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Levobupivacaine

Levobupivacaine

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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

Levobupivacaine

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 Formula	C₁₈H₂₉ClN₂O
Molecular Weight	324.9 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	5
Exact Mass	324.1968412 g/mol
Monoisotopic Mass	324.1968412 g/mol
Topological Polar Surface Area	32.3 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	321
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

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.)