Paclitaxel 紫杉醇

CAS 33069-62-4 MFCD00869953

化学结构图

33069-62-4
SMILES: CC1(C)C2[C@@H](OC(C)=O)C(=O)[C@@]3(C)[C@H]([C@H](OC(=O)C4C=CC=CC=4)[C@]1(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)C1C=CC=CC=1)C1C=CC=CC=1)C=2C)[C@@]1(CO[C@@H]1C[C@@H]3O)OC(C)=O |&1:4,11,13,14,24,27,31,33,51,54,56|

化学属性

Mol. FormulaC47H51NO14
Mol. Weight854
Melting Point213
TSCANo
Density0.200
Appearance white solid powder
SolubilitySoluble in DMSO, not in water
pH:A

别名和识别编码

Chemical NamePaclitaxel
PubChem Substance ID87558555
Beilstein Registry Number1420457
MDL NumberMFCD00869953
CAS Number33069-62-4
Synonym BMS 181339-01; BMS181339-01; BMS-181339-01; Brand name: Taxol; Anzatax; Asotax; Bristaxol; Praxel; Taxol Konzentrat. TAX. Taxol Taxol A
Merck Number6982
Chemical Name Translation紫杉醇
Reaxys-RN1420457
FormulaC47H51NO14
IUPAC Name(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
InChIKeyRCINICONZNJXQF-MZXODVADSA-N
InChIInChI=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
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分类

  • {SNA} Antibiotics A to Z, Antibiotics N-S, Antibiotics by Application, Antineoplastic and Immunosuppressive Antibiotics, Application Index, Approved Therapeutics/Drug Candidates, Bioactive Small Molecule Alphabetical Index, Bristol-Myers Squibb, Cell Signaling Enzymes, Chemical Structure Class, Drug and Xenobiotic Metabolism, Fluorination Ready Pharma-Developed Compounds, Interferes with DNA Synthesis, Isoprenoids, Mechanism of Action, Microtubule Inhibitors, Multi-Drug Resistance and Drug Metabolism, P-PH, Prenols, Substrates, Inducers, Inhibitors, Taxoides, Xenobiotics And Drug Metabolism Substrates, Xenobiotics and Drug Metabolism,

产品应用

  • Paclitaxel is a compound with antineoplastic activity extracted from the Pacific yew tree Taxus brevifolia. Paclitaxel binds to tubulin and inhibits the disassembly of microtubules, thereby inhibiting 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).

相关文献及参考

  • [2]. Dziadyk JM, et al. Paclitaxel-induced apoptosis may occur without a prior G2/M-phase arrest. Anticancer Res. 2004 Jan-Feb;24(1):27-36.
  • [3]. Li Q, et al. Low doses of paclitaxel enhance liver metastasis of breast cancer cells in the mouse model. FEBS J. 2016 Aug;283(15):2836-52.
  • [4]. Pan Z, et al. Paclitaxel attenuates Bcl-2 resistance to apoptosis in breast cancer cells through an endoplasmic reticulum-mediated calciumrelease in a dosage dependent manner. Biochem Biophys Res Commun. 2013 Feb 13. pii: S0006-291X(13)00259-3.
  • [5]. Cadamuro M, et al. Low dose paclitaxel reduces S100A4 nuclear import to inhibit invasion and hematogenous metastasis of cholangiocarcinoma. Cancer Res. 2016 Jun 21.
  • [6]. Li Q, et al. Low doses of paclitaxel enhance liver metastasis of breast cancer cells in the mouse model. FEBS J. 2016 Jun 16.
  • [7]. Yilmaz E, et al. Sensory neuron subpopulation-specific dysregulation of intracellular calcium in a rat

安全信息

GHS Symbol
WGK Germany3
Hazard statements
  • H302+H312+H332
  • H315 Causes skin irritation 会刺激皮肤
  • H317 May cause an allergic skin reaction 可能导致皮肤过敏
  • H334 May cause allergy or asthma symptoms or breathing difficulties if inhaled 吸入可能导致过敏或哮喘症状或呼吸困难
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
  • H341 Suspected of causing genetic defects 怀疑导致遗传性缺陷
  • H318 Causes serious eye damage 严重伤害眼睛
  • H361 Suspected of damaging fertility or the unborn child 怀疑对生育能力或未出生婴儿造成伤害
  • H371 May cause damage to organs 可能导致器官损伤
  • H413 Maycauselonglastingharmfuleffectstoaquaticlife 可能对水生生物造成长期持续有害影响。
Personal Protective Equipment Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
RTECSDA8340700
Precautionary statements
  • P201 Obtain special instructions before use. 使用前获取专门指示。
  • P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西，喝水或吸烟。
  • P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P284 Wear respiratory protection.? 佩戴呼吸保护装置。
  • P285 In case of inadequate ventilation wear respiratory protection. 在通风不足的情况下，戴呼吸防护。
  • P301+P312+P330
  • P304+P340+P312
  • P305+P351+P338
  • P308+P313
  • P337+P313
  • P342+P311
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Signal word Danger
Hazard Codes Xn
Risk Statements
  • R20/21/22 Harmful by inhalation, in contact with skin and if swallowed 吸入、皮肤接触和不慎吞咽有害
  • R37/38 Irritating to respiratory system and skin 对呼吸系统和皮肤有刺激性
  • R41 Risk of serious damage to eyes 有严重损伤眼睛的危险
  • R42/43
  • R62 Possible risk of impaired fertility 有削弱生殖能力的危险
  • R68 Possible risk of irreversible effects 可能有不可挽回的作用的危险
  • R68/20/21/22
Safety Statements
  • S22 Do not breathe dust 不要吸入粉尘；
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护；
  • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时，立即求医（可能时出示标签）；
  • S60 This material and its container must be disposed of as hazardous waste 该物质及其容器必须作为危险废物处置；
  • S9 Keep container in a well-ventilated place 保持容器在通风良好的场所；
Packing GroupIII
Storage condition Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). 储存温度2-8°C 
TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 85 mg/kg
TOXIC EFFECTS :
   Lungs, Thorax, or Respiration - other changes
   Blood - changes in bone marrow (not otherwise specified)
REFERENCE :
   JTSCDR Journal of Toxicological Sciences.  (Japanese Soc. of Toxicological
   Sciences, 4th Floor, Gakkai

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 32530 ug/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Lungs, Thorax, or Respiration - dyspnea
   Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
   NTIS** National Technical Information Service.  (Springfield, VA 22161)
   Formerly U.S. Clearinghouse for Scientific & Technical Information.
   Volume(issue)/page/year: PB83-170969

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Human - woman
DOSE/DURATION           : 4995 mg/kg/3H-C
TOXIC EFFECTS :
   Cardiac - cardiomyopathy including infarction
   Blood - leukopenia
   Blood - thrombocytopenia
REFERENCE :
   LANCAO Lancet.  (7 Adam St., London WC2N 6AD, UK)  V.1-    1823-
   Volume(issue)/page/year: 343,727,1994

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 128 mg/kg
TOXIC EFFECTS :
   Skin and Appendages - hair
   Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
   NTIS** National Technical Information Service.  (Springfield, VA 22161)
   Formerly U.S. Clearinghouse for Scientific & Technical Information.
   Volume(issue)/page/year: PB83-170969

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 6600 ug/kg
SEX/DURATION            : female 7-17 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - musculoskeletal system
   Reproductive - Effects on Newborn - delayed effects
REFERENCE :
   JTSCDR Journal of Toxicological Sciences.  (Japanese Soc. of Toxicological
   Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku,
   Tokyo 113, Japan)  V.1-    1976-  Volume(issue)/page/year: 19(Suppl
   1),69,1994

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 84 mg/kg
SEX/DURATION            : male 9 week(s) pre-mating
                          female 2 week(s) pre-mating
                          female 1-7 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Maternal Effects - other effects
   Reproductive - Fertility - pre-implantation mortality (e.g. reduction in
   number of implants per female; total number of implants per corpora lutea)
   Reproductive - Effects on Embryo or Fetus - extra-embryonic structures
   (e.g., placenta, umbilical cord)
REFERENCE :
   JTSCDR Journal of Toxicological Sciences.  (Japanese Soc. of Toxicological
   Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku,
   Tokyo 113, Japan)  V.1-    1976-  Volume(issue)/page/year: 19(Suppl
   1),57,1994

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 26 mg/kg
SEX/DURATION            : female 17-21 day(s) after conception
                          lactating female 21 day(s) post-birth
TOXIC EFFECTS :
   Reproductive - Effects on Newborn - growt

其他信息

  • Paclitaxel是一种微管聚合物稳定剂，作用于人内皮细胞，IC50为0.1 pM

系列性分类

  1. Life Science 生命科学
  2. Antibiotics 抗生素
  3. Antibiotics A to Z - Antibiotics
  4. Antibiotics N-S - Antibiotics A to Z
  1. Life Science 生命科学
  2. Antibiotics 抗生素
  3. Antibiotics by Application - Antibiotics
  4. Antineoplastic and Immunosuppressive Antibiotics - Antibiotics by Application
  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Bioactive Small Molecules - Cell Biology
  4. P - Bioactive Small Molecules
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Antibiotics
  4. Antibiotics by Application
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Antibiotics
  4. Chemical Structure Class
  5. Sulfonamides
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Antibiotics
  4. Mechanism of Action
  5. Interferes with Cell Wall Synthesis
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Antibiotics
  4. Spectrum of Activity
  5. Antiparasitic / Antiprotozoal / Anthelminthic
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Cell Signaling and Neuroscience
  4. Multi-Drug Resistance and Drug Metabolism
  5. Drug and Xenobiotic Metabolism
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Enzymes, Inhibitors, and Substrates
  4. Cell Signaling Enzymes
  5. Xenobiotics and Drug Metabolism
  6. Inhibitors
  1. Medical Research Areas
  2. Angiogenesis
  3. Bcl-2
  1. Medical Research Areas
  2. Cytosketetal Signaling
  3. Microtubule/Tubulin  (微管/微管蛋白)

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