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Epothilone B

Epothilone B structure

CAS No:
152044-54-7
Formula:
C27H41NO6S
Chemical Name:
Epothilone B
Synonyms:
4,17-Dioxabicyclo[14.1.0]heptadecane-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)-;4,17-Dioxabicyclo[14.1.0]heptadecane-5,9-dione,7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-;(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;Epothilone B;(-)-Epothilone B;EPO 906;Patupilone;EPO 906A;Epo B;(1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione;681125-91-7
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Epothilone B is a microtubule stabilizer with a Ki of 0.71μM. It acts by binding to the αβ-tubulin heterodimer subunit which causes decreasing of αβ-tubulin dissociation.

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 apoptosis inducer, an antineoplastic agent and a microtubule-stabilising agent. It is an epothilone and an epoxide.|Epothilone B is a 16-membered macrolide that mimics the biological effects of taxol.|Patupilone is a compound isolated from the myxobacterium Sorangium cellulosum. Similar to paclitaxel, patupilone induces microtubule polymerization and stabilizes microtubules against depolymerization conditions. In addition to promoting tubulin polymerization and stabilization of microtubules, this agent is cytotoxic for cells overexpressing P-glycoprotein, a characteristic that distinguishes it from the taxanes. Patupilone may cause complete cell-cycle arrest.

Epothilone B Basic Attributes

Molecular Weight：

507.68

Exact Mass：

507.68

EC Number：

1533716-785-6

UNII：

UEC0H0URSE

NSC Number：

684363

DSSTox ID：

DTXSID4046862

NCI Thesaurus Code：

C1623

HScode：

29419090

Characteristics

PSA：

138

XLogP3：

2.29

Appearance：

colorless

Density：

1.1±0.1 g/cm3

Melting Point：

117-118 °C

Boiling Point：

680.2±55.0 °C at 760 mmHg

Flash Point：

365.2±31.5 °C

Refractive Index：

1.532

Storage Conditions：

Store at -20°C

Vapor Pressure：

0mmHg at 25°C

Specific rotation：

D21 -35° (c = 0.7 in methanol)

Safety Information

Transport codes：

NONH for all modes of transport

Precautionary statement(s)：

P201, P202, P260, P261, P262, P264, P270, P272, P273, P280, P281, P301+P310, P302+P350, P302+P352, P308+P313, P310, P314, P321, P322, P330, P332+P313, P333+P313, P361, P362, P363, P391, P405, P501

Hazard Statements：

H300

GHS Classification：

|Danger|H300 (80%): Fatal if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P261, P262, P264, P270, P271, P272, P273, P280, P281, P301+P310, P302+P350, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P312, P314, P321, P322, P330, P332+P313, P333+P313, P361, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 5 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

Drug Indication：

Investigated for use/treatment in ovarian cancer, lung cancer, brain cancer, breast cancer, and gastric cancer.|Malignant neoplasm of other and unspecified genital organs - Fallopian tube (oviduct, uterine tube), Malignant neoplasm of the retroperitoneum and peritoneum - Peritoneum, unspecified

MeSH：

Agents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES. (See all compounds classified as Tubulin Modulators.)|Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

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 Entry Terms：

EPO906

Epothilone B Use and Manufacturing

Uses

Epothilone 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.

Use Classification：

Human drugs -> Rare disease (orphan)|Human Drugs -> EU pediatric investigation plans|Polyketides [PK] -> Macrolides and lactone polyketides [PK04]

Computed Properties

Molecular Weight:507.7
XLogP3:4.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:2
Exact Mass:507.26545920
Monoisotopic Mass:507.26545920
Topological Polar Surface Area:138
Heavy Atom Count:35
Complexity:816
Defined Atom Stereocenter Count:7
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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