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    Naropin

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: 84057-95-4, (s)-ropivacaine, Naropin, Ropivacaine [inn], Ropivacaine hydrochloride, Ropivacaina
    Molecular Formula
    C17H26N2O
    Molecular Weight
    274.4  g/mol
    InChI Key
    ZKMNUMMKYBVTFN-HNNXBMFYSA-N
    FDA UNII
    7IO5LYA57N
    An anilide used as a long-acting local anesthetic. It has a differential blocking effect on sensory and motor neurons.
    Ropivacaine is an Amide Local Anesthetic. The physiologic effect of ropivacaine is by means of Local Anesthesia.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S)-N-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide
    2.1.2 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
    2.1.3 InChI Key
    ZKMNUMMKYBVTFN-HNNXBMFYSA-N
    2.1.4 Canonical SMILES
    CCCN1CCCCC1C(=O)NC2=C(C=CC=C2C)C
    2.1.5 Isomeric SMILES
    CCCN1CCCC[C@H]1C(=O)NC2=C(C=CC=C2C)C
    2.2 Other Identifiers
    2.2.1 UNII
    7IO5LYA57N
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 1 Propyl 2',6' Pipecoloxylidide

    2. 1-propyl-2',6'-pipecoloxylidide

    3. Al 381

    4. Al-381

    5. Al381

    6. Lea 103

    7. Lea-103

    8. Lea103

    9. Naropeine

    10. Naropin

    11. Ropivacaine Hydrochloride

    12. Ropivacaine Monohydrochloride

    13. Ropivacaine Monohydrochloride, (s)-isomer

    2.3.2 Depositor-Supplied Synonyms

    1. 84057-95-4

    2. (s)-ropivacaine

    3. Naropin

    4. Ropivacaine [inn]

    5. Ropivacaine Hydrochloride

    6. Ropivacaina

    7. Ropivacainum

    8. Ropivacaina [spanish]

    9. (s)-n-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide

    10. Ropivacainum [inn-latin]

    11. Ropivacaina [inn-spanish]

    12. (2s)-n-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide

    13. Ropivicaine

    14. 7io5lya57n

    15. (-)-1-propyl-2',6'-pipecoloxylidide

    16. Lea 103

    17. Chebi:8890

    18. Tlc590

    19. (2s)-n-(2,6-dimethylphenyl)-1-propyl-2-piperidinecarboxamide

    20. (2s)-n-(2,6-dimethylphenyl)-1-propyl-piperidine-2-carboxamide

    21. Tlc-590

    22. Ropivacaine (inn)

    23. L-n-n-propylpipecolic Acid-2,6-xylidide

    24. Lea-103

    25. 2-piperidinecarboxamide, N-(2,6-dimethylphenyl)-1-propyl-, (2s)-

    26. S-ropivacaine

    27. (s)-(-)-1-propyl-2',6'-pipecoloxylidide

    28. 1-propyl-2',6'-pipecoloxylidide

    29. Noropine

    30. Narop

    31. Lea-103 Hcl

    32. Naropin (tn)

    33. Ncgc00164597-01

    34. Ropivacaine [inn:ban]

    35. 98717-15-8

    36. Unii-7io5lya57n

    37. Ropivacaine Base

    38. Mfcd00864425

    39. Al-381

    40. Ropivacaine [mi]

    41. Ropivacaine [vandf]

    42. Schembl33292

    43. Ropivacaine [usp-rs]

    44. Ropivacaine [who-dd]

    45. Bidd:gt0203

    46. Narop; Noropine; Lea-103

    47. Gtpl7602

    48. (-)-1-propyl-2',6'-dimethyl-2-piperidylcarboxyanilid

    49. Chembl1077896

    50. Dtxsid4040187

    51. Zinc897002

    52. Hy-b0563

    53. Bbl102321

    54. S5504

    55. Stl556120

    56. Akos017343283

    57. Ccg-267197

    58. Db00296

    59. As-35173

    60. Cs-0009514

    61. R0251

    62. C07532

    63. D08490

    64. Ab00698466-07

    65. Ab00698466_10

    66. 057r954

    67. A840710

    68. Q279504

    69. (s)-(-)-1-propyl-2',6'-pipecoloxylidine

    70. Q-201677

    71. (-)-1-propyl-2',6'-dimethyl-2-piperidylcarboxyanilide

    72. (s)-n-(2,6-dimethylphenyl)-1-propyl-2-piperidinecarboxamide

    73. (s)-(-)-1-propylpiperidine-2-carboxylic Acid (2,6-dimethylphenyl)amide

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 274.4 g/mol
    Molecular Formula C17H26N2O
    XLogP32.9
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count4
    Exact Mass274.204513457 g/mol
    Monoisotopic Mass274.204513457 g/mol
    Topological Polar Surface Area32.3 Ų
    Heavy Atom Count20
    Formal Charge0
    Complexity308
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameNaropin
    PubMed HealthRopivacaine (Injection)
    Drug ClassesAnesthetic, Local
    Drug LabelNaropin Injection contains ropivacaine HCl which is a member of the amino amide class of local anesthetics. Naropin Injection is a sterile, isotonic solution that contains the enantiomerically pure drug substance, sodium chloride for isotonicity an...
    Active IngredientRopivacaine hydrochloride
    Dosage FormInjectable
    RouteInjection
    Strength2mg/ml; 10mg/ml; 5mg/ml; 7.5mg/ml
    Market StatusPrescription
    CompanyFresenius Kabi Usa

    2 of 2  
    Drug NameNaropin
    PubMed HealthRopivacaine (Injection)
    Drug ClassesAnesthetic, Local
    Drug LabelNaropin Injection contains ropivacaine HCl which is a member of the amino amide class of local anesthetics. Naropin Injection is a sterile, isotonic solution that contains the enantiomerically pure drug substance, sodium chloride for isotonicity an...
    Active IngredientRopivacaine hydrochloride
    Dosage FormInjectable
    RouteInjection
    Strength2mg/ml; 10mg/ml; 5mg/ml; 7.5mg/ml
    Market StatusPrescription
    CompanyFresenius Kabi Usa

    4.2 Drug Indication

    Used in obstetric anesthesia and regional anesthesia for surgery.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    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.

    5.2 MeSH Pharmacological Classification

    Anesthetics, Local

    Drugs that block nerve conduction when applied locally to nerve tissue in appropriate concentrations. They act on any part of the nervous system and on every type of nerve fiber. In contact with a nerve trunk, these anesthetics can cause both sensory and motor paralysis in the innervated area. Their action is completely reversible. (From Gilman AG, et. al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed) Nearly all local anesthetics act by reducing the tendency of voltage-dependent sodium channels to activate. (See all compounds classified as Anesthetics, Local.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    ROPIVACAINE
    5.3.2 FDA UNII
    7IO5LYA57N
    5.3.3 Pharmacological Classes
    Amides [CS]; Local Anesthesia [PE]; Amide Local Anesthetic [EPC]
    5.4 ATC Code

    N01BB09

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    N - Nervous system

    N01 - Anesthetics

    N01B - Anesthetics, local

    N01BB - Amides

    N01BB09 - Ropivacaine

    5.5 Absorption, Distribution and Excretion

    Absorption

    Bioavailability is 87%98% following epidural administration.

    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.

    Clearance

    387+/- 107 mL/min

    unbound plasma clearance=7.2 +/- 1.6 L/min

    5.6 Metabolism/Metabolites

    Hepatic

    Ropivacaine has known human metabolites that include 3-hydroxy-ropivacaine and PPX.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.7 Biological Half-Life

    Approximately 4.2 hours.

    5.8 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.