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Substance Name: Paclitaxel [USAN:USP:INN:BAN]
RN: 33069-62-4
UNII: P88XT4IS4D
InChIKey: RCINICONZNJXQF-MZXODVADSA-N

Note

  • A cyclodecane isolated from the bark of the Pacific yew tree, TAXUS BREVIFOLIA. It stabilizes MICROTUBULES in their polymerized form leading to cell death.

    NCI: A compound extracted from the Pacific yew tree Taxus brevifolia with antineoplastic activity. Paclitaxel binds to tubulin and inhibits the disassembly of microtubules, thereby resulting in the inhibition of cell division. This agent also induces apoptosis by binding to and blocking the function of the apoptosis inhibitor protein Bcl-2 (B-cell Leukemia 2). (NCI Thesaurus)

Molecular Formula

  • C47-H51-N-O14

Molecular Weight

  • 853.9129
 

Classification Codes

  • Antimitotic Agents
  • Antineoplastic
  • Antineoplastic Agents
  • Antineoplastic Agents, Phytogenic
  • Drug / Therapeutic Agent
  • Human Data
  • Mitosis Modulators
  • Reproductive Effect
  • Tubulin Modulators
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Names and Synonyms

Name of Substance

  • Infinnium
  • Paclitaxel
  • Paclitaxel [USAN:USP:INN:BAN]
  • Taxol

MeSH Heading

  • Paclitaxel

Synonyms

  • (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
  • (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
  • (NAB)-Paclitaxel
  • 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
  • ABI 007
  • ABI-007
  • Abraxane
  • Abraxane I.V. Suspension
  • BMS 181339-01
  • BMS-181339-01
  • Capxol
  • CCRIS 8143
  • Coroflex Please
  • Cyclopax
  • Cynviloq
  • Cypher select
  • DHP 107
  • DRG-0190
  • Ebetaxel
  • EmPAC
  • EndoTAG 1
  • EndoTAG-1
  • Genaxol
  • Genetaxyl
  • Genexol
  • HSDB 6839
  • IG 001
  • Intaxel
  • LEP-ETU
  • LipoPac
  • Liposome-entrapped paclitaxel easy-to-use
  • MBT 0206
  • Mitotax
  • Nab-paclitaxel
  • Nanoparticle albumin bound paclitaxel
  • Nanoxel
  • NK 105
  • NSC 125973
  • NSC-125973
  • OncoGel
  • Onxol
  • Pacliex
  • Paclitaxel
  • Padexol
  • Paxceed
  • Paxene
  • Plaxicel
  • QW 8184
  • Sindaxel
  • TaxAlbin
  • Taxol
  • Taxol A
  • Taxus Express
  • Taxus Liberte
  • Taxus stent
  • UNII-P88XT4IS4D
  • Yewtaxan
  • Zisu

Systematic Names

  • 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)-
  • 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))-
  • 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))-
  • 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

Superlist Name

  • Paclitaxel

Registry Numbers

CAS Registry Number

  • 33069-62-4

FDA UNII

  • P88XT4IS4D

Other Registry Numbers

  • 1203669-79-7
  • 157069-30-2

System Generated Number

  • 0033069624

Structure Descriptors

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

InChIKey

RCINICONZNJXQF-MZXODVADSA-N

Smiles

CC(=O)O[C@H]1C(=O)[C@]2(C)[C@@H](O)C[C@H]3OC[C@@]3(OC(=O)C)[C@H]2[C@H](OC(=O)c4ccccc4)[C@]5(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)c6ccccc6)c7ccccc7)C(=C1C5(C)C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 15mg/kg (15mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION		 National Technical Information Service. Vol. PB83-170969,
mouse LD50 intraperitoneal 128mg/kg (128mg/kg)   National Technical Information Service. Vol. PB83-170969,
mouse LD50 intraperitoneal 128mg/kg (128mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER National Technical Information Service. Vol. PB83-170969,
mouse LD50 intravenous 12mg/kg (12mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Pharmaceutical Research. Vol. 4, Pg. 162, 1987.
rat LD50 intraperitoneal 32530ug/kg (32.53mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 National Technical Information Service. Vol. PB83-170969,
rat LDLo intravenous 85mg/kg (85mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE		 Journal of Toxicological Sciences. Vol. 19(Suppl,
women LDLo intravenous 4995mg/kg/3H- (4995mg/kg) BLOOD: LEUKOPENIA

CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION

BLOOD: THROMBOCYTOPENIA		 Lancet. Vol. 343, Pg. 727, 1994.