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Chemistry

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Also known as: 1-butyl-n-(2,6-dimethylphenyl)piperidine-2-carboxamide, 2180-92-9, Dl-bupivacaine, 38396-39-3, Marcaine, Bupivacaina
Molecular Formula
C18H28N2O
Molecular Weight
288.4  g/mol
InChI Key
LEBVLXFERQHONN-UHFFFAOYSA-N
FDA UNII
Y8335394RO

Bupivacaine
A widely used local anesthetic agent.
Bupivacaine is an Amide Local Anesthetic. The physiologic effect of bupivacaine is by means of Local Anesthesia.
1 2D Structure

Bupivacaine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
2.1.2 InChI
InChI=1S/C18H28N2O/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)
2.1.3 InChI Key
LEBVLXFERQHONN-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCCN1CCCCC1C(=O)NC2=C(C=CC=C2C)C
2.2 Other Identifiers
2.2.1 UNII
Y8335394RO
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 Anhydrous

7. Bupivacaine Carbonate

8. Bupivacaine Hydrochloride

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

2. 2180-92-9

3. Dl-bupivacaine

4. 38396-39-3

5. Marcaine

6. Bupivacaina

7. Anekain

8. (+-)-bupivacaine

9. Bupivacainum

10. Sensorcaine

11. 1-butyl-2',6'-pipecoloxylidide

12. Exparel

13. Bupivacainum [inn-latin]

14. Bupivacaina [inn-spanish]

15. Dl-1-butyl-2',6'-pipecoloxylidide

16. Bucaine

17. 2-piperidinecarboxamide, 1-butyl-n-(2,6-dimethylphenyl)-

18. Ah 250

19. Win 11318

20. Bloqueina

21. (+/-)-bupivacaine

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

23. Posimir

24. Sky0402

25. 2',6'-pipecoloxylidide, 1-butyl-

26. 1-butyl-n-(2,6-dimethylphenyl)-piperidine-2-carboxamide

27. Marcain

28. Liq865

29. (1)-1-butyl-n-(2,6-dimethylphenyl)piperidine-2-carboxamide

30. Chebi:77431

31. Liq-865

32. Sky-0402

33. Xaracoll

34. Lac-43

35. Y8335394ro

36. Cbupivacaine

37. Bupivacaine Hcl Kit

38. Bupivacaine Base

39. (r)-bupivacaine Hcl

40. Bucaine (tn)

41. Dur-843

42. Einecs 218-553-3

43. Einecs 253-911-2

44. Bupivacaine [usan:inn:ban]

45. Unii-y8335394ro

46. Hsdb 7790

47. Racemic Bupivacaine

48. (rs)-bupivacaine

49. Bupivacaine Liposome

50. Sky 0402

51. Exparel (tn)

52. Liposomal Bupivacaine

53. Bupivacaine Free Base

54. Bupivacaine-[13c]

55. Spectrum_001524

56. Bupivacaine Liposome Injectable Suspension

57. Marcaine And Sensorcaine

58. Bupivacaine [mi]

59. Prestwick0_000305

60. Prestwick1_000305

61. Prestwick2_000305

62. Prestwick3_000305

63. Spectrum2_001589

64. Spectrum3_000974

65. Spectrum4_001098

66. Spectrum5_001483

67. Bupivacaine [inn]

68. (.+/-.)-1-butyl-2',6'-pipecoloxylidide

69. (.+/-.)-bupivacaine

70. Bupivacaine (usan/inn)

71. Bupivacaine [hsdb]

72. Bupivacaine [usan]

73. Lac-43 (salt/mix)

74. Epitope Id:122662

75. Bupivacaine [vandf]

76. Marcaine Spinal (salt/mix)

77. Chembl1098

78. Schembl25438

79. Bspbio_000270

80. Bspbio_002607

81. Bupivacaine [who-dd]

82. Kbiogr_001516

83. Kbioss_002004

84. Divk1c_000758

85. Spbio_001558

86. Spbio_002489

87. Bpbio1_000298

88. Chebi:3215

89. Gtpl2397

90. Bupivacaine [green Book]

91. Dtxsid2022703

92. Kbio1_000758

93. Kbio2_002004

94. Kbio2_004572

95. Kbio2_007140

96. Kbio3_001827

97. Bupivacaine [orange Book]

98. Dl-1-butyl-2,6-pipecoloxylidide

99. Ninds_000758

100. 1-butyl-n-(2,6-dimethylphenyl)-2-piperidinecarboximidic Acid

101. Ah250

102. Hms2090f12

103. Hms3428p06

104. Marcaine Hydrochloride (salt/mix)

105. 1217442-06-2

106. 3-ethyl-2-methylbenzoxazoliumiodide

107. Bcp12242

108. Bcp21825

109. Hy-b0405

110. 2-piperidinecarboxamide, 1-butyl-n-(2,6-dimethylphenyl)-, (+-)-

111. Ah-250

112. Bdbm50350790

113. Mfcd00243007

114. Stl484283

115. Zynrelef Component Bupivacaine

116. Akos001637202

117. Akos016842516

118. Ac-2096

119. Bs-5224

120. Cs-w023182

121. Db00297

122. Bupivacaine Component Of Zynrelef

123. Idi1_000758

124. Ncgc00178579-01

125. Ncgc00178579-02

126. Bb166160

127. Sbi-0051846.p002

128. Db-119016

129. Ab00053674

130. Ft-0623286

131. Ft-0660567

132. Ft-0699781

133. Ft-0771900

134. C07529

135. D07552

136. Ropivacaine Hydrochloride Impurity, Bupivacaine-

137. Ab00053674-08

138. Ab00053674-09

139. Ab00053674_10

140. Ab00053674_11

141. 180b929

142. A873847

143. L000695

144. Q422806

145. Q-100271

146. Brd-a01636364-003-05-2

147. Brd-a01636364-003-08-6

148. (plusmn)-1-butyl-n-(2,6-dimethylphenyl)piperidine-2-carboxamide

149. 2-piperidinecarboxamide, 1-butyl-n-(2,6-dimethylphenyl)-, (+/-)-

150. 2-piperidinecarboxamide, 1-butyl-n-(2,6-dimethylphenyl)-, (.+/-.)-

151. Ropivacaine Hydrochloride Impurity, Bupivacaine- [usp Impurity]

152. 119427-31-5

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 288.4 g/mol
Molecular Formula C18H28N2O
XLogP33.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count5
Exact Mass288.220163521 g/mol
Monoisotopic Mass288.220163521 g/mol
Topological Polar Surface Area32.3 Ų
Heavy Atom Count21
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 Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 6  
Drug NameExparel
PubMed HealthBupivacaine Liposome (Injection)
Drug ClassesAnesthetic, Local
Drug LabelEXPAREL is a sterile, non-pyrogenic white to off-white preservative-free aqueous suspension of multivesicular liposomes (DepoFoam drug delivery system) containing bupivacaine. Bupivacaine is present at a concentration of 13.3 mg/mL. After injection...
Active IngredientBupivacaine
Dosage FormInjectable, liposomal
RouteInjection
Strength266mg/20ml (13.3mg/ml)
Market StatusPrescription
CompanyPacira Pharms

2 of 6  
Drug NameMarcaine
PubMed HealthBupivacaine/Epinephrine (Injection)
Drug ClassesAnesthetic, Amino Amide Combination, Anesthetic, 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
PubMed HealthBupivacaine (Injection)
Drug ClassesAnesthetic, 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; epinephrine bitartrate
Dosage FormInjectable
RouteSpinal; Injection
Strength0.5%; 0.0091mg/ml; 0.75%; 0.25%
Market StatusPrescription
CompanyFresenius Kabi Usa

4 of 6  
Drug NameExparel
PubMed HealthBupivacaine Liposome (Injection)
Drug ClassesAnesthetic, Local
Drug LabelEXPAREL is a sterile, non-pyrogenic white to off-white preservative-free aqueous suspension of multivesicular liposomes (DepoFoam drug delivery system) containing bupivacaine. Bupivacaine is present at a concentration of 13.3 mg/mL. After injection...
Active IngredientBupivacaine
Dosage FormInjectable, liposomal
RouteInjection
Strength266mg/20ml (13.3mg/ml)
Market StatusPrescription
CompanyPacira Pharms

5 of 6  
Drug NameMarcaine
PubMed HealthBupivacaine/Epinephrine (Injection)
Drug ClassesAnesthetic, Amino Amide Combination, Anesthetic, 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
PubMed HealthBupivacaine (Injection)
Drug ClassesAnesthetic, 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; epinephrine bitartrate
Dosage FormInjectable
RouteSpinal; Injection
Strength0.5%; 0.0091mg/ml; 0.75%; 0.25%
Market StatusPrescription
CompanyFresenius Kabi Usa

4.2 Therapeutic Uses

Bupivacaine hydrochloride is used for infiltration anesthesia and for peripheral, sympathetic nerve, and epidural (including caudal) block anesthesia. A 0.75% solution of the drug in 8.25% dextrose is used for spinal anesthesia. Bupivacaine is not used for obstetric paracervical block or topical anesthesia. /Use Included in US product label/

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 3334


Bupivacaine Hydrochloride is indicated for the production of local or regional anesthesia or analgesia for surgery, dental and oral surgery procedures, diagnostic and therapeutic procedures, and for obstetrical procedures. Only the 0.25% and 0.5% concentrations are indicated for obstetrical anesthesia. /Use Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for BUPIVACAINE HYDROCHLORIDE, injection, solution; BUPIVACAINE HYDROCHLORIDE WITH EPINEPHRINE, injection, solution (August 2008). Available from, as of February 22, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=8962


4.3 Drug Warning

The 0.75% solution of bupivacaine hydrochloride is no longer recommended for obstetric anesthesia, since use of this concentration for epidural anesthesia in obstetric patients has been associated with cardiac arrest with difficult resuscitation or death. Cardiac arrest has occurred after seizures resulting from systemic toxicity, apparently following inadvertent intravascular injection.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 3335


Local anesthetics should only be employed by clinicians who are well versed in diagnosis and management of dose-related toxicity and other acute emergencies which might arise from the block to be employed, and then only after insuring the immediate availability of oxygen, other resuscitative drugs, cardiopulmonary resuscitative equipment, and the personnel resources needed for proper management of toxic reactions and related emergencies. delay in proper management of dose-related toxicity, under ventilation from any cause, and/or altered sensitivity may lead to the development of acidosis, cardiac arrest and, possibly, death. /Local anesthetics/

US Natl Inst Health; DailyMed. Current Medication Information for BUPIVACAINE HYDROCHLORIDE, injection, solution; BUPIVACAINE HYDROCHLORIDE WITH EPINEPHRINE, injection, solution (August 2008). Available from, as of February 22, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=8962


Pending accumulation of further data on the use of the drug in pediatric patients, bupivacaine hydrochloride solutions should not be used in children younger than 12 years of age and the solution for spinal anesthesia should not be used in children younger than 18 years of age.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 3335


Some commercially available formulations of bupivacaine hydrochloride contain sodium metabisulfite, a sulfite that may cause allergic-type reactions, including anaphylaxis and life-threatening or less severe asthmatic episodes, in certain susceptible individuals. The overall prevalence of sulfite sensitivity in the general population is unknown but probably low; such sensitivity appears to occur more frequently in asthmatic than in nonasthmatic individuals.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 3335


For more Drug Warnings (Complete) data for Bupivacaine (18 total), please visit the HSDB record page.


4.4 Drug Indication

Bupivacaine 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. Bupivacaine is indicated to induce post-surgical analgesia in adults for up to 72 hours following arthroscopic subacromial decompression by administration into the subacromial space under direct arthroscopic visualization. Bupivacaine, together with the NSAID [meloxicam], is indicated for the production of postsurgical analgesia in adult patients for up to 72 hours following bunionectomy, open inguinal herniorrhaphy or total knee arthroplasty.


FDA Label


Exparel is indicated as a brachial plexus block or femoral nerve block for treatment of post-operative pain in adults, and as a field block for treatment of somatic post-operative pain from small- to medium-sized surgical wounds in adults.


Postsurgical analgesia


5 Pharmacology and Biochemistry
5.1 Pharmacology

Bupivacaine is a widely used local anesthetic agent. Bupivacaine is often administered by spinal injection prior to total hip arthroplasty. It is also commonly injected into surgical wound sites to reduce pain for up to 20 hours after surgery. In comparison to other local anesthetics it has a long duration of action. It is also the most toxic to the heart when administered in large doses. This problem has led to the use of other long-acting local anaesthetics:ropivacaine and levobupivacaine. Levobupivacaine is a derivative, specifically an enantiomer, of bupivacaine. Systemic absorption of local anesthetics produces effects on the cardiovascular and central nervous systems. At blood concentrations achieved with therapeutic doses, changes in cardiac conduction, excitability, refractoriness, contractility, and peripheral vascular resistance are minimal. However, toxic blood concentrations depress cardiac conduction and excitability, which may lead to atrioventricular block, ventricular arrhythmias and to cardiac arrest, sometimes resulting in fatalities. In addition, myocardial contractility is depressed and peripheral vasodilation occurs, leading to decreased cardiac output and arterial blood pressure. Following systemic absorption, local anesthetics can produce central nervous system stimulation, depression or both.


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
BUPIVACAINE
5.3.2 FDA UNII
Y8335394RO
5.3.3 Pharmacological Classes
Amides [CS]; Local Anesthesia [PE]; Amide Local Anesthetic [EPC]
5.4 ATC Code

N01BB01


N01BB01

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

N01BB01 - Bupivacaine


5.5 Absorption, Distribution and Excretion

Absorption

Systemic absorption of local anesthetics is dose- and concentration-dependendent on the total drug administered. Other factors that affect the rate of systemic absorption include the route of administration, blood flow at the administration site, and the presence or absence of epinephrine in the anesthetic solution. Bupivacaine formulated for instillation with [meloxicam] produced varied systemic measures following a single dose of varying strength. In patients undergoing bunionectomy, 60 mg of bupivacaine produced a Cmax of 54 33 ng/mL, a median Tmax of 3 h, and an AUC of 1718 1211 ng\*h/mL. For a 300 mg dose used in herniorrhaphy, the corresponding values were 271 147 ng/mL, 18 h, and 15,524 8921 ng\*h/mL. Lastly, a 400 mg dose used in total knee arthroplasty produced values of 695 411 ng/mL, 21 h, and 38,173 29,400 ng\*h/mL.


Route of Elimination

Only 6% of bupivacaine is excreted unchanged in the urine.


After absorption into the blood, bupivacaine hydrochloride is more highly bound to plasma proteins than are any other local anesthetics; bupivacaine is reportedly 82-96% bound. Bupivacaine hydrochloride has the lowest degree of placental transmission of parenteral local anesthetics and may cause the least fetal depression.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 3335


Pregnant rats received an intravenous infusion of bupivacaine at a rate of 0.33 mg. kg-1. min-1 over a period of 15 min. The fetuses were delivered either at the end of infusion or at 2 or 4 hr after dosing. Maternal and fetal blood and tissue samples were obtained for the assays of bupivacaine and its metabolites using capillary gas chromatography-mass spectrometry. The elimination half-life of bupivacaine was 37.7 min. The major metabolite was 3'-hydroxybupivacaine. Bupivacaine and 3'-hydroxybupivacaine were present in all samples at the end of administration. The fetal to maternal concentration ratio of bupivacaine in plasma was 0.29, and in the placenta was 0.63. The amnion contained the highest bupivacaine concentration: threefold higher in the maternal and 11-fold higher than in the fetal plasma. At 4 hr after dosing, bupivacaine was no longer detectable in any maternal and fetal samples, whereas 3'-hydroxybupivacaine was still present in all tissues except the fetal plasma and heart. These data indicate that a considerable amount of bupivacaine is taken up by both sides of the placenta, as well as the amnion and myometrium. 3'-Hydroxybupivacaine was present in all tissues except the fetal plasma and heart samples, even after the parent compound became no longer detectable.

PMID:11020763 Morishima HO et al; Anesthesiology. 93 (4): 1069-74 (2000).


After injection of Bupivacaine Hydrochloride for caudal, epidural, or peripheral nerve block in man, peak levels of bupivacaine in the blood are reached in 30 to 45 minutes, followed by a decline to insignificant levels during the next three to six hours.

US Natl Inst Health; DailyMed. Current Medication Information for BUPIVACAINE HYDROCHLORIDE, injection, solution; BUPIVACAINE HYDROCHLORIDE WITH EPINEPHRINE, injection, solution (August 2008). Available from, as of February 22, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=8962


Pharmacokinetic studies on the plasma profile of Bupivacaine Hydrochloride after direct intravenous injection suggest a three-compartment open model. The first compartment is represented by the rapid intravascular distribution of the drug. The second compartment represents the equilibration of the drug throughout the highly perfused organs such as the brain, myocardium, lungs, kidneys, and liver. The third compartment represents an equilibration of the drug with poorly perfused tissues, such as muscle and fat. The elimination of drug from tissue distribution depends largely upon the ability of binding sites in the circulation to carry it to the liver where it is metabolized.

US Natl Inst Health; DailyMed. Current Medication Information for BUPIVACAINE HYDROCHLORIDE, injection, solution; BUPIVACAINE HYDROCHLORIDE WITH EPINEPHRINE, injection, solution (August 2008). Available from, as of February 22, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=8962


For more Absorption, Distribution and Excretion (Complete) data for Bupivacaine (6 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Amide-type local anesthetics such as bupivacaine are metabolized primarily in the liver via conjugation with glucuronic acid. The major metabolite of bupivacaine is 2,6-pipecoloxylidine, which is mainly catalyzed via cytochrome P450 3A4.


Pregnant rats received an intravenous infusion of bupivacaine at a rate of 0.33 mg. kg-1. min-1 over a period of 15 min. The fetuses were delivered either at the end of infusion or at 2 or 4 hr after dosing. Maternal and fetal blood and tissue samples were obtained for the assays of bupivacaine and its metabolites using capillary gas chromatography-mass spectrometry. The elimination half-life of bupivacaine was 37.7 min. The major metabolite was 3'-hydroxybupivacaine. Bupivacaine and 3'-hydroxybupivacaine were present in all samples at the end of administration. The fetal to maternal concentration ratio of bupivacaine in plasma was 0.29, and in the placenta was 0.63. The amnion contained the highest bupivacaine concentration: threefold higher in the maternal and 11-fold higher than in the fetal plasma. At 4 hr after dosing, bupivacaine was no longer detectable in any maternal and fetal samples, whereas 3'-hydroxybupivacaine was still present in all tissues except the fetal plasma and heart. These data indicate that a considerable amount of bupivacaine is taken up by both sides of the placenta, as well as the amnion and myometrium. 3'-Hydroxybupivacaine was present in all tissues except the fetal plasma and heart samples, even after the parent compound became no longer detectable.

PMID:11020763 Morishima HO et al; Anesthesiology. 93 (4): 1069-74 (2000).


Bupivacaine hydrochloride is principally metabolized to pipecolylxylidine (PPX) by N-dealkylation, probably in the liver. Bupivacaine is excreted in urine as small amounts of PPX, unchanged drug (5%), and other metabolites as yet unidentified.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 3335


5.7 Biological Half-Life

2.7 hours in adults and 8.1 hours in neonates. Bupivacaine applied together with [meloxicam] for postsurgical analgesia had a median half-life of 15-17 hours, depending on dose and application site.


Pregnant rats received an intravenous infusion of bupivacaine at a rate of 0.33 mg. kg-1. min-1 over a period of 15 min. The fetuses were delivered either at the end of infusion or at 2 or 4 hr after dosing. Maternal and fetal blood and tissue samples were obtained for the assays of bupivacaine and its metabolites using capillary gas chromatography-mass spectrometry. The elimination half-life of bupivacaine was 37.7 min.

PMID:11020763 Morishima HO et al; Anesthesiology. 93 (4): 1069-74 (2000).


The elimination half-life of bupivacaine hydrochloride is 1.5-5.5 hours in adults and 8.1 hours in neonates.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 3335


5.8 Mechanism of Action

Local anesthetics such as bupivacaine 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. Bupivacaine prevents depolarization by bindng to the intracellular portion of sodium channels and blocking sodium ion influx into neurons. In general, the progression of anesthesia is related to the diameter, myelination and conduction velocity of affected nerve fibers. Clinically, the order of loss of nerve function is as follows: (1) pain, (2) temperature, (3) touch, (4) proprioception, and (5) skeletal muscle tone. The analgesic effects of Bupivicaine are thought to potentially be due to its binding to the prostaglandin E2 receptors, subtype EP1 (PGE2EP1), which inhibits the production of prostaglandins, thereby reducing fever, inflammation, and hyperalgesia.


Local anesthetics 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. In general, the progression of anesthesia is related to the diameter, myelination, and conduction velocity of affected nerve fibers. Clinically, the order of loss of nerve function is as follows: (1) pain, (2) temperature, (3) touch, (4) proprioception, and (5) skeletal muscle tone.

US Natl Inst Health; DailyMed. Current Medication Information for BUPIVACAINE HYDROCHLORIDE, injection, solution; BUPIVACAINE HYDROCHLORIDE WITH EPINEPHRINE, injection, solution (August 2008). Available from, as of February 22, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=8962


API SUPPLIERS

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01

Nortec Quimica

Brazil

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02

LGM Pharma

U.S.A

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Virtual BoothLGM Pharma accelerates & optimizes the new product pathway from early development through commercialization.

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03

Moehs Iberica

Spain

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Virtual BoothMoehs Group, a reference company in the production of pharmaceutical active ingredients.

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04

Shandong Chenghui Shuangda Pharmac...

China

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05

Jiangsu Hengrui Medicine

China

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Jiangsu Hengrui Medicine

China

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06

Dishman Carbogen Amcis

India

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Dishman Carbogen Amcis

India

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07

MSN Laboratories

India

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MSN Laboratories

India

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Cambrex Corporation

U.S.A

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Cambrex Corporation

U.S.A

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Siegfried AG

Switzerland

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Siegfried AG

Switzerland

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Ishita API

India

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D6 D8, SY.NO. 234\/2,234\/3,","city":"TURKAPALLY(V),SHAMEERPET, HYDERABAD","supplier":"USP","supplierCountry":"INDIA","foreign_port":"WASHINGTON, DULLES I","customer":"UNITED STATES PHARMACOPEIA - INDIA PRIVATE LIMITED","customerCountry":"INDIA","quantity":"0.00","actualQuantity":"0.0003","unit":"KGS","unitRateFc":"910000","totalValueFC":"281.1","currency":"USD","unitRateINR":"77806066.7","date":"01-Aug-2024","totalValueINR":"23341.82","totalValueInUsd":"281.1","indian_port":"Hyderabad Air","hs_no":"29333990","bill_no":"4827338","productDescription":"Re-Import","marketType":"REGULATED MARKET","country":"INDIA","selfForZScoreResived":"Pharma Grade","supplierPort":"WASHINGTON, DULLES I","supplierAddress":"7135 ENGLISH MUFFIN WAY FREDERICK,MD 21704 USA Frederick, , United States United States","customerAddress":"P.NO. D6 D8, SY.NO. 234\/2,234\/3,"}]
08-Jan-2021
30-Aug-2024
KGS
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Average Price (USD/KGS)

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country Total Quantity
(KGS)
Average Price
(USD/KGS)
Number of Transactions

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INTERMEDIATES SUPPLIERS

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01

26th North American ISSX
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26th North American ISSX
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CAS Number : 110-52-1

End Use API : Bupivacaine

About The Company : Maisuriya Pharma Solutions is a research-driven & technology-oriented company. Continuous innovations & improvement are the lifeblood of our business. Our major...

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