| Identification | Back Directory | [Name]
Telatinib | [CAS]
75747-14-7 | [Synonyms]
17-AG
17-AGG
17-AAG
Gld-36
KOS 953
CP 127374
TELATINIB
NSC-330507
Tanespimycin
17-AAG,17AAG
17-AAG (KOS953)
CP127374,NSC-330507
17-AAG, CP 127374
17-AAG(GeldanaMycin)
17-AAG (TanespiMycin)
ALLYLAMINOGELDANAMYCIN
17-ALLYLAMINOGELDANAMYCIN
Telatinib/ 17-AAG
17-DEMETHOXY-17-ALLYLAMINO GELDANAMYCIN
17-(ALLYLAMINO)-17-DIMETHOXYGELDANAMYCIN
17-(ALLYLAMINO)-17-DEMETHOXYGELDANAMYCIN
17-(Allylamino)-17-desmethylgeldanamycin
Geldanamycin, 17-allylamino-17-demethoxy-
Geldanamycin, des-o-methyl-17-allylamino-
17-(ALLYLAMINO)-17-DESMETHOXYGELDANAMYCIN
17-DEMETHOXY-17-(2-PROPENYLAMINO)-GELDANAMYCIN
GELDANAMYCIN,17-DEMETHOXY-17-(2-PROPENYLAMINO)-
17-ALLYLAMINO-17-DEMETHOXYGELDANAMYCIN (17-AAG)
17-ALLYLAMINO-17-DIMETHOXYGELDANAMYCIN (17-AAG)
Telatinib(TanespiMycin,KOS-953, 17-AAG,NSC 330507)
17AAG (17-(AllylaMino)-17-deMethoxy-geldanaMycin)
Telatinib
17-Demethoxy-17-allylaminogeldanamycin
17-(Allylamino)geldanamycin, 17-AAG, 17-Demethoxy-17-allylamino geldanamycin, CP 127374, Geldanamycin,17-demethoxy-17-(2-propenylamino)-, NSC 330507
17-demethoxy-17-(2-propenylamino)-[(3R,5R,6S,7R,8E,10R,11R,12Z,14E)-6-Hydroxy-5,11,21-trimethoxy-3,7,9,15-tetramethyl-16,20,22-trioxo-17-azabicyclo[16.3.1]docosa-1(21),8,12,14,18-pentaen-10-yl] carbamate | [Molecular Formula]
C31H43N3O8 | [MDL Number]
MFCD04973892 | [MOL File]
75747-14-7.mol | [Molecular Weight]
585.69 |
| Chemical Properties | Back Directory | [Appearance]
Dark Purple Solid | [Melting point ]
201-203°C | [Boiling point ]
797.8±60.0 °C(Predicted) | [density ]
1.21 | [RTECS ]
LX8932000 | [Fp ]
>110°(230°F) | [storage temp. ]
−20°C
| [solubility ]
DMSO: soluble
| [form ]
solid
| [pka]
8.62±0.70(Predicted) | [color ]
Purple or dark red | [Water Solubility ]
Soluble in DMSO at 150 mg/mL; soluble in ethanol at 5 mg/mL. Very poorly soluble in water | [Sensitive ]
Light Sensitive | [Stability:]
Stable for 1 year from date of purchase as supplied. Protect from moisture. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months. | [InChIKey]
AYUNIORJHRXIBJ-HTLBVUBBSA-N | [SMILES]
C12C(=O)C(=CC(=O)C=1NCC=C)NC(=O)C(C)=CC=C[C@H](OC)[C@@H](OC(=O)N)C(C)=C[C@H](C)[C@@H](O)[C@@H](OC)C[C@H](C)C2 |t:17,19,30| | [CAS DataBase Reference]
75747-14-7 |
| Questions And Answer | Back Directory | [Description]
Tanespimycin (17-AAG, CP127374, NSC-330507, KOS 953) (75747-14-7) is a potent HSP90 inhibitor with IC50 of 5 nM in a cell-free assay, having a 100-fold higher binding affinity for HSP90 derived from tumour cells than HSP90 from normal cells. Tanespimycin (17-AAG) induces apoptosis, necrosis, autophagy and mitophagy. Phase 3.
| [Targets]
HSP90 5 nM. | [In vitro]
17-AAG, an analog of geldanamycin, exhibits greater than 100 times higher binding affinity for Hsp90 derived from HER-2-overexpressing cancer cells (BT474, N87, SKOV3 and SKBR3) or BT474 breast carcinoma cells with IC50 values of 5-6 nM. 17-AAG causes the degradation of HER2, HER3, Akt, and both mutant and wild-type androgen receptor (AR), leading to the RB-dependent G1 growth arrest of prostate cancer cells such as LNCaP, LAPC-4, DU-145, and PC-3 with IC50 values of 25-45 nM. [2] In addition to inducing apoptosis of Ba/F3 cells transformed with wild-type BCR-ABL with an IC50 of 5.2 μM, 17-AAG has the ability to induce apoptosis of cells transformed with imatinib mesylate-resistant T315I and E255K BCR-ABL mutants with IC50 values of 2.3 μM and 1.0 μM, respectively, by inducing the degradation of both wild-type BCR-ABL protein and mutants. |
| Hazard Information | Back Directory | [Chemical Properties]
Dark Purple Solid | [Usage]
Potent inhibitor of heat shock protein 90 (Hsp90). 17-AAG is a less toxic analog than Geldanamycin. It induces apoptosis and displays antitumor effects. 17-AAG inhibits the activity of oncogenic proteins such as N-ras, Ki-ras, c-Akt, and p185erB2.
| [Biological Activity]
Inhibitor of heat shock protein 90 (Hsp90) chaperone activity, and an analog of geldanamycin (9,13-Dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-2-azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaene-3,20,22-trione, 9-carbamate ). Subsequently inhibits the activity of oncogenic proteins such as p185 erbB-2 (IC 50 = 31 nM), N-ras, Ki-ras and c-Akt. Antitumor in vivo . | [Uses]
Geldanamycin is a potent inhibitor of Hsp90 that exhibits severe hepatotoxicity when used in vivo. 17-AAG is an analog of geldanamycin which has potent in vivo activity and reduced toxicity. Like other Hsp90 inhibitors, 17-AAG has diverse anti-tumor actions and has potential in treating certain types of cancer. 17-AAG inhibits the growth of prostate cancer cell lines (IC50 = 25-45 nM). 17-AAG promotes the degradation of HER2 and induces growth arrest and apoptosis in breast cancer cells overexpressing HER2 (IC50 = 4-72 nM). | [Uses]
Potent inhibitor of heat shock protein 90 (Hsp90). 17-AAG is a less toxic analog than Geldanamycin. It induces apoptosis and displays antitumor effects. 17-AAG inhibits the activity of oncogenic proteins such as N-ras, Ki-ras, c-Akt, and p185erB2.
| [Definition]
ChEBI: 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,
t induces apoptosis and displays antitumour effects. | [General Description]
Chemical structure: benzenoid | [Biochem/physiol Actions]
17-(Allylamino)-17-demethoxygeldanamycin (17-AAG) is a benzoquinone and is an analog of geldanamycin. | [storage]
4°C, protect from light | [References]
1) Schulte et al. (1998), The benzoquinone ansamycin 17-allylamino-17-demethoxygeldanamycin binds to HSP90 and shares important biologic activities with geldanamycin; Cancer Chemother. Pharmacol. 42 273
2) Kamal et al. (2003), A high-affinity conformation of Hsp90 confers tumour selectivity on Hsp90 inhibitors; Nature, (b>425 407
3) Kaur et al. (2004), Therapeutic and diagnostic implications of Hsp90 activation; Clinical Cancer Res. 10 4813 |
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