CAS 189453-10-9

Epothilone D

Description:

Epothilone D is a natural product and a member of the epothilone family, which are macrocyclic compounds known for their ability to stabilize microtubules, similar to the mechanism of action of taxanes like paclitaxel. It is characterized by its complex structure, which includes a 16-membered macrolide ring and multiple stereocenters, contributing to its biological activity. Epothilone D exhibits potent antitumor properties, making it a subject of interest in cancer research and drug development. It has shown efficacy against various cancer cell lines and is being investigated for its potential use in treating resistant tumors. The compound is soluble in organic solvents and has a relatively low solubility in water, which can influence its bioavailability and formulation in therapeutic applications. Its mechanism involves binding to the β-tubulin subunit of microtubules, leading to cell cycle arrest and apoptosis in cancer cells. Overall, Epothilone D represents a promising avenue for developing new cancer therapies, particularly for tumors that are resistant to conventional treatments.

Formula: C₂₇H₄₁NO₅S

InChI: InChI=1/C27H41NO5S/c1-16-9-8-10-17(2)25(31)19(4)26(32)27(6,7)23(29)14-24(30)33-22(12-11-16)18(3)13-21-15-34-20(5)28-21/h11,13,15,17,19,22-23,25,29,31H,8-10,12,14H2,1-7H3/b16-11-,18-13+/t17-,19+,22?,23-,25-/m0/s1

InChI key: InChIKey=XOZIUKBZLSUILX-GIQCAXHBSA-N

SMILES: C(=C\C=1N=C(C)SC1)(\C)/[C@H]2OC(=O)C[C@H](O)C(C)(C)C(=O)[C@H](C)[C@@H](O)[C@@H](C)CCC/C(/C)=C\C2

Synonyms:

• (-)-Desoxyepothilone B
• (4R,7S,8S,9S,13Z,16S)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]oxacyclohexadec-13-ene-2,6-dione
• (4S,7R,8S,9S,13Z)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]oxacyclohexadec-13-ene-2,6-dione
• (4S,7R,8S,9S,13Z,16S)-4,8-Dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]oxacyclohexadec-13-ene-2,6-dione
• 12,13-Deoxyepothilone B
• 12,13-Desoxyepothilone B
• Epo D
• Epothilone D
• Kos 862
• NSC 703147
• Oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9,13-pentamethyl -16-(1-methyl-2-(2-methyl-4-thiazolyl)ethenyl)-, (4S-(4R*,7S,8R*,9R*,1 3Z,16R*(E)))-
• Oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-, [4S-[4R*,7S*,8R*,9R*,13Z,16R*(E)]]-

Epothilone D

CAS: 189453-10-9

Epothilone D

Formula: C₂₇H₄₁NO₅S

Purity: ≥95%

Molecular weight: 491.68

Ref: 54-BUP23122

Oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-, (4S,7R,8S,9S,13Z,16S)-

CAS: 189453-10-9

Formula: C₂₇H₄₁NO₅S

Purity: 97%

Color and Shape: Solid

Molecular weight: 491.6831

Ref: IN-DA002DOU

Epothilone D (synthetic)

Controlled Product

CAS: 189453-10-9

Applications Epothilones are polyketide natural products that inhibit cancer cells by a mechanism similar to paclitaxel, and also are effective against paclitaxel-resistant tumours. Epothilone D is in phase I clinical testing of in patients with advanced solid tumours. Epothilone D is a cytotoxic macrolide that stabilises malignant cells' microtubules and arrests mitosis, a characteristic it shares with other epothilones. They bind to the same hepatic sites as does paclitaxel (Taxol) in a 1:1 stoichiometric ratio of a, b-tubulin heterodimers.
References Bollag, D.M., et al.: Cancer. Res., 55, 2325 (1995), Hardt, I.H., et al.: J. Nat. Prod., 64, 847 (2001), Gerth, K., et al.: J. Antibiot., 55, 41, 45 (2002)

Formula: C₂₆H₃₉NO₅S

Color and Shape: Neat

Molecular weight: 477.66

Ref: TR-E589000

Epothilone D

CAS: 189453-10-9

Formula: C₂₇H₄₁NO₅S

Molecular weight: 491.69

Ref: 4Z-E-119002

Epothilone D (synthetic)

CAS: 189453-10-9

Microtubule stabilizer; natural polyketide compound; antineoplastic

Formula: C₂₇H₄₁NO₅S

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 491.69 g/mol

Ref: 3D-FE22752

Epothilone D

CAS: 189453-10-9

Formula: C₂₇H₄₁NO₅S

Molecular weight: 491.7

Ref: BE-RMCE093002

Epothilone D

CAS: 189453-10-9

Epothilone D is a natural polyketide compound isolated from the myxobacterium Sorangium cellulosum that binds to tubulin and inhibits microtubule disassembly, thereby blocking mitosis, cellular proliferation, and cell motility, Epothilone D is extensively utilized in cancer research to study microtubule dynamics, mitotic arrest, and cytoskeleton-targeted anticancer mechanisms.

Formula: C₂₇H₄₁NO₅S

Color and Shape: White Solid

Molecular weight: 491.683

Ref: TM-TQ0202

Epothilone D

CAS: 189453-10-9

Formula: C₂₇H₄₁NO₅S

Molecular weight: 491.69

Ref: ST-EA-CP-E298000