|
|
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
* denotes mobile formatted website
Links to Resources
NLM Resources (File Locators)
Regulatory Agencies (Superlist Locators)
Other Resources (Internet Locators)
Search for this InChIKey on the Web
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/s1InChIKey
RCINICONZNJXQF-MZXODVADSA-NSmiles
CC(=O)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. |