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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

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 Formula	C₁₈H₂₈N₂O
Molecular Weight	288.4 g/mol
XLogP3	3.4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	5
Exact Mass	288.220163521 g/mol
Monoisotopic Mass	288.220163521 g/mol
Topological Polar Surface Area	32.3 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	321
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 6
Drug Name	Exparel
PubMed Health	Bupivacaine Liposome (Injection)
Drug Classes	Anesthetic, Local
Drug Label	EXPAREL 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 Ingredient	Bupivacaine
Dosage Form	Injectable, liposomal
Route	Injection
Strength	266mg/20ml (13.3mg/ml)
Market Status	Prescription
Company	Pacira Pharms

2 of 6
Drug Name	Marcaine
PubMed Health	Bupivacaine/Epinephrine (Injection)
Drug Classes	Anesthetic, Amino Amide Combination, Anesthetic, Local
Drug Label	MarcaineBupivacaine 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 Ingredient	Bupivacaine hydrochloride
Dosage Form	Injectable
Route	Spinal
Strength	0.75%
Market Status	Prescription
Company	Hospira

3 of 6
Drug Name	Sensorcaine
PubMed Health	Bupivacaine (Injection)
Drug Classes	Anesthetic, Local
Drug Label	Sensorcaine (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 Ingredient	Bupivacaine hydrochloride; epinephrine bitartrate
Dosage Form	Injectable
Route	Spinal; Injection
Strength	0.5%; 0.0091mg/ml; 0.75%; 0.25%
Market Status	Prescription
Company	Fresenius Kabi Usa

4 of 6
Drug Name	Exparel
PubMed Health	Bupivacaine Liposome (Injection)
Drug Classes	Anesthetic, Local
Drug Label	EXPAREL 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 Ingredient	Bupivacaine
Dosage Form	Injectable, liposomal
Route	Injection
Strength	266mg/20ml (13.3mg/ml)
Market Status	Prescription
Company	Pacira Pharms

5 of 6
Drug Name	Marcaine
PubMed Health	Bupivacaine/Epinephrine (Injection)
Drug Classes	Anesthetic, Amino Amide Combination, Anesthetic, Local
Drug Label	MarcaineBupivacaine 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 Ingredient	Bupivacaine hydrochloride
Dosage Form	Injectable
Route	Spinal
Strength	0.75%
Market Status	Prescription
Company	Hospira

6 of 6
Drug Name	Sensorcaine
PubMed Health	Bupivacaine (Injection)
Drug Classes	Anesthetic, Local
Drug Label	Sensorcaine (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 Ingredient	Bupivacaine hydrochloride; epinephrine bitartrate
Dosage Form	Injectable
Route	Spinal; Injection
Strength	0.5%; 0.0091mg/ml; 0.75%; 0.25%
Market Status	Prescription
Company	Fresenius 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/

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

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 C_max of 54 33 ng/mL, a median T_max 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.

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.

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.

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.

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.

API SUPPLIERS

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USDMF

01

Nortec Quimica Sa

Brazil

Biotech Showcase

Not Confirmed

Nortec Quimica is the largest API manufacturer in Latin America.

Contact Supplier

Brazil

Virtual Booth

Digital Content

BUPIVACAINE

GDUFA

DMF Review : Complete

Rev. Date : 2019-03-25

Pay. Date : 2018-11-13

DMF Number : 33285

Submission : 2018-11-21

Status : Active

Type : II

02

Cambrex Karlskoga Ab

U.S.A

Biotech Showcase

Not Confirmed

03

Dishman Carbogen Amcis Ltd

India

Switzerland

BIO Partnering at JPM

Not Confirmed

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KDMF

01

Dishman Carbogen Amcis

India

Biotech Showcase

Not Confirmed

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NDC API

01

Nortec Quimica SA

Brazil

BIO Partnering at JPM

Not Confirmed

Nortec Quimica is the largest API manufacturer in Latin America.

Contact Supplier

Brazil

Virtual Booth

Digital Content

BUPIVACAINE

NDC Package Code : 59014-0053

Start Marketing Date : 2018-04-13

End Marketing Date : 2025-12-31

Dosage Form (Strength) : POWDER (25kg/25kg)

Marketing Category : BULK INGREDIENT

Portfolio PDF

Product Web Link

Virtual Booth

Switzerland

Biotech Showcase

Not Confirmed

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Listed Suppliers

01

Nortec Quimica

Brazil

BIO Partnering at JPM

Not Confirmed

Nortec Quimica is the largest API manufacturer in Latin America.

Contact Supplier

Brazil

Virtual Booth

Digital Content

Bupivacaine

About the Company : Nortec Química stands as the largest manufacturer of Active Pharmaceutical Ingredients (IFAs) in Latin America, embarking on its mission to ensure the availability of quality medi...

Nortec Química stands as the largest manufacturer of Active Pharmaceutical Ingredients (IFAs) in Latin America, embarking on its mission to ensure the availability of quality medicines with IFAs developed in Brazil. The company's approach involves leveraging the expertise of major National Research Centers and tapping into the experience of the Brazilian Chemical and Petrochemical Industry. Nortec Química plays a significant role in the Brazilian pharmaceutical landscape and the Unified Health System (SUS), producing APIs for branded, generic, and similar medicines, as well as medicines dedicated to addressing neglected diseases.

02

LGM Pharma

U.S.A

BIO Partnering at JPM

Not Confirmed

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

Contact Supplier

U.S.A

Virtual Booth

Digital Content

Bupivacaine

About the Company : LGM Pharma is a global leader in sourcing hard-to-find APIs and intermediates for the pharmaceutical and biotech industries. LGM is also a full service CDMO providing formulation, ...

LGM Pharma is a global leader in sourcing hard-to-find APIs and intermediates for the pharmaceutical and biotech industries. LGM is also a full service CDMO providing formulation, analytical method development and testing, and commercial manufacturing. LGM Pharma offers custom API synthesis, analytical development, and regulatory services. With a network of over 300 accredited CGMP manufacturing partners, LGM provides unparalleled supply chain security. And, with over 100,000 square feet of FDA-inspected cGMP manufacturing and warehouse capacity, LGM Pharma provides a one-stop solution for solid dose, powder, semi-solid and liquid drugs.

03

Shandong Chenghui Shuangda Pharmace...

China

CPhI China

Attending

China's leading API and intermediate manufacturer, offering CMO/CDMO services and exports to 70+ countries, enhancing global health.

Contact Supplier

China

Virtual Booth

Digital Content

Bupivacaine

About the Company : Shandong Chenghui Shuangda Pharmaceutical Co., Ltd. is specialized in R&D and production of APIs and advanced intermediates. With 22 years of production experience,the company has ...

Shandong Chenghui Shuangda Pharmaceutical Co., Ltd. is specialized in R&D and production of APIs and advanced intermediates. With 22 years of production experience,the company has 6 workshops and 9 production lines which has 100t/month production capacity.The company is committed to maintain the standards with continuous improvements to the current standards throughout the product lifecycle.The main products include local anesthetic drugs, antiviral drugs, cardiovascular and cerebrovascular drugs, antitumor drugs, gastrointestinal drugs, diabetic drugs, veterinary drugs, and CDMO products.

04

Cambrex Corporation

U.S.A

BIO Partnering at JPM

Not Confirmed

05

Cerata Pharmaceuticals

India

BIO Partnering at JPM

Not Confirmed

06

Dishman Carbogen Amcis

BIO Partnering at JPM

Not Confirmed

Only 10 entries up to this point, click to access all

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API Reference Price

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,","city":"HYDERABAD","supplier":"MOEHS IBERICA","supplierCountry":"SPAIN","foreign_port":"NA","customer":"EUGIA PHARMA SPECIALITIES ","customerCountry":"INDIA","quantity":"400.00","actualQuantity":"400","unit":"KGS","unitRateFc":"295","totalValueFC":"119064","currency":"USD","unitRateINR":"24410.5","date":"08-Aug-2023","totalValueINR":"9862827.04","totalValueInUsd":"119064","indian_port":"HYDERABAD AIR","hs_no":"29333990","bill_no":"0","productDescription":"API","marketType":"REGULATED MARKET","country":"SPAIN","selfForZScoreResived":"Pharma Grade","supplierPort":"NA","supplierAddress":"","customerAddress":"PLOT NO.2, MAITHRIVIHAR,,AMEERPET, ,"},{"dataSource":"API Import","activeIngredients":"","year":"2023","qtr":"Q3","strtotime":1691519400,"product":"BUPIVACAINE HYDROCHLORIDE (BATCH:0000141175,0000141178)","address":"PLOT NO.B3,B4&B5 PT SIPCOT,INDUSTR","city":"SRIPERUMPUDUR,TAMIL NADU","supplier":"PFIZER SERVICE COMPANY 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CESAR MARTINELI I BRUNET 12A C\/ROMA, 8-12 08191-RUBI-BCN 08191 RUBI Barcelona, SPAIN SPAIN","customerAddress":"CLARIS CORPORATE HEAD QUARTERS,"},{"dataSource":"API Import","activeIngredients":"","year":"2023","qtr":"Q4","strtotime":1697135400,"product":"75630 BUPIVACAINE HYDROCHLORIDE CAS: 73360-54-0 NDC: 52932-0729 BATCH NO: 78","address":"PLOT No.30, GALAXY ,","city":"BENGALURU","supplier":"MOEHS IBERICA","supplierCountry":"SPAIN","foreign_port":"BARCELONA","customer":"STERISCIENCE SPECIALTIES PRIVATE ","customerCountry":"INDIA","quantity":"125.00","actualQuantity":"125","unit":"KGS","unitRateFc":"590","totalValueFC":"74565.8","currency":"USD","unitRateINR":"49648.5","date":"13-Oct-2023","totalValueINR":"6206062.5","totalValueInUsd":"74565.8","indian_port":"Bangalore Air","hs_no":"29349990","bill_no":"8274991","productDescription":"API","marketType":"REGULATED MARKET","country":"SPAIN","selfForZScoreResived":"Pharma Grade","supplierPort":"BARCELONA","supplierAddress":"C\/. CESAR MARTINELL I BRUNET12A CORRESPOND C\/ROMA 8-12 08191-RUBI-BCN 08191 RUBI ES","customerAddress":"PLOT No.30, GALAXY ,"},{"dataSource":"API Import","activeIngredients":"","year":"2023","qtr":"Q4","strtotime":1698258600,"product":"BUPIVACAINE HYDROCHLORIDE","address":"PLOT NO.2, MAITHRIVIHAR,","city":"HYDERABAD, AP.","supplier":"MOEHS IBERICA","supplierCountry":"SPAIN","foreign_port":"BARCELONA","customer":"EUGIA PHARMA SPECIALITIES ","customerCountry":"INDIA","quantity":"600.00","actualQuantity":"600","unit":"KGS","unitRateFc":"295","totalValueFC":"190016.6","currency":"EUR","unitRateINR":"26358.3","date":"26-Oct-2023","totalValueINR":"15814950","totalValueInUsd":"190016.6","indian_port":"Hyderabad Air","hs_no":"29333990","bill_no":"8467713","productDescription":"API","marketType":"REGULATED MARKET","country":"SPAIN","selfForZScoreResived":"Pharma Grade","supplierPort":"BARCELONA","supplierAddress":"POLIGONO INDUSTRIAL RUBI SUR CESARMARTINELL I BRUNET 12A 08191,RUBI (BARCELONA) \/\/ C\/ CESAR MARTINELL I Spain","customerAddress":"PLOT NO.2, MAITHRIVIHAR,"},{"dataSource":"API Import","activeIngredients":"","year":"2023","qtr":"Q4","strtotime":1698777000,"product":"4902371 BUPIVACAINE BASE 100 G * 3 BATCHES","address":"221, GOREGAON-MULUND LINK ROAD,","city":"BHANDUP WEST, MUMBAI","supplier":"CAMBREX CORPORATION","supplierCountry":"SWEDEN","foreign_port":"GOTHENBURG","customer":"RUBICON RESEARCH","customerCountry":"INDIA","quantity":"0.30","actualQuantity":"0.3","unit":"KGS","unitRateFc":"7500","totalValueFC":"2275.1","currency":"USD","unitRateINR":"631500","date":"01-Nov-2023","totalValueINR":"189450","totalValueInUsd":"2275.1","indian_port":"Bombay Air","hs_no":"29339990","bill_no":"8566137","productDescription":"API","marketType":"REGULATED MARKET","country":"SWEDEN","selfForZScoreResived":"Pharma Grade","supplierPort":"GOTHENBURG","supplierAddress":"SE-691 85 KARLSKOGASWEDENSDNF SE","customerAddress":"221, GOREGAON-MULUND LINK ROAD,"},{"dataSource":"API Import","activeIngredients":"","year":"2023","qtr":"Q4","strtotime":1703010600,"product":"BUPIVACAINE BASE (BATCH#0000107038)(TOTAL 0.500KG) - 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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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Drugs in Development

FULL SCREEN VIEW Click here to open all results in a new tab [this preview display 10 results]

INTERMEDIATES SUPPLIERS

01

Maisuriya Pharma Solutions

India

Pharma, Lab & Chemical Expo

Not Confirmed

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FDF Dossiers

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FDA Orange Book

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Europe

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South Africa

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Listed Dossiers

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Related Excipient Companies

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Excipients by Applications

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Topical

Parenteral

01

DKSH

Switzerland

Pharma, Lab & Chemical Expo

Not Confirmed

DKSH is your trusted partner for companies looking to grow their business in Asia & beyond.

Dosage Form : Capsule, Emulsion, Solution, Suspension, Tablet

Grade : Parenteral, Oral, Topical

Category : Fillers, Diluents & Binders, Lubricants & Glidants, Parenteral, Topical

Brand Name : CAPTEX 300

Application : Fillers, Diluents & Binders, Lubricants & Glidants, Parenteral, Topical

Excipient Details : Captex 300 is used in parenteral solutions and suspensions, topical emulsions, and as filler and lubricant in capsules and tablets.

Pharmacopoeia Ref : EP, USP/NF, JP, US FDA

Technical Specs : LOW C6

Ingredient(s) : Glyceryl Tricaprylate Excipient

02

DKSH

Switzerland

Pharma, Lab & Chemical Expo

Not Confirmed

DKSH is your trusted partner for companies looking to grow their business in Asia & beyond.

Dosage Form : Solution, Suspension

Grade : Parenteral

Category : Parenteral

Brand Name : CAPTEX 355 INJ

Application : Parenteral

Excipient Details : Captex 355 INJ is used in parenteral solutions and suspensions.

Pharmacopoeia Ref : EP, USP/NF, JP, US FDA

Technical Specs : INJ Grade

Ingredient(s) : Glyceryl Tricaprylate Excipient

03

DKSH

Switzerland

Pharma, Lab & Chemical Expo

Not Confirmed

DKSH is your trusted partner for companies looking to grow their business in Asia & beyond.

Dosage Form : Capsule, Emulsion, Solution, Suspension, Tablet

Grade : Parenteral, Oral, Topical

Category : Fillers, Diluents & Binders, Lubricants & Glidants, Parenteral, Topical

Brand Name : CAPTEX 8000

Application : Fillers, Diluents & Binders, Lubricants & Glidants, Parenteral, Topical

Excipient Details : Captex 8000 is used in parenteral solutions and suspensions, topical emulsions, and as filler and lubricant in capsules and tablets.

Pharmacopoeia Ref : JP, US FDA

Technical Specs : N/A

Ingredient(s) : Glyceryl Tricaprylate Excipient

04

DKSH

Switzerland

Pharma, Lab & Chemical Expo

Not Confirmed

DKSH is your trusted partner for companies looking to grow their business in Asia & beyond.

Dosage Form : Capsule, Emulsion, Solution, Suspension, Tablet

Grade : Parenteral, Oral, Topical

Category : Fillers, Diluents & Binders, Lubricants & Glidants, Parenteral, Topical

Brand Name : CAPTEX INJ 8000

Application : Fillers, Diluents & Binders, Lubricants & Glidants, Parenteral, Topical

Excipient Details : Captex INJ 8000 is used in topical emulsions, parenteral suspensions and solutions, and as a lubricant and filler in tablets and capsules.

Pharmacopoeia Ref : JP, US FDA

Technical Specs : N/A

Ingredient(s) : Glyceryl Tricaprylate Excipient

05

Nippon Fine Chemical

Japan

Pharma, Lab & Chemical Expo

Not Confirmed

Lubricants & Glidants

Fillers, Diluents & Binders

Solubilizers

Co-Processed Excipients

Surfactant & Foaming Agents

Emulsifying Agents

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US Medicaid Prescriptions

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Finished Drug Prices

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APIs

Bupivacaine (10 kg - 100 kg) API needed in the U.S.A [ENA20880]

A CDMO that focuses on development and manufacturing of various APIs and finished formulations is looking for suppliers of Bupivacaine (10 kg - 100 kg) API for commercial purposes. The suppliers must support this enquiry with USDMF, GMP & CoA .

18 Oct 2024

Various APIs needed in Egypt [ENA17016]

A company that focuses on research, development & manufacturing of tablets, capsules, oral liquids and injectables is looking for suppliers of Various APIs for development purposes. The suppliers must support this enquiry with GMP & CoA. 1. Bupivacaine API 2. Meloxicam API

02 May 2023

Various APIs needed in India [ENA15188]

A company that focuses on the manufacturing of ampoules, dry powder, lyophilized and liquid products is looking for suppliers of Various APIs for commercial purpose. The suppliers must support this enquiry with DMF, GMP & CoA. 1. BP/ USP Grade Tranexamic Acid (5 kg) API 2. BP/ USP Grade Iron Sucrose (1 kg) API 3. BP/ USP Grade Hyoscine Butyl Bromide (500 g) API 4. BP/ USP Grade Ketorolac Tromethamine (500 g) API 5. BP/ USP Grade Bupivacaine (2 kg) API 6. BP/ USP Grade Dextrose (1 kg) API

01 Oct 2022

Various APIs needed in Bangladesh [ENA12269]

A company based in Bangladesh that provides world-class solutions to the local pharmaceutical industry & deals in active pharmaceutical ingredients and excipients is looking for suppliers of Various APIs. 1. Baricitinib API 2. Bupivacaine API 3. Fidaxomicin API 4. Ingenol Mebutate API 5. Lorcaserin HCl API

30 Dec 2021

USP grade Labetalol, Lidocaine and other APIs needed in the United States [ENA05176]

A healthcare company operates specialty pharmacies focused on conditions such as diabetes, HIV, hepatitis C, and rheumatological and gastrointestinal diseases is looking for APIs mentioned below. The supplier must support this enquiry with USFDA and USDMF. 1. Labetalol 2. Lidocaine 3. Bupivacaine 4. Sodium Chloride 5. Sodium Bicarbonate 6. Ketorolac.

17 Sep 2019

Enquiry// Various Injectable grade APIs needed in India (Part 1/4) [ENA00697]

A pharmaceutical manufacturing company based in India and catering to domestic and international markets is looking for a number of APIs to be used at their Small Volume Parentals' manufacturing facility. 1. Acyclovir 2. Adenosine 3. Adrenaline 4. Alprostadil 5. Amikacin 6. Aminocaproic Acid 7. Aminophylline 8. Amiodarone Sterile Concentrate 9. Amphotericin-B 10. Atracurium Besylate 11. Atropine Sulfate 12. Atropine Sulphate ( Veterinary Use) 13. Betamethasone 14. Bupivacaine 15. Bupivacaine Heavy 16. Bupivacaine Hydrochloride 17. Calcium Gluconate 18. Capreomycin 19. Carboprost Tromethamine 20. Chloramphenicol Sodium Succinate 21. Chloroquine Phosphate 22. Chlorpheniramine 23. Clindamycin 24. Colistimethate Sodium 25. Dalteparin Sodium 26. Dexamethasone 27. Dextrose 28. Diazepam 29. Diclofenac 30. Dicyclomine HCl 31. Digoxin 32. Diltiazem 33. Dimercaprol 34. Dipyridamole 35. Dobutamine

07 Feb 2018

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FDF DOSSIERS

BUPIVACAINE

Pharma, Lab & Chemical Expo

Not Confirmed

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US Exclusivities

01

INNOCOLL

BUPIVACAINE

BUPIVACAINE; MELOXICAM

Pharma, Lab & Chemical Expo

Not Confirmed

10

PACIRA PHARMS INC

BUPIVACAINE

Pharma, Lab & Chemical Expo

Not Confirmed

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REF. STANDARDS & IMPURITIES

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USP

Others

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ABOUT THIS PAGE

Bupivacaine Manufacturers

A Bupivacaine manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Bupivacaine, including repackagers and relabelers. The FDA regulates Bupivacaine manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Bupivacaine API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Bupivacaine manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Bupivacaine Suppliers

A Bupivacaine supplier is an individual or a company that provides Bupivacaine active pharmaceutical ingredient (API) or Bupivacaine finished formulations upon request. The Bupivacaine suppliers may include Bupivacaine API manufacturers, exporters, distributors and traders.

click here to find a list of Bupivacaine suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Bupivacaine USDMF

A Bupivacaine DMF (Drug Master File) is a document detailing the whole manufacturing process of Bupivacaine active pharmaceutical ingredient (API) in detail. Different forms of Bupivacaine DMFs exist exist since differing nations have different regulations, such as Bupivacaine USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Bupivacaine DMF submitted to regulatory agencies in the US is known as a USDMF. Bupivacaine USDMF includes data on Bupivacaine's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Bupivacaine USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Bupivacaine suppliers with USDMF on PharmaCompass.

Bupivacaine KDMF

In Korea, the Ministry of Food and Drug Safety (MFDS) is in charge of regulating pharmaceutical products and services.

Pharmaceutical companies submit a Bupivacaine Drug Master File in Korea (Bupivacaine KDMF) to the MFDS, which includes comprehensive information about the production, processing, facilities, materials, packaging, and testing of Bupivacaine. The MFDS reviews the Bupivacaine KDMF as part of the drug registration process and uses the information provided in the Bupivacaine KDMF to evaluate the safety and efficacy of the drug.

After submitting a Bupivacaine KDMF to the MFDS, the registered manufacturer can provide importers or distributors with the registration number without revealing confidential information to Korean business partners. Applicants seeking to register their Bupivacaine API can apply through the Korea Drug Master File (KDMF).

click here to find a list of Bupivacaine suppliers with KDMF on PharmaCompass.

Bupivacaine NDC

National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Bupivacaine as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Bupivacaine API and other APIs are published in this directory by the FDA.

Unfinished drugs

The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

Pharmaceutical companies that manufacture Bupivacaine as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

Compounded drug products

The NDC directory also contains data on finished compounded human drug products that contain Bupivacaine and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Bupivacaine NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of Bupivacaine suppliers with NDC on PharmaCompass.

Bupivacaine GMP

Bupivacaine Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Bupivacaine GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Bupivacaine GMP manufacturer or Bupivacaine GMP API supplier for your needs.

Bupivacaine CoA

A Bupivacaine CoA (Certificate of Analysis) is a formal document that attests to Bupivacaine's compliance with Bupivacaine specifications and serves as a tool for batch-level quality control.

Bupivacaine CoA mostly includes findings from lab analyses of a specific batch. For each Bupivacaine CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Bupivacaine may be tested according to a variety of international standards, such as European Pharmacopoeia (Bupivacaine EP), Bupivacaine JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Bupivacaine USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.

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ACTIVE PHARMA INGREDIENTS

13 API Suppliers

6 USDMF

1 KDMF

6 NDC API

11 Listed Suppliers

$ API Reference Price

DEVELOPMENTS

41 Drugs in Development

INTERMEDIATES

1 Intermediates Suppliers

FINISHED DOSAGE FORMULATIONS

108 FDF Dossiers

9 FDA Orange Book

79 Europe

4 South Africa

16 Listed Dossiers

RELATED EXCIPIENT COMPANIES

5 DKSH

2 Nippon Fine Chemical

EXCIPIENTS BY APPLICATIONS

5 Topical

5 Parenteral

4 Lubricants & Glidants

4 Fillers, Diluents & Binders

1 Solubilizers

1 Co-Processed Excipients

1 Surfactant & Foaming Agents

1 Emulsifying Agents

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1 US Medicaid Prescriptions

78 Finished Drug Prices

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104 US Patents

13 US Exclusivities

REF. STANDARDS & IMPURITIES

2 USP

3 Others

ACTIVE PHARMA INGREDIENTS

API REF. PRICE (USD/KG)

$ 898

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