Epothilone B

HCID 448013CAS 152044-54-7

기본 정보

표준 SMILES
C/C(=C\c1csc(C)n1)[C@@H]1C[C@@H]2O[C@]2(C)CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1
InChIKey
QXRSDHAAWVKZLJ-PVYNADRNSA-N
분자식
C27H41NO6S
평균 분자량
507.7 g/mol
단동위원소 질량
507.26545903

개요

Epothilone B is an epithilone that is epithilone D in which the double bond in the macrocyclic ring has been oxidised to the corresponding epoxide (the S,S stereoisomer). It has a role as an antineoplastic agent, a microtubule-stabilising agent and an apoptosis inducer. It is an epoxide and an epothilone.

이름 및 식별자

우선 이름
Epothilone B
IUPAC
(1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
영어명
Epothilone B
분자식
C27H41NO6S
분자량
507.68

이름 및 동의어

Epothilone BPatupilone152044-54-7(-)-Epothilone BEpo BEpothilon BEPO 906patupilonaEpithilone bEPO 906AGNF-PF-193EPO-906
이름 더 보기
EPOTHILONECS-556atupiloneEbomycin BOncology API
patupilonumDTXSID4046862UEC0H0URSEEPO906AEPO-906ACHEBI:31550(1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione(1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione

데이터베이스 식별자

CAS
152044-54-7
PubChem CID
448013
DTXSID
DTXSID4046862
ChEMBL
CHEMBL94657
ChEBI
CHEBI:31550
UNII
UEC0H0URSE
EC Number
604-822-6

물성

구조 계산 물성

XLogP
4.2
극성 표면적
137 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
8
회전 가능 결합 수
2
무거운 원자 수
35

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Listed in ZINC15
LipidsPolyketides [PK] -> Macrolides and lactone polyketides [PK04]
Endocrine DisruptorsPotential endocrine disrupting compound

물리화학적 성질

녹는점
95 · 95-97°C
끓는 점
680.2 · 680.2±55.0 °C(Predicted)
밀도
1.136 · 1.136
저장 조건
-20 °C · Store at -20°C
용해도
DMSO(최대 40mg/ml) 또는 에탄올(최대 35mg/ml)에 용해됩니다.
물리적 상태
흰색에서 회백색 고체

화학적 성질

White Powder

안전 및 규제

GHS 분류

GHS Classification · 4건

Danger

H300 (75%): Fatal if swallowed [Danger Acute toxicity, oral]

P203, P260, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P302+P352, P304+P340, P305+P354+P338, P316, P317, P318, P319, P321, P330, P332+P317, P333+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 4 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Regulatory Information · 1건

4,17-Dioxabicyclo14.1.0heptadecane-5,9-dione, 7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl-, (1S,3S,7S,10R,11S,12S,16R)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Hazard Classes and CategoriesAcute Tox. 1 (75%)

안전 데이터

wgk
3
HS 번호
29419090
스토리지 클래스
11 - Combustible Solids

화학 및 산업

약리 정보

Mechanism of Action · 1건

The principal mechanism of the epothilone class is inhibition of microtubule function. Microtubules are essential to cell division, and epothilones therefore stop cells from properly dividing. Epothilone B possess the same biological effects as taxol both in vitro and in cultured cells. This is because they share the same binding site, as well as binding affinity to the microtubule. Like taxol, epothilone B binds to the αβ-tubulin heterodimer subunit. Once bound, the rate of αβ-tubulin dissociation decreases, thus stabilizing the microtubules. Furthermore, epothilone B has also been shown to induce tubulin polymerization into microtubules without the presence of GTP. This is caused by formation of microtubule bundles throughout the cytoplasm. Finally, epothilone B also causes cell cycle arrest at the G2-M transition phase, thus leading to cytotoxicity and eventually cell apoptosis.

MeSH Pharmacological Classification · 2건

Substances that inhibit or prevent the proliferation of NEOPLASMS.

Agents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES.

응용 분야 · 2건

용도Epothilones are polyketide natural products that inhibit cancer cells by a mechanism similar to paclitaxel, and also are effective against paclitaxel-resistant tumours. Epothilone B is what is known as a microtubule stabilizer. When a cell divides, the chromosomes that will end up in each cell are separated by thin filaments called microtubules. Normally these microtubules then break down as the cell division progresses. This class of cytotoxic chemo drugs prevents that break down and thus prevents cells from completing division.

일반 설명Epothilones has antimitotic properties. It prevents microtubule depolymerization and competitively blocks paclitaxel binding to microtubules. Epothilone B is used to treat metastatic breast cancer (MBC).

공급사50 곳

北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
浙江荣大化工有限公司571-88086013

추가 설명

정의ChEBI: An epithilone that is epithilone D in which the double bond in the macrocyclic ring has been oxidised to the corresponding epoxide (the S,S stereoisomer).

관련 반응

24건

연결된 노트

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