Description Targets In vitro
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17-AAG

Description Targets In vitro
Product Name
17-AAG
CAS No.
75747-14-7
Chemical Name
17-AAG
Synonyms
17-AG;17-AAG;17-AGG;Gld-36;CS-480;KOS 953;CP 127374;TELATINIB;Tiratinib;NSC-330507
CBNumber
CB1195912
Molecular Formula
C31H43N3O8
Formula Weight
585.69
MOL File
75747-14-7.mol
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17-AAG Property

Melting point:
201-203°C
Boiling point:
797.8±60.0 °C(Predicted)
Density 
1.21
RTECS 
LX8932000
Flash point:
>110°(230°F)
storage temp. 
Keep in dark place,Sealed in dry,Store in freezer, under -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
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
22-24/25-36-26
WGK Germany 
3
HS Code 
29419090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H317May cause an allergic skin reaction

H319Causes serious eye irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P272Contaminated work clothing should not be allowed out of the workplace.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
A8476
Product name
17-(Allylamino)-17-demethoxygeldanamycin
Purity
≥98% (HPLC), solid
Packaging
500μg
Price
$96.4
Updated
2024/03/01
Sigma-Aldrich
Product number
100068
Product name
17-AAG-CAS75747-14-7-Calbiochem
Purity
Alesstoxic,potent,syntheticderivativeoftheansamycinbenzoquinoneantibio
Packaging
500μg
Price
$303
Updated
2024/03/01
Alfa Aesar
Product number
J66960
Product name
17-(Allylamino)-17-demethoxygeldanamycin, 99%
Packaging
25mg
Price
$109.65
Updated
2024/03/01
Alfa Aesar
Product number
J66960
Product name
17-(Allylamino)-17-demethoxygeldanamycin, 99%
Packaging
100mg
Price
$258.65
Updated
2024/03/01
Cayman Chemical
Product number
11039
Product name
17-AAG
Purity
≥98%
Packaging
1mg
Price
$37
Updated
2024/03/01
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17-AAG Chemical Properties,Usage,Production

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.

Description

17-AAG (75747-14-7) is a semi-synthetic analog of geldanamycin (Cat.# 10-1084) which is less toxic and more stable. 17-AAG selectively binds to and inhibits HSP90 from tumor cells. Anti-angiogenic activity. Cell permeable.

Chemical Properties

Dark Purple Solid

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

17-(Allylamino)-17-demethoxygeldanamycin (17-AAG) inhibits heat shock protein 90 (Hsp90), the expression of heat shock factor-1, and the activity of oncogenic proteins such as N-ras, Ki-ras, c-Akt, and p185erB2. In addition to its anti-tumor effects, 17-AAG also induces apoptosis.

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

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 .

Biochem/physiol Actions

17-(Allylamino)-17-demethoxygeldanamycin (17-AAG) is a benzoquinone and is an analog of geldanamycin.

storage

-20°C

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

17-AAG Preparation Products And Raw materials

Raw materials

Preparation Products

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17-AAG Suppliers

Shanghai Chaolan Chemical Technology Center
Tel
021-QQ:65489617 15618227136
Fax
21-5161 9052
Email
Sales@ATKchemical.com
Country
China
ProdList
7296
Advantage
58
Shaanxi Cuikang Pharmaceutical Technology Co., Ltd
Tel
18049165724 13186333400
Email
cuichengbio@163.com
Country
China
ProdList
2775
Advantage
58
Shaanxi Kebele Pharmaceutical R&D Co., Ltd
Tel
13119135307 13119135307
Email
3866620171@qq.com
Country
China
ProdList
1841
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
94657
Advantage
76
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15839
Advantage
69
Chembest Research Laboratories Limited
Tel
+86-21-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6005
Advantage
61
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
Advantage
70
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32321
Advantage
50
China DongFan Chemical Co.,LTD
Tel
86-0571-85151182
Fax
86-0571-85151182
Country
China
ProdList
5691
Advantage
66
Jinan Trio PharmaTech Co., Ltd.
Tel
+86 (531) 88811783
Fax
+86 (531) 55696010 QQ 1762738062
Email
sales@trio-pharmatech.com (International market)
Country
China
ProdList
1856
Advantage
62
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View Lastest Price from 17-AAG manufacturers

Career Henan Chemical Co
Product
17-AAG 75747-14-7
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
200kg
Release date
2020-01-02

75747-14-7, 17-AAGRelated Search:


  • GELDANAMYCIN,17-DEMETHOXY-17-(2-PROPENYLAMINO)-
  • CP 127374
  • ALLYLAMINOGELDANAMYCIN
  • NSC-330507
  • 17-(ALLYLAMINO)-17-DEMETHOXYGELDANAMYCIN
  • 17-(ALLYLAMINO)-17-DESMETHOXYGELDANAMYCIN
  • 17-(ALLYLAMINO)-17-DIMETHOXYGELDANAMYCIN
  • 17-ALLYLAMINOGELDANAMYCIN
  • 17-AG
  • 17-AGG
  • 17-AAG
  • 17-DEMETHOXY-17-(2-PROPENYLAMINO)-GELDANAMYCIN
  • 17-DEMETHOXY-17-ALLYLAMINO GELDANAMYCIN
  • 17-ALLYLAMINO-17-DEMETHOXYGELDANAMYCIN (17-AAG)
  • 17-AAG, CP 127374
  • 17-(Allylamino)-17-desmethylgeldanamycin
  • KOS 953
  • Tanespimycin
  • TELATINIB
  • 17-ALLYLAMINO-17-DIMETHOXYGELDANAMYCIN (17-AAG)
  • 17-AAG,17AAG
  • 17-(Allylamino)geldanamycin, 17-AAG, 17-Demethoxy-17-allylamino geldanamycin, CP 127374, Geldanamycin,17-demethoxy-17-(2-propenylamino)-, NSC 330507
  • Geldanamycin, 17-allylamino-17-demethoxy-
  • Geldanamycin, des-o-methyl-17-allylamino-
  • Gld-36
  • 17-AAG(GeldanaMycin)
  • Telatinib(TanespiMycin,KOS-953, 17-AAG,NSC 330507)
  • 17-AAG (KOS953)
  • 17-AAG (TanespiMycin)
  • 17AAG (17-(AllylaMino)-17-deMethoxy- geldanaMycin)
  • 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
  • CP127374,NSC-330507
  • Telatinib 17-Demethoxy-17-allylaminogeldanamycin
  • Telatinib/ 17-AAG
  • Tanespimycin, >=98%
  • Tanespimycin (17-AAG)
  • 17 AAG (Tanespimyciin)
  • CS-480
  • Geldanamycin Impurity 1(17-Allylamino-17-Demethoxygeldanamycin)
  • Geldanamycin 17-Allylamino
  • 17-AAG USP/EP/BP
  • (4E,6Z,8S,9S,10E,12S,13R,14S,16R)-19-(Allylamino)-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl carbamate
  • [(3S,5R,6S,7R,8Z,11R,14E)-6-hydroxy-5,11-dimethoxy-3,7,9,15-tetramethyl-16,20,22-trioxo-21-(prop-2-enylamino)-17-azabicyclo[16.3.1]docosa-1(21),8,12,14,18-pentaen-10-yl] carbamate
  • anespimycin
  • Tiratinib
  • Allylamino-17-demethoxygeldanamycin, 17-
  • 75747-14-7
  • C31H43N3O8
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