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ChemicalBook--->CAS DataBase List--->75747-14-7

75747-14-7

75747-14-7 Structure

75747-14-7 Structure
IdentificationBack 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 PropertiesBack 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 AnswerBack 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 InformationBack 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
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

36/37/38
[Safety Statements ]

22-24/25-36-26
[WGK Germany ]

3
[HS Code ]

29419090
Spectrum DetailBack Directory
[Spectrum Detail]

17-AAG(75747-14-7)MS
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