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Chemistry

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Also known as: 183133-96-2, Jevtana, Taxoid xrp6258, Txd 258, Xrp-6258, Cabazitaxelum
Molecular Formula
C45H57NO14
Molecular Weight
835.9  g/mol
InChI Key
BMQGVNUXMIRLCK-OAGWZNDDSA-N
FDA UNII
51F690397J

Cabazitaxel
Cabazitaxel is a semi-synthetic derivative of the natural taxoid 10-deacetylbaccatin III with potential antineoplastic activity. Cabazitaxel binds to and stabilizes tubulin, resulting in the inhibition of microtubule depolymerization and cell division, cell cycle arrest in the G2/M phase, and the inhibition of tumor cell proliferation. Unlike other taxane compounds, this agent is a poor substrate for the membrane-associated, multidrug resistance (MDR), P-glycoprotein (P-gp) efflux pump and may be useful for treating multidrug-resistant tumors. In addition, cabazitaxel penetrates the blood-brain barrier (BBB).
Cabazitaxel is a Microtubule Inhibitor. The physiologic effect of cabazitaxel is by means of Microtubule Inhibition.
1 2D Structure

Cabazitaxel

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-1-hydroxy-15-[(2R,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]oxy-9,12-dimethoxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
2.1.2 InChI
InChI=1S/C45H57NO14/c1-24-28(57-39(51)33(48)32(26-17-13-11-14-18-26)46-40(52)60-41(3,4)5)22-45(53)37(58-38(50)27-19-15-12-16-20-27)35-43(8,36(49)34(55-10)31(24)42(45,6)7)29(54-9)21-30-44(35,23-56-30)59-25(2)47/h11-20,28-30,32-35,37,48,53H,21-23H2,1-10H3,(H,46,52)/t28-,29-,30+,32-,33+,34+,35-,37-,43+,44-,45+/m0/s1
2.1.3 InChI Key
BMQGVNUXMIRLCK-OAGWZNDDSA-N
2.1.4 Canonical SMILES
CC1=C2C(C(=O)C3(C(CC4C(C3C(C(C2(C)C)(CC1OC(=O)C(C(C5=CC=CC=C5)NC(=O)OC(C)(C)C)O)O)OC(=O)C6=CC=CC=C6)(CO4)OC(=O)C)OC)C)OC
2.1.5 Isomeric SMILES
CC1=C2[C@H](C(=O)[C@@]3([C@H](C[C@@H]4[C@]([C@H]3[C@@H]([C@@](C2(C)C)(C[C@@H]1OC(=O)[C@@H]([C@H](C5=CC=CC=C5)NC(=O)OC(C)(C)C)O)O)OC(=O)C6=CC=CC=C6)(CO4)OC(=O)C)OC)C)OC
2.2 Other Identifiers
2.2.1 UNII
51F690397J
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Jevtana

2. Kabazitaxel

2.3.2 Depositor-Supplied Synonyms

1. 183133-96-2

2. Jevtana

3. Taxoid Xrp6258

4. Txd 258

5. Xrp-6258

6. Cabazitaxelum

7. Xrp6258

8. Xrp 6258

9. Jevtana (tn)

10. Nsc-761432

11. Chebi:63584

12. Txd-258

13. 51f690397j

14. Kabazitaxel

15. Jevtana Kit

16. Cabazitaxel (jevtana)

17. (2ar,4s,4as,6r,9s,11s,12s,12ar,12bs)-12b-acetoxy-9-(((2r,3s)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-3-phenylpropanoyl)oxy)-11-hydroxy-4,6-dimethoxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1h-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl Benzoate.

18. Cabazitaxel Acetonate

19. Cabazitaxel Acetonate [jan]

20. Cabazitaxel Injection

21. Cabazitaxel [usan:inn]

22. Jevanta

23. Txd258

24. Unii-51f690397j

25. Rpr 116258a

26. Rpr-116258a

27. Cabazitaxel [mi]

28. Cabazitaxel [inn]

29. Cabazitaxel (usan/inn)

30. Cabazitaxel [usan]

31. Cabazitaxel [vandf]

32. Cabazitaxel [mart.]

33. Cabazitaxel [who-dd]

34. Schembl179674

35. Cabazitaxel [ema Epar]

36. Gtpl6798

37. Chembl1201748

38. Amy4317

39. Cabazitaxel [orange Book]

40. Dtxsid40171389

41. Ex-a838

42. Mfcd18827611

43. Nsc761432

44. Nsc794609

45. S3022

46. Zinc85536932

47. Akos032947285

48. Ccg-270519

49. Cs-0972

50. Db06772

51. Nsc 761432

52. Nsc-794609

53. Ncgc00346704-01

54. Ncgc00346704-03

55. As-75355

56. Hy-15459

57. A25044

58. D09755

59. Ab01273971-01

60. Ab01273971_02

61. Q412963

62. Sr-01000941585

63. J-011721

64. J-519981

65. Sr-01000941585-1

66. (((tertbutoxy)carbonyl)amino)-2-hydroxy-3-phenylpropanoate1-hydroxy-7beta,10beta-dimethoxy-9-oxo-5beta,20-epoxytax-11-ene-2alpha,4,13alpha-triyl 4-acetate 2-benzoate 13-((2r,3s)-3-

67. (1s)-5beta,20-epoxy-9-oxo-7beta,10beta-dimethoxytaxa-11-ene-1,2alpha,4alpha,13alpha-tetraol 2-benzoate 4-acetate 13-[(2r,3s)-2-hydroxy-3-(tert-butoxycarbonylamino)-3-phenylpropionate]

68. (1s,2s,3r,4s,7r,9s,10s,12r,15s)-4-(acetyloxy)-15-{[(2r,3s)-3-{[(tert-butoxy)carbonyl]amino}-2-hydroxy-3-phenylpropanoyl]oxy}-1-hydroxy-9,12-dimethoxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3),(1)?.0?,?]heptadec-13-en-2-yl Benzoate

69. (1s,2s,3r,4s,7r,9s,10s,12r,15s)-4-(acetyloxy)-15-{[(2r,3s)-3-{[(tert-butoxy)carbonyl]amino}-2-hydroxy-3-phenylpropanoyl]oxy}-1-hydroxy-9,12-dimethoxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-2-yl Benzoate

70. (2alpha,5beta,7beta,10beta,13alpha)-4-acetoxy-13-({(2r,3s)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl}oxy)-1-hydroxy-7,10-dimethoxy-9-oxo-5,20-epoxytax-11-en-2-yl Benzoate

71. (2ar,4s,4as,6r,9s,11s,12s,12ar,12bs)-12b-acetoxy-9-(((2r,3s)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-3-phenylpropanoyl)oxy)-11-hydroxy-4,6-dimethoxy-4a,8,13,1

72. (2ar,4s,4as,6r,9s,11s,12s,12ar,12bs)-12b-acetoxy-9-(((2r,3s)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-3-phenylpropanoyl)oxy)-11-hydroxy-4,6-dimethoxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1h-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl Benzoate

73. [(1s,2s,3r,4s,7r,9s,10s,12r,15s)-4-acetyloxy-1-hydroxy-15-[(2r,3s)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]oxy-9,12-dimethoxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] Benzoate

74. 1-hydroxy-7,10-dimethoxy-9-oxo-5,20-epoxytax-11-ene-2,4,13-triyl 4-acetate 2-benzoate 13-((2r,3s)-3-(((tertbutoxy)carbonyl)amino)-2-hydroxy-3-phenylpropanoate)

75. 1-hydroxy-7.beta.,10.beta.-dimethoxy-9-oxo-5.beta.,20-epoxytax-11-ene-2.alpha.,4,13.alpha.-triyl 4-acetate 2-benzoate 13-((2r,3s)-3-(((tert-butoxy)carbonyl)amino)-2-hydroxy-3-phenylpropanoate)

76. Benzenepropanoic Acid, Beta-[[(1,1-dimethylethoxy)carbonyl]amino]-alpha-hydroxy-, (2ar,4s,4as,6r,9s,11s,12s,12ar,12bs)-12b-(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-11-hydroxy-4,6-dimethoxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1h-cyclodeca[3,4]benz[1,2-b]oxet-9-yl Ester, (alphar,betas)-

2.4 Create Date
2006-10-25
3 Chemical and Physical Properties
Molecular Weight 835.9 g/mol
Molecular Formula C45H57NO14
XLogP32.7
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count14
Rotatable Bond Count15
Exact Mass835.37790549 g/mol
Monoisotopic Mass835.37790549 g/mol
Topological Polar Surface Area202 Ų
Heavy Atom Count60
Formal Charge0
Complexity1690
Isotope Atom Count0
Defined Atom Stereocenter Count11
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameJevtana kit
Active IngredientCabazitaxel
Dosage FormSolution
RouteIv (infusion)
Strength60mg/1.5ml (40mg/ml)
Market StatusPrescription
CompanySanofi Aventis Us

2 of 2  
Drug NameJevtana kit
Active IngredientCabazitaxel
Dosage FormSolution
RouteIv (infusion)
Strength60mg/1.5ml (40mg/ml)
Market StatusPrescription
CompanySanofi Aventis Us

4.2 Drug Indication

For treatment of patients with hormone-refractory metastatic prostate cancer previously treated with a docetaxel-containing treatment regimen.


FDA Label


Jevtana in combination with prednisone or prednisolone is indicated for the treatment of patients with hormone-refractory metastatic prostate cancer previously treated with a docetaxel-containing regimen.


Treatment of prostate cancer


Treatment of patients with hormone refractory metastatic prostate cancer previously treated with a docetaxel-containing regimen.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Cabaitaxel has anti-tumour properties and is effective against docetaxel-sensitive and -insensitive tumours.


5.2 FDA Pharmacological Classification
5.2.1 Active Moiety
CABAZITAXEL
5.2.2 FDA UNII
51F690397J
5.2.3 Pharmacological Classes
Established Pharmacologic Class [EPC] - Microtubule Inhibitor
5.3 ATC Code

L01CD


L01CD04


L01CD04


L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01C - Plant alkaloids and other natural products

L01CD - Taxanes

L01CD04 - Cabazitaxel


5.4 Absorption, Distribution and Excretion

Absorption

After an intravenous dose of cabazitaxel 25 mg/m2 every three weeks to a population of 170 patients with solid tumors, the mean Cmax in patients with metastatic prostate cancer was 226 ng/mL (CV 107%) and was reached at the end of the one-hour infusion (Tmax). The mean AUC in patients with metastatic prostate cancer was 991 ng.h/mL (CV 34%). Administration with prednisone or prednisolone do not effect the pharmacokinetic profile of cabazitaxel.


Route of Elimination

After a one-hour intravenous infusion [14C]-cabazitaxel 25 mg/m2, approximately 80% of the administered dose was eliminated within 2 weeks. Cabazitaxel is mainly excreted in the feces as numerous metabolites (76% of the dose); while renal excretion of cabazitaxel and metabolites account for 3.7% of the dose (2.3% as unchanged drug in urine).


Volume of Distribution

The volume of distribution (Vss) was 4,864 L (2,643 L/m2 for a patient with a median BSA of 1.84 m2) at steady state. Compared to other taxanes, penetrates the CNS to a greater extent.


Clearance

Cabazitaxel has a plasma clearance of 48.5 L/h (CV 39%; 26.4 L/h/m2 for a patient with a median BSA of 1.84 m2) in patients with metastatic prostate cancer.


5.5 Metabolism/Metabolites

Cabazitaxel is extensively metabolized in the liver (>95%), mainly by the CYP3A4/5 isoenzyme (80% to 90%), and to a lesser extent by CYP2C8 which results in 20 different metabolites. Two of these metabolites are active demethylated derivatives of cabaxitaxel and referred to as RPR112698 and RPR123142 respectively. Docetaxel is another metabolite of cabazitaxel. Cabazitaxel is the main circulating moiety in human plasma.


5.6 Biological Half-Life

Following a one-hour intravenous infusion, plasma concentrations of cabazitaxel can be described by a three-compartment pharmacokinetic model with -, -, and - half-lives of 4 minutes, 2 hours, and 95 hours, respectively.


5.7 Mechanism of Action

Cabazitaxel is a microtubule inhibitor. Cabazitaxel binds to tubulin and promotes its assembly into microtubules while simultaneously inhibiting disassembly. This leads to the stabilization of microtubules, which results in the interference of mitotic and interphase cellular functions. The cell is then unable to progress further into the cell cycle, being stalled at metaphase, thus triggering apoptosis of the cancer cell.


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Protheragen

U.S.A
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Cabazitaxel

About the Company : Protheragen helps clients achieve cost-effective improvements in R\&D productivity by providing reliable products and solutions to the global chemical industry. Our offerings inclu...

Protheragen helps clients achieve cost-effective improvements in R\&D productivity by providing reliable products and solutions to the global chemical industry. Our offerings include chemical products, packaging, equipment, and custom synthesis. With state-of-the-art manufacturing facilities, professional R\&D teams, and ISO9001 certification, we are committed to becoming a leading supplier of pharmaceutical ingredients and specialty chemicals, delivering quality and innovation to meet diverse industry needs worldwide.
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Cabazitaxel

About the Company : Shilpa Medicare Limited (SML) started its operations as API manufacturer way back in 1987 at Raichur, Karnataka- India. The commercial production in the SML was started in November...

Shilpa Medicare Limited (SML) started its operations as API manufacturer way back in 1987 at Raichur, Karnataka- India. The commercial production in the SML was started in November 1989. Today Shilpa Medicare Limited is a global brand in manufacturing and supplying of affordable API and Formulation globally in different regulated markets.
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10

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Cabazitaxel

About the Company : Founded in 1980, Sichuan Xieli Pharmaceutical Co., Ltd. operates with the guiding principle of "collaborating to build a healthy enterprise." The company specializes in the cultiva...

Founded in 1980, Sichuan Xieli Pharmaceutical Co., Ltd. operates with the guiding principle of "collaborating to build a healthy enterprise." The company specializes in the cultivation of ecological medicinal materials, extraction of natural active ingredients from plants and animals, and the synthesis and R&D of their derivatives. Its core focus lies in producing high value-added products for export. The company’s diverse portfolio includes dozens of products such as rutin-based cardiovascular and cerebrovascular medications, plant flavonoid capillary drugs, plant-derived anti-tumor agents, animal and plant extracts, etc.
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28-Mar-2022
20-May-2025
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ABOUT THIS PAGE

Looking for 183133-96-2 / Cabazitaxel API manufacturers, exporters & distributors?

Cabazitaxel manufacturers, exporters & distributors 1

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

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Cabazitaxel manufacturer or Cabazitaxel supplier.

PharmaCompass also assists you with knowing the Cabazitaxel API Price utilized in the formulation of products. Cabazitaxel API Price is not always fixed or binding as the Cabazitaxel Price is obtained through a variety of data sources. The Cabazitaxel Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Cabazitaxel

Synonyms

183133-96-2, Jevtana, Taxoid xrp6258, Txd 258, Xrp-6258, Cabazitaxelum

Cas Number

183133-96-2

Unique Ingredient Identifier (UNII)

51F690397J

About Cabazitaxel

Cabazitaxel is a semi-synthetic derivative of the natural taxoid 10-deacetylbaccatin III with potential antineoplastic activity. Cabazitaxel binds to and stabilizes tubulin, resulting in the inhibition of microtubule depolymerization and cell division, cell cycle arrest in the G2/M phase, and the inhibition of tumor cell proliferation. Unlike other taxane compounds, this agent is a poor substrate for the membrane-associated, multidrug resistance (MDR), P-glycoprotein (P-gp) efflux pump and may be useful for treating multidrug-resistant tumors. In addition, cabazitaxel penetrates the blood-brain barrier (BBB).

Cabazitaxel Manufacturers

A Cabazitaxel manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Cabazitaxel, including repackagers and relabelers. The FDA regulates Cabazitaxel manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Cabazitaxel 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 Cabazitaxel manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Cabazitaxel Suppliers

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

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

Cabazitaxel USDMF

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

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

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

Cabazitaxel WC

A Cabazitaxel written confirmation (Cabazitaxel WC) is an official document issued by a regulatory agency to a Cabazitaxel manufacturer, verifying that the manufacturing facility of a Cabazitaxel active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting Cabazitaxel APIs or Cabazitaxel finished pharmaceutical products to another nation, regulatory agencies frequently require a Cabazitaxel WC (written confirmation) as part of the regulatory process.

click here to find a list of Cabazitaxel suppliers with Written Confirmation (WC) on PharmaCompass.

Cabazitaxel 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 Cabazitaxel as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Cabazitaxel 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 Cabazitaxel 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 Cabazitaxel and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Cabazitaxel NDC to their finished compounded human drug products, they may choose to do so.

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

Cabazitaxel GMP

Cabazitaxel 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 Cabazitaxel 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 Cabazitaxel GMP manufacturer or Cabazitaxel GMP API supplier for your needs.

Cabazitaxel CoA

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

Cabazitaxel CoA mostly includes findings from lab analyses of a specific batch. For each Cabazitaxel 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.

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