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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyRopivacaine
Identification
- Name
- Ropivacaine
- Accession Number
- DB00296 (APRD00492)
- Type
- Small Molecule
- Groups
- Approved
- Description
Ropivacaine is a local anaesthetic drug belonging to the amino amide group. The name ropivacaine refers to both the racemate and the marketed S-enantiomer. Ropivacaine hydrochloride is commonly marketed by AstraZeneca under the trade name Naropin.
- 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 - Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Naropin Solution 10 mg Epidural Aspen Pharmacare Canada Inc. 1997-04-30 Not applicable Canada 
Naropin Injection, solution 7.5 mg/1mL Epidural; Perineural 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 5 mg/1mL Epidural; Infiltration; Perineural General Injectables & Vaccines 2014-03-11 Not applicable US Naropin Injection, solution 2 mg/1mL Epidural; Infiltration Fresenius Kabi 2011-05-31 Not applicable US Naropin Injection, solution 10 mg/1mL Epidural Fresenius Kabi 2011-05-31 Not applicable US Naropin Solution 5 mg Epidural; Infiltration Aspen Pharmacare Canada Inc. 1997-04-30 Not applicable Canada Naropin Injection, solution 5 mg/1mL Epidural; Infiltration; Perineural Fresenius Kabi 2011-05-31 Not applicable US Naropin Inj 7.5mg/ml Liquid 7.5 mg Parenteral Astra Zeneca 1997-04-30 2003-11-18 Canada Ropivacaine Hydrochloride Injection Solution 2 mg Epidural; Infiltration Teva Not applicable Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Ropivacaine Hydrochloride Injection 5 mg/1mL Epidural; Infiltration; Perineural Somerset Therapeutics, Llc 2018-06-19 Not applicable US Ropivacaine Hydrochloride Injection, solution 2 mg/1mL Epidural; Infiltration; Perineural Hospira, Inc. 2014-11-07 Not applicable US Ropivacaine Hydrochloride Injection, solution 5 mg/1mL Epidural; Infiltration; Perineural Auro Medics Pharma Llc 2016-09-15 Not applicable US Ropivacaine Hydrochloride Injection, solution 2 mg/1mL Epidural; Infiltration; Perineural Akorn 2018-03-16 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 5 mg/1mL Parenteral Sandoz 2014-07-24 Not applicable US Ropivacaine Hydrochloride Injection, solution 2 mg/1mL Epidural; Infiltration; Perineural Auro Medics Pharma Llc 2016-09-15 Not applicable US Ropivacaine Hydrochloride Injection, solution 10 mg/1mL Epidural Auro Medics Pharma Llc 2016-09-15 Not applicable US Ropivacaine Hydrochloride Injection, solution 10 mg/1mL Epidural Sagent Pharmaceuticals 2014-09-23 2019-07-31 US Ropivacaine Hydrochloride Injection 10 mg/1mL Epidural Somerset Therapeutics, Llc 2018-06-19 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End 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
- Anesthetics
- Anesthetics, Local
- Central Nervous System Agents
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 CYP2B6 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Hypotensive Agents
- Local Anesthesia
- Nervous System
- 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
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
Systemic exposure to excessive quantities of ropivacaine mainly result in central nervous system (CNS) and cardiovascular effects – CNS effects usually occur at lower blood plasma concentrations and additional cardiovascular effects present at higher concentrations, though cardiovascular collapse may also occur with low concentrations. CNS effects may include CNS excitation (nervousness, tingling around the mouth, tinnitus, tremor, dizziness, blurred vision, seizures) followed by depression (drowsiness, loss of consciousness, respiratory depression and apnea). Cardiovascular effects include hypotension, bradycardia, arrhythmias, and/or cardiac arrest – some of which may be due to hypoxemia secondary to respiratory depression.
- Affected organisms
- Humans and other mammals
- Pathways
Pathway Category Ropivacaine Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction (R)-warfarin The metabolism of (R)-warfarin can be decreased when combined with Ropivacaine. (S)-Warfarin The metabolism of (S)-Warfarin can be decreased when combined with Ropivacaine. 3-isobutyl-1-methyl-7H-xanthine The serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with Ropivacaine. 3,5-diiodothyropropionic acid The metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Ropivacaine. 4-hydroxycoumarin The metabolism of 4-hydroxycoumarin can be decreased when combined with Ropivacaine. 5-androstenedione The metabolism of 5-androstenedione can be decreased when combined with Ropivacaine. 6-Deoxyerythronolide B The metabolism of Ropivacaine can be decreased when combined with 6-Deoxyerythronolide B. 6-O-benzylguanine The serum concentration of 6-O-benzylguanine can be increased when it is combined with Ropivacaine. 7-Deazaguanine The serum concentration of 7-Deazaguanine can be increased when it is combined with Ropivacaine. 7-ethyl-10-hydroxycamptothecin The metabolism of Ropivacaine can be decreased when combined with 7-ethyl-10-hydroxycamptothecin. - 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 Injection, solution Epidural; Infiltration 2 mg/1mL Liquid Parenteral 7.5 mg 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 10 mg/1mL Injection, solution Epidural; Infiltration; Perineural 2 mg/1mL Injection, solution Epidural; Infiltration; Perineural 5 mg/1mL Injection, solution Epidural; Perineural 7.5 mg/1mL Injection, solution Parenteral 10 mg/1mL Injection, solution Parenteral 5 mg/1mL Solution Epidural; Infiltration 2 mg Solution Epidural 10 mg Solution Epidural 7.5 mg Solution Epidural; Infiltration 5 mg - 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) US5670524 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
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]
- Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
- 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
- Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
- 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
- Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Drug created on June 13, 2005 07:24 / Updated on January 22, 2019 21:01