Details of the Drug

General Information of Drug (ID: DMYNMDP)

Drug Name

Tocainide

Synonyms

Taquidil; Tocainida; Tocainidum; Tonocard; Astra W 36095; Tocainida [INN-Spanish]; Tocainidum [INN-Latin]; W-36095; Tocainide (USAN/INN); Tocainide [USAN:BAN:INN]; Alanyl-2,6-xylidide; N-(2,6-dimethylphenyl)alaninamide; (-)-2-Amino-N-(2,6-dimethylphenyl)propanamide; 2-AMINO-N-(2,6-DIMETHYLPHENYL)PROPANAMIDE; 2-Amino-2',6'-propionoxylidide; 2-Amino-N-(2,6-dimethylphenyl)propionamid

Indication

Disease Entry	ICD 11	Status	REF
Ventricular arrhythmias	BC71	Approved	[1]
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Therapeutic Class

Antiarrhythmic Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

192.26

Logarithm of the Partition Coefficient (xlogp)

0.8

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 3: high solubility and low permeability [2]
Bioavailability: 89% of drug becomes completely available to its intended biological destination(s) [3]
Clearance: The drug present in the plasma can be removed from the body at the rate of 2.2 mL/min/kg [4]
Elimination: 38% of drug is excreted from urine in the unchanged form [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 15 hours [4]
Metabolism: The drug is metabolized via the hepatic []
Unbound Fraction: The unbound fraction of drug in plasma is 0.87% [4]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 1.8 L/kg [4]
Water Solubility: The ability of drug to dissolve in water is measured as 10 mg/mL [2]

Adverse Drug Reaction (ADR)

ADR Term	Variation	Related DOT	DOT ID	REF
Poisoning and toxicity	Not Available	CYP2D6	OTZJC802	[5]
Sudden cardiac death	Not Available	KCNQ1	OT8SPJNX	[5]
Sudden cardiac death	Not Available	SCN5A	OTGYZWR6	[5]
Sudden cardiac death	Not Available	KCNE1	OTZNQUW9	[5]
Sudden cardiac death	Not Available	KCNH2	OTZX881H	[5]
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Chemical Identifiers

Formula: C11H16N2O
IUPAC Name: 2-amino-N-(2,6-dimethylphenyl)propanamide
Canonical SMILES: CC1=C(C(=CC=C1)C)NC(=O)C(C)N
InChI: InChI=1S/C11H16N2O/c1-7-5-4-6-8(2)10(7)13-11(14)9(3)12/h4-6,9H,12H2,1-3H3,(H,13,14)
InChIKey: BUJAGSGYPOAWEI-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 38945
ChEBI ID: CHEBI:9611
CAS Number: 41708-72-9
DrugBank ID: DB01056
TTD ID: D01PJR
INTEDE ID: DR1607

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
E3 ubiquitin-protein ligase COP1 (RFWD2)	TT05DLS	COP1_HUMAN	Modulator	[6]
Voltage-gated sodium channel (Nav)	TTIG65Q	NOUNIPROTAC	Modulator	[6]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 1A2 (CYP1A2)_{Main DME}	DEJGDUW	CP1A2_HUMAN	Substrate	[7]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Cytochrome P450 2D6 (CYP2D6)	OTZJC802	CP2D6_HUMAN	Drug Response	[5]
Potassium voltage-gated channel subfamily E member 1 (KCNE1)	OTZNQUW9	KCNE1_HUMAN	Drug Response	[5]
Potassium voltage-gated channel subfamily H member 2 (KCNH2)	OTZX881H	KCNH2_HUMAN	Drug Response	[5]
Potassium voltage-gated channel subfamily KQT member 1 (KCNQ1)	OT8SPJNX	KCNQ1_HUMAN	Drug Response	[5]
Sodium channel protein type 5 subunit alpha (SCN5A)	OTGYZWR6	SCN5A_HUMAN	Drug Response	[5]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

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

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Ocrelizumab	DMEZ2KH	Moderate	Additive immunosuppressive effects by the combination of Tocainide and Ocrelizumab.	Multiple sclerosis [8A40]	[8]
Omacetaxine mepesuccinate	DMPU2WX	Moderate	Additive immunosuppressive effects by the combination of Tocainide and Omacetaxine mepesuccinate.	Myeloproliferative neoplasm [2A20]	[9]
Valganciclovir	DMS2IUH	Moderate	Additive myelosuppressive effects by the combination of Tocainide and Valganciclovir.	Virus infection [1A24-1D9Z]	[10]
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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: 7309).
2	BDDCS applied to over 900 drugs
3	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
4	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5	ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
6	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
7	The effect of tocainide on theophylline metabolism. Br J Clin Pharmacol. 1993 Apr;35(4):437-40.
8	Product Information. Ocrevus (ocrelizumab). Genentech, South San Francisco, CA.
9	Product Information. Synribo (omacetaxine). Teva Pharmaceuticals USA, North Wales, PA.
10	Cerner Multum, Inc. "Australian Product Information.".