Details of the Drug

General Information of Drug (ID: DMSPJG2)

Drug Name
Ropivacaine
Synonyms
Naropin; ROPIVACAINE HCl; Ropivacaine hydrochloride; Ropivacaine monohydrochloride; Naropin (TN); Ropivacaine monohydrochloride, (S)-isomer; (2S)-N-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide; (2S)-N-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide hydrochloride
Indication
Disease Entry ICD 11 Status REF
Anaesthesia 9A78.6 Approved [1]
Appendicitis DB10 Approved [2]
Therapeutic Class
Anesthetics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 274.4
Logarithm of the Partition Coefficient (xlogp) 2.9
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [3]
Bioavailability
The bioavailability of drug is 87%C98% []
Clearance
The drug present in the plasma can be removed from the body at the rate of 5.5 mL/min/kg [4]
Elimination
1% of drug is excreted from urine in the unchanged form [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 4.2 hours [4]
Metabolism
The drug is metabolized via the hepatic []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 15.618 micromolar/kg/day [5]
Unbound Fraction
The unbound fraction of drug in plasma is 0.06% [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 0.75 L/kg [4]
Water Solubility
The ability of drug to dissolve in water is measured as 53.8 mg/mL [3]
Chemical Identifiers
Formula
C17H26N2O
IUPAC Name
(2S)-N-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide
Canonical SMILES
CCCN1CCCC[C@H]1C(=O)NC2=C(C=CC=C2C)C
InChI
InChI=1S/C17H26N2O/c1-4-11-19-12-6-5-10-15(19)17(20)18-16-13(2)8-7-9-14(16)3/h7-9,15H,4-6,10-12H2,1-3H3,(H,18,20)/t15-/m0/s1
InChIKey
ZKMNUMMKYBVTFN-HNNXBMFYSA-N
Cross-matching ID
PubChem CID
175805
ChEBI ID
CHEBI:8890
CAS Number
84057-95-4
DrugBank ID
DB00296
TTD ID
D09RHQ
INTEDE ID
DR1442
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Voltage-gated sodium channel alpha Nav1.8 (SCN10A) TT90XZ8 SCNAA_HUMAN Modulator [6]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [7]
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [8]
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Substrate [9]
Cytochrome P450 2B6 (CYP2B6) DEPKLMQ CP2B6_HUMAN Substrate [8]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Gene/Protein Processing [10]
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Drug Response [11]
Apoptosis-inducing factor 1, mitochondrial (AIFM1) OTKPWB7Q AIFM1_HUMAN Gene/Protein Processing [12]
Beclin-1 (BECN1) OT4X293M BECN1_HUMAN Gene/Protein Processing [10]
Caspase-1 (CASP1) OTZ3YQFU CASP1_HUMAN Protein Interaction/Cellular Processes [13]
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Gene/Protein Processing [14]
Caspase-9 (CASP9) OTD4RFFG CASP9_HUMAN Gene/Protein Processing [14]
Clusterin (CLU) OTQGG0JM CLUS_HUMAN Drug Response [11]
Gasdermin-D (GSDMD) OTH39BKI GSDMD_HUMAN Protein Interaction/Cellular Processes [13]
Heme oxygenase 1 (HMOX1) OTC1W6UX HMOX1_HUMAN Gene/Protein Processing [13]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Anaesthesia
ICD Disease Classification 9A78.6
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Voltage-gated sodium channel alpha Nav1.8 (SCN10A) DTT SCN10A 9.89E-01 -0.16 -0.31
Cytochrome P450 2B6 (CYP2B6) DME CYP2B6 4.74E-01 2.25E-01 1.65E-01
Cytochrome P450 1A2 (CYP1A2) DME CYP1A2 7.57E-07 -1.95E-01 -4.24E-01
Cytochrome P450 2D6 (CYP2D6) DME CYP2D6 1.21E-04 -2.33E-01 -5.09E-01
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 6.90E-01 2.35E-02 7.88E-02
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Ropivacaine
DDI Drug Name DDI Drug ID Severity Mechanism Disease REF
Alfentanil DMVO0UB Minor Decreased metabolism of Ropivacaine caused by Alfentanil mediated inhibition of CYP450 enzyme. Corneal disease [9A76-9A78] [15]
Coadministration of a Drug Treating the Disease Different from Ropivacaine (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Tacrine DM51FY6 Minor Increased plasma concentrations of Ropivacaine and Tacrine due to competitive inhibition of the same metabolic pathway. Alzheimer disease [8A20] [16]
Dronedarone DMA8FS5 Minor Decreased metabolism of Ropivacaine caused by Dronedarone mediated inhibition of CYP450 enzyme. Angina pectoris [BA40] [17]
Nifedipine DMSVOZT Minor Decreased metabolism of Ropivacaine caused by Nifedipine mediated inhibition of CYP450 enzyme. Angina pectoris [BA40] [17]
Voriconazole DMAOL2S Minor Decreased metabolism of Ropivacaine caused by Voriconazole mediated inhibition of CYP450 enzyme. Aspergillosis [1F20] [17]
Posaconazole DMUL5EW Minor Decreased metabolism of Ropivacaine caused by Posaconazole mediated inhibition of CYP450 enzyme. Aspergillosis [1F20] [17]
Zafirlukast DMHNQOG Minor Decreased metabolism of Ropivacaine caused by Zafirlukast mediated inhibition of CYP450 enzyme. Asthma [CA23] [17]
Obeticholic acid DM3Q1SM Moderate Decreased metabolism of Ropivacaine caused by Obeticholic acid mediated inhibition of CYP450 enzyme. Autoimmune liver disease [DB96] [18]
Ciprofloxacin XR DM2NLS9 Minor Decreased metabolism of Ropivacaine caused by Ciprofloxacin XR mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [19]
Dalfopristin DM4LTKV Minor Decreased metabolism of Ropivacaine caused by Dalfopristin mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [17]
Clarithromycin DM4M1SG Minor Decreased metabolism of Ropivacaine caused by Clarithromycin mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [17]
Chloramphenicol DMFXEWT Minor Decreased metabolism of Ropivacaine caused by Chloramphenicol mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [17]
Troleandomycin DMUZNIG Minor Decreased metabolism of Ropivacaine caused by Troleandomycin mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [17]
Telithromycin DMZ4P3A Minor Decreased metabolism of Ropivacaine caused by Telithromycin mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [17]
Pexidartinib DMS2J0Z Moderate Increased metabolism of Ropivacaine caused by Pexidartinib mediated induction of CYP450 enzyme. Bone/articular cartilage neoplasm [2F7B] [20]
Lapatinib DM3BH1Y Minor Decreased metabolism of Ropivacaine caused by Lapatinib mediated inhibition of CYP450 enzyme. Breast cancer [2C60-2C6Y] [17]
Tucatinib DMBESUA Minor Decreased metabolism of Ropivacaine caused by Tucatinib mediated inhibition of CYP450 enzyme. Breast cancer [2C60-2C6Y] [17]
Grepafloxacin DMGLX0T Moderate Decreased metabolism of Ropivacaine caused by Grepafloxacin mediated inhibition of CYP450 enzyme. Bronchitis [CA20] [21]
Sotalol DML60TN Moderate Increased risk of atrioventricular block by the combination of Ropivacaine and Sotalol. Cardiac arrhythmia [BC9Z] [22]
Mifepristone DMGZQEF Minor Decreased metabolism of Ropivacaine caused by Mifepristone mediated inhibition of CYP450 enzyme. Cushing syndrome [5A70] [17]
Osilodrostat DMIJC9X Moderate Decreased metabolism of Ropivacaine caused by Osilodrostat mediated inhibition of CYP450 enzyme. Cushing syndrome [5A70] [23]
MK-8228 DMOB58Q Minor Decreased metabolism of Ropivacaine caused by MK-8228 mediated inhibition of CYP450 enzyme. Cytomegaloviral disease [1D82] [17]
Aprepitant DM053KT Minor Decreased metabolism of Ropivacaine caused by Aprepitant mediated inhibition of CYP450 enzyme. Depression [6A70-6A7Z] [17]
Imipramine DM2NUH3 Minor Increased plasma concentrations of Ropivacaine and Imipramine due to competitive inhibition of the same metabolic pathway. Depression [6A70-6A7Z] [16]
Nefazodone DM4ZS8M Minor Decreased metabolism of Ropivacaine caused by Nefazodone mediated inhibition of CYP450 enzyme. Depression [6A70-6A7Z] [17]
Stiripentol DMMSDOY Minor Decreased metabolism of Ropivacaine caused by Stiripentol mediated inhibition of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [17]
Itraconazole DMCR1MV Minor Decreased metabolism of Ropivacaine caused by Itraconazole mediated inhibition of CYP450 enzyme. Fungal infection [1F29-1F2F] [17]
Terbinafine DMI6HUW Moderate Decreased metabolism of Ropivacaine caused by Terbinafine mediated inhibition of CYP450 enzyme. Fungal infection [1F29-1F2F] [24]
Miconazole DMPMYE8 Minor Decreased metabolism of Ropivacaine caused by Miconazole mediated inhibition of CYP450 enzyme. Fungal infection [1F29-1F2F] [17]
Ketoconazole DMPZI3Q Minor Decreased metabolism of Ropivacaine caused by Ketoconazole mediated inhibition of CYP450 enzyme. Fungal infection [1F29-1F2F] [17]
Cimetidine DMH61ZB Minor Decreased metabolism of Ropivacaine caused by Cimetidine mediated inhibition of CYP450 enzyme. Gastro-oesophageal reflux disease [DA22] [17]
Boceprevir DMBSHMF Minor Decreased metabolism of Ropivacaine caused by Boceprevir mediated inhibition of CYP450 enzyme. Hepatitis virus infection [1E50-1E51] [17]
Telaprevir DMMRV29 Minor Decreased metabolism of Ropivacaine caused by Telaprevir mediated inhibition of CYP450 enzyme. Hepatitis virus infection [1E50-1E51] [17]
Isoniazid DM5JVS3 Minor Decreased metabolism of Ropivacaine caused by Isoniazid mediated inhibition of CYP450 enzyme. HIV-infected patients with tuberculosis [1B10-1B14] [17]
Rifampin DMA8J1G Minor Increased metabolism of Ropivacaine caused by Rifampin mediated induction of CYP450 enzyme. HIV-infected patients with tuberculosis [1B10-1B14] [25]
Rifapentine DMCHV4I Minor Increased metabolism of Ropivacaine caused by Rifapentine mediated induction of CYP450 enzyme. HIV-infected patients with tuberculosis [1B10-1B14] [25]
Delavirdine DM3NF5G Minor Decreased metabolism of Ropivacaine caused by Delavirdine mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [17]
Fosamprenavir DM4W9B3 Minor Decreased metabolism of Ropivacaine caused by Fosamprenavir mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [17]
Cobicistat DM6L4H2 Minor Decreased metabolism of Ropivacaine caused by Cobicistat mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [17]
Saquinavir DMG814N Minor Decreased metabolism of Ropivacaine caused by Saquinavir mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [17]
Amprenavir DMLMXE0 Minor Decreased metabolism of Ropivacaine caused by Amprenavir mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [17]
Darunavir DMN3GCH Minor Decreased metabolism of Ropivacaine caused by Darunavir mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [17]
Ritonavir DMU764S Minor Decreased metabolism of Ropivacaine caused by Ritonavir mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [17]
Teriflunomide DMQ2FKJ Moderate Increased metabolism of Ropivacaine caused by Teriflunomide mediated induction of CYP450 enzyme. Hyper-lipoproteinaemia [5C80] [26]
Verapamil DMA7PEW Minor Decreased metabolism of Ropivacaine caused by Verapamil mediated inhibition of CYP450 enzyme. Hypertension [BA00-BA04] [17]
Diltiazem DMAI7ZV Minor Decreased metabolism of Ropivacaine caused by Diltiazem mediated inhibition of CYP450 enzyme. Hypertension [BA00-BA04] [17]
Conivaptan DM1V329 Minor Decreased metabolism of Ropivacaine caused by Conivaptan mediated inhibition of CYP450 enzyme. Hypo-osmolality/hyponatraemia [5C72] [17]
Givosiran DM5PFIJ Moderate Decreased metabolism of Ropivacaine caused by Givosiran mediated inhibition of CYP450 enzyme. Inborn porphyrin/heme metabolism error [5C58] [27]
Berotralstat DMWA2DZ Minor Decreased metabolism of Ropivacaine caused by Berotralstat mediated inhibition of CYP450 enzyme. Innate/adaptive immunodeficiency [4A00] [17]
Melatonin DMKWFBT Minor Increased plasma concentrations of Ropivacaine and Melatonin due to competitive inhibition of the same metabolic pathway. Insomnia [7A00-7A0Z] [16]
Crizotinib DM4F29C Minor Decreased metabolism of Ropivacaine caused by Crizotinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [17]
Ceritinib DMB920Z Minor Decreased metabolism of Ropivacaine caused by Ceritinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [17]
PF-06463922 DMKM7EW Moderate Increased metabolism of Ropivacaine caused by PF-06463922 mediated induction of CYP450 enzyme. Lung cancer [2C25] [28]
Capmatinib DMYCXKL Moderate Decreased metabolism of Ropivacaine caused by Capmatinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [29]
Selpercatinib DMZR15V Minor Decreased metabolism of Ropivacaine caused by Selpercatinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [17]
Lumefantrine DM29GAD Moderate Decreased metabolism of Ropivacaine caused by Lumefantrine mediated inhibition of CYP450 enzyme. Malaria [1F40-1F45] [26]
Idelalisib DM602WT Minor Decreased metabolism of Ropivacaine caused by Idelalisib mediated inhibition of CYP450 enzyme. Mature B-cell leukaemia [2A82] [17]
IPI-145 DMWA24P Minor Decreased metabolism of Ropivacaine caused by IPI-145 mediated inhibition of CYP450 enzyme. Mature B-cell leukaemia [2A82] [17]
Vemurafenib DM62UG5 Moderate Decreased metabolism of Ropivacaine caused by Vemurafenib mediated inhibition of CYP450 enzyme. Melanoma [2C30] [30]
Danazol DML8KTN Minor Decreased metabolism of Ropivacaine caused by Danazol mediated inhibition of CYP450 enzyme. Menstrual cycle bleeding disorder [GA20] [17]
Exjade DMHPRWG Moderate Decreased metabolism of Ropivacaine caused by Exjade mediated inhibition of CYP450 enzyme. Mineral absorption/transport disorder [5C64] [31]
Riluzole DMECBWN Minor Increased plasma concentrations of Ropivacaine and Riluzole due to competitive inhibition of the same metabolic pathway. Motor neuron disease [8B60] [16]
Rifabutin DM1YBHK Minor Increased metabolism of Ropivacaine caused by Rifabutin mediated induction of CYP450 enzyme. Mycobacterium infection [1B10-1B21] [25]
Fedratinib DM4ZBK6 Minor Decreased metabolism of Ropivacaine caused by Fedratinib mediated inhibition of CYP450 enzyme. Myeloproliferative neoplasm [2A20] [17]
Nilotinib DM7HXWT Minor Decreased metabolism of Ropivacaine caused by Nilotinib mediated inhibition of CYP450 enzyme. Myeloproliferative neoplasm [2A20] [17]
Imatinib DM7RJXL Minor Decreased metabolism of Ropivacaine caused by Imatinib mediated inhibition of CYP450 enzyme. Myeloproliferative neoplasm [2A20] [17]
Dasatinib DMJV2EK Minor Decreased metabolism of Ropivacaine caused by Dasatinib mediated inhibition of CYP450 enzyme. Myeloproliferative neoplasm [2A20] [17]
Netupitant DMEKAYI Minor Decreased metabolism of Ropivacaine caused by Netupitant mediated inhibition of CYP450 enzyme. Nausea/vomiting [MD90] [17]
Entrectinib DMMPTLH Minor Decreased metabolism of Ropivacaine caused by Entrectinib mediated inhibition of CYP450 enzyme. Non-small cell lung cancer [2C25] [17]
Olaparib DM8QB1D Moderate Increased metabolism of Ropivacaine caused by Olaparib mediated induction of CYP450 enzyme. Ovarian cancer [2C73] [26]
Rucaparib DM9PVX8 Moderate Decreased metabolism of Ropivacaine caused by Rucaparib mediated inhibition of CYP450 enzyme. Ovarian cancer [2C73] [32]
Prilocaine DMI7DZ2 Major Increased risk of methemoglobinemia by the combination of Ropivacaine and Prilocaine. Pain [MG30-MG3Z] [33]
Abametapir DM2RX0I Moderate Decreased metabolism of Ropivacaine caused by Abametapir mediated inhibition of CYP450 enzyme. Pediculosis [1G00] [34]
Lefamulin DME6G97 Moderate Decreased metabolism of Ropivacaine caused by Lefamulin mediated inhibition of CYP450 enzyme. Pneumonia [CA40] [17]
Lonafarnib DMGM2Z6 Minor Decreased metabolism of Ropivacaine caused by Lonafarnib mediated inhibition of CYP450 enzyme. Premature ageing appearance [LD2B] [17]
Flutamide DMK0O7U Minor Increased plasma concentrations of Ropivacaine and Flutamide due to competitive inhibition of the same metabolic pathway. Prostate cancer [2C82] [35]
Bicalutamide DMZMSPF Minor Decreased metabolism of Ropivacaine caused by Bicalutamide mediated inhibition of CYP450 enzyme. Prostate cancer [2C82] [17]
Celecoxib DM6LOQU Moderate Decreased metabolism of Ropivacaine caused by Celecoxib mediated inhibition of CYP450 enzyme. Rheumatoid arthritis [FA20] [36]
Olanzapine DMPFN6Y Minor Increased plasma concentrations of Ropivacaine and Olanzapine due to competitive inhibition of the same metabolic pathway. Schizophrenia [6A20] [16]
Voxelotor DMCS6M5 Minor Decreased metabolism of Ropivacaine caused by Voxelotor mediated inhibition of CYP450 enzyme. Sickle-cell disorder [3A51] [17]
Larotrectinib DM26CQR Minor Decreased metabolism of Ropivacaine caused by Larotrectinib mediated inhibition of CYP450 enzyme. Solid tumour/cancer [2A00-2F9Z] [17]
LEE011 DMMX75K Minor Decreased metabolism of Ropivacaine caused by LEE011 mediated inhibition of CYP450 enzyme. Solid tumour/cancer [2A00-2F9Z] [17]
Ibutilide DMKXY2R Moderate Increased risk of atrioventricular block by the combination of Ropivacaine and Ibutilide. Supraventricular tachyarrhythmia [BC81] [22]
Fostamatinib DM6AUHV Moderate Decreased metabolism of Ropivacaine caused by Fostamatinib mediated inhibition of CYP450 enzyme. Thrombocytopenia [3B64] [37]
Brilinta DMBR01X Minor Decreased metabolism of Ropivacaine caused by Brilinta mediated inhibition of CYP450 enzyme. Thrombosis [DB61-GB90] [17]
Bretylium DM1FX74 Moderate Increased risk of bradycardia by the combination of Ropivacaine and Bretylium. Ventricular tachyarrhythmia [BC71] [22]
Mexiletine DMCTE9R Minor Increased plasma concentrations of Ropivacaine and Mexiletine due to competitive inhibition of the same metabolic pathway. Ventricular tachyarrhythmia [BC71] [35]
Amiodarone DMUTEX3 Moderate Increased risk of bradycardia by the combination of Ropivacaine and Amiodarone. Ventricular tachyarrhythmia [BC71] [22]
⏷ Show the Full List of 87 DDI Information of This Drug

References

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