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    Levobupivacaine

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    MARKET PLACE

    PharmaCompass
    $ API Ref.Price (USD/KG) : 1,704Xls

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    2D Structure
    Also known as: Levobupivacaine hcl, 27262-48-2, Chirocaine, Levobupivacaine hydrochloride [usan], Levobupivacaine (hydrochloride), (s)-1-butyl-2',6'-pipecoloxylidide monohydrochloride
    Molecular Formula
    C18H29ClN2O
    Molecular Weight
    324.9  g/mol
    InChI Key
    SIEYLFHKZGLBNX-NTISSMGPSA-N
    FDA UNII
    J998RDZ51I
    S-enantiomer of bupivacaine that is used as a local anesthetic and for regional nerve blocks, including EPIDURAL ANESTHESIA.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide;hydrochloride
    2.1.2 InChI
    InChI=1S/C18H28N2O.ClH/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3;/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21);1H/t16-;/m0./s1
    2.1.3 InChI Key
    SIEYLFHKZGLBNX-NTISSMGPSA-N
    2.1.4 Canonical SMILES
    CCCCN1CCCCC1C(=O)NC2=C(C=CC=C2C)C.Cl
    2.1.5 Isomeric SMILES
    CCCCN1CCCC[C@H]1C(=O)NC2=C(C=CC=C2C)C.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    J998RDZ51I
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Chirocaine

    2. Levobupivacaine

    2.3.2 Depositor-Supplied Synonyms

    1. Levobupivacaine Hcl

    2. 27262-48-2

    3. Chirocaine

    4. Levobupivacaine Hydrochloride [usan]

    5. Levobupivacaine (hydrochloride)

    6. (s)-1-butyl-2',6'-pipecoloxylidide Monohydrochloride

    7. (s)-1-butyl-n-(2,6-dimethylphenyl)piperidine-2-carboxamide Hydrochloride

    8. (s)-(-)-bupivacaine Hydrochloride

    9. J998rdz51i

    10. Chebi:31772

    11. Bupivacaine (-)-form Hydrochloride

    12. (2s)-1-butyl-n-(2,6-dimethylphenyl)piperidine-2-carboxamide Hydrochloride

    13. (s)-1-butyl-n-(2,6-dimethylphenyl)-2-piperidinecarboxamide Monohydrochloride

    14. (s)-(-)-bupivacaine Monohydrochloride

    15. 27262-48-2 (hcl)

    16. Dsstox_cid_26071

    17. Dsstox_rid_81319

    18. Dsstox_gsid_46071

    19. (s)-bupivacaine Hydrochloride

    20. Levobupivacaine Free Base

    21. Bupicaine Hydrochloride (-)

    22. Cas-27262-48-2

    23. Ncgc00159482-02

    24. Unii-j998rdz51i

    25. Popscaine

    26. Chirocaine (tn)

    27. Levobupivacaine Hydrochloride (anhydrous)

    28. Schembl34174

    29. (s)-(-)-bupivacaine Hcl

    30. (-)-bupivacaine Hydrochloride

    31. Levobupivacaine Monohydrochloride

    32. Chembl1200749

    33. Dtxsid9046071

    34. Hy-b0653a

    35. 2',6'-pipecoloxylidide, 1-butyl-, Hydrochloride, (-)-

    36. Mr-8-a2

    37. (s)-(-)-bupivacainehydrochloride

    38. Levobupivacaine Hcl [vandf]

    39. (-)-(s)-bupivacaine Hydrochloride

    40. Act04726

    41. Tox21_111706

    42. Mfcd01704265

    43. S4061

    44. Akos016001444

    45. Tox21_111706_1

    46. Ac-2097

    47. Ccg-267755

    48. Cs-4301

    49. 2-piperidinecarboxamide, 1-butyl-n-(2,6-dimethylphenyl)-, Monohydrochloride, (2s)-

    50. Ncgc00178579-04

    51. As-15053

    52. Levobupivacaine Hydrochloride (jan/usan)

    53. Levobupivacaine Hydrochloride [jan]

    54. Levobupivacaine Hydrochloride [mart.]

    55. Levobupivacaine Hydrochloride [who-dd]

    56. Levobupivacaine Hydrochloride, >=98% (hplc)

    57. D01287

    58. Bupivacaine (-)-form Hydrochloride [mi]

    59. (s)-1-butyl-2',6'-pipecoloxylidide Hydrochloride

    60. 262b482

    61. Levobupivacaine Hydrochloride [orange Book]

    62. Q27114682

    63. (2s)-1-butyl-2-[(2,6-dimethylphenyl)carbamoyl]piperidinium Chloride

    64. (2s)-1-butyl-n-(2,6-dimethylphenyl)piperidine-2-carboxamide;hydrochloride

    65. 2-piperidinecarboxamide, 1-butyl-n-(2,6-dimethylphenyl)-,monohydrochloride, (2s)-

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 324.9 g/mol
    Molecular Formula C18H29ClN2O
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count5
    Exact Mass324.1968412 g/mol
    Monoisotopic Mass324.1968412 g/mol
    Topological Polar Surface Area32.3 Ų
    Heavy Atom Count22
    Formal Charge0
    Complexity321
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Pharmacology and Biochemistry
    4.1 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.)