Epothilone B

HCID 448013CAS 152044-54-7

Grundinformationen

Standard-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
Summenformel
C27H41NO6S
Durchschnittliche Molmasse
507,7 g/mol
Monoisotopische Masse
507,26545903

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
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
Englischer Name
Epothilone B
Summenformel
C27H41NO6S
Molmasse
507.68

Namen und Synonyme

Epothilone BPatupilone152044-54-7(-)-Epothilone BEpo BEpothilon BEPO 906patupilonaEpithilone bEPO 906AGNF-PF-193EPO-906
Weitere Namen anzeigen
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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP
4,2
Polarare Oberfläche (TPSA)
137 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
8
Frei drehbare Bindungen
2
Schwere Atome
35

Experimentelle und physikochemische Eigenschaften

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

Physikochemische Eigenschaften

Schmelzpunkt
95 · 95-97°C
Siedepunkt
680.2 · 680.2±55.0 °C(Predicted)
Dichte
1.136 · 1.136
storage temp.
-20 °C · Store at -20°C
Löslichkeit
Soluble in DMSO (up to 40 mg/ml) or in Ethanol (up to 35 mg/ml).
Aggregatzustand
White to off-white solid

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Regulatory Information · 1 Eintrag

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%)

Sicherheitsdaten

wgk
3
hs_code
29419090
Speicherklasse
11 - Combustible Solids

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 1 Eintrag

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 · 2 Einträge

Substances that inhibit or prevent the proliferation of NEOPLASMS.

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

Anwendungen · 1 Eintrag

VerwendenEpothilones 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.

Anbieter50 Anbieter

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

Ergänzende Hinweise

DefinitionChEBI: 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).

Zugehörige Reaktionen

24

Verknüpfte Notizen

Wird geladen…