All Manufacturers, Suppliers, Distributors and Exporters of Paclitaxel with approved in Europe Marketing Authorisations (MA) of Finished Dosage Form listed on PharmaCompass.com

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Chemistry

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Also known as: 33069-62-4, P88xt4is4d, Taxol, Taxol a, Yewtaxan, Abraxane
Molecular Formula
C47H51NO14
Molecular Weight
853.9  g/mol
InChI Key
RCINICONZNJXQF-MZXODVADSA-N
FDA UNII
P88XT4IS4D

Paclitaxel
Nab-paclitaxel is a Cremophor EL-free, albumin-stabilized nanoparticle formulation of the natural taxane paclitaxel with antineoplastic activity. Paclitaxel binds to and stabilizes microtubules, preventing their depolymerization and so inhibiting cellular motility, mitosis, and replication. This formulation solubilizes paclitaxel without the use of the solvent Cremophor, thereby permitting the administration of larger doses of paclitaxel while avoiding the toxic effects associated with Cremophor.
Paclitaxel is a Microtubule Inhibitor. The physiologic effect of paclitaxel is by means of Microtubule Inhibition.
1 2D Structure

Paclitaxel

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-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/C47H51NO14/c1-25-31(60-43(56)36(52)35(28-16-10-7-11-17-28)48-41(54)29-18-12-8-13-19-29)23-47(57)40(61-42(55)30-20-14-9-15-21-30)38-45(6,32(51)22-33-46(38,24-58-33)62-27(3)50)39(53)37(59-26(2)49)34(25)44(47,4)5/h7-21,31-33,35-38,40,51-52,57H,22-24H2,1-6H3,(H,48,54)/t31-,32-,33+,35-,36+,37+,38-,40-,45+,46-,47+/m0/s1
2.1.3 InChI Key
RCINICONZNJXQF-MZXODVADSA-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)C6=CC=CC=C6)O)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)O)C)OC(=O)C
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)C6=CC=CC=C6)O)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)O)C)OC(=O)C
2.2 Other Identifiers
2.2.1 UNII
P88XT4IS4D
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 33069-62-4

2. P88xt4is4d

3. Taxol

4. Taxol A

5. Yewtaxan

6. Abraxane

7. Plaxicel

8. Genaxol

9. Ebetaxel

10. Genetaxyl

11. Capxol

12. Paxene

13. Onxol

14. Oncogel

15. Cyclopax

16. Genexol

17. Intaxel

18. Mitotax

19. Pacliex

20. Paxceed

21. Taxalbin

22. Empac

23. Abi-007

24. Onxal

25. Zisu

26. Lipopac

27. Taxus Liberte

28. Taxus Stent

29. Paclitaxel (taxol)

30. Endotag 1

31. Lep-etu

32. Genexol-pm

33. Tocosol Paclitaxel

34. Nsc-125973

35. (-)-paclitaxel

36. Taxus

37. Abi 007

38. Bms 181339-01

39. Mbt 0206

40. Nsc 125973

41. Bms-181339-01

42. Hsdb 6839

43. Dhp 107

44. Dhp-107

45. Drg-0190

46. Nk 105

47. Nsc125973

48. Qw 8184

49. Liposome-entrapped Paclitaxel Easy-to-use

50. Paclitaxel (taxus Canadensis)

51. Chembl428647

52. (2ar,4s,4as,6r,9s,11s,12s,12ar,12bs)-9-(((2r,3s)-3-benzamido-2-hydroxy-3-phenylpropanoyl)oxy)-12-(benzoyloxy)-4,11-dihydroxy-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]oxete-6,12b-diyl Diacetate

53. 5beta,20-epoxy-1,2-alpha,4,7beta,10beta,13alpha-hexahydroxytax-11-en-9-one 4,10-diacetate 2-benzoate 13-ester With (2r,3s)-n-benzoyl-3-phenylisoserine

54. Chebi:45863

55. Nab-paclitaxel

56. Mbt-0206

57. Abi-007 Component Paclitaxel

58. Nk-105

59. (2ar-(2aalpha,4beta,4abeta,6beta,9alpha(alpha R*,betas*),11alpha,12alpha,12balpha))-beta-(benzoylamino)-alpha-hydroxybenzenepropanoic Acid 6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1h-cyclodeca(3,4)benz(1,2-b)oxet-9-yl Ester

60. Qw-8184

61. Ncgc00164367-01

62. Padexol

63. Mfcd00869953

64. Cynviloq

65. Nanoxel

66. Sindaxel

67. Xorane

68. Cypher Select

69. Coroflex Please

70. Taxus Express

71. 7,11-methano-1h-cyclodeca[3,4]benz[1,2-b]oxete, Benzenepropanoic Acid Deriv.

72. (1s,2s,3r,4s,7r,9s,10s,12r,15s)-4,12-bis(acetyloxy)-1,9-dihydroxy-15-{[(2r,3s)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-2-yl Benzoate

73. (nab)-paclitaxel

74. [(1s,2s,3r,4s,7r,9s,10s,12r,15s)-4,12-diacetyloxy-15-[(2r,3s)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] Benzoate

75. Smr000857385

76. Endotag-1

77. Sr-01000075350

78. Abraxane I.v. Suspension

79. Unii-p88xt4is4d

80. Anzatax

81. Infinnium

82. Nanotaxel

83. Paclical

84. Pacligel

85. Paxoral

86. Ccris 8143

87. Paclitaxel,(s)

88. Paclitaxel [usan:usp:inn:ban]

89. Abraxane (tn)

90. (2alpha,5beta,7beta,10beta,13alpha)-4,10-bis(acetyloxy)-1,7-dihydroxy-13-({(2r,3s)-2-hydroxy-3-phenyl-3-[(phenylcarbonyl)amino]propanoyl}oxy)-9-oxo-5,20-epoxytax-11-en-2-yl Benzoate

91. [diacetoxy-[(2r,3s)-3-benzamido-2-hydroxy-3-phenyl-propanoyl]oxy-dihydroxy-tetramethyl-oxo-[?]yl] Benzoate

92. 5?,20-epoxy-1,7?-dihydroxy-9-oxotax-11-ene-2?,4,10?,13?-tetrayl 4,10-diacetate 2-benzoate 13-[(2r,3s)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoate]

93. Nanoparticle Albumin Bound Paclitaxel

94. Cas-33069-62-4

95. Ig 001

96. Bms-181339

97. Paclitaxel-ssmm-vip

98. P-ssmm-vip

99. Paclitaxel [mi]

100. Paclitaxel [inn]

101. Paclitaxel [jan]

102. Prestwick3_000155

103. Paclitaxel [hsdb]

104. Paclitaxel [usan]

105. Dsstox_cid_3413

106. Taxol (tn)

107. Paclitaxel [vandf]

108. Paclitaxel [mart.]

109. Schembl3976

110. Dsstox_rid_77016

111. Nova-12005

112. Paclitaxel [usp-rs]

113. Paclitaxel [who-dd]

114. Paclitaxel, Taxus Brevifolia

115. Bidd:pxr0046

116. Dsstox_gsid_23413

117. Bspbio_000290

118. Kbiogr_002509

119. Kbioss_002517

120. Paclitaxel (jan/usp/inn)

121. Mls002154218

122. Mls002695976

123. Oas-pac-100

124. Paclitaxel [ema Epar]

125. Bpbio1_000320

126. Gtpl2770

127. Megxp0_001940

128. Taxol (tn) (bristol Meyers)

129. Paclitaxel [green Book]

130. Dtxsid9023413

131. Paclitaxel [orange Book]

132. Tsd-001 [who-dd]

133. Acon1_002231

134. Kbio2_002509

135. Kbio2_005077

136. Kbio2_007645

137. Kbio3_002987

138. Anx-513

139. Dhp-208

140. Dts-301

141. Paclitaxel [ep Monograph]

142. Paclitaxel [usp Impurity]

143. Sdp-013

144. Cmap_000068

145. Oraxol Component Paclitaxel

146. Hms2090d07

147. Hms2095o12

148. Hms2231a16

149. Hms3712o12

150. Paclitaxel [usp Monograph]

151. Abraxane (albumin-bound Suspension)

152. Abraxane Component Paclitaxel

153. Act02709

154. Hy-b0015

155. Mpi-5018

156. Tox21_112107

157. Bdbm50001839

158. Nsc745099

159. Zinc96006020

160. Abi 007 Component Paclitaxel

161. Akos007930675

162. Akos015969673

163. Akos025312303

164. Ccg-220155

165. Cs-1145

166. Db01229

167. Gs-6554

168. Nsc-745099

169. Ncgc00164367-02

170. Ncgc00164367-03

171. Ncgc00164367-04

172. Ncgc00164367-05

173. Ncgc00164367-10

174. Paclitaxel, From Taxus Brevifolia, 95%

175. (2ar,4s,4as,6r,9s,11s,12s,12ar,12bs)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-dodecahydro-4,6,9,11,12,12b-hexahydroxy-4a,8,13,13-tetramethyl-7,11-methano-5h-cyclodeca(3,4)benz(1,2-b)oxet-5-one 6,12b-diacetate, 12-benzoate, 9-ester With (2r,3s)-n-benzoyl-3-phenylisoserine

176. Nab-paclitaxel Component Paclitaxel

177. Nci60_000601

178. Paclitaxel, From Taxus Yannanensis, Powder

179. Ab00513812

180. N1361

181. D00491

182. M02242

183. N88686

184. Ab00513812-02

185. Ab00513812-03

186. 069p624

187. Paclitaxel, Antibiotic For Culture Media Use Only

188. Q423762

189. 7,4]benz[1,2-b]oxete,benzenepropanoic Acid Deriv.

190. Q-201533

191. Sr-01000075350-1

192. Sr-01000075350-3

193. Sr-01000075350-6

194. Sr-01000075350-7

195. Sr-01000075350-9

196. Brd-k62008436-001-03-1

197. Brd-k62008436-001-05-6

198. Brd-k62008436-001-22-1

199. Paclitaxel, From Semisynthetic (from Taxus Sp.), >=97%

200. Paclitaxel, European Pharmacopoeia (ep) Reference Standard

201. Paclitaxel, From Taxus Brevifolia, >=95% (hplc), Powder

202. Paclitaxel, United States Pharmacopeia (usp) Reference Standard

203. 12-benzoate, 9-ester With (2r,3s)-n-benzoyl-3-phenylisoserine

204. Paclitaxel, Pharmaceutical Secondary Standard; Certified Reference Material

205. Paclitaxel Natural For Peak Identification, European Pharmacopoeia (ep) Reference Standard

206. (2ar,4s,4as,6r,9s,11s,12s,12ar,12bs)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-dodecahydro 4,6,9,11,12,12b-hexahydroxy-4a,8,13,13-tetramethyl-7,11-methano 5hcyclodeca(3,4)benz(1,2-b)oxet-5-one 6,12b-diacetate,

207. (2ar,4s,4as,6r,9s,11s,12s,12ar,12bs)-6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1h-cyclodeca[3,4]benz[1,2-b]oxet-9-yl (ar,bs)-b-(benzoylamino)-a-hydroxybenzenepropanoate

208. (2ar,4s,4as,6r,9s,11s,12s,12ar,12bs)-9-(((2r,3s)-3-benzamido-2-hydroxy-3-phenylpropanoyl)oxy)-12-(benzoyloxy)-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-3,4,4a,5,6,9,10,11,12,12a-decahydro-1h-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2ah)-diyl Diacetate

209. (2ar-(2aalpha,4beta,4abeta,6beta,9alpha(alpha R*,betas*),11alpha,12alpha,12balpha))-beta-(benzoylamino)-alpha-hydroxybenzenepropanoic Acid 6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12

210. (2beta,5beta,7alpha,8alpha,10alpha,13alpha)-4,10-bis(acetyloxy)-1,7-dihydroxy-13-({(2r,3s)-2-hydroxy-3-phenyl-3-[(phenylcarbonyl)amino]propanoyl}oxy)-9-oxo-5,20-epoxytax-11-en-2-yl Benzoate

211. 1203669-79-7

212. 4alpha,10beta-bis(acetyloxy)-13alpha-[(2s,3s)-3-benzamido-2-hydroxy-3-phenylpropanoyloxy]-1,7beta-dihydroxy-9-oxo-5beta,20-epoxytax-11-en-2alpha-yl Benzoate

213. Benzenepropanoic Acid, .beta.-(benzoylamino)-.alpha.-hydroxy-, (2ar,4s,4as,6r,9s,11s,12s,12ar,12bs)-6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1h-cyclodeca(3,4)benz(1,2-b)oxet-9-yl Ester, (.alpha.r,.beta.s)-

214. Benzenepropanoic Acid, 6,12b-bis(acetyl Oxy)-12-(benzoyloxy)- 2a,3,4,4a,5,6,9,10,11,12,12a,12b,- Dodecahydro-4,11- Dihydroxy-4a,8,13,13-tetramethyl-5-oxo- 7,11-methano- 1h-cyclodeca[3,4]benz[1,2-b]oxet-9-yl Ester, [2ar- [2a.alpha.,4.beta.,4a.beta.,6.beta.,9.alpha.(alpha. R*,.beta.s*),11.alpha.,12.alpha.,12a.alpha.,12b.alpha.]]-

215. Benzenepropanoic Acid, B-(benzoylamino)-.alpha.-hydroxy-, (2ar,4s,4as,6r,9s,11s,12s,12ar,12bs)-6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1h-cyclodeca[3,4]benz[1,2-b]oxet-9-yl Ester, (ar,bs)-

216. Benzenepropanoic Acid, Beta-(benzoylamino)-alpha-hydroxy-, (2ar,4s,4as,6r,9s,11s,12s,12ar,12bs)-6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13

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

218. Benzenepropanoic Acid, Beta-(benzoylamino)-alpha-hydroxy-, 6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1h

219. Benzenepropanoic Acid, Beta-(benzoylamino)-alpha-hydroxy-, 6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1h-cyclodeca(3,4)benz(1,2-b)oxet-9-yl Ester, (2ar-(2a-alpha,4-beta,4a-beta,6-beta,9-alpha(alpha-r*,beta-s*),11-alpha,12-alpha,12a-alpha, 12b-alpha))-

220. Benzenepropanoic Acid, Beta-(benzoylamino)-alpha-hydroxy-, 6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1h-cyclodeca(3,4)benz(1,2-b)oxet-9-yl Ester, (2ar-(2aalpha,4beta,4abeta,6beta,9alpha(alphar*,betas*),11alpha,12alpha,12aalpha,12balpha))-

221. Paclitaxel Semi-synthetic For Peak Identification, European Pharmacopoeia (ep) Reference Standard

222. Paclitaxel Semi-synthetic For System Suitability, European Pharmacopoeia (ep) Reference Standard

223. Tax-11-en-9-one, 5beta,20-epoxy-1,2alpha,4,7beta,10beta,13alpha- Hexahydroxy-, 4,10-diacetate 2-benzoate, 13-ester With (2r,3s)-n-benzoyl-3-phenylisoserine

224. Tax-11-en-9-one, 5beta,20-epoxy-1,2alpha,4,7beta,10beta,13alpha-hexahydroxy-, 4,10-diacetate 2-benzoate 13-ester With (2r,3s)-n-benzoyl-3-phenylisoserine (8ci)

225. Tax-11-en-9-one,20-epoxy-1,2.alpha.,4,7.beta., 10.beta.,13.alpha.- Hexahydroxy-, 4,10-diacetate 2- Benzoate,13-ester With (2r,3s)-n-benzoyl-3-phenylisoserine

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 853.9 g/mol
Molecular Formula C47H51NO14
XLogP32.5
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count14
Rotatable Bond Count14
Exact Mass853.33095530 g/mol
Monoisotopic Mass853.33095530 g/mol
Topological Polar Surface Area221 Ų
Heavy Atom Count62
Formal Charge0
Complexity1790
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 6  
Drug NameAbraxane
PubMed HealthPaclitaxel Protein-bound (Injection)
Drug ClassesAntineoplastic Agent
Active IngredientPaclitaxel
Dosage FormFor suspension
RouteIv (infusion)
Strength100mg/vial
Market StatusPrescription
CompanyAbraxis Bioscience

2 of 6  
Drug NamePaclitaxel
PubMed HealthPaclitaxel (Injection)
Drug ClassesAntineoplastic Agent
Active IngredientPaclitaxel
Dosage FormInjectable
RouteInjection
Strength6mg/ml
Market StatusPrescription
CompanyHospira; Fresenius Kabi Oncol; Actavis Elizabeth; Teva Pharms; Ebewe Pharma; Onco Therapies; Eurohlth Intl

3 of 6  
Drug NameTaxol
PubMed HealthPaclitaxel (Injection)
Drug ClassesAntineoplastic Agent
Drug LabelPaclitaxel Injection, USP is a clear colorless to slightly yellow viscous solution. It is supplied as a nonaqueous solution intended for dilution with a suitable parenteral fluid prior to intravenous infusion. Paclitaxel Injection, USP is available i...
Active IngredientPaclitaxel
Dosage FormInjectable
RouteInjection
Strength6mg/ml
Market StatusPrescription
CompanyHq Spclt Pharma

4 of 6  
Drug NameAbraxane
PubMed HealthPaclitaxel Protein-bound (Injection)
Drug ClassesAntineoplastic Agent
Active IngredientPaclitaxel
Dosage FormFor suspension
RouteIv (infusion)
Strength100mg/vial
Market StatusPrescription
CompanyAbraxis Bioscience

5 of 6  
Drug NamePaclitaxel
PubMed HealthPaclitaxel (Injection)
Drug ClassesAntineoplastic Agent
Active IngredientPaclitaxel
Dosage FormInjectable
RouteInjection
Strength6mg/ml
Market StatusPrescription
CompanyHospira; Fresenius Kabi Oncol; Actavis Elizabeth; Teva Pharms; Ebewe Pharma; Onco Therapies; Eurohlth Intl

6 of 6  
Drug NameTaxol
PubMed HealthPaclitaxel (Injection)
Drug ClassesAntineoplastic Agent
Drug LabelPaclitaxel Injection, USP is a clear colorless to slightly yellow viscous solution. It is supplied as a nonaqueous solution intended for dilution with a suitable parenteral fluid prior to intravenous infusion. Paclitaxel Injection, USP is available i...
Active IngredientPaclitaxel
Dosage FormInjectable
RouteInjection
Strength6mg/ml
Market StatusPrescription
CompanyHq Spclt Pharma

4.2 Therapeutic Uses

Antineoplastic Agents, Phytogenic; Radiation-Sensitizing Agents

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


Standard formulation paclitaxel requires the use of solvents, such as Cremphor-EL, which contribute to some of the toxicities commonly associated with paclitaxel-based therapy. Nanoparticle albumin-bound paclitaxel (nab-paclitaxel) is a novel solvent-free formulation of paclitaxel. The formulation is prepared by high-pressure homogenization of paclitaxel in the presence of serum albumin into a nanoparticle colloidal suspension. The human albumin-stabilized paclitaxel particles have an average size of 130 nm. Nab-paclitaxel has several practical advantages over Cremphor-EL-paclitaxel, including a shorter infusion time (30 min) and no need for premedications for hypersensitivity reactions. The nab-paclitaxel formulation eliminates the impact of Cremphor-EL on paclitaxel pharmacokinetics and utilizes the endogenous albumin transport mechanisms to concentrate nab-paclitaxel within the tumor. A recent Phase III trial compared nab- and Cremphor-EL-paclitaxel in patients with metastatic breast cancer. Patients treated with nab-paclitaxel experienced a higher response, longer time to tumor progression and, in patients receiving second-line or greater therapy, a longer median survival. Patients treated with nab-paclitaxel had a significantly lower rate of severe neutropenia and a higher rate of sensory neuropathy. The preclinical and clinical data indicate that the nab-paclitaxel formulation has significant advantages over Cremphor-EL-paclitaxel.

PMID:17716129 Stinchcombe TE; Nanomed 2 (4): 415-23 (2007)


As first line and subsequent therapy for the treatment of advanced carcinoma of the ovary. As first-line therapy, paclitaxel is indicated in combination with cisplatin.

Novak, K.M. (ed.). Drug Facts and Comparisons2008 Edition. Wolters Kluwer Health. St. Louis, Missouri 2008., p. 2833


Adjuvant treatment of node-positive breast cancer administration sequentially to standard doxorubicin-containing combination chemotherapy. In the clinical trial, there was an overall favorable effect on disease-free and overall survival in the total population of patients with receptor-positive and receptor-negative tumors, but the benefit has been specifically demonstrated by available data (mean follow-up, 30 months) only in the patients with estrogen and progesterone receptor-negative tumors. Indicated for the treatment of breast cancer after failure of combination chemotherapy for metastatic disease or relapse within 6 months of adjuvant chemotherapy. Previous therapy should have included an anthracycline unless clinically contraindicated.

Novak, K.M. (ed.). Drug Facts and Comparisons2008 Edition. Wolters Kluwer Health. St. Louis, Missouri 2008., p. 2833


For more Therapeutic Uses (Complete) data for TAXOL (9 total), please visit the HSDB record page.


4.3 Drug Warning

Administer paclitaxel under the supervision of a health care provider experienced in the use of cancer chemotherapeutic agents. Appropriate management of complications is possible only when adequate diagnostic and treatment facilitates are readily available.

Novak, K.M. (ed.). Drug Facts and Comparisons2008 Edition. Wolters Kluwer Health. St. Louis, Missouri 2008., p. 2833


Do not give paclitaxel therapy to patients with solid tumors who have baseline neutrophil counts of less than 1,500 cells/cu mm, and do not give to patients with AIDS-related Kaposi sarcoma if the baseline neutrophil count is less than 1,000 cells/cu mm. In order to monitor the occurrence of bone marrow suppression, primarily neutropenia, which may be severe and result in infection, perform frequent peripheral blood cell counts on all patients receiving paclitaxel.

Novak, K.M. (ed.). Drug Facts and Comparisons2008 Edition. Wolters Kluwer Health. St. Louis, Missouri 2008., p. 2833


Anaphylaxis and severe hypersensitivity reactions characterized by dyspnea and hypotension requiring treatment, angioedema, and generalized urticaria have occurred in 2% to 4% of patients receiving paclitaxel in clinical trials. Fatal reactions have occurred in patients despite premedication. Pretreat all patients with corticosteroids, diphenhydramine, and H2 antagonists. Do not rechallenge patients who experience severe hypersensitivity reactions to paclitaxel with the drug.

Novak, K.M. (ed.). Drug Facts and Comparisons2008 Edition. Wolters Kluwer Health. St. Louis, Missouri 2008., p. 2833


An albumin form of paclitaxel may substantially affect a drug's functional properties relative to those of drug in solution. Do not substitute for or with other paclitaxel formulations. /Paclitaxel (albumin-bound)/

Novak, K.M. (ed.). Drug Facts and Comparisons2008 Edition. Wolters Kluwer Health. St. Louis, Missouri 2008., p. 2833


For more Drug Warnings (Complete) data for TAXOL (62 total), please visit the HSDB record page.


4.4 Drug Indication

Used in the treatment of Kaposi's sarcoma and cancer of the lung, ovarian, and breast. Abraxane is specfically indicated for the treatment of metastatic breast cancer and locally advanced or metastatic non-small cell lung cancer.


FDA Label


Pazenir monotherapy is indicated for the treatment of metastatic breast cancer in adult patients who have failed first-line treatment for metastatic disease and for whom standard, anthracycline containing therapy is not indicated.

Pazenir in combination with carboplatin is indicated for the first-line treatment of non-small cell lung cancer in adult patients who are not candidates for potentially curative surgery and/or radiation therapy.


Abraxane monotherapy is indicated for the treatment of metastatic breast cancer in adult patients who have failed first-line treatment for metastatic disease and for whom standard, anthracycline containing therapy is not indicated.

Abraxane in combination with gemcitabine is indicated for the first-line treatment of adult patients with metastatic adenocarcinoma of the pancreas.

Abraxane in combination with carboplatin is indicated for the first-line treatment of non-small cell lung cancer in adult patients who are not candidates for potentially curative surgery and/or radiation therapy.


Apealea in combination with carboplatin is indicated for the treatment of adult patients with first relapse of platinumsensitive epithelial ovarian cancer , primary peritoneal cancer and fallopian tube cancer .


Paxene is indicated for the treatment of patients with:

advanced AIDS-related Kaposi's sarcoma (AIDS-KS) who have failed prior liposomal anthracycline therapy;

metastatic carcinoma of the breast (MBC) who have failed, or are not candidates for standard anthracycline-containing therapy;

advanced carcinoma of the ovary (AOC) or with residual disease (> 1 cm) after initial laparotomy, in combination with cisplatin as first-line treatment;

metastatic carcinoma of the ovary (MOC) after failure of platinum-containing combination therapy without taxanes as second-line treatment;

non-small cell lung carcinoma (NSCLC) who are not candidates for potentially curative surgery and/or radiation therapy, in combination with cisplatin. Limited efficacy data supports this indication (see section 5. 1).


Treatment of solid malignant tumours


Treatment of soft tissue sarcoma


5 Pharmacology and Biochemistry
5.1 Pharmacology

Paclitaxel is a taxoid antineoplastic agent indicated as first-line and subsequent therapy for the treatment of advanced carcinoma of the ovary, and other various cancers including breast cancer. Paclitaxel is a novel antimicrotubule agent that promotes the assembly of microtubules from tubulin dimers and stabilizes microtubules by preventing depolymerization. This stability results in the inhibition of the normal dynamic reorganization of the microtubule network that is essential for vital interphase and mitotic cellular functions. In addition, paclitaxel induces abnormal arrays or "bundles" of microtubules throughout the cell cycle and multiple asters of microtubules during mitosis.


5.2 FDA Pharmacological Classification
5.2.1 Active Moiety
PACLITAXEL
5.2.2 FDA UNII
P88XT4IS4D
5.2.3 Pharmacological Classes
Microtubule Inhibitor [EPC]; Microtubule Inhibition [PE]
5.3 ATC Code

L01CD01


L01CD01


L01CD01


L01CD01


L01CD01

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

L01C - Plant alkaloids and other natural products

L01CD - Taxanes

L01CD01 - Paclitaxel


5.4 Absorption, Distribution and Excretion

Absorption

When a 24 hour infusion of 135 mg/m^2 is given to ovarian cancer patients, the maximum plasma concentration (Cmax) is 195 ng/mL, while the AUC is 6300 ngh/mL.


Route of Elimination

In 5 patients administered a 225 or 250 mg/m2 dose of radiolabeled paclitaxel as a 3-hour infusion, a mean of 71% of the radioactivity was excreted in the feces in 120 hours, and 14% was recovered in the urine.


Volume of Distribution

227 to 688 L/m^2 [apparent volume of distribution at steady-state, 24 hour infusion]


Clearance

21.7 L/h/m2 [Dose 135 mg/m2, infusion duration 24 h]

23.8 L/h/m2 [Dose 175 mg/m2, infusion duration 24 h]

7 L/h/m2 [Dose 135 mg/m2, infusion duration 3 h]

12.2 L/h/m2 [Dose 175 mg/m2, infusion duration 3 h]


Paclitaxel bound to nanoparticles of the serum protein albumin is delivered via endothelial transport mediated by albumin receptors, and the resulting concentration of paclitaxel in tumor cells is increased compared with that achieved using an equivalent dose of conventional paclitaxel. Like conventional paclitaxel, albumin-bound paclitaxel has a large volume of distribution. Following 30-minute or 3-hour IV infusion of 80-375 mg/sq m albumin-bound paclitaxel, the volume of distribution averaged 632 L/sq m. The volume of distribution of albumin-bound paclitaxel 260 mg/sq m by 30-minute IV infusion was 53% larger than the volume of distribution of conventional paclitaxel 175 mg/sq m by 3-hour IV infusion. /Paclitaxel (albumin-bound)/

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 1188


Following IV administration, paclitaxel is widely distributed into body fluids and tissues. Paclitaxel has a large volume of distribution that appears to be affected by dose and duration of infusion. Following administration of paclitaxel doses of 135 or 175 mg/sq m by IV infusion over 24 hours in patients with advanced ovarian cancer, the mean apparent volume of distribution at steady state ranged from 227-688 L/sq m. The steady-state volume of distribution ranged from 18.9-260 L/sq m in children with solid tumors or refractory leukemia receiving paclitaxel 200-500 mg/sq m by 24-hour IV infusion. Paclitaxel does not appear to readily penetrate the CNS, but paclitaxel has been detected in ascitic fluid following IV infusion of the drug. It is not known whether paclitaxel is distributed into human milk, but in lactating rats given radiolabeled paclitaxel, concentrations of radioactivity in milk were higher than those in plasma and declined in parallel with plasma concentrations of the drug.

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 1188


For the dose range 80-375 mg/sq m, increase in dose of albumin-bound paclitaxel was associated with a proportional increase in AUC.354 The duration of infusion did not affect the pharmacokinetic disposition of albumin-bound paclitaxel. Following 30-minute or 3-hour IV infusion of albumin-bound paclitaxel 260 mg/sq m, the peak plasma concentration averaged 18,741 ng/mL. /Paclitaxel (albumin-bound)/

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 1188


Peak plasma concentrations and areas under the plasma concentration-time curve (AUCs) following IV administration of paclitaxel exhibit marked interindividual variation. Plasma concentrations of paclitaxel increase during continuous IV administration of the drug and decline immediately following completion of the infusion. Following 24-hour IV infusion of paclitaxel at doses of 135 or 175 mg/sq m in patients with advanced ovarian cancer, peak plasma concentrations averaged 195 or 365 ng/mL, respectively; the increase in dose (30%) was associated with a disproportionately greater increase in peak plasma concentration (87%), but the increase in AUC was proportional. When paclitaxel was administered by continuous IV infusion over 3 hours at doses of 135 or 175 mg/sq m in patients with advanced ovarian cancer, peak plasma concentrations averaged 2.17 or 3.65 ug/mL, respectively; the increase in dose (30%) was associated with disproportionately greater increases in peak plasma concentration (68%) and AUC (89%).

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 1188


For more Absorption, Distribution and Excretion (Complete) data for TAXOL (8 total), please visit the HSDB record page.


5.5 Metabolism/Metabolites

Hepatic. In vitro studies with human liver microsomes and tissue slices showed that paclitaxel was metabolized primarily to 6a-hydrox-ypaclitaxel by the cytochrome P450 isozyme CYP2C8; and to two minor metabolites, 3’-p-hydroxypaclitaxel and 6a, 3’-p-dihydroxypaclitaxel, by CYP3A4.


Paclitaxel is extensively metabolized in the liver. Metabolism of paclitaxel to its major metabolite, 6alpha-hydroxypaclitaxel, is mediated by cytochrome P-450 isoenzyme CYP2C8,1 185 187 202 354 while metabolism to 2 of its minor metabolites, 3'-p-hydroxypaclitaxel and 6alpha,3'-p-dihydroxypaclitaxel, is catalyzed by CYP3A4.

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 1188


The elimination of nonradioactive taxol in bile and urine was investigated in the rat after administration via the caudal vein (10 mg/kg). As in humans, no metabolites of taxol were detected by HPLC in rat urine, and only 10% of the injected taxol was recovered in urine over a 24 hr period. In contrast, 11.5% and 29% of the injected taxol was recovered in rat bile as unchanged taxol and metabolites, respectively. Among the nine taxol metabolites detected by HPLC, the side chain at C13, which is required for pharmacological activity, had been removed in only one minor metabolite, baccatin III. The chemical structures of the two major hydroxylated metabolites were determined by MS (fast atom bombardment and desorption chemical ionization) and (1)H NMR spectroscopy. One was a taxol derivative hydroxylated on the phenyl group at C3 of the side chain at C13, while the other corresponded to a taxol derivative hydroxylated in the m-position on the benzoate of the side chain at C2. Although these two major taxol metabolites were as active as taxol in preventing cold microtubule disassembly, they were, respectively, 9 and 39 times less cytotoxic as taxol on in vitro L1210 leukemia growth. These results show for the first time that there is a significant hepatic metabolism of taxol.

PMID:1981534 Monsarrat B et al; Drug Metab Dispos Biol Fate Chem 18 (6): 895-901 (1990)


To investigate how taxane's substituents at C3' affect its metabolism, ... the metabolism of cephalomannine and paclitaxel, a pair of analogs that differ slightly at the C3' position /was compared/. After cephalomannine was incubated with human liver microsomes in an NADPH-generating system, two monohydroxylated metabolites (M1 and M2) were detected by liquid chromatography/tandem mass spectrometry. C4'' (M1) and C6alpha (M2) were proposed as the possible hydroxylation sites, and the structure of M1 was confirmed by (1)H NMR. Chemical inhibition studies and assays with recombinant human cytochromes P450 (P450s) indicated that 4''-hydroxycephalomannine was generated predominantly by CYP3A4 and 6alpha-hydroxycephalomannine by CYP2C8. The overall biotransformation rate between paclitaxel and cephalomannine differed slightly (184 vs. 145 pmol/min/mg), but the average ratio of metabolites hydroxylated at the C13 side chain to C6alpha for paclitaxel and cephalomannine varied significantly (15:85 vs. 64:36) in five human liver samples. Compared with paclitaxel, the major hydroxylation site transferred from C6alpha to C4'', and the main metabolizing P450 changed from CYP2C8 to CYP3A4 for cephalomannine. In the incubation system with rat or minipig liver microsomes, only 4''-hydroxycephalomannine was detected, and its formation was inhibited by CYP3A inhibitors. Molecular docking by AutoDock suggested that cephalomannine adopted an orientation in favor of 4''-hydroxylation, whereas paclitaxel adopted an orientation favoring 3'-p-hydroxylation. Kinetic studies showed that CYP3A4 catalyzed cephalomannine more efficiently than paclitaxel due to an increased V(m). Our results demonstrate that relatively minor modification of taxane at C3' has major consequence on the metabolism.

PMID:18039807 Zhang JW et al; Drug Metab Dispos 36 (2): 418-26 (2008)


5.6 Biological Half-Life

When a 24 hour infusion of 135 mg/m^2 is given to ovarian cancer patients, the elimination half=life is 52.7 hours.


5.3-17.4 hours after 1 and 6 hour infusions at dosing levels of 15-275 mg/sq m

Lelkin, J.B., Paloucek, F.P., Poisoning & Toxicology Compendium. LEXI-COMP Inc. & American Pharmaceutical Association, Hudson, OH 1998., p. 433


Following IV infusion of paclitaxel over periods ranging from 6-24 hours in adults with malignancy, plasma concentrations of paclitaxel appeared to decline in a biphasic manner in some studies, with an average distribution half-life of 0.34 hours and an average elimination half-life of 5.8 hours. However, additional studies, particularly those in which paclitaxel is administered over shorter periods of infusion, show that the drug exhibits nonlinear pharmacokinetic behavior. In patients receiving paclitaxel 175 mg/sq m administered by 3-hour IV infusion, the distribution half-life averages 0.27 hours and the elimination half-life averages 2.33 hours.

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 1188


Following 30-minute or 3-hour IV infusion of 80-375 mg/sq m albumin-bound paclitaxel, ... terminal half-life albumin-bound paclitaxel was about 27 hours. ... /Paclitaxel (albumin-bound)/

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 1188


5.7 Mechanism of Action

Paclitaxel interferes with the normal function of microtubule growth. Whereas drugs like colchicine cause the depolymerization of microtubules in vivo, paclitaxel arrests their function by having the opposite effect; it hyper-stabilizes their structure. This destroys the cell's ability to use its cytoskeleton in a flexible manner. Specifically, paclitaxel binds to the β subunit of tubulin. Tubulin is the "building block" of mictotubules, and the binding of paclitaxel locks these building blocks in place. The resulting microtubule/paclitaxel complex does not have the ability to disassemble. This adversely affects cell function because the shortening and lengthening of microtubules (termed dynamic instability) is necessary for their function as a transportation highway for the cell. Chromosomes, for example, rely upon this property of microtubules during mitosis. Further research has indicated that paclitaxel induces programmed cell death (apoptosis) in cancer cells by binding to an apoptosis stopping protein called Bcl-2 (B-cell leukemia 2) and thus arresting its function.


Evidence suggests that paclitaxel also may induce cell death by triggering apoptosis. In addition, paclitaxel and docetaxel enhance the effects of ionizing radiation, possibly by blocking cells in the G2 phase, the phase of the cell cycle in which cells are most radiosensitive.

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 1187


Paclitaxel is an antimicrotubule antineoplastic agent. Unlike some other common antimicrotubule agents (e.g., vinca alkaloids, colchicine, podophyllotoxin), which inhibit microtubule assembly, paclitaxel and docetaxel (a semisynthetic taxoid) promote microtubule assembly. Microtubules are organelles that exist in a state of dynamic equilibrium with their components, tubulin dimers. They are an essential part of the mitotic spindle and also are involved in maintenance of cell shape and motility, and transport between organelles within the cell. By binding in a reversible, concentration-dependent manner to the beta-subunit of tubulin at the N-terminal domain, paclitaxel enhances the polymerization of tubulin, the protein subunit of the spindle microtubules, even in the absence of factors that are normally required for microtubule assembly (e.g., guanosine triphosphate [GTP]), and induces the formation of stable, nonfunctional microtubules. Paclitaxel promotes microtubule stability even under conditions that typically cause depolymerization in vitro (e.g., cold temperature, the addition of calcium, the presence of antimitotic drugs). While the precise mechanism of action of the drug is not understood fully, paclitaxel disrupts the dynamic equilibrium within the microtubule system and blocks cells in the late G2 phase and M phase of the cell cycle, inhibiting cell replication.

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 1187


... Taxol induces tubulin polymerization and forms extremely stable and nonfunctional microtubules. Taxol has demonstrated broad activity in preclinical screening studies, and antineoplastic activity has been observed in several classically refractory tumors. These tumors include cisplatin resistant ovarian carcinoma in phase II trials and malignant melanoma and non-small cell lung carcinoma in phase I studies.

PMID:1973737 Rowinsky EK et al; J Natl Cancer Inst 82 (15): 1247-59 (1990)


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04-Jan-2021
14-Aug-2024
KGS
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DOSAGE - INJECTABLE;INJECTION - 6MG/ML **Fede...DOSAGE - INJECTABLE;INJECTION - 6MG/ML **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20262

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DOSAGE - POWDER;INTRAVENOUS - 100MG/VIAL

USFDA APPLICATION NUMBER - 211875

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