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Ixabepilone

CAT: 0013-GTR19162741-09Size: 200 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19162741-09Size:200 mg
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Description
A semisynthetic Epothilone B analogue and potent, orally active microtubule stabilizer; shows a broad spectrum of activity against a panel of tumor cell lines in vitro (IC50=1.4-34.5 nM), retains the antineoplastic activity against human cancers that are resistance to paclitaxel both in vitro and in vivo.Breast Cancer Approved (In Vitro) :BMS-247550 is a highly potent cytotoxic agent capable of killing cancer cells at low nanomolar concentrations and retains its antineoplastic activity against human cancers that are naturally insensitive to paclitaxel or that have developed resistance to paclitaxel. (In Vivo) :BMS-247550 demonstrates antitumor activity that is superior to paclitaxel in both paclitaxel-resistant and -sensitive tumors. BMS-247550 is more efficacious than paclitaxel in all five paclitaxel-resistant tumors evaluated in this study (four human and one murine) : the clinically derived paclitaxel resistant Pat-7 ovarian carcinoma, the A2780Tax ovarian carcinoma that is resistant to paclitaxel because of tubulin mutations, theHCT116/VM46 MDR colon carcinoma, the clinically derived paclitaxel-resistant Pat-21 breast carcinoma, and the murine fibrosarcoma M5076. Against three paclitaxel-sensitive human tumor xenografts, BMS-247550 produces antitumor activity equivalent to paclitaxel: A2780 human ovarian carcinoma, HCT116, and LS174T human colon carcinoma.
CAS Number
219989-84-1
Product Name Alternative
Azaepothilone B | BMS-247550 | BMS247550
Field of Research
Pharmacology & Drug Discovery
Purity
>98% (HPLC)
Solubility
10 mM in DMSO
Smiles
O=C (C[C@@H]1O) N[C@H] (/C (C) =C/C2=CSC (C) =N2) C[C@H]3[C@@] (O3) (C) CCC[C@H] (C) [C@H] (O) [C@@H] (C) C (C1 (C) C) =O
Molecular Formula
C27H42N2O5S
Molecular Weight
506.6978
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.
Other Product Names
17-Oxa-4-azabicyclo[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) -

Chemical Information

Ixabepilone

Ixabepilone is a macrocycle that is a lactam analogue of epothilone B. Binds directly to beta-tubulin subunits on microtubules, leading to suppression of microtubule dynamics. It has a role as an antineoplastic agent and a microtubule-destabilising agent. It is a lactam, an epoxide, a member of 1,3-thiazoles, a macrocycle and a beta-hydroxy ketone.

CAS Number219989-84-1
PubChem CID6445540
IUPAC Name(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]-17-oxa-4-azabicyclo[14.1.0]heptadecane-5,9-dione
Molecular FormulaC27H42N2O5S
Molecular Weight506.7
XLogP3.6
Topological Polar Surface Area140
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count7
Rotatable Bond Count2
Heavy Atom Count35
Formal Charge0
Complexity817
SMILES
C[C@H]1CCC[C@@]2([C@@H](O2)C[C@H](NC(=O)C[C@@H](C(C(=O)[C@@H]([C@H]1O)C)(C)C)O)/C(=C/C3=CSC(=N3)C)/C)C
InChI
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
InChIKey
FABUFPQFXZVHFB-PVYNADRNSA-N
Chemical Structure
2D Structure
2D structure of Ixabepilone
CAS: 219989-84-1
CID: 6445540
Formula: C27H42N2O5S
MW: 506.7
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight506.7
XLogP33.6
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count7
Rotatable Bond Count2
Exact Mass506.28144362
Monoisotopic Mass506.28144362
Topological Polar Surface Area140 Ų
Heavy Atom Count35
Formal Charge0
Complexity817
Isotope Atom Count0
Defined Atom Stereocenter Count7
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
TRC-I941990-25MGIxabepilone
A11449-50Ixabepilone 50mg

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