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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyRopivacaine
Identification
- Name
- Ropivacaine
- Accession Number
- DB00296 (APRD00492)
- Type
- Small Molecule
- Groups
- Approved
- Description
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.
- Structure
Structure for Ropivacaine (DB00296)
- Synonyms
- (S)-(−)-1-propyl-2',6'-pipecoloxylidide
- (S)-ropivacaine
- L-N-n-propylpipecolic acid-2,6-xylidide
- Ropivacaina
- Ropivacaine
- Ropivacainum
- Product Ingredients
Ingredient UNII CAS InChI Key Ropivacaine hydrochloride V910P86109 132112-35-7 VSHFRHVKMYGBJL-CKUXDGONSA-N Ropivacaine hydrochloride anhydrous 35504LBE2T 98717-15-8 NDNSIBYYUOEUSV-RSAXXLAASA-N - Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataNaropin Solution 5 mg Epidural; Infiltration Aspen Pharmacare Canada Inc. 1997-04-30 Not applicable Canada 
Naropin Injection, solution 2 mg/1mL Epidural; Infiltration Fresenius Kabi 2011-05-31 Not applicable US 
Naropin Solution 2 mg Epidural; Infiltration Aspen Pharmacare Canada Inc. 1997-04-30 Not applicable Canada Naropin Injection, solution 10 mg/1mL Epidural Fresenius Kabi 2011-05-31 Not applicable US Naropin Injection, solution 7.5 mg/1mL Epidural; Perineural Fresenius Kabi 2011-05-31 Not applicable US Naropin Injection, solution 5 mg/1mL Epidural; Infiltration; Perineural Fresenius Kabi 2011-05-31 Not applicable US Naropin Solution 10 mg Epidural Aspen Pharmacare Canada Inc. 1997-04-30 Not applicable Canada Naropin Injection, solution 5 mg/1mL Epidural; Infiltration; Perineural General Injectables & Vaccines, Inc 2014-03-11 Not applicable US Naropin Inj 7.5mg/ml Liquid Parenteral Astra Zeneca 1997-04-30 2003-11-18 Canada ReadyfusOR Ropivacaine Fixed Rate Delivery System Injection, solution 2 mg/1mL Infiltration BioQ Pharma Incorporated 2018-03-05 Not applicable US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataRopivacaine Hydrochloride Injection, solution 10 mg/1mL Epidural AuroMedics Pharma LLC 2016-09-15 Not applicable US Ropivacaine Hydrochloride Injection, solution 2 mg/1mL Epidural; Infiltration; Perineural AuroMedics Pharma LLC 2016-09-15 Not applicable US Ropivacaine Hydrochloride Injection 10 mg/1mL Epidural Somerset Therapeutics, Llc 2018-06-19 Not applicable US Ropivacaine Hydrochloride Injection 2 mg/1mL Epidural; Infiltration; Perineural Somerset Therapeutics, Llc 2018-06-19 Not applicable US Ropivacaine Hydrochloride Injection, solution 10 mg/1mL Epidural Hospira, Inc. 2014-09-23 Not applicable US Ropivacaine Hydrochloride Injection, solution 200 mg/20mL Epidural Mylan Institutional LLC 2019-05-23 Not applicable US Ropivacaine Hydrochloride Injection, solution 10 mg/1mL Epidural AuroMedics Pharma LLC 2016-09-15 Not applicable US Ropivacaine Hydrochloride Injection, solution 2 mg/1mL Epidural; Infiltration; Perineural AuroMedics Pharma LLC 2016-09-15 Not applicable US Ropivacaine Hydrochloride Injection 7.5 mg/1mL Epidural; Perineural Somerset Therapeutics, Llc 2018-06-19 Not applicable US Ropivacaine Hydrochloride Injection, solution 10 mg/1mL Epidural Sagent Pharmaceuticals 2014-09-23 2019-07-31 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Dexopin Ropivacaine hydrochloride (5 mg/1mL) + Dexamethasone sodium phosphate (10 mg/1mL) + Povidone-iodine (10 mg/1mL) Kit Topical Asclemed Usa, Inc. 2019-06-10 Not applicable US Ropidex Ropivacaine hydrochloride (5 mg/1mL) + Dexamethasone sodium phosphate (10 mg/1mL) + Povidone-iodine (10 mg/1mL) Kit Topical Asclemed Usa, Inc. 2019-06-10 Not applicable US Ropivacaine HCl Ropivacaine hydrochloride (2 mg/1mL) Injection, solution Epidural Cantrell Drug Company 2012-05-29 2015-01-14 US - Categories
- Amide Local Anesthetic
- Amides
- Amines
- Anesthetics
- Anesthetics, Local
- Anilides
- Aniline Compounds
- Central Nervous System Agents
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 CYP2B6 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Drugs that are Mainly Renally Excreted
- Hypotensive Agents
- Local Anesthesia
- Nervous System
- Neuraxial Anesthetics
- Peripheral Nervous System Agents
- Sensory System Agents
- UNII
- 7IO5LYA57N
- CAS number
- 84057-95-4
- Weight
- Average: 274.4011
Monoisotopic: 274.204513464 - Chemical Formula
- C17H26N2O
- 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
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Pharmacology
- Indication
Used in obstetric anesthesia and regional anesthesia for surgery.
- Associated Conditions
- Associated Therapies
- 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.
Target Actions Organism ASodium channel protein type 10 subunit alpha inhibitorHumans - Absorption
Bioavailability is 87%–98% following epidural administration.
- Volume of distribution
- Not Available
- Protein binding
94%, mainly to a1-acid glycoprotein
- Metabolism
Hepatic
- 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
- 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.
- Affected organisms
- Humans and other mammals
- Pathways
Pathway Category Ropivacaine Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Unlock Additional Data
Additional Data Available
Adverse Effects
Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.
Learn more Additional Data Available
Contraindications
Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.
Learn more Additional Data Available
Blackbox Warnings
Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.
Learn moreInteractions
- 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.
Drug Interaction Unlock Additional Data(R)-warfarin The metabolism of (R)-warfarin can be decreased when combined with Ropivacaine. 6-O-benzylguanine The metabolism of 6-O-benzylguanine can be decreased when combined with Ropivacaine. 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the orthostatic hypotensive activities of Ropivacaine. 8-azaguanine The metabolism of 8-azaguanine can be decreased when combined with Ropivacaine. 8-chlorotheophylline The metabolism of 8-chlorotheophylline can be decreased when combined with Ropivacaine. 9-Deazaguanine The metabolism of 9-Deazaguanine can be decreased when combined with Ropivacaine. 9-Methylguanine The metabolism of 9-Methylguanine can be decreased when combined with Ropivacaine. Abacavir Ropivacaine may decrease the excretion rate of Abacavir which could result in a higher serum level. Abatacept The metabolism of Ropivacaine can be increased when combined with Abatacept. Abiraterone The serum concentration of Ropivacaine can be increased when it is combined with Abiraterone. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
References
- Synthesis Reference
Peter Jaksch, "Process for the preparation of ropivacaine hydrochloride monohydrate." U.S. Patent US5959112, issued February, 1970.
US5959112- General References
- 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. [PubMed:12772136]
- Picard J, Meek T: Lipid emulsion to treat overdose of local anaesthetic: the gift of the glob. Anaesthesia. 2006 Feb;61(2):107-9. [PubMed:16430560]
- 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. [PubMed:16810015]
- External Links
- Human Metabolome Database
- HMDB0014441
- KEGG Compound
- C07532
- PubChem Compound
- 175805
- PubChem Substance
- 46504712
- ChemSpider
- 153165
- ChEBI
- 8890
- ChEMBL
- CHEMBL1077896
- Therapeutic Targets Database
- DAP001230
- PharmGKB
- PA451271
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Ropivacaine
- ATC Codes
- N01BB09 — Ropivacaine
- AHFS Codes
- 72:00.00 — Local Anesthetics
- FDA label
- Download (274 KB)
- MSDS
- Download (57 KB)
Clinical Trials
- Clinical Trials
Pharmacoeconomics
- Manufacturers
- App pharmaceuticals llc
- Packagers
- APP Pharmaceuticals
- Astra Pharma Inc.
- AstraZeneca Inc.
- Pharmakon
- Pharmedium
- Dosage forms
Form Route Strength Kit Topical Injection, solution Epidural 10 mg/1mL Injection, solution Epidural; Infiltration 2 mg/1mL Injection, solution Epidural; Infiltration; Perineural 5 mg/1mL Injection, solution Epidural; Perineural 7.5 mg/1mL Solution Epidural 10 mg Solution Epidural; Infiltration 2 mg Solution Epidural; Infiltration 5 mg Liquid Parenteral Injection, solution Infiltration 2 mg/1mL Injection, solution Epidural 2 mg/1mL Injection Epidural 10 mg/1mL Injection Epidural; Infiltration; Perineural 2 mg/1mL Injection Epidural; Infiltration; Perineural 5 mg/1mL Injection Epidural; Perineural 7.5 mg/1mL Injection, solution Epidural 200 mg/20mL Injection, solution Epidural; Infiltration 5 mg/1mL Injection, solution Epidural; Infiltration; Perineural 150 mg/30mL Injection, solution Epidural; Infiltration; Perineural 2 mg/1mL Injection, solution Epidural; Infiltration; Perineural 40 mg/20mL Injection, solution Epidural; Perineural 150 mg/20mL Injection, solution Parenteral 10 mg/1mL Injection, solution Parenteral 5 mg/1mL Solution Epidural; Infiltration Solution Epidural - Prices
Unit description Cost Unit Ropivacaine hcl-ns 0.5% 1.84USD ml Ropivacaine hcl 0.2% on-q pump 0.99USD ml Naropin 10 mg/ml ampule 0.97USD ml Ropivacaine hcl-ns 0.3% 0.9USD ml Ropivacaine-ns 0.1% on-q pump 0.71USD ml Naropin 7.5 mg/ml ampule 0.62USD ml Naropin 5 mg/ml vial 0.58USD ml Ropivacaine hcl-ns 0.15% 0.51USD ml Ropivacaine hcl-ns 0.125% 0.48USD ml Naropin 5 mg/ml ampule 0.46USD ml Naropin 2 mg/ml ampule 0.44USD 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 btl 0.23USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Unlock Additional DataUS5670524 No 1997-09-23 2014-05-26 US US4870086 No 1989-09-26 2010-09-24 US CA2165446 No 2005-07-05 2014-05-26 Canada CA1337549 No 1995-11-14 2012-11-14 Canada US8118802 No 2012-02-21 2023-05-18 US US7857802 No 2010-12-28 2026-11-28 US US7828787 No 2010-11-09 2025-10-18 US US8162915 No 2012-04-24 2024-05-23 US Additional Data Available- Filed On
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility 57.6 mg/L Not Available logP 2.90 HANSCH,C ET AL. (1995) pKa 8.07 Not Available - Predicted Properties
Property Value Source Water Solubility 0.253 mg/mL ALOGPS logP 2.91 ALOGPS logP 4.07 ChemAxon logS -3 ALOGPS pKa (Strongest Acidic) 13.62 ChemAxon pKa (Strongest Basic) 7.82 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 32.34 Å2 ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 85.59 m3·mol-1 ChemAxon Polarizability 32.67 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 0.9705 Blood Brain Barrier + 0.9377 Caco-2 permeable + 0.5912 P-glycoprotein substrate Substrate 0.8037 P-glycoprotein inhibitor I Inhibitor 0.8768 P-glycoprotein inhibitor II Non-inhibitor 0.6339 Renal organic cation transporter Non-inhibitor 0.6611 CYP450 2C9 substrate Non-substrate 0.819 CYP450 2D6 substrate Substrate 0.8919 CYP450 3A4 substrate Substrate 0.723 CYP450 1A2 substrate Non-inhibitor 0.5499 CYP450 2C9 inhibitor Non-inhibitor 0.9246 CYP450 2D6 inhibitor Inhibitor 0.8821 CYP450 2C19 inhibitor Non-inhibitor 0.8773 CYP450 3A4 inhibitor Non-inhibitor 0.5902 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6116 Ames test Non AMES toxic 0.8507 Carcinogenicity Non-carcinogens 0.8763 Biodegradation Not ready biodegradable 0.9783 Rat acute toxicity 2.2964 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8009 hERG inhibition (predictor II) Inhibitor 0.8438
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Taxonomy
- 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
- Alpha-amino acid amide / 2-piperidinecarboxamide / Piperidinecarboxamide / Anilide / M-xylene / Xylene / N-arylamide / Monocyclic benzene moiety / Benzenoid / Piperidine show 16 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- piperidinecarboxamide, ropivacaine (CHEBI:8890)
Targets
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- 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. [PubMed:17016423]
- 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. [PubMed:10781449]
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
- 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. [PubMed:9834040]
- 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
- 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. [PubMed:7832304]
- 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
- 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. [PubMed:7832304]
Drug created on June 13, 2005 07:24 / Updated on December 08, 2019 20:10