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2D Structure
Also known as: Bupivacaine hcl, 18010-40-7, 14252-80-3, Carbostesin, Vivacaine, Sensorcaine
Molecular Formula
C18H29ClN2O
Molecular Weight
324.9  g/mol
InChI Key
SIEYLFHKZGLBNX-UHFFFAOYSA-N
FDA UNII
AKA908P8J1

A widely used local anesthetic agent.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
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
2.1.3 InChI Key
SIEYLFHKZGLBNX-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCCN1CCCCC1C(=O)NC2=C(C=CC=C2C)C.Cl
2.2 Other Identifiers
2.2.1 UNII
AKA908P8J1
2.3 Synonyms
2.3.1 MeSH Synonyms

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

2. Bupivacain Janapharm

3. Bupivacain Rpr

4. Bupivacain-rpr

5. Bupivacaina Braun

6. Bupivacaine

7. Bupivacaine Anhydrous

8. Bupivacaine Carbonate

9. Bupivacaine Monohydrochloride, Monohydrate

10. Buvacaina

11. Carbostesin

12. Dolanaest

13. Marcain

14. Marcaine

15. Sensorcaine

16. Svedocain Sin Vasoconstr

2.3.2 Depositor-Supplied Synonyms

1. Bupivacaine Hcl

2. 18010-40-7

3. 14252-80-3

4. Carbostesin

5. Vivacaine

6. Sensorcaine

7. Bupivacaine (hydrochloride)

8. 1-butyl-n-(2,6-dimethylphenyl)piperidine-2-carboxamide Hydrochloride

9. Marcain

10. Ah-2250

11. Bupivacaine Hydrochloride Anhydrous

12. Lac-43

13. Nsc-758631

14. 1-butyl-n-(2,6-dimethylphenyl)piperidine-2-carboxamide;hydrochloride

15. 2-piperidinecarboxamide, 1-butyl-n-(2,6-dimethylphenyl)-, Monohydrochloride

16. Win 11,318

17. Aka908p8j1

18. Chebi:31322

19. 1-butyl-n-(2,6-dimethylphenyl)-2-piperidinecarboxamide Monohydrochloride

20. Bloqueina

21. Xaracoll

22. 2-piperidinecarboxamide, 1-butyl-n-(2,6-dimethylphenyl)-, Hydrochloride (1:1)

23. (s)-bupivacaine Hydrochloride

24. Bicain

25. Marcaine Spinal

26. Smr000058218

27. (+-)-bupivacaine Hydrochloride

28. Bupivacaine Hydrochloride [jan]

29. Mnarcaine Hydrochloride

30. Einecs 241-917-8

31. Bupivacaine Hydrochloride Kit

32. Unii-aka908p8j1

33. Lac 43

34. Sr-05000001874

35. 1-butyl-n-(2,6-dimethylphenyl)-2-piperidinecarboxamide

36. Levobupivacaine Hydrochloride (anhydrous)

37. 2',6'-pipecoloxylidide, 1-butyl-, Hydrochloride

38. Sky 0302

39. Prestwick_894

40. 2',6'-pipecoloxylidide, 1-butyl-, Monohydrochloride

41. Ah 2250

42. Marcaine Hydrochloride Preservation Free

43. Bupivacain Hydrochloride

44. Bupivacaine Hydrochloride Preservation Free

45. Bupivacaini Hydrochloridum

46. Bupivacaine Hydrochloride Rs

47. Bupivacaine Monohydrochloride

48. Win 11318 Hcl

49. Schembl34374

50. Mls001361336

51. Mls002154259

52. Spectrum1503818

53. Bupivacaine-[d9] Hydrochloride

54. Chembl1200396

55. Dtxsid0030877

56. Chebi:77441

57. Hy-b0405a

58. Bupivacaine Hydrochloride(marcain)

59. Hms1568n12

60. Hms1922i12

61. Pharmakon1600-01503818

62. Bupivacaine Hydrochloride (marcain)

63. Act04725

64. Bcp22697

65. Bcp22708

66. Bupivacaine Hydrochloride (anhydrous)

67. Ccg-39367

68. Mfcd00078956

69. Nsc119660

70. Nsc758631

71. S2454

72. Bupivacaine Hydrochloride [mi]

73. Akos015889322

74. Bcp9000461

75. Fd-0235

76. Nsc 758631

77. Nsc-119660

78. Ncgc00095072-01

79. Ncgc00095072-02

80. Anhydrous Bupivacaine Hydrochloride

81. Bupivacaine Hydrochloride [who-dd]

82. Bupivacaine Hydrochloride, Anhydrous

83. B3925

84. Ft-0607564

85. Ft-0623287

86. Ft-0658830

87. Ft-0663897

88. Ft-0663899

89. Sw197015-3

90. 52b803

91. Bupivacaine Hydrochloride [usp Impurity]

92. J-011502

93. Q-100158

94. Sr-05000001874-3

95. Q27888209

96. 1-butyl-2-piperidylformo-2',6'-xylidide Hydrochloride

97. 2-piperidinecarboxamide,6-dimethylphenyl)-, Hydrochloride

98. 1-butyl-2-[(2,6-dimethylphenyl)carbamoyl]piperidinium Chloride

99. (+/-)-1-butyl-2',6'-pipecoloxylidide Monohydrochloride

100. Rac-1-butyl-2-[(2,6-dimethylphenyl)carbamoyl]piperidinium Chloride

101. Rac-1-butyl-n-(2,6-dimethylphenyl)piperidine-2-carboxamide Hydrochloride

102. 15233-43-9

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 Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 6  
Drug NameBupivacaine hydrochloride
PubMed HealthBupivacaine/Epinephrine (Injection)
Drug ClassesAnesthetic, Amino Amide Combination, Anesthetic, Local
Drug LabelSensorcaine (bupivacaine HCl) injections are sterile isotonic solutions that contain a local anesthetic agent with and without epinephrine (as bitartrate) 1:200,000 and are administered parenterally by injection. See INDICATIONS AND USAGE for spe...
Active IngredientBupivacaine hydrochloride
Dosage FormInjectable
Routeinjection; Spinal; Injection
Strength0.5%; 0.75%; 0.25%
Market StatusPrescription
CompanySagent Agila; Hospira

2 of 6  
Drug NameMarcaine
PubMed HealthBupivacaine (Injection)
Drug ClassesAnesthetic, Local
Drug LabelMarcaineBupivacaine Hydrochloride Injection, USPMarcaineWith Epinephrine 1:200,000 (as bitartrate)Bupivacaine Hydrochloride and Epinephrine Injection, USP Rx onlyBupivacaine hydrochloride is 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylpheny...
Active IngredientBupivacaine hydrochloride
Dosage FormInjectable
RouteSpinal
Strength0.75%
Market StatusPrescription
CompanyHospira

3 of 6  
Drug NameSensorcaine
Drug LabelSensorcaine (bupivacaine HCl) injections are sterile isotonic solutions that contain a local anesthetic agent with and without epinephrine (as bitartrate) 1:200,000 and are administered parenterally by injection. See INDICATIONS AND USAGE for spe...
Active IngredientBupivacaine hydrochloride; epinephrine bitartrate
Dosage FormInjectable
RouteSpinal; Injection
Strength0.5%; 0.0091mg/ml; 0.75%; 0.25%
Market StatusPrescription
CompanyFresenius Kabi Usa

4 of 6  
Drug NameBupivacaine hydrochloride
PubMed HealthBupivacaine/Epinephrine (Injection)
Drug ClassesAnesthetic, Amino Amide Combination, Anesthetic, Local
Drug LabelSensorcaine (bupivacaine HCl) injections are sterile isotonic solutions that contain a local anesthetic agent with and without epinephrine (as bitartrate) 1:200,000 and are administered parenterally by injection. See INDICATIONS AND USAGE for spe...
Active IngredientBupivacaine hydrochloride
Dosage FormInjectable
Routeinjection; Spinal; Injection
Strength0.5%; 0.75%; 0.25%
Market StatusPrescription
CompanySagent Agila; Hospira

5 of 6  
Drug NameMarcaine
PubMed HealthBupivacaine (Injection)
Drug ClassesAnesthetic, Local
Drug LabelMarcaineBupivacaine Hydrochloride Injection, USPMarcaineWith Epinephrine 1:200,000 (as bitartrate)Bupivacaine Hydrochloride and Epinephrine Injection, USP Rx onlyBupivacaine hydrochloride is 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylpheny...
Active IngredientBupivacaine hydrochloride
Dosage FormInjectable
RouteSpinal
Strength0.75%
Market StatusPrescription
CompanyHospira

6 of 6  
Drug NameSensorcaine
Drug LabelSensorcaine (bupivacaine HCl) injections are sterile isotonic solutions that contain a local anesthetic agent with and without epinephrine (as bitartrate) 1:200,000 and are administered parenterally by injection. See INDICATIONS AND USAGE for spe...
Active IngredientBupivacaine hydrochloride; epinephrine bitartrate
Dosage FormInjectable
RouteSpinal; Injection
Strength0.5%; 0.0091mg/ml; 0.75%; 0.25%
Market StatusPrescription
CompanyFresenius Kabi Usa

5 Pharmacology and Biochemistry
5.1 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.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Amides [CS]; Local Anesthesia [PE]; Amide Local Anesthetic [EPC]