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SML2615

Sigma-Aldrich

Ixabepilone

≥98% (HPLC)

Synonym(s):

(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]-17-oxa-4-azabicyclo[14.1.0]heptadecane-5,9-dione, Azaepothilone B, BMS-247550, NSC-710428

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About This Item

Empirical Formula (Hill Notation):
C27H42N2O5S
CAS Number:
219989-84-1
Molecular Weight:
506.70
MDL number:
MFCD04307791
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -35 to -45°, c = 1.0 in chloroform-d

storage condition

protect from light

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

InChI

1S/C27H42N2O5S/c1-15-9-8-10-27(7)22(34-27)12-20(16(2)11-19-14-35-18(4)28-19)29-23(31)13-21(30)26(5,6)25(33)17(3)24(15)32/h11,14-15,17,20-22,24,30,32H,8-10,12-13H2,1-7H3,(H,29,31)/b16-11+/t15-,17+,20-,21-,22-,24-,27+/m0/s1

InChI key

FABUFPQFXZVHFB-PVYNADRNSA-N

Biochem/physiol Actions

Ixabepilone is a microtubule stabilizing semisynthetic lactam analog of epothilone B. It appears that Ixabepilone is unaffected by BCRP mediated chemoresistance.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H341,H361fd,H372

Hazard Classifications

Acute Tox. 3 Oral - Muta. 2 - Repr. 2 - STOT RE 1

Target Organs

Gastro-intestinal system,hematopoietic system,Nervous system,lymphatics

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Cynthia Osborne et al.
Clinical breast cancer, 18(1), e89-e95 (2017-08-07)
Hormonal therapies and single-agent sequential chemotherapeutic regimens are the standards of care for HER2- metastatic breast cancer (MBC). However, treating patients with hormone-refractory and triple negative (TN) MBC remains challenging. We report the results of combined ixabepilone and carboplatin in
John T Hunt
Molecular cancer therapeutics, 8(2), 275-281 (2009-01-29)
The discovery of the antineoplastic agent paclitaxel and its unique activity as a microtubule-stabilizing agent resulted in dramatic improvements in the treatment of breast, ovarian, and non-small cell lung cancers. Despite the potent antitumor activity of taxanes such as paclitaxel
Jennifer A Smith et al.
Cancer research, 76(17), 5115-5123 (2016-08-05)
Peripheral neuropathy is a serious, dose-limiting side effect of cancer treatment with microtubule-targeting drugs. Symptoms present in a "stocking-glove" distribution, with longest nerves affected most acutely, suggesting a length-dependent component to the toxicity. Axonal transport of ATP-producing mitochondria along neuronal

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