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파클리탁셀

Paclitaxel

HCID 441276
노트반응

데이터를 보충하는 중입니다. 잠시 후 페이지를 새로 고치면 최신 내용을 볼 수 있습니다

기본 정보이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
33069-62-4
표준 SMILES
CC(=O)O[C@H]1C(=O)[C@@]2(C)C([C@H](OC(=O)c3ccccc3)[C@]3(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)c4ccccc4)c4ccccc4)C(C)=C1C3(C)C)[C@]1(OC(C)=O)CO[C@@H]1C[C@@H]2O
분자식
C47H51NO14
평균 분자량
853.92 g/mol

이름 및 식별자

우선 이름
Paclitaxel
현지명
파클리탁셀
영어명
Paclitaxel
분자식
C47H51NO14
분자량
853.92

이름 및 동의어

파클리탁셀TAXOLBACCATIN IIIAbraxanePaclitaxe5β,20-Epoxy-1,7β-dihydroxy-9-oxotax-11-ene-2α,4,10β,13α-tetrayl 4,10-diacetate 2-benzoate 13-[(2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoate][2aR-[2aα,4β,4aβ,6α,9α(αR*,βS*),11α,12α,12aα,12bα]]-β-(Benzoylamino)-α-hydroxy-6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-ylesterbenzenepropanoicacid6,12b-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-ylester, (αR, βS)-αR-hydroxy-βS-(benzoylamino)-benzenepropanoic acid, (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 esterBenzenepropanoic acid, β-(benzoylamino)-α-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, (αR,βS)-TAXUS

데이터베이스 식별자

물성

물리화학적 성질

녹는점
213 °C · 213 °C (dec.)(lit.)
끓는 점
774.66 °C · 774.66°C (rough estimate)
밀도
0.2 · 0.200
굴절률
-49 ° · -49 ° (C=1, MeOH)
인화점
9 ℃ · 9℃
저장 조건
2 · 2-8°C
용해도
50 mg/mL, · 메탄올: 50 mg/mL, 투명, 무색
물리적 상태
가루
산도 계수 (pKa)
11.9 · 11.90±0.20(Predicted)
색상
하얀색
수용성
0.3 mg/L · 0.3mg/L(37 ºC)
Merck
14 · 14,6982
BRN
1420457 · 1420457
안정성
안정적인. 강한 산화제와 호환되지 않습니다. 타기 쉬운.
InChIKey
RCINICONZNJXQF-MZXODVADSA-N
SMILES
N([C@H]([C@@H](O)C(=O)O[C@H]3C[C@]4([C@H](C6[C@]7([C@H](OC7)C[C@@H]([C@]6(C(=O)[C@@H](C(=C3C)C4(C)C)OC(=O)C)C)O)OC(=O)C)OC(=O)c5ccccc5)O)c2ccccc2)C(=O)c1ccccc1
LogP
3.95 · 3.950 (est)
EPA
Paclitaxel (33069-62-4)

화학적 성질

White Powder

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

안전 데이터

wgk
3
rtecs
DA8340700
ridadr
1544
독성
LD50 intraperitoneal in mouse: 128mg/kg
HS 번호
29329990
risk_code
37/38-41-42/43-62-68-40-48-20/21/22-68/20/21/22
hazard_code
Xn
safety_code
22-26-36/37/39-45
포장분류
III
위험 등급
6.1(b)
F 고인화성물질
10-21
Hazard Classifications
Muta. 2Repr. 1BSTOT RE 2
스토리지 클래스
6.1C - Combustible, acute toxic Cat.3toxic compounds or compounds which causing chronic effects
유해 물질 데이터
33069-62-4(Hazardous Substances Data)

화학 및 산업

응용 분야 · 4건

개요Paclitaxel, a natural product isolated from the bark of the Pacific yew, is effective in treating refractory metastatic ovarian cancer. Unlike any other antineoplastic agents, paclitaxel appears to have several possible mechanisms of action, including an antimicrotubule action through the promotion of tubulin polymerization and stabilization of microtubules, thereby, halting mitosis and promoting cell death. The supply of paclitaxel is limited by its low natural abundance and currently it is being manufactured by a semi-synthetic route from deacetylbaccatin Ⅲ that is isolated from the needles of the yew tree. Recent completion of two total syntheses of taxol conquered the structural complexity of the title compound and may be useful in obtaining certain closely related analogs, some of which have been found to have antitumor activity. Paclitaxel has potential uses in the treatment of metastatic breast cancer, lung cancer, head and neck cancer, and malignant melanoma.

역사Paclitaxel, initially named taxol, is a naturally occurring diterpenoid compound extracted from the Pacific yew tree, Taxus brevifolia. Paclitaxel was discovered by National Cancer Institute (NCI) in 1960s. Scientists were conducting screenings of plant extracts in search of potential anticancer agents when they discovered the distinctive cytotoxic properties of paclitaxel against cancer cells. In October of 1995, China became the second country with formal production of paclitaxel and its injection in the world.Paclitaxel/Taxol is on the World Health Organization’s Model List of Essential Medicines, and was at one point the best-selling cancer drug ever manufactured, with annual sales of $1.6 billion in 2000.

용도Paclitaxel is an antineoplastic that used to treat patients with lung, ovarian, breast cancer, head and neck cancer, and advanc ed forms of Kaposi's sarcoma. Paclitaxel is a mitotic inhibitor used in cancer chemotherapy. It is also used in the study of structure and function of microtubles into tubulin.

일반 설명Paclitaxel (commercial name, Taxol) a complex diterpene alkaloid isnaturally obtained from Taxus species (family Taxaceae). Paclitaxel has been provedas highly effective in the treatment of various types of cancers, since it acts as amicrotubule-stabilizing agent to protect against disassembly. Paclitaxel was developed by the National Cancer Institute, USA, as a drug for cancer therapy andused for the treatment of refractory ovarian cancer, metastatic breast and lung cancer,and Kaposi’s sarcoma (Srivastava et al. 2005). The natural source of paclitaxelis the bark of several Taxus species; however, the cost of extraction is very highsince the concentration of paclitaxel accumulation is very low (0.02% of dry weight)and also entails the destruction of natural resources (Cusido et al. 2014). Eventhough, paclitaxel can be chemically synthesized, but this process is not commerciallyviable. Plant cell cultures have been developed for the production of paclitaxelby Phyton Biotech in 1995, and in 2004 the FDA has approved the use of plantculture supply of paclitaxel/Taxol (Leone and Roberts 2013).

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화합물 노트

불러오는 중…

이 페이지에서기본 정보이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
CAS
33069-62-4
PubChem CID
441276
ChEMBL
CHEMBL48
Nikkaji
J2.961.919K
제조 방법 · 1건

The total synthesis of paclitaxel (Taxol) is described. Double Rubottom oxidation of the bis(silyl enol ether) derived from a tricarbocyclic diketone effectively installed a bridgehead olefin and C-5/C-13 hydroxy groups in a one-step operation. The novel Ag-promoted oxetane formation smoothly constructed the tetracyclic framework of paclitaxel.Total Synthesis of PaclitaxelThe biosynthesis of paclitaxel involves the condensation of the three isoprenyl diphosphate (IPP) units with dimethylallyl diphosphate (DMAPP). Plants are unique in producing IPP and DMAPP by both the mevalonic pathway (MVA) in the cytosol or via the methylerythritol phosphate (MEP) pathway in the plastids.Paclitaxel: biosynthesis, production and future prospects

상·하류 제품 정보

상류 원료

실리카겔Column초산에틸규조토불화 트리에틸암모늄염화벤조일hydrogen fluoride삼차-뷰틸 아이소시아네이트중탄산나트륨(중조)4-나이트로벤젠설포닐 염화물벤즈알데히드디메틸아세탈트리에틸아민트리메틸클로로실란티오페놀P-톨루엔설폰 산포타슘터셔리부톡사이드불산

하류 제품

(αR,βS)-β-(BenzoylaMino)-α-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-benzenepropanoic Acid (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-dodeca

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