Identification

Summary

Ropivacaine is an analgesic drug used for local or regional anesthesia for surgery and short-term management of pain.

Brand Names
Naropin
Generic Name
Ropivacaine
DrugBank Accession Number
DB00296
Background

Ropivacaine is an aminoamide local anaesthetic drug commonly marketed by AstraZeneca under the trade name Naropin. It is present as a racemic mixture of the enantiomers containing equal proportions of the “S” and “R” forms. The marketed form contains the single S-enantiomer as the active ingredient.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 274.4011
Monoisotopic: 274.204513464
Chemical Formula
C17H26N2O
Synonyms
  • (S)-(−)-1-propyl-2',6'-pipecoloxylidide
  • (S)-ropivacaine
  • L-N-n-propylpipecolic acid-2,6-xylidide
  • Ropivacaina
  • Ropivacaine
  • Ropivacainum

Pharmacology

Indication

Used in obstetric anesthesia and regional anesthesia for surgery.

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Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Ropivacaine, a local anesthetic agent, is indicated for the production of local or regional anesthesia or analgesia for surgery, for oral surgery procedures, for diagnostic and therapeutic procedures, and for obstetrical procedures.

Mechanism of action

Local anesthetics such as Ropivacaine block the generation and the conduction of nerve impulses, presumably by increasing the threshold for electrical excitation in the nerve, by slowing the propagation of the nerve impulse, and by reducing the rate of rise of the action potential. Specifically, they block the sodium-channel and decrease chances of depolarization and consequent action potentials. In general, the progression of anesthesia is related to the diameter, myelination and conduction velocity of affected nerve fibers.

TargetActionsOrganism
ASodium channel protein type 10 subunit alpha
inhibitor
Humans
Absorption

Bioavailability is 87%–98% following epidural administration.

Volume of distribution

Not Available

Protein binding

94%, mainly to a1-acid glycoprotein

Metabolism

Hepatic

Hover over products below to view reaction partners

Route of elimination

Ropivacaine is extensively metabolized in the liver, predominantly by aromatic hydroxylation mediated by cytochrome P4501A to 3-hydroxy ropivacaine. After a single IV dose approximately 37% of the total dose is excreted in the urine as both free and conjugated 3-hydroxy ropivacaine. In total, 86% of the ropivacaine dose is excreted in the urine after intravenous administration of which only 1% relates to unchanged drug.

Half-life

Approximately 4.2 hours.

Clearance
  • 387 +/- 107 mL/min
  • unbound plasma clearance=7.2 +/- 1.6 L/min
Adverse Effects
Adverseeffects
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Toxicity

High systemic doses of ropivacaine can result in central nervous system (CNS) and cardiovascular effects, with the CNS effects usually occurring at lower blood plasma concentrations and additional cardiovascular effects occurring at higher concentrations. However, cardiovascular collapse may bee seen at low concentrations. CNS effects include CNS excitation involving nervousness, tingling around the mouth, tinnitus, tremor, dizziness, blurred vision, seizures. CNS depressant effects may follow, associated with drowsiness, loss of consciousness, respiratory depression and apnea. Cardiovascular events may be caused by hypoxemia secondary to respiratory depression and include hypotension, bradycardia, arrhythmias, and/or cardiac arrest.

Pathways
PathwayCategory
Ropivacaine Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Ropivacaine is combined with 1,2-Benzodiazepine.
AbacavirRopivacaine may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbametapirThe serum concentration of Ropivacaine can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Ropivacaine can be increased when combined with Abatacept.
AbirateroneThe serum concentration of Ropivacaine can be increased when it is combined with Abiraterone.
AcebutololThe risk or severity of adverse effects can be increased when Ropivacaine is combined with Acebutolol.
AceclofenacAceclofenac may decrease the excretion rate of Ropivacaine which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Ropivacaine which could result in a higher serum level.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Ropivacaine.
AcetaminophenThe risk or severity of methemoglobinemia can be increased when Ropivacaine is combined with Acetaminophen.
Interactions
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Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Ropivacaine hydrochlorideV910P86109132112-35-7VSHFRHVKMYGBJL-CKUXDGONSA-N
Ropivacaine hydrochloride anhydrous35504LBE2T98717-15-8NDNSIBYYUOEUSV-RSAXXLAASA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
NaropinInjection, solution7.5 mg/1mLEpidural; PerineuralFresenius Kabi USA, LLC1996-09-24Not applicableUS flag
NaropinSolution2 mg / mLEpidural; InfiltrationAspen Pharmacare Canada Inc.1997-04-30Not applicableCanada flag
NaropinInjection, solution5 mg/1mLEpidural; Infiltration; PerineuralGeneral Injectables & Vaccines, Inc2014-03-11Not applicableUS flag
NaropinSolution10 mg / mLEpiduralAspen Pharmacare Canada Inc.1997-04-30Not applicableCanada flag
NaropinInjection, solution5 mg/1mLEpidural; Infiltration; PerineuralFresenius Kabi USA, LLC2009-08-04Not applicableUS flag
NaropinInjection, solution2 mg/1mLEpidural; InfiltrationFresenius Kabi USA, LLC2009-08-04Not applicableUS flag
NaropinSolution5 mg / mLEpidural; InfiltrationAspen Pharmacare Canada Inc.1997-04-30Not applicableCanada flag
NaropinInjection, solution10 mg/1mLEpiduralFresenius Kabi USA, LLC2009-08-04Not applicableUS flag
Naropin Inj 7.5mg/mlLiquid7.5 mg / mLParenteralAstra Zeneca1997-04-302003-11-18Canada flag
ReadyfusOR Ropivacaine Fixed Rate Delivery SystemInjection, solution2 mg/1mLInfiltrationBioQ Pharma Incorporated2018-03-05Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ropivacaine HydrochlorideInjection5 mg/1mLEpidural; InfiltrationHikma Pharmaceuticals USA Inc.2020-07-20Not applicableUS flag
Ropivacaine HydrochlorideInjection2 mg/1mLEpidural; Infiltration; PerineuralSomerset Therapeutics, Llc2018-06-15Not applicableUS flag
Ropivacaine HydrochlorideInjection, solution10 mg/1mLEpiduralSagent Pharmaceuticals2014-09-232019-07-31US flag
Ropivacaine HydrochlorideInjection10 mg/1mLEpiduralSomerset Therapeutics, Llc2018-06-15Not applicableUS flag
Ropivacaine HydrochlorideInjection, solution7.5 mg/1mLEpidural; PerineuralHospira, Inc.2014-09-23Not applicableUS flag
Ropivacaine HydrochlorideInjection10 mg/1mLEpiduralCaplin Steriles Limited2020-04-24Not applicableUS flag
Ropivacaine HydrochlorideInjection, solution5 mg/1mLEpidural; Infiltration; PerineuralAuroMedics Pharma LLC2016-09-15Not applicableUS flag
Ropivacaine HydrochlorideInjection, solution150 mg/30mLEpidural; Infiltration; PerineuralMylan Institutional LLC2019-05-232021-03-31US flag
Ropivacaine HydrochlorideInjection, solution2 mg/1mLEpidural; InfiltrationSagent Pharmaceuticals2018-12-15Not applicableUS flag
Ropivacaine HydrochlorideInjection5 mg/1mLEpidural; Infiltration; PerineuralSomerset Therapeutics, Llc2018-06-15Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
DexopinRopivacaine hydrochloride (5 mg/1mL) + Dexamethasone sodium phosphate (10 mg/1mL) + Povidone-iodine (10 mg/1mL)KitTopicalAsclemed Usa, Inc.2019-06-10Not applicableUS flag
RopidexRopivacaine hydrochloride (5 mg/1mL) + Dexamethasone sodium phosphate (10 mg/1mL) + Povidone-iodine (10 mg/1mL)KitEpidural; Infiltration; Intramuscular; Intravenous; Perineural; TopicalAsclemed Usa, Inc.2019-06-10Not applicableUS flag
Ropivacaine HClRopivacaine hydrochloride (2 mg/1mL)Injection, solutionEpiduralCantrell Drug Company2012-05-292015-01-14US flag

Categories

ATC Codes
N01BB09 — Ropivacaine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acid amides
Alternative Parents
Piperidinecarboxamides / Anilides / m-Xylenes / N-arylamides / Trialkylamines / Secondary carboxylic acid amides / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
2-piperidinecarboxamide / Alpha-amino acid amide / Amine / Anilide / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Hydrocarbon derivative
show 16 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
piperidinecarboxamide, ropivacaine (CHEBI:8890)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
7IO5LYA57N
CAS number
84057-95-4
InChI Key
ZKMNUMMKYBVTFN-HNNXBMFYSA-N
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
IUPAC Name
(2S)-N-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide
SMILES
CCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C

References

Synthesis Reference

Peter Jaksch, "Process for the preparation of ropivacaine hydrochloride monohydrate." U.S. Patent US5959112, issued February, 1970.

US5959112
General References
  1. Weinberg G, Ripper R, Feinstein DL, Hoffman W: Lipid emulsion infusion rescues dogs from bupivacaine-induced cardiac toxicity. Reg Anesth Pain Med. 2003 May-Jun;28(3):198-202. [Article]
  2. Picard J, Meek T: Lipid emulsion to treat overdose of local anaesthetic: the gift of the glob. Anaesthesia. 2006 Feb;61(2):107-9. [Article]
  3. Rosenblatt MA, Abel M, Fischer GW, Itzkovich CJ, Eisenkraft JB: Successful use of a 20% lipid emulsion to resuscitate a patient after a presumed bupivacaine-related cardiac arrest. Anesthesiology. 2006 Jul;105(1):217-8. [Article]
Human Metabolome Database
HMDB0014441
KEGG Compound
C07532
PubChem Compound
175805
PubChem Substance
46504712
ChemSpider
153165
BindingDB
50239375
RxNav
35780
ChEBI
8890
ChEMBL
CHEMBL1077896
ZINC
ZINC000000897002
Therapeutic Targets Database
DAP001230
PharmGKB
PA451271
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Ropivacaine
FDA label
Download (274 KB)
MSDS
Download (57 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingSupportive CarePostoperative pain1
4Active Not RecruitingTreatmentCaudal epidural block therapy / Postoperative pain1
4CompletedNot AvailableCholecystectomy / Laparoscopy1
4CompletedNot AvailableElective Surgery of the Spine by Laparotomy1
4CompletedNot AvailableKidney Transplantation1
4CompletedNot AvailableSurgery, Cardiac1
4CompletedBasic ScienceFetal Cardiac Rhythm Abnormalities1
4CompletedBasic ScienceHemodynamics / Lumbar epidural anesthesia therapy / Ropivacaine Concentration1
4CompletedBasic SciencePeripheral Nerve Blocks1
4CompletedDiagnosticAtelectasis / Pregnant State1

Pharmacoeconomics

Manufacturers
  • App pharmaceuticals llc
Packagers
  • APP Pharmaceuticals
  • Astra Pharma Inc.
  • AstraZeneca Inc.
  • Pharmakon
  • Pharmedium
Dosage Forms
FormRouteStrength
KitTopical
InjectionEpidural; Perineural
Injection, solutionEpidural; Infiltration2 mg/1mL
Injection, solutionParenteral
Injection, solutionEpidural
InjectionEpidural; Subcutaneous2 mg/ml
LiquidParenteral7.5 mg / mL
InjectionEpidural; Subcutaneous10 mg/ml
Injection, solutionEpidural10 MG/ML
Injection, solutionEpidural7.5 MG/ML
Injection, solutionEpidural; Infiltration2 MG/ML
Injection, solutionIntrathecal5 MG/ML
Injection, solutionInfiltration2 mg/1mL
KitEpidural; Infiltration; Intramuscular; Intravenous; Perineural; Topical
SolutionParenteral
Injection, solution
Injection, solution10 MG/ML
Injection, solution2 MG/ML
Injection, solution5 MG/ML
Injection, solution7.5 MG/ML
Injection, solutionEpidural2 mg/1mL
InjectionEpidural10 mg/1mL
InjectionEpidural7.5 mg/1mL
InjectionEpidural; Infiltration2 mg/1mL
InjectionEpidural; Infiltration5 mg/1mL
InjectionEpidural; Infiltration; Perineural10 mg/1mL
InjectionEpidural; Infiltration; Perineural2 mg/1mL
InjectionEpidural; Infiltration; Perineural5 mg/1mL
InjectionEpidural; Perineural7.5 mg/1mL
Injection, solutionEpidural10 mg/1mL
Injection, solutionEpidural200 mg/20mL
Injection, solutionEpidural; Infiltration5 mg/1mL
Injection, solutionEpidural; Infiltration; Perineural150 mg/30mL
Injection, solutionEpidural; Infiltration; Perineural2 mg/1mL
Injection, solutionEpidural; Infiltration; Perineural40 mg/20mL
Injection, solutionEpidural; Infiltration; Perineural5 mg/1mL
Injection, solutionEpidural; Perineural150 mg/20mL
Injection, solutionEpidural; Perineural7.5 mg/1mL
Injection, solutionParenteral10 mg/1mL
Injection, solutionParenteral5 mg/1mL
SolutionEpidural; Infiltration2 mg / mL
SolutionEpidural10 mg / mL
SolutionEpidural7.5 mg / mL
SolutionEpidural; Infiltration5 mg / mL
SolutionEpidural2 mg/mL
Injection, solutionEpidural2 mg/mL
Injection
Prices
Unit descriptionCostUnit
Ropivacaine hcl-ns 0.5%1.84USD ml
Ropivacaine hcl 0.2% on-q pump0.99USD ml
Naropin 10 mg/ml ampule0.97USD ml
Ropivacaine hcl-ns 0.3%0.9USD ml
Ropivacaine-ns 0.1% on-q pump0.71USD ml
Naropin 7.5 mg/ml ampule0.62USD ml
Naropin 5 mg/ml vial0.58USD ml
Ropivacaine hcl-ns 0.15%0.51USD ml
Ropivacaine hcl-ns 0.125%0.48USD ml
Naropin 5 mg/ml ampule0.46USD ml
Naropin 2 mg/ml ampule0.44USD ml
Ropivacaine hcl-ns 0.1%0.39USD ml
Ropivacaine hcl-ns 0.25%0.34USD ml
Ropivacaine hcl-ns 0.2%0.29USD ml
Naropin 2 mg/ml infusion btl0.23USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5670524No1997-09-232014-05-26US flag
US4870086No1989-09-262010-09-24US flag
CA2165446No2005-07-052014-05-26Canada flag
CA1337549No1995-11-142012-11-14Canada flag
US8118802No2012-02-212023-05-18US flag
US7857802No2010-12-282026-11-28US flag
US7828787No2010-11-092025-10-18US flag
US8162915No2012-04-242024-05-23US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility57.6 mg/LNot Available
logP2.90HANSCH,C ET AL. (1995)
pKa8.07Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.253 mg/mLALOGPS
logP2.91ALOGPS
logP4.07ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)13.62ChemAxon
pKa (Strongest Basic)7.82ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.34 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity85.59 m3·mol-1ChemAxon
Polarizability32.67 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9705
Blood Brain Barrier+0.9377
Caco-2 permeable+0.5912
P-glycoprotein substrateSubstrate0.8037
P-glycoprotein inhibitor IInhibitor0.8768
P-glycoprotein inhibitor IINon-inhibitor0.6339
Renal organic cation transporterNon-inhibitor0.6611
CYP450 2C9 substrateNon-substrate0.819
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateSubstrate0.723
CYP450 1A2 substrateNon-inhibitor0.5499
CYP450 2C9 inhibitorNon-inhibitor0.9246
CYP450 2D6 inhibitorInhibitor0.8821
CYP450 2C19 inhibitorNon-inhibitor0.8773
CYP450 3A4 inhibitorNon-inhibitor0.5902
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6116
Ames testNon AMES toxic0.8507
CarcinogenicityNon-carcinogens0.8763
BiodegradationNot ready biodegradable0.9783
Rat acute toxicity2.2964 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8009
hERG inhibition (predictor II)Inhibitor0.8438
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Voltage-gated sodium channel activity
Specific Function
Tetrodotoxin-resistant channel that mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference acro...
Gene Name
SCN10A
Uniprot ID
Q9Y5Y9
Uniprot Name
Sodium channel protein type 10 subunit alpha
Molecular Weight
220623.605 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Liu BG, Zhuang XL, Li ST, Xu GH: The effects of ropivacaine on sodium currents in dorsal horn neurons of neonatal rats. Anesth Analg. 2000 May;90(5):1034-8. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Arlander E, Ekstrom G, Alm C, Carrillo JA, Bielenstein M, Bottiger Y, Bertilsson L, Gustafsson LL: Metabolism of ropivacaine in humans is mediated by CYP1A2 and to a minor extent by CYP3A4: an interaction study with fluvoxamine and ketoconazole as in vivo inhibitors. Clin Pharmacol Ther. 1998 Nov;64(5):484-91. [Article]
  2. Ropivacaine FDA label [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Oda Y, Furuichi K, Tanaka K, Hiroi T, Imaoka S, Asada A, Fujimori M, Funae Y: Metabolism of a new local anesthetic, ropivacaine, by human hepatic cytochrome P450. Anesthesiology. 1995 Jan;82(1):214-20. doi: 10.1097/00000542-199501000-00026. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Oda Y, Furuichi K, Tanaka K, Hiroi T, Imaoka S, Asada A, Fujimori M, Funae Y: Metabolism of a new local anesthetic, ropivacaine, by human hepatic cytochrome P450. Anesthesiology. 1995 Jan;82(1):214-20. doi: 10.1097/00000542-199501000-00026. [Article]

Drug created at June 13, 2005 13:24 / Updated at October 26, 2021 21:40