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]
Premature ejaculation HA03.0Z Investigative [2]
Therapeutic Class
Anesthetics
Affected Organisms
Humans and other mammals
ATC Code
N01BB04: Prilocaine
N01BB: Amides
N01B: ANESTHETICS, LOCAL
N01: ANESTHETICS
N: NERVOUS SYSTEM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 220.31
Logarithm of the Partition Coefficient (xlogp) 2.1
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
Clearance
The drug present in the plasma can be removed from the body at the rate of 29 mL/min/kg [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 1.8 hours [3]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 33.5136 micromolar/kg/day [4]
Unbound Fraction
The unbound fraction of drug in plasma is 0.72% [3]
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 [3]
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
CHEMBL1194
CAS Number
721-50-6
UNII
046O35D44R
DrugBank ID
DB00750
TTD ID
D06LYG
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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 Nav1.5 (SCN5A) TTZOVE0 SCN5A_HUMAN Blocker [5]
Molecular Interaction Atlas (MIA) 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] [6]
Amyl nitrite DMJKO05 Major Increased risk of methemoglobinemia by the combination of Prilocaine and Amyl nitrite. Angina pectoris [BA40] [6]
Sulfamethoxazole DMB08GE Major Increased risk of methemoglobinemia by the combination of Prilocaine and Sulfamethoxazole. Bacterial infection [1A00-1C4Z] [6]
Silver sulfadiazine DMVTHWQ Major Increased risk of methemoglobinemia by the combination of Prilocaine and Silver sulfadiazine. Bacterial infection [1A00-1C4Z] [7]
Levobupivacaine DM783CH Major Increased risk of methemoglobinemia by the combination of Prilocaine and Levobupivacaine. Corneal disease [9A76-9A78] [6]
Benzocaine DMI18HW Major Increased risk of methemoglobinemia by the combination of Prilocaine and Benzocaine. Corneal disease [9A76-9A78] [7]
Phenobarbital DMXZOCG Major Increased risk of methemoglobinemia by the combination of Prilocaine and Phenobarbital. Epilepsy/seizure [8A61-8A6Z] [6]
Isosorbide mononitrate DMYLMU0 Major Increased risk of methemoglobinemia by the combination of Prilocaine and Isosorbide mononitrate. Hydrocephalus [8D64] [6]
Tafenoquine DM1XT4N Major Increased risk of methemoglobinemia by the combination of Prilocaine and Tafenoquine. Malaria [1F40-1F45] [6]
Primaquine DMWQ16I Major Increased risk of methemoglobinemia by the combination of Prilocaine and Primaquine. Malaria [1F40-1F45] [6]
Sulphadoxine DMZI2UF Major Increased risk of methemoglobinemia by the combination of Prilocaine and Sulphadoxine. Malaria [1F40-1F45] [6]
Metoclopramide DMFA5MY Major Increased risk of methemoglobinemia by the combination of Prilocaine and Metoclopramide. Nausea/vomiting [MD90] [6]
Sulfasalazine DMICA9H Major Increased risk of methemoglobinemia by the combination of Prilocaine and Sulfasalazine. Rheumatoid arthritis [FA20] [6]
Tetracaine DM9J6C2 Major Increased risk of methemoglobinemia by the combination of Prilocaine and Tetracaine. Sensation disturbance [MB40] [7]
Mepivacaine DMH2NMY Major Increased risk of methemoglobinemia by the combination of Prilocaine and Mepivacaine. Sensation disturbance [MB40] [6]
Bretylium DM1FX74 Moderate Increased risk of bradycardia by the combination of Prilocaine and Bretylium. Ventricular tachyarrhythmia [BC71] [8]
Amiodarone DMUTEX3 Moderate Increased risk of bradycardia by the combination of Prilocaine and Amiodarone. Ventricular tachyarrhythmia [BC71] [8]
⏷ 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 Prilocaine FDA Label
3 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4 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
5 Monoamine transporter and sodium channel mechanisms in the rapid pressor response to cocaine. Pharmacol Biochem Behav. 1998 Feb;59(2):305-12.
6 Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".
7 Cerner Multum, Inc. "Australian Product Information.".
8 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]