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TXD258

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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 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 Formula	C₄₅H₅₇NO₁₄
Molecular Weight	835.9 g/mol
XLogP3	2.7
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	14
Rotatable Bond Count	15
Exact Mass	835.37790549 g/mol
Monoisotopic Mass	835.37790549 g/mol
Topological Polar Surface Area	202 Å²
Heavy Atom Count	60
Formal Charge	0
Complexity	1690
Isotope Atom Count	0
Defined Atom Stereocenter Count	11
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	Jevtana kit
Active Ingredient	Cabazitaxel
Dosage Form	Solution
Route	Iv (infusion)
Strength	60mg/1.5ml (40mg/ml)
Market Status	Prescription
Company	Sanofi Aventis Us

2 of 2
Drug Name	Jevtana kit
Active Ingredient	Cabazitaxel
Dosage Form	Solution
Route	Iv (infusion)
Strength	60mg/1.5ml (40mg/ml)
Market Status	Prescription
Company	Sanofi 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

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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