Extended Release Oral Tablet	Oral
Lamotrigine 300 mg tablet	300 mg	24 HR Extended Release Oral Tablet	Oral
Lamotrigine 50 mg tablet	50 mg	24 HR Extended Release Oral Tablet	Oral
Lamotrigine 25 mg tablet	25 mg	Chewable Tablet	Oral
Lamotrigine 5 mg tablet	5 mg	Chewable Tablet	Oral
Lamotrigine 200 mg tablet	200 mg	24 HR Extended Release Oral Tablet	Oral
Lamotrigine 25 mg tablet	25 mg	24 HR Extended Release Oral Tablet	Oral
Lamotrigine 100 mg tablet	100 mg	Oral Tablet	Oral
Lamotrigine 200 mg tablet	200 mg	Oral Tablet	Oral
Lamotrigine 2 mg tablet	2 mg	Chewable Tablet	Oral
Lamotrigine 150 mg tablet	150 mg	Oral Tablet	Oral
Lamotrigine 25 mg tablet	25 mg	Oral Tablet	Oral
Lamotrigine 250 mg tablet	250 mg	Oral Tablet	Oral
Lamotrigine 50 mg tablet	50 mg	Oral Tablet	Oral

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References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2622).
2	BDDCS applied to over 900 drugs
3	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
4	Lamictal FDA Label
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7	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
8	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.
9	Lamotrigine is a substrate for OCT1 in brain endothelial cells. Biochem Pharmacol. 2012 Mar 15;83(6):805-14.
10	Several major antiepileptic drugs are substrates for human P-glycoprotein. Neuropharmacology. 2008 Dec;55(8):1364-75.
11	Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8.
12	Variation in glucuronidation of lamotrigine in human liver microsomes. Xenobiotica. 2009 May;39(5):355-63.
13	Studies on induction of lamotrigine metabolism in transgenic UGT1 mice. Xenobiotica. 2009 Nov;39(11):826-35.
14	Effects of anticonvulsants on human p450c17 (17alpha-hydroxylase/17,20 lyase) and 3beta-hydroxysteroid dehydrogenase type 2. Epilepsia. 2005 Mar;46(3):444-8.
15	Genetic association study of treatment response with olanzapine/fluoxetine combination or lamotrigine in bipolar I depression. J Clin Psychiatry. 2010 May;71(5):599-605. doi: 10.4088/JCP.08m04632gre. Epub 2009 Dec 15.
16	Functional evaluation of polymorphisms in the human ABCB1 gene and the impact on clinical responses of antiepileptic drugs. Pharmacogenet Genomics. 2008 May;18(5):390-402. doi: 10.1097/FPC.0b013e3282f85e36.
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19	Expression of the human UGT1 locus in transgenic mice by 4-chloro-6-(2,3-xylidino)-2-pyrimidinylthioacetic acid (WY-14643) and implications on drug metabolism through peroxisome proliferator-activated receptor alpha activation. Drug Metab Dispos. 2007 Mar;35(3):419-27.
20	Belcastro V, Costa C, Striano P "Levetiracetam-associated hyponatremia." Seizure 17 (2008): 389-90. [PMID: 18584781]
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24	Ebert U, Thong NQ, Oertel R, Kirch W "Effects of rifampicin and cimetidine on pharmacokinetics and pharmacodynamics of lamotrigine in healthy subjects." Eur J Clin Pharmacol 56 (2000): 299-304. [PMID: 10954343]
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26	Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA.
27	Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN.
28	Product Information. Addyi (flibanserin). Sprout Pharmaceuticals, Raleigh, NC.
29	Product Information. Thalomid (thalidomide). Celgene Corporation, Warren, NJ.
30	Bigham S, McGuigan C, MacDonald BK "Reduced absorption of lipophilic anti-epileptic medications when used concomitantly with the anti-obesity drug orlistat." Epilepsia 47 (2006): 2207. [PMID: 17201727]
31	Product Information. Alphagan (brimonidine ophthalmic). Allergan Inc, Irvine, CA.
32	Hansen BS, Dam M, Brandt J, et al "Influence of dextropropoxyphene on steady state serum levels and protein binding of three anti-epileptic drugs in man." Acta Neurol Scand 61 (1980): 357-67. [PMID: 6998251]
33	Sekar M, Mimpriss TJ "Buprenorphine, benzodiazepines and prolonged respiratory depression." Anaesthesia 42 (1987): 567-8. [PMID: 3592200]
34	Product Information. Zanaflex (tizanidine). Acorda Therapeutics, Hawthorne, NY.