Epothilone B

HCID 448013CAS 152044-54-7
Substructure searchFind similar structures

Basic information

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
Molecular formula
C27H41NO6S
Average molar mass
507.7 g/mol
Monoisotopic mass
507.26545903

Overview

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.

Names & identifiers

Preferred 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
English name
Epothilone B
Molecular formula
C27H41NO6S
Molecular weight
507.68

Names & synonyms

Epothilone BPatupilone152044-54-7(-)-Epothilone BEpo BEpothilon BEPO 906patupilonaEpithilone bEPO 906AGNF-PF-193EPO-906
Show more names
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

Database identifiers

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

Properties

Computed structural properties

XLogP
4.2
Topological polar surface area
137 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
8
Rotatable bonds
2
Heavy atoms
35

Experimental & physicochemical properties

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

Physicochemical properties

Melting point
95 · 95-97°C
alpha
21 · D21 -35° (c = 0.7 in methanol)
Boiling point
680.2 · 680.2±55.0 °C(Predicted)
Density
1.136 · 1.136
storage temp.
-20 °C · Store at -20°C
solubility
Soluble in DMSO (up to 40 mg/ml) or in Ethanol (up to 35 mg/ml).

Safety & regulation

GHS classification

GHS Classification · 4 items

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.

Hazard information

Regulatory Information · 1 item

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%)

Safety data

wgk
3
hs_code
29419090
Signal word
Danger
Symbol(GHS)
GHS08,GHS09,GHS06
Storage Class
11 - Combustible Solids
Hazard statements
H310-H341-H360-H372-H315-H317-H410-H300

Chemistry & industry

Pharmacology

Mechanism of Action · 1 item

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 items

Substances that inhibit or prevent the proliferation of NEOPLASMS.

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

Applications · 5 items

DescriptionEpothilone B (152044-54-7) induces microtubule polymerization. Causes cell cycle arrest at the G2-M transition (EC50 = 32 nM for HeLa cells). Induces apoptosis. Cell permeable.

UsesEpothilone B (Epo B) is a macrolide that causes the formation of bundles of intracellular microtubules in non-mitotic cells, induces the formation of hyperstable tubulin polymers, and arrests cell cycling in mitosis. It induces mitotic arrest at the G2-M transition in Hs578T and HeLa cells (IC50 = 3 and 32 nM, respectively) as well as in multidrug resistant KB3-1 and KBV-1 cells (IC50 = 16 and 92 nM, respectively). Epo B causes cell cycle arrest at nanomolar IC50 values in cell lines from ovarian, breast, lung, colon, prostate, and squamous cancer.

UsesEpothilones 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.

UsesEpothilone B is a microtubule inhibitor isolated from the myxobacteria, Sorangium cellulosum. Like epothilone A, epothilone B acts by stabilising microtubule formation at the taxol binding site, and causes cell cycle arrest at the G2/M transition, leading to cytotoxicity.

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

Upstream & downstream products

Downstream products

Suppliers50 total

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

Additional notes

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).

Related reactions

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Linked notes

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