Details of the Drug

General Information of Drug (ID: DMI7DZ2)

Drug Name

Prilocaine

Synonyms

Citanest; Prilocaina; Prilocainum; Propitocaine; Prilocaine [USAN]; Prilocaine base; Astra 1512; Astra 1515; L 67; Citanest (TN); Prilocaina [INN-Spanish]; Prilocainum [INN-Latin]; Propitocaine (JAN); Prilocaine (USP/INN); O-Methyl-2-propylaminopropionanilide; O-Methyl-alpha-propylaminopropionanilide; Alpha-n-Propylamino-2-methylpropionanilide; N-[2-Methylphenyl]-2-[propylamino]propanamide; N-(2-methylphenyl)-N2-propylalaninamide; N-(2-Methylphenyl)-2-(propylamino)propanamide; N-(2-methylphenyl)-N(2)-propylalaninamide; Propanamide, N-(2-methylphenyl)-2-(propylamino)-(9CI); 2-(Propylamino)-o-propionotoluidide; 2-Methyl-.alpha.-propylaminopropionanilide; 2-Methyl-alpha-propylaminopropionanilide

Indication

Disease Entry	ICD 11	Status	REF
Pain	MG30-MG3Z	Approved	[1], [2], [3]

Therapeutic Class

Anesthetics

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

220.31

Topological Polar Surface Area (xlogp)

2.1

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Clearance: The drug present in the plasma can be removed from the body at the rate of 29 mL/min/kg [4]
Half-life: The concentration or amount of drug in body reduced by one-half in 1.8 hours [4]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 33.5136 micromolar/kg/day [5]
Unbound Fraction: The unbound fraction of drug in plasma is 0.72% [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 3.7 L/kg [4]

Chemical Identifiers

Formula: C13H20N2O
IUPAC Name: N-(2-methylphenyl)-2-(propylamino)propanamide
Canonical SMILES: CCCNC(C)C(=O)NC1=CC=CC=C1C
InChI: InChI=1S/C13H20N2O/c1-4-9-14-11(3)13(16)15-12-8-6-5-7-10(12)2/h5-8,11,14H,4,9H2,1-3H3,(H,15,16)
InChIKey: MVFGUOIZUNYYSO-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 4906
ChEBI ID: CHEBI:8404
CAS Number: 721-50-6
DrugBank ID: DB00750
TTD ID: D06LYG

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Voltage-gated sodium channel alpha Nav1.5 (SCN5A)	TTZOVE0	SCN5A_HUMAN	Blocker	[6]

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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 Prilocaine (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Isosorbide dinitrate	DMBI4JG	Major	Increased risk of methemoglobinemia by the combination of Prilocaine and Isosorbide dinitrate.	Anal fissure/fistula [DB50]	[13]
Amyl nitrite	DMJKO05	Major	Increased risk of methemoglobinemia by the combination of Prilocaine and Amyl nitrite.	Angina pectoris [BA40]	[13]
Sulfamethoxazole	DMB08GE	Major	Increased risk of methemoglobinemia by the combination of Prilocaine and Sulfamethoxazole.	Bacterial infection [1A00-1C4Z]	[13]
Silver sulfadiazine	DMVTHWQ	Major	Increased risk of methemoglobinemia by the combination of Prilocaine and Silver sulfadiazine.	Bacterial infection [1A00-1C4Z]	[14]
Levobupivacaine	DM783CH	Major	Increased risk of methemoglobinemia by the combination of Prilocaine and Levobupivacaine.	Corneal disease [9A76-9A78]	[13]
Benzocaine	DMI18HW	Major	Increased risk of methemoglobinemia by the combination of Prilocaine and Benzocaine.	Corneal disease [9A76-9A78]	[14]
Phenobarbital	DMXZOCG	Major	Increased risk of methemoglobinemia by the combination of Prilocaine and Phenobarbital.	Epilepsy/seizure [8A61-8A6Z]	[13]
Isosorbide mononitrate	DMYLMU0	Major	Increased risk of methemoglobinemia by the combination of Prilocaine and Isosorbide mononitrate.	Hydrocephalus [8D64]	[13]
Tafenoquine	DM1XT4N	Major	Increased risk of methemoglobinemia by the combination of Prilocaine and Tafenoquine.	Malaria [1F40-1F45]	[13]
Primaquine	DMWQ16I	Major	Increased risk of methemoglobinemia by the combination of Prilocaine and Primaquine.	Malaria [1F40-1F45]	[13]
Sulphadoxine	DMZI2UF	Major	Increased risk of methemoglobinemia by the combination of Prilocaine and Sulphadoxine.	Malaria [1F40-1F45]	[13]
Metoclopramide	DMFA5MY	Major	Increased risk of methemoglobinemia by the combination of Prilocaine and Metoclopramide.	Nausea/vomiting [MD90]	[13]
Sulfasalazine	DMICA9H	Major	Increased risk of methemoglobinemia by the combination of Prilocaine and Sulfasalazine.	Rheumatoid arthritis [FA20]	[13]
Tetracaine	DM9J6C2	Major	Increased risk of methemoglobinemia by the combination of Prilocaine and Tetracaine.	Sensation disturbance [MB40]	[14]
Mepivacaine	DMH2NMY	Major	Increased risk of methemoglobinemia by the combination of Prilocaine and Mepivacaine.	Sensation disturbance [MB40]	[13]
Bretylium	DM1FX74	Moderate	Increased risk of bradycardia by the combination of Prilocaine and Bretylium.	Ventricular tachyarrhythmia [BC71]	[15]
Amiodarone	DMUTEX3	Moderate	Increased risk of bradycardia by the combination of Prilocaine and Amiodarone.	Ventricular tachyarrhythmia [BC71]	[15]
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⏷ Show the Full List of 17 DDI Information of This Drug

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: 7276).
2	FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 076290.
3	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
4	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5	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
6	Monoamine transporter and sodium channel mechanisms in the rapid pressor response to cocaine. Pharmacol Biochem Behav. 1998 Feb;59(2):305-12.
7	Lacosamide: a new approach to target voltage-gated sodium currents in epileptic disorders. CNS Drugs. 2009;23(7):555-68.
8	Effect of sodium channel blockers on ST segment, QRS duration, and corrected QT interval in patients with Brugada syndrome. J Cardiovasc Electrophysiol. 2000 Dec;11(12):1320-9.
9	Medicinal chemistry of neuronal voltage-gated sodium channel blockers. J Med Chem. 2001 Jan 18;44(2):115-37.
10	Halothane attenuates the cerebroprotective action of several Na+ and Ca2+ channel blockers via reversal of their ion channel blockade. Eur J Pharmacol. 2002 Oct 4;452(2):175-81.
11	From first class to third class: recent upheaval in antiarrhythmic therapy--lessons from clinical trials. Am J Cardiol. 1996 Aug 29;78(4A):28-33.
12	How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
13	Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".
14	Cerner Multum, Inc. "Australian Product Information.".
15	Keidar S, Grenadier E, Palant A "Sinoatrial arrest due to lidocaine injection in sick sinus syndrome during amiodarone administration." Am Heart J 104 (1982): 1384-5. [PMID: 7148661]