Epothilone B
Completing data — refresh the page later to see the latest
Basic information
- CAS
152044-54-7- 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 propertiesFilling in
- XLogP
- 4.2
- Topological polar surface area
- 137 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 2
- Heavy atoms
- 35
- Formal charge
- 0
- Complexity
- 815
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).
- pka
- 13.57 · 13.57±0.70(Predicted)
- form
- White to off-white solid
- color
- colorless
- biological source
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
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
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
- Precautionary statements
- P262-P264-P270-P280-P302+P350-P310-P322-P361-P363-P405-P501-P260-P264-P270-P314-P501-P273-P391-P501-P201-P202-P281-P308+P313-P405-P501-P264-P280-P302+P352-P321-P332+P313-P362-P264-P270-P301+P310-P321-P330-P405-P501-P261-P272-P280-P302+P352-P333+P313-P321-P363-P501
Chemistry & industry
Pharmacology
Mechanism of Action
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
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Agents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES.
Applications
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.
Related reactions
24 records
Compound notes
Loading…