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Chemistry

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Also known as: 179324-69-7, Velcade, Ps-341, Ldp-341, Bortezomib (ps-341), Radiciol

Molecular Formula

C₁₉H₂₅BN₄O₄

Molecular Weight

384.2 g/mol

InChI Key

GXJABQQUPOEUTA-RDJZCZTQSA-N

FDA UNII

69G8BD63PP

A pyrazine and boronic acid derivative that functions as a reversible PROTEASOME INHIBITOR. It is used as an ANTINEOPLASTIC AGENT in the treatment of MULTIPLE MYELOMA and MANTLE CELL LYMPHOMA.

Bortezomib is a Proteasome Inhibitor. The mechanism of action of bortezomib is as a Proteasome Inhibitor.

1 2D Structure

Bortezomib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(1R)-3-methyl-1-[[(2S)-3-phenyl-2-(pyrazine-2-carbonylamino)propanoyl]amino]butyl]boronic acid

2.1.2 InChI

InChI=1S/C19H25BN4O4/c1-13(2)10-17(20(27)28)24-18(25)15(11-14-6-4-3-5-7-14)23-19(26)16-12-21-8-9-22-16/h3-9,12-13,15,17,27-28H,10-11H2,1-2H3,(H,23,26)(H,24,25)/t15-,17-/m0/s1

2.1.3 InChI Key

GXJABQQUPOEUTA-RDJZCZTQSA-N

2.1.4 Canonical SMILES

B(C(CC(C)C)NC(=O)C(CC1=CC=CC=C1)NC(=O)C2=NC=CN=C2)(O)O

2.1.5 Isomeric SMILES

B([C@H](CC(C)C)NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)C2=NC=CN=C2)(O)O

2.2 Other Identifiers

2.2.1 UNII

69G8BD63PP

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 341, Ps

2. Ldp 341

3. Ldp-341

4. Ldp341

5. Ps 341

6. Ps-341

7. Ps341

8. Velcade

2.3.2 Depositor-Supplied Synonyms

1. 179324-69-7

2. Velcade

3. Ps-341

4. Ldp-341

5. Bortezomib (ps-341)

6. Radiciol

7. Ps 341

8. ((r)-3-methyl-1-((s)-3-phenyl-2-(pyrazine-2-carboxamido)propanamido)butyl)boronic Acid

9. Dpba

10. Ldp 341

11. Bortezomib Accord

12. Nsc-681239

13. [(1r)-3-methyl-1-[[(2s)-3-phenyl-2-(pyrazine-2-carbonylamino)propanoyl]amino]butyl]boronic Acid

14. Bortezomib (velcade)

15. N-[(1r)-1-(dihydroxyboryl)-3-methylbutyl]-n-(pyrazin-2-ylcarbonyl)-l-phenylalaninamide

16. Mln-341

17. [(1r)-3-methyl-1-[[(2s)-1-oxo-3-phenyl-2-[(pyrazinylcarbonyl)amino]propyl]amino]butyl]boronic Acid

18. Mg 341

19. Mg-341

20. Boronic Acid, B-[(1r)-3-methyl-1-[[(2s)-1-oxo-3-phenyl-2-[(2-pyrazinylcarbonyl)amino]propyl]amino]butyl]-

21. Nsc 681239

22. 69g8bd63pp

23. Chembl325041

24. Peptide Boronate

25. Chebi:52717

26. Nsc681239

27. Ncgc00242506-02

28. S1013

29. Dsstox_cid_20980

30. Dsstox_rid_79609

31. N-[(1r)-1-(dihydroxyboranyl)-3-methylbutyl]-nalpha-(pyrazin-2-ylcarbonyl)-l-phenylalaninamide

32. Dsstox_gsid_40980

33. Pyz-phe-boroleu

34. (r)-3-methyl-1-((s)-3-phenyl-2-(pyrazine-2-carboxamido)propanamido)butylboronic Acid

35. ((1r)-3-methyl-1-(((2s)-3-phenyl-2-((pyrazinylcarbonyl)amino)propanoyl)amino)butyl)boronic Acid

36. [(1r)-3-methyl-1-({(2s)-3-phenyl-2-[(pyrazin-2-ylcarbonyl)amino]propanoyl}amino)butyl]boronic Acid

37. Boronic Acid, ((1r)-3-methyl-1-(((2s)-1-oxo-3-phenyl-2-((pyrazinylcarbonyl)amino)propyl)amino)butyl)-

38. N-((1s)-1-benzyl-2-(((1r)-1-(dihydroxyboranyl)-3-methylbutyl)amino)-2-oxoethyl)pyrazinecarboxamide

39. Velcade (tn)

40. Cas-179324-69-7

41. Ps 341 (pharmaceutical)

42. Unii-69g8bd63pp

43. Brotezamide

44. Proscript Boronic Acid

45. Bortezomib [usan:inn:ban]

46. Hsdb 7666

47. Bortezomib Hydrate

48. Bortezomib,velcade

49. Lpd 341

50. Lpd-341

51. Ncgc00168751-01

52. Ncgc00181022-01

53. Bortezomib- Bio-x

54. Bortezomib [usan]

55. Mfcd09056737

56. Velcade (millenium)

57. 3mg0

58. Bortezomib [mi]

59. Bortezomib [inn]

60. Bortezomib [jan]

61. Bortezomib [hsdb]

62. Bortezomib [vandf]

63. Bortezomib [mart.]

64. Bortezomib [who-dd]

65. Mls004774142

66. Bortezomib (jan/usan/inn)

67. Bortezomib [ema Epar]

68. Schembl192129

69. Gtpl6391

70. Bortezomib [orange Book]

71. Bortezomib Hydrate [jan]

72. Dtxsid3040980

73. Tox21_112630

74. Tox21_112672

75. Bdbm50069989

76. Nsc756655

77. Akos015909706

78. Tox21_112672_1

79. Zinc169746649

80. Am81235

81. Ccg-268449

82. Cs-1039

83. Db00188

84. Nsc-756655

85. Bortezomib (velcade,mg-341,ps-341)

86. Ncgc00242506-01

87. Ncgc00242506-06

88. Ncgc00242506-07

89. As-15721

90. Bb164258

91. Hy-10227

92. Nci60_029010

93. Smr003500787

94. B5741

95. Sw208077-3

96. A18332

97. D03150

98. Ab01273951-01

99. Ab01273951-02

100. Ab01273951_03

101. 324b697

102. Q419319

103. Sr-01000939863

104. Sr-01000939863-2

105. Brd-k88510285-001-02-0

106. ((r)-3-methyl-1-((s)-3-phenyl-2-(pyrazine-2-carboxamido)propanamido)butyl)boronicacid

107. (r)-3-methyl-1-((s)-3-phenyl-2-(pyrazine-6-carboxamido)propanamido)butylboronic Acid

108. (1r)-3-methyl-1-({(2s)-3-phenyl-2-[(2-pyrazinylcarbonyl)amino]propanoyl}amino)butylboronic Acid, Aldrichcpr

109. (r)-3-methyl-1-((s)-3-phenyl-2-(pyrazine-2-carboxamido)propanamido)butan-2-ylboronic Acid

110. [(1r)-3-methyl-1-[[(2s)-1-oxo-3-phenyl-2-[(pyrazinylcarbonyl)amino]propyl]amino]-butyl]boronic Acid

111. 1610526-91-4

112. Boronic Acid, (3-methyl-1-((1-oxo-3-phenyl-2-((pyrazinylcarbonyl)amino)propyl)amino)butyl)-, (s-(r*,s*))-

113. Boronic Acid, [(1(r)-3-methyl-1-[[(2s)-1-oxo-3-phenyl-2-[(pyrazinylcarbonyl)amino]propyl]amino]butyl]-

114. N-((1s)-1-benzyl-2-(((1r)-1-(dihydroxyboranyl)-3-methylbutyl)amino)2-oxoethylpyrazinecarboxamide

115. N-[(1r)-1-(dihydroxyboranyl)-3-methylbutyl]-n(alpha)-(pyrazin-2-ylcarbonyl)-l-phenylalaninamide

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₂₅BN₄O₄
Molecular Weight	384.2 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	9
Exact Mass	384.1968855 g/mol
Monoisotopic Mass	384.1968855 g/mol
Topological Polar Surface Area	124 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	500
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
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 2
Drug Name	Velcade
PubMed Health	Bortezomib (Injection)
Drug Classes	Antineoplastic Agent
Drug Label	VELCADE (bortezomib) for Injection is an antineoplastic agent available for intravenous injection or subcutaneous use. Each single use vial contains 3.5 mg of bortezomib as a sterile lyophilized powder. Inactive ingredient: 35 mg mannitol, USP.Bort...
Active Ingredient	Bortezomib
Dosage Form	Injectable
Route	Intravenous, subcutaneous
Strength	3.5mg/vial
Market Status	Prescription
Company	Millennium Pharms

2 of 2
Drug Name	Velcade
PubMed Health	Bortezomib (Injection)
Drug Classes	Antineoplastic Agent
Drug Label	VELCADE (bortezomib) for Injection is an antineoplastic agent available for intravenous injection or subcutaneous use. Each single use vial contains 3.5 mg of bortezomib as a sterile lyophilized powder. Inactive ingredient: 35 mg mannitol, USP.Bort...
Active Ingredient	Bortezomib
Dosage Form	Injectable
Route	Intravenous, subcutaneous
Strength	3.5mg/vial
Market Status	Prescription
Company	Millennium Pharms

4.2 Therapeutic Uses

Antineoplastic Agents; Protease Inhibitors

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

Bortezomib injection is indicated for the treatment of patients with multiple myeloma who have received at least 1 prior therapy. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for Velcade (Bortezomib) (January 2008). Available from, as of November 25, 2008: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=6358

Bortezomib injection is indicated for the treatment of patients with mantle cell lymphoma who have received at least 1 prior therapy. /Included in US product label/

4.3 Drug Warning

Known hypersensitivity to bortezomib, boron, or mannitol.

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 929

Bortezomib mainly causes sensory peripheral neuropathy, but severe motor peripheral neuropathy also has been reported. In the phase III trial, peripheral neuropathy occurred in 36% of patients receiving bortezomib and 9% of patients receiving dexamethasone. Grade 3 or 4 peripheral neuropathy occurred in 7 or less than 1%, respectively, of patients receiving bortezomib. Following dosage adjustments, amelioration or resolution of peripheral neuropathy was reported in 51% of patients with grade 2 or higher peripheral neuropathy within a median of 3.5 months from onset. About 8% of patients discontinued bortezomib therapy because of peripheral neuropathy.

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 929

Patients receiving bortezomib should be monitored for manifestations of neuropathy (eg, burning sensation, hyperesthesia, hypoesthesia, paresthesia, discomfort, neuropathic pain). Dose and/or frequency of administration of bortezomib should be adjusted in patients who experience new-onset or exacerbation of peripheral neuropathy.

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 929

In the phase III trial, asthenia (ie, fatigue, malaise, weakness) was reported in 61% of patients receiving bortezomib and 45% of patients receiving dexamethasone. Grade 3 asthenia occurred in 12 versus 6%, respectively, of patients receiving bortezomib or dexamethasone. About 3% of patients receiving bortezomib and 2% of patients receiving dexamethasone discontinued therapy because of asthenia.

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 929

For more Drug Warnings (Complete) data for BORTEZOMIB (26 total), please visit the HSDB record page.

4.4 Drug Indication

Bortezomib is indicated for the treatment of adult patients with multiple myeloma or mantle cell lymphoma.

FDA Label

Velcade as monotherapy or in combination with pegylated liposomal doxorubicin or dexamethasone is indicated for the treatment of adult patients with progressive multiple myeloma who have received at least 1 prior therapy and who have already undergone or are unsuitable for haematopoietic stem cell transplantation.

Velcade in combination with melphalan and prednisone is indicated for the treatment of adult patients with previously untreated multiple myeloma who are not eligible for high dose chemotherapy with haematopoietic stem cell transplantation.

Velcade in combination with dexamethasone, or with dexamethasone and thalidomide, is indicated for the induction treatment of adult patients with previously untreated multiple myeloma who are eligible for high dose chemotherapy with haematopoietic stem cell transplantation.

Velcade in combination with rituximab, cyclophosphamide, doxorubicin and prednisone is indicated for the treatment of adult patients with previously untreated mantle cell lymphoma who are unsuitable for haematopoietic stem cell transplantation.

Bortezomib Hospira as monotherapy or in combination with pegylated liposomal doxorubicin or dexamethasone is indicated for the treatment of adult patients with progressive multiple myeloma who have received at least 1 prior therapy and who have already undergone or are unsuitable for haematopoietic stem cell transplantation.

Bortezomib Hospira in combination with melphalan and prednisone is indicated for the treatment of adult patients with previously untreated multiple myeloma who are not eligible for high-dose chemotherapy with haematopoietic stem cell transplantation.

Bortezomib Hospira in combination with dexamethasone, or with dexamethasone and thalidomide, is indicated for the induction treatment of adult patients with previously untreated multiple myeloma who are eligible for high-dose chemotherapy with haematopoietic stem cell transplantation.

Bortezomib Hospira in combination with rituximab, cyclophosphamide, doxorubicin and prednisone is indicated for the treatment of adult patients with previously untreated mantle cell lymphoma who are unsuitable for haematopoietic stem cell transplantation.

Bortezomib as monotherapy or in combination with pegylated liposomal doxorubicin or dexamethasone is indicated for the treatment of adult patients with progressive multiple myeloma who have received at least 1 prior therapy and who have already undergone or are unsuitable for haematopoietic stem cell transplantation.

Bortezomib in combination with melphalan and prednisone is indicated for the treatment of adult patients with previously untreated multiple myeloma who are not eligible for high-dose chemotherapy with haematopoietic stem cell transplantation.

Bortezomib in combination with dexamethasone, or with dexamethasone and thalidomide, is indicated for the induction treatment of adult patients with previously untreated multiple myeloma who are eligible for high-dose chemotherapy with haematopoietic stem cell transplantation.

Bortezomib in combination with rituximab, cyclophosphamide, doxorubicin and prednisone is indicated for the treatment of adult patients with previously untreated mantle cell lymphoma who are unsuitable for haematopoietic stem cell transplantation.

Bortezomib SUN as monotherapy or in combination with pegylated liposomal doxorubicin or dexamethasone is indicated for the treatment of adult patients with progressive multiple myeloma who have received at least 1 prior therapy and who have already undergone or are unsuitable for haematopoietic stem cell transplantation.

Bortezomib SUN in combination with melphalan and prednisone is indicated for the treatment of adult patients with previously untreated multiple myeloma who are not eligible for high-dose chemotherapy with haematopoietic stem cell transplantation.

Bortezomib SUN in combination with dexamethasone, or with dexamethasone and thalidomide, is indicated for the induction treatment of adult patients with previously untreated multiple myeloma who are eligible for high-dose chemotherapy with haematopoietic stem cell transplantation.

Bortezomib SUN in combination with rituximab, cyclophosphamide, doxorubicin and prednisone is indicated for the treatment of adult patients with previously untreated mantle cell lymphoma who are unsuitable for haematopoietic stem cell transplantation.

Bortezomib Accord as monotherapy or in combination with pegylated liposomal doxorubicin or dexamethasone is indicated for the treatment of adult patients with progressive multiple myeloma who have received at least 1 prior therapy and who have already undergone or are unsuitable for haematopoietic stem cell transplantation.

Bortezomib Accord in combination with melphalan and prednisone is indicated for the treatment of adult patients with previously untreated multiple myeloma who are not eligible for highdose chemotherapy with haematopoietic stem cell transplantation.

Bortezomib Accord in combination with dexamethasone, or with dexamethasone and thalidomide, is indicated for the induction treatment of adult patients with previously untreated multiple myeloma who are eligible for highdose chemotherapy with haematopoietic stem cell transplantation.

Bortezomib Accord in combination with rituximab, cyclophosphamide, doxorubicin and prednisone is indicated for the treatment of adult patients with previously untreated mantle cell lymphoma who are unsuitable for haematopoietic stem cell transplantation.

Treatment of mantle cell lymphoma

5 Pharmacology and Biochemistry

5.1 Pharmacology

Bortezomib works to target the ubiquitin-proteasome pathway, an essential molecular pathway that regulates intracellular concentrations of proteins and promotes protein degradation. The ubiquitin-proteasome pathway is often dysregulated in pathological conditions, leading to aberrant pathway signalling and the formation of malignant cells. In one study, patient-derived chronic lymphocytic leukemia (CLL) cells contained 3-fold higher levels of chymotrypsin-like proteasome activity than normal lymphocytes. By reversibly inhibiting proteasome, bortezomib prevents proteasome-mediated proteolysis. Bortezomib exerts a cytotoxic effect on various cancer cell types _in vitro_ and delays tumour growth _in vivo_ in nonclinical tumour models. Bortezomib inhibits the proteasome activity in a dose-dependent manner. In one pharmacodynamic study, more than 75% of proteasome inhibition was observed in whole blood samples within one hour after dosing of bortezomib.

5.2 MeSH Pharmacological Classification

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

BORTEZOMIB

5.3.2 FDA UNII

69G8BD63PP

5.3.3 Pharmacological Classes

Proteasome Inhibitors [MoA]; Proteasome Inhibitor [EPC]

5.4 ATC Code

L01XG01

L01XX32

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

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01X - Other antineoplastic agents

L01XG - Proteasome inhibitors

L01XG01 - Bortezomib

5.5 Absorption, Distribution and Excretion

Absorption

Following intravenous administration of 1 mg/m² and 1.3 mg/m² doses, the mean C_max of bortezomib were 57 and 112 ng/mL, respectively. In a twice-weekly dosing regimen, the C_max ranged from 67 to 106 ng/mL at the dose of 1 mg/m² and 89 to 120 ng/mL for the 1.3 mg/m² dose. In patients with multiple myeloma, the C_max of bortezomib followig subcutaneous administration was lower than that of intravenously-administered dose; however, the total systemic exposure of the drug was equivalent for both routes of administration. There is a wide interpatient variability in drug plasma concentrations.

Route of Elimination

Bortezomib is eliminated by both renal and hepatic routes.

Volume of Distribution

The mean distribution volume of bortezomib ranged from approximately 498 to 1884 L/m² in patients with multiple myeloma receiving a single- or repeat-dose of 1 mg/m² or 1.3 mg/m². Bortezomib distributes into nearly all tissues, except for the adipose and brain tissue.

Clearance

Following the administration of a first dose of 1 mg/m² and 1.3 mg/m², the mean mean total body clearances were 102 and 112 L/h, respectively. The clearances were 15 and 32 L/h after the subsequent dose of 1 and 1.3 mg/m², respectively.

Following intravenous administration of 1 mg/sq m and 1.3 mg/sq m doses to 24 patients with multiple myeloma (n=12, per each dose level), the mean maximum plasma concentrations of bortezomib (Cmax) after the first dose (Day 1) were 57 and 112 ng/mL, respectively.

In subsequent doses, when administered twice weekly, the mean maximum observed plasma concentrations ranged from 67 to 106 ng/mL for the 1 mg/sq m dose and 89 to 120 ng/mL for the 1.3 mg/sq m dose. The mean elimination half-life of bortezomib upon multiple dosing ranged from 40 to 193 hours after the 1 mg/sq m dose and 76 to 108 hours after the 1.3 mg/sq m dose. The mean total body clearances was 102 and 112 L/hr following the first dose for doses of 1 mg/sq m and 1.3 mg/sq m, respectively, and ranged from 15 to 32 L/hr following subsequent doses for doses of 1 and 1.3 mg/sq m, respectively.

The mean distribution volume of bortezomib ranged from approximately 498 to 1884 L/sq m following single- or repeat-dose administration of 1 mg/sq m or 1.3mg/sq m to patients with multiple myeloma. This suggests bortezomib distributes widely to peripheral tissues. The binding of bortezomib to human plasma proteins averaged 83% over the concentration range of 100 to 1000 ng/mL.

It is not known whether bortezomib is excreted in human milk.

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

5.6 Metabolism/Metabolites

Bortezomib is primarily metabolized by CYP3A4, CYP2C19, and CYP1A2. CYP2D6 and CYP2C9 are also involved in drug metabolism, but to a smaller extent. Oxidative deboronation, which involves the removal of boronic acid from the parent compound, is the main metabolic pathway. Metabolites of bortezomib are pharmacologically inactive and more than 30 metabolites have been identified in human and animal studies.

In vitro studies with human liver microsomes and human cDNA-expressed cytochrome P450 isozymes indicate that bortezomib is primarily oxidatively metabolized via cytochrome P450 enzymes 3A4, 2C19, and 1A2. Bortezomib metabolism by CYP 2D6 and 2C9 enzymes is minor. The major metabolic pathway is deboronation to form 2 deboronated metabolites that subsequently undergo hydroxylation to several metabolites. Deboronated bortezomib metabolites are inactive as 26S proteasome inhibitors. Pooled plasma data from 8 patients at 10 min and 30 min after dosing indicate that the plasma levels of metabolites are low compared to the parent drug.

... The P450 inhibition potential of bortezomib and its major deboronated metabolites M1 and M2 and their dealkylated metabolites M3 and M4 was evaluated in human liver microsomes for the major P450 isoforms 1A2, 2C9, 2C19, 2D6, and 3A4/5. Bortezomib, M1, and M2 were found to be mild inhibitors of CYP2C19 (IC(50) approximately 18.0, 10.0, and 13.2 microM, respectively), and M1 was also a mild inhibitor of CYP2C9 (IC(50) approximately 11.5 microM). However, bortezomib, M1, M2, M3, and M4 did not inhibit other P450s (IC(50) values > 30 microM). There also was no time-dependent inhibition of CYP3A4/5 by bortezomib or its major metabolites. ...

PMID:16443666 LU C et al; Drug Metab Dispos 34 (4): 702-8 (2006)

... Bortezomib binds the proteasome via the boronic acid moiety, and therefore, the presence of this moiety is necessary to achieve proteasome inhibition. Metabolites in plasma obtained from patients receiving a single intravenous dose of bortezomib were identified and characterized by liquid chromatography/mass spectrometry (LC/MS) and liquid chromatography/tandem mass spectrometry (LC/MS/MS). Metabolite standards that were synthesized and characterized by LC/MS/MS and high field nuclear magnetic resonance spectroscopy (NMR) were used to confirm metabolite structures. The principal biotransformation pathway observed was oxidative deboronation, most notably to a pair of diastereomeric carbinolamide metabolites. Further metabolism of the leucine and phenylalanine moieties produced tertiary hydroxylated metabolites and a metabolite hydroxylated at the benzylic position, respectively. Conversion of the carbinolamides to the corresponding amide and carboxylic acid was also observed. Human liver microsomes adequately modeled the in vivo metabolism of bortezomib, as the principal circulating metabolites were observed in vitro. Using cDNA-expressed cytochrome P450 isoenzymes, it was determined that several isoforms contributed to the metabolism of bortezomib, including CYP3A4, CYP2C19, CYP1A2, CYP2D6, and CYP2C9. ...

PMID:15764713 Pekol T et al; Drug Metab Dispos 33 (6): 771-7 (2005)

5.7 Biological Half-Life

The mean elimination half-life of bortezomib ranged from 40 to 193 hours following a multiple dosing regimen at a 1 mg/m² dose. The half-life ranged from 76 to 108 hours after multiple dosing of 1.3 mg/m² bortezomib.

The mean elimination half-life of bortezomib upon multiple dosing ranged from 40 to 193 hours after the 1 mg/sq m dose and 76 to 108 hours after the 1.3 mg/sq m dose.

5.8 Mechanism of Action

The ubiquitin-proteasome pathway is a homeostatic proteolytic pathway for intracellular protein degradation: proteins marked with a poly-ubiquitin chain are degraded to small peptides and free ubiquitin by the proteasome, which is a large multimeric protease. Aberrant proteasome-dependent proteolysis, as seen in some malignancies, can lead to uncontrolled cell division, leading to tumorigenesis, cancer growth, and spread. Bortezomib is a reversible inhibitor of the 26S proteasome, which is made up of a 20S core complexed with a 19S regulatory complex. Individual -subunits allow specific catalytic action of the 20S core. In mammalian cells, bortezomib is a potent inhibitor of the proteasomes chymotryptic-like activity, which is attributed to the 5-subunit of the 20S core particle. Bortezomib binds to the active site of the threonine hydroxyl group in the 5-subunit. A probing study showed bortezomib also binding to and inhibiting the 1-subunit, which mediates the caspase-like activity of the proteasome, and 1i-subunit, which is an altered subunit that is expressed to form immunoproteasomes in response to cell stress or inflammation. By inhibiting the proteasome-mediated degradation of key proteins that promote cell apoptosis, bortezomib induces a cell cycle arrest during the G2-M phase. It is believed that multiple mechanisms, other than proteasome inhibition, may be involved in the anticancer activity of bortezomib. The anticancer activity of bortezomib was largely associated with suppression of the NF-B signalling pathway, resulting in the downregulation of anti-apoptotic target genes and expression of anti-apoptic proteins. This may be explained by bortezomib preventing uncontrolled degradation of IB, which is an inhibitory protein of NF-B. NOXA, which is a pro-apoptotic factor, induced by bortezomib selectively in cancer cells; thus, it is suggested to be another key mechanism of bortezomib.

Bortezomib, a modified dipeptidyl boronic acid, is an antineoplastic agent. The drug reversibly inhibits the 26S proteasome, a large protein complex that degrades ubiquitinated proteins. The ubiquitin-proteasome pathway plays an essential role in regulating the intracellular concentration of specific proteins, thereby maintaining homeostasis within cells. Inhibition of the 26S proteasome by bortezomib prevents targeted proteolysis and causes disruption of normal homeostatic mechanisms, which can lead to cell death. In vitro studies indicate that bortezomib is cytotoxic to a variety of cancer cell types. Bortezomib has been shown to cause a delay in tumor growth in vivo in tumor models, including multiple myeloma.

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 931

... The mechanisms underlying /bortezomib/ cancer cell toxicity are complex. A growing body of evidence suggests proteasome inhibition-dependent regulation of the BCL-2 family is a critical requirement. In particular, the stabilization of BH3-only proteins BIK, NOXA and BIM, appear to be essential for effecting BAX- and BAK-dependent cell death. ...

PMID:17828309 Fennell DA et al; Oncogene 27 (9): 1189-97 (2008)

Proteasome inhibition is a novel, targeted approach in cancer therapy. Both natural and synthetic proteasome inhibitors selectively penetrate cancer cells, disrupting the orderly destruction of key regulatory proteins involved in tumorigenesis and metastasis. Disrupting the orderly destruction of regulatory proteins causes an imbalance of these proteins within the cell, which interferes with the systematic activation of signaling pathways required to maintain tumor cell growth and survival; therefore, cellular replication is inhibited and apoptosis ensues. ...

PMID:15688597 Jung L et al; Oncology (Williston Park) 18 (14 Suppl 11): 4-13 (2004)

Bortezomib (PS-341, Velcade) is a potent and selective inhibitor of the proteasome that is currently under investigation for the treatment of solid malignancies. /Investigators/ have shown previously that bortezomib has activity in pancreatic cancer models and that the drug induces endoplasmic reticulum (ER) stress but also suppresses the unfolded protein response (UPR). Because the UPR is an important cytoprotective mechanism, /investigators/ hypothesized that bortezomib would sensitize pancreatic cancer cells to ER stress-mediated apoptosis. Here, /the authors/ show that bortezomib promotes apoptosis triggered by classic ER stress inducers (tunicamycin and thapsigargin) via a c-Jun NH(2)-terminal kinase (JNK)-dependent mechanism. /They/ also show that cisplatin stimulates ER stress and interacts with bortezomib to increase ER dilation, intracellular Ca(2+) levels, and cell death. Importantly, combined therapy with bortezomib plus cisplatin induced JNK activation and apoptosis in orthotopic pancreatic tumors resulting in a reduction in tumor burden. Taken together, the data establish that bortezomib sensitizes pancreatic cancer cells to ER stress-induced apoptosis and show that bortezomib strongly enhances the anticancer activity of cisplatin.

PMID:16357177 Nawrocki ST et al; Cancer Res 65 (24): 11658-66 (2005)

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REDDY\\'S LABORATORIES","customerCountry":"CHILE","quantity":"0.00","actualQuantity":"0.1","unit":"GMS","unitRateFc":"500","totalValueFC":"19.7","currency":"USD","unitRateINR":16580,"date":"01-Oct-2024","totalValueINR":"1658","totalValueInUsd":"19.7","indian_port":"Vizag-EPZ\/SEZ","hs_no":"29349930","bill_no":"4517983","productDescription":"API","marketType":"REGULATED MARKET","country":"CHILE","selfForZScoreResived":"Pharma Grade","supplierPort":"Vizag-EPZ\/SEZ","supplierAddress":"H.NO. 8-2-337,BESIDE TV9 OFFICE, HYDERABAD ANDHRA PRADESH","customerAddress":""},{"dataSource":"API Export","activeIngredients":"","year":"2024","qtr":"Q4","strtotime":1729881000,"product":"BORTEZOMIB IHS","address":"HETERO HOUSE,H.NO.8-3-166\/7\/1ERRAGADDA","city":"HYDERABAD","supplier":"HETERO DRUGS","supplierCountry":"INDIA","foreign_port":"BUENOS AIRES","customer":"LABORATORIO KEMEX SA","customerCountry":"ARGENTINA","quantity":"0.02","actualQuantity":"0.02","unit":"KGS","unitRateFc":"1290000","totalValueFC":"24793.2","currency":"USD","unitRateINR":104164500,"date":"26-Oct-2024","totalValueINR":"2083290","totalValueInUsd":"24793.2","indian_port":"Hyderabad Air","hs_no":"29241900","bill_no":"5161924","productDescription":"API","marketType":"LESS REGULATED MARKET","country":"ARGENTINA","selfForZScoreResived":"Pharma Grade","supplierPort":"Hyderabad Air","supplierAddress":"HETERO HOUSE,H.NO.8-3-166\/7\/1ERRAGADDA, HYDERABAD","customerAddress":""},{"dataSource":"API Import","activeIngredients":"","year":"2022","qtr":"Q1","strtotime":1643308200,"product":"BORTEZOMIB (QTY: 45GMS, VALUE: USD 500\/GM)","address":"PLOT NO.2, MAITHRIVIHAR AMEERPET,","city":"HYDERABAD","supplier":"HANSOH PHARMA","supplierCountry":"CHINA","foreign_port":"#N\/A","customer":"EUGIA PHARMA SPECIALITIES ","customerCountry":"INDIA","quantity":"0.05","actualQuantity":"0.045","unit":"KGS","unitRateFc":"500000","totalValueFC":"22743.6","currency":"USD","unitRateINR":"37650000","date":"28-Jan-2022","totalValueINR":"1694250","totalValueInUsd":"22743.6","indian_port":"HYDERABAD AIR","hs_no":"29339990","bill_no":"7266478","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"#N\/A","supplierAddress":"","customerAddress":"PLOT NO.2, MAITHRIVIHAR AMEERPET,"},{"dataSource":"API Import","activeIngredients":"","year":"2023","qtr":"Q1","strtotime":1676226600,"product":"BORTEZOMIB (AS PER INVOICE)","address":"PLOT NO.2, MAITHRIVIHAR AMEERPET,","city":"HYDERABAD","supplier":"JIANGSU HANSOH PHARMACEUTICAL GROUP CO., LTD","supplierCountry":"CHINA","foreign_port":"NA","customer":"EUGIA PHARMA SPECIALITIES ","customerCountry":"INDIA","quantity":"0.28","actualQuantity":"278.95","unit":"GMS","unitRateFc":"300","totalValueFC":"83847.1","currency":"USD","unitRateINR":"24825","date":"13-Feb-2023","totalValueINR":"6924933.75","totalValueInUsd":"83847.1","indian_port":"HYDERABAD AIR","hs_no":"29339990","bill_no":"4618443","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"NA","supplierAddress":"","customerAddress":"PLOT NO.2, MAITHRIVIHAR AMEERPET,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q4","strtotime":1727893800,"product":"BORTEZOMIB WORKING STANDARD","address":"H.NO. 8-2-337, BESIDE TV9 OFFICE,,","city":"HYDERABAD,TELANGANA","supplier":"DR. REDDY\\'S LABORATORIES","supplierCountry":"INDIA","foreign_port":"VISAKHAPATNAM SEZ","customer":"DR. REDDY\\'S LABORATORIES","customerCountry":"INDIA","quantity":"0.00","actualQuantity":"0.001","unit":"KGS","unitRateFc":"94777","totalValueFC":"95.4","currency":"USD","unitRateINR":"8018130","date":"03-Oct-2024","totalValueINR":"8018.13","totalValueInUsd":"95.4","indian_port":"Vizag-EPZ\/SEZ","hs_no":"29339990","bill_no":"5932426","productDescription":"Re-Import","marketType":"REGULATED MARKET","country":"INDIA","selfForZScoreResived":"Pharma Grade","supplierPort":"VISAKHAPATNAM SEZ","supplierAddress":"FTO -7, PLOT NO.P1 TO P9 V.S.E.Z., DUVVADA,VISAKHAPATNAM SDNF India","customerAddress":"H.NO. 8-2-337, BESIDE TV9 OFFICE,,"}]

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

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INTERMEDIATES SUPPLIERS

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FDF Dossiers

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FDA Orange Book

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Europe

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Canada

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Australia

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Listed Dossiers

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Related Excipient Companies

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Excipients by Applications

Click here to find the perfect excipient manufacturers by their capabilities

Fillers, Diluents & Binders

Chewable & Orodispersible Aids

Direct Compression

01

SPI Pharma

U.S.A

CPhI India 2024

Booth #8.Q31

SPI Pharma has been solving formulation challenges using superior functional materials.

Dosage Form : Orodispersible Tablet, Tablet

Grade : Oral

Category : Chewable & Orodispersible Aids, Direct Compression, Fillers, Diluents & Binders, Taste Masking

Brand Name : Pharmaburst 500

Application : Chewable & Orodispersible Aids, Direct Compression, Fillers, Diluents & Binders, Taste Masking

Excipient Details : Pharmaburst® 500 is a directly compressible pharmaceutical excipient used to create orally disintegrating tablets quickly and easily.

Pharmacopoeia Ref : NA

Technical Specs : NA

Ingredient(s) : Mannitol

02

SPI Pharma

U.S.A

CPhI India 2024

Booth #8.Q31

SPI Pharma has been solving formulation challenges using superior functional materials.

Dosage Form : Orodispersible Tablet, Tablet

Grade : Oral

Category : Chewable & Orodispersible Aids, Direct Compression, Fillers, Diluents & Binders, Taste Masking

Brand Name : Advantol 300

Application : Chewable & Orodispersible Aids, Direct Compression, Fillers, Diluents & Binders, Taste Masking

Excipient Details : Advantol® 300 is a DC pharmaceutical excipient used to create soft chewable or soft melt oral dosage forms & enables rapid product development.

Pharmacopoeia Ref : NA

Technical Specs : NA

Ingredient(s) : Mannitol

03

SPI Pharma

U.S.A

CPhI India 2024

Booth #8.Q31

SPI Pharma has been solving formulation challenges using superior functional materials.

Dosage Form : Tablet, Orodispersible Tablet

Grade : Oral

Category : Chewable & Orodispersible Aids, Co-Processed Excipients, Direct Compression, Fillers, Diluents & Binders, Taste Masking

Brand Name : Compressol SM

Application : Chewable & Orodispersible Aids, Co-Processed Excipients, Direct Compression, Fillers, Diluents & Binders, Taste Masking

Excipient Details : Compressol® SM, co-processed polyol, is a DC excipient of mannitol & sorbitol with superior compactibility, lower disintegration time & hygroscopicity

Pharmacopoeia Ref : NA

Technical Specs : NA

Ingredient(s) : Mannitol

04

SPI Pharma

U.S.A

CPhI India 2024

Booth #8.Q31

SPI Pharma has been solving formulation challenges using superior functional materials.

Dosage Form : Orodispersible Tablet, Tablet

Grade : Oral

Category : Chewable & Orodispersible Aids, Direct Compression, Fillers, Diluents & Binders

Brand Name : Mannogem EZ Spray-Dried

Application : Chewable & Orodispersible Aids, Direct Compression, Fillers, Diluents & Binders

Excipient Details : Mannogem EZ Spray-Dried, a mannitol product, dissolves rapidly and can increase the rate of tablet disintegration, drug dissolution & drug release.

Pharmacopoeia Ref : NA

Technical Specs : NA

Ingredient(s) : Mannitol

05

SPI Pharma

U.S.A

CPhI India 2024

Booth #8.Q31

SPI Pharma has been solving formulation challenges using superior functional materials.

Dosage Form : Orodispersible Tablet, Tablet

Grade : Oral

Category : Chewable & Orodispersible Aids, Direct Compression, Fillers, Diluents & Binders

Brand Name : Mannogem Granular

Application : Chewable & Orodispersible Aids, Direct Compression, Fillers, Diluents & Binders

Excipient Details : Mannogem Granular (mannitol) dissolves rapidly and can increase the rate of tablet disintegration, subsequent drug dissolution and drug release.

Pharmacopoeia Ref : NA

Technical Specs : NA

Ingredient(s) : Mannitol

06

SPI Pharma

U.S.A

CPhI India 2024

Booth #8.Q31

SPI Pharma has been solving formulation challenges using superior functional materials.

Dosage Form : Tablet

Grade : Oral

Category : Direct Compression, Fillers, Diluents & Binders, Taste Masking

Brand Name : Mannogem® XL Opal

Application : Direct Compression, Fillers, Diluents & Binders, Taste Masking

Excipient Details : Mannogem® XL Opal, directly compressible 160 µm spray-dried mannitol provides superior binding properties and tabletability.

Pharmacopoeia Ref : NA

Technical Specs : 160 µm Powder Mannitol

Ingredient(s) : Mannitol

07

Sigachi Industries

India

The Pharmacy Technology

Not Confirmed

08

Microlex e.U

Austria

The Pharmacy Technology

Not Confirmed

09

BASF

Germany

The Pharmacy Technology

Not Confirmed

Taste Masking

Parenteral

Co-Processed Excipients

Disintegrants & Superdisintegrants

Granulation

01

SPI Pharma

U.S.A

CPhI India 2024

Booth #8.Q31

SPI Pharma has been solving formulation challenges using superior functional materials.

Dosage Form : Granule / Pellet, Tablet

Grade : Oral

Category : Fillers, Diluents & Binders, Granulation

Brand Name : Mannogem Powder

Application : Fillers, Diluents & Binders, Granulation

Excipient Details : Mannogem (mannitol powder) is a pharmaceutical excipient that dissolves rapidly and increases tablet disintegration rate, drug dissolution & release.

Pharmacopoeia Ref : NA

Technical Specs : NA

Ingredient(s) : Mannitol

02

Microlex e.U

Austria

Compamed

Not Confirmed

03

BASF

Germany

Compamed

Not Confirmed

Topical

Thickeners and Stabilizers

API Stability Enhancers

Digital Content

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DATA COMPILATION #PharmaFlow

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Global Sales Information

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US Medicaid Prescriptions

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Finished Drug Prices

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Annual Reports

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Market Place

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APIs

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FDF DOSSIERS

Bortezomib (3.5 mg/ 10 ml) Injections needed in Trinidad & Tobago [ENA16220]

A company that deals in wholesale, import, export & distribution of various pharmaceutical products is looking for suppliers of Bortezomib (3.5 mg/ 10 ml) Injections for commercial purposes. The required quantity is 5,000 units - 10,000 units.

27 Jan 2023

Tender// Bortezomib (3.5 mg) Vials needed in the United States [ENA14873]

U.S. Department of Veterans Affairs is looking for supplies of Bortezomib (3.5 mg) Vials for commercial purpose. The required quantity is 17,804 units. The deadline is 31-Aug-2022.

31 Aug 2022

Various Finished Dosage Formulations needed in Vietnam [ENA12409]

A large pharmaceutical company based in India that deals in various segments such as gynecology, cardiovascular, diabetology, asthma, pediatric, CNS, GI and NSAIDs is looking for suppliers of Various Finished Dosage Formulations for commercial purposes. The Indian suppliers must support this enquiry with USFDA or EUGMP & European suppliers must support this enquiry with WHO GMP. The final market is South East Asian countries. 1. Thiamine Hydrochloride (100 mg) + Pyridoxine hydrochloride (200 mg) + Cyanocobalamin (0.2 mg) Tablets 2. Bortezomib (3.5 mg) Injections 3. Amoxicillin (500 mg & 875 mg) + Clavulanic Acid (125 mg) Tablets 4. Amoxicillin (400 mg) + Clavulanic Acid (57 mg) Suspensions 5. Amoxicillin (1 g) + Clavulanic Acid (0.2 g) Injections

14 Jan 2022

Various Finished Dosage Formulations needed in Vietnam [ENA12275]

A large pharmaceutical company based in India that deals in various segments such as gynecology, cardiovascular, diabetology, asthma, pediatric, CNS, GI and NSAIDs is looking for suppliers of Various Finished Dosage Formulations for commercial purposes. The Indian suppliers must support this enquiry with USFDA or EUGMP & European suppliers must support this enquiry with WHO GMP. The final market is South East Asian countries. 1. Pazopanib (200 mg & 400 mg) Film Coated Tablet 2. Ticagrelor (60 mg & 90 mg) Film Coated Tablet 3. Bortezomib (3.5 mg) Powder for Injection 4. Iron (III)-Hydroxide Sucrose (100 mg/ 5 ml) Conc. Solution for Infusion 5. Sildenafil Citrate (100 mg) Film Coated Tablet

31 Dec 2021

Tender// Various Finished Dosage Formulations needed in Poland [ENA11289]

University Hospital In Krakow is looking for supplies of Various Finished Dosage Formulations for commercial purpose. The deadline is 22-Sep-2021. 1. Darbepoetin Alfa (500 mcg / ml in 1 ml) Solution for Injection. The required quantity is 100 units. 2. Bortezomib (3.5 mg) Powder for Solution for Injection. The required quantity is 1,800 units. 3. Certolizumab Pegol (200 mg / ml) Solution for Injection. The required quantity is 450 units. 4. Levodopa (20 mg) + Carbidopa (5 mg / ml) Enteric Gel. The required quantity is 1,000 units. 5. Nilotinib (200 mg) Hard Capsules. The required quantity is 650 units. 6. Pertuzumab (420 mg /14 ml) Concentrate for Solution for Infusion. The required quantity is 1,000 units. 7. Fosfomycin (4 g) Powder for Solution for Infusion. The required quantity is 3,600 units.

03 Sep 2021

Pemetrexed and Bortezomib and other formulations needed in the Middle East [ENA02683]

A private international healthcare group based in Switzerland is searching for suppliers/manufacturers of following products: 1. Pemetrexed 2. Bortezomib 3. Sunitinib 4. Erlotinib 5. Gefitinib 6. Afinitor 7. Abiraterone 8. Everolimus 9. Lenalidomide The manufacturing site must be GMP/EU/FDA approved.

20 Nov 2018

Enquiry// Pemetrexed and Bortezomib formulations needed for GCC and Egypt market [ENA00983]

A private international healthcare group based in Switzerland is searching for suppliers/manufacturers of Pemetrexed and Bortezomib formulations. The manufacturing site must be GMP/EU/FDA approved.

06 Jun 2018

Enquiry// Bortezomib, Docetaxel and other formulations needed for Colombia [ENA00950]

A leading distribution company in Colombia, which provides complete sourcing solutions to its customers is looking for following formulations: 1. Bortezomib 3.5 2. Docetaxel 80 mg Lyophilized Injectable 3. Cabazitaxel 60 mg/1.5 mL solution for injection 4. Doxorubicin Liposomal 20 mg/10 mL solution for injection 5. Plerixafor 20 mg x Vial 1.2 mL solution for injection 6. Pegfilgrastim 6 MG/0.6ML solution for injection 7. Clofarabine 20 mg/20 mL solution for injection 8. Amphotericin liposomal 50 mg powder for solution for injection

26 May 2018

Enquiry// Sunitinib, Bortezomib and Various other GMP grade finished dosage formulations needed in Switzerland [ENA00363]

A private, international healthcare group based in Switzerland is searching for European/US manufacturers of following products: i) Sunitinib: 12.5 mg 400 packs ii) Bortezomib: 3.5 mg 600 packs iii) Lenalidomide: 10 mg 450 packs; 25 mg 360 packs; 5 mg 240 packs iv) Abiraterone: 250mg 600 packs v) Pemetrexed: 500mg 840 packs vi) Everolimus: 5mg 480 packs The suppliers/manufacturers should support the products with EU CTD dossier and GMP certificate.

10 Jun 2017

Enquiry//Various Finished Formulations Needed for Sri Lanka [ENA00002]

Unicorn International Ltd., a leading marketing company in Sri Lanka is searching for manufacturers who can supply 100,000 tablets/injections of the following - 1)Voriconazole 200mg tablets 2) Voriconazole 200mg injection 3) Diazepam tablet 2mg/ 5mg /10mg 4) Diazepam injections 10mg/2ml 5) Dapsone 50mg /100mg tablets 6) Bortezomib 2mg injection 7) Rituximab 500mg / 50 ml 8) Clofazimine 100mg Interested companies should contact Thanuj Fernando M.D (M. A.) CEO/ Director Unicorn International Pvt Ltd No.207,Lion City , Liyangemulla , Seeduwa , Sri Lanka Tel : 0094 710387600 Fax : 0094 711001209 Mob : 0094 772387600 Web Site : http://www.unicornintl.com

25 Mar 2016

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ACTIVE PHARMA INGREDIENTS

66 API Suppliers

27 USDMF

6 JDMF

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21 NDC API

41 Listed Suppliers

$ API Reference Price

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20 Europe

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RELATED EXCIPIENT COMPANIES

1 Evonik

1 Rochem International Inc

12 SPI Pharma

1 DKSH

1 Faran Shimi Pharmaceutical

1 Pfanstiehl

1 BASF

2 Gangwal Chemicals

1 Ingredion Pharma Solutions

2 Kerry

2 Microlex e.U

1 Pluviaendo

3 Roquette

1 Shanghai Shenmei Pharmaceutical Technology Co., Ltd

1 Shijiazhuang Huaxu Pharmaceutical

1 Sigachi Industries

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17 Fillers, Diluents & Binders

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9 Direct Compression

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4 Parenteral

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4 Disintegrants & Superdisintegrants

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PATENTS & EXCLUSIVITIES

11 US Patents

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ACTIVE PHARMA INGREDIENTS

API REF. PRICE (USD/KG)

$ 1,143,477

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REF. STANDARDS OR IMPURITIES

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64EXCIPIENTS BY APPLICATIONS