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17-AAG

CAT: 0013-GTR19161561-07Size: 25 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19161561-07Size:25 mg
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Description
A potent Hsp90 inhibitor with IC50 of 5 nM in cell-free assays; induces cytosolic accumulation of cytochrome c and cleavage and activities of caspase-9 and caspase-3, triggering apoptosis of HL-60/Bcr-Abl and K562 cells; causes the degradation of HER2, HER3, Akt, and both mutant and wild-type androgen receptor; inhibits prostate cancer xenografts growth in mice.Skin Cancer Phase 2 Discontinued (In Vitro) :Tanespimycin causes the degradation of HER2, Akt, and both mutant and wild-type AR and the retinoblastoma-dependent G1 growth arrest of prostate cancer cells. Tanespimycin inhibits prostate cancer cell lines with IC50s ranged from 25-45 nM (LNCaP, 25 nM; LAPC-4, 40 nM; DU-145, 45 nM; and PC-3, 25 nM) .Tanespimycin (0.1-1 μM) induces a nearly complete loss of ErbB2 on ErbB2-overexpressing breast cancer cells. Tanespimycin inhibits cell growth and induces G2/M cell cycle arrest and apoptosis in CCA cells together with the down-regulation of Bcl-2, Survivin and Cyclin B1, and the up-regulation of cleaved PARP. (In Vivo) :Tanespimycin (25-200 mg/kg, i.p.) causes a dose-dependent decline in AR, HER2, and Akt expression in prostate cancer xenografts. Tanespimycin treatment at doses sufficient to induce AR, HER2, and Akt degradation results in the dose-dependent inhibition of androgen-dependent and -independent prostate cancer xenograft growth without toxicity.Tanespimycin (60 mg/kg) with Rapamycin (30 mg/kg) inhibits A549 and MDA-MB-231 tumor growth and effects tumor cures in MDA-MB-231 tumor-bearing animals by tail vein injection.
CAS Number
75747-14-7
Product Name Alternative
Tanespimycin | NSC 330507 | CP 127374 | 17AAG | 17 AAG
Purity
>98% (HPLC)
Solubility
DMSO: ≥ 55 mg/mL
Smiles
NC (O[C@@H] (/C (C) =C/[C@H] (C) [C@@H] (O) [C@@H] (OC) C[C@H] (C) CC1=C2NCC=C) [C@@H] (OC) /C=C/C=C (C) /C (NC (C1=O) =CC2=O) =O) =O
Molecular Formula
C31H43N3O8
Molecular Weight
585.6884
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.
Other Product Names
Geldanamycin, 17-demethoxy-17- (2-propenylamino) -

Chemical Information

Tanespimycin

Tanespimycin is a 19-membered macrocyle that is geldanamycin in which the methoxy substituent attached to the benzoquinone moiety has been replaced by an allylamino group. It is a potent inhibitor of heat shock protein 90 (Hsp90). A less toxic analogue than geldanamycin, it induces apoptosis and displays antitumour effects. It has a role as an antineoplastic agent, a Hsp90 inhibitor and an apoptosis inducer. It is a member of 1,4-benzoquinones, an ansamycin, a carbamate ester, an organic heterobicyclic compound and a secondary amino compound. It is functionally related to a geldanamycin.

CAS Number75747-14-7
PubChem CID6505803
IUPAC Name[(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-19-(prop-2-enylamino)-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl] carbamate
Molecular FormulaC31H43N3O8
Molecular Weight585.7
XLogP2.6
Topological Polar Surface Area166
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count9
Rotatable Bond Count7
Heavy Atom Count42
Formal Charge0
Complexity1210
SMILES
C[C@H]1C[C@@H]([C@@H]([C@H](/C=C(/[C@@H]([C@H](/C=C\C=C(\C(=O)NC2=CC(=O)C(=C(C1)C2=O)NCC=C)/C)OC)OC(=O)N)\C)C)O)OC
InChI
InChI=1S/C31H43N3O8/c1-8-12-33-26-21-13-17(2)14-25(41-7)27(36)19(4)15-20(5)29(42-31(32)39)24(40-6)11-9-10-18(3)30(38)34-22(28(21)37)16-23(26)35/h8-11,15-17,19,24-25,27,29,33,36H,1,12-14H2,2-7H3,(H2,32,39)(H,34,38)/b11-9-,18-10+,20-15+/t17-,19+,24+,25+,27-,29+/m1/s1
InChIKey
AYUNIORJHRXIBJ-TXHRRWQRSA-N
Chemical Structure
2D Structure
2D structure of Tanespimycin
CAS: 75747-14-7
CID: 6505803
Formula: C31H43N3O8
MW: 585.7
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight585.7
XLogP32.6
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count9
Rotatable Bond Count7
Exact Mass585.30501534
Monoisotopic Mass585.30501534
Topological Polar Surface Area166 Ų
Heavy Atom Count42
Formal Charge0
Complexity1210
Isotope Atom Count0
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count3
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes