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
$235.6
Updated
2025/07/31
Sigma-Aldrich
Product number
100068
Product name
17-AAG-CAS75747-14-7-Calbiochem
Purity
Alesstoxic,potent,syntheticderivativeoftheansamycinbenzoquinoneantibio
Packaging
500μg
Price
$312
Updated
2025/07/31
Cayman Chemical
Product number
11039
Product name
17-AAG
Purity
≥98%
Packaging
1mg
Price
$37
Updated
2024/03/01
Cayman Chemical
Product number
11039
Product name
17-AAG
Purity
≥98%
Packaging
5mg
Price
$90
Updated
2024/03/01
Cayman Chemical
Product number
11039
Product name
17-AAG
Purity
≥98%
Packaging
10mg
Price
$161
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.

Synthesis

107-11-9

30562-34-6

75747-14-7

The reaction of (+)-geldanamycin (5.1 mg, 9.0 μmol) with allylamine (10.0 μL, 0.13 mmol) was dissolved in chloroform (1.5 mL) at room temperature and stirred. The progress of the reaction was monitored by thin-layer chromatography (TLC), and complete conversion of geldanamycin was confirmed after 18 hours. The reaction mixture was subsequently washed with saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent. Purification was carried out by rapid column chromatography on silica gel, the eluent being a mixed petroleum ether/ethyl acetate solvent, to give the target product as a purple solid (5.3 mg, 99% yield). The product characterization data were as follows: IR (KBr, cm?1) 3464, 3333, 2958, 2929, 2825, 1728, 1691, 1652, 1571, 1485, 1372, 1323, 1189, 1101, 1057; UV (95% ethanol, λmax/nm) 332 (ε=2.0×10?); 1H NMR (CDCl?, 500 MHz) δ 9.14 (s, 1H), 7.28 (s, 1H), 6.93 (bd, J=11.5 Hz, 1H), 6.56 (bdd, J=11.5, 11.0 Hz, 1H), 6.38 (bt, J=6.0 Hz, 1H), 5.94-5.81 (m, 3H), 5.30- 5.24 (m, 2H), 5.17 (s, 1H), 4.82 (bs, 2H), 4.29 (bd, J=10.0 Hz, 1H), 4.21 (bs, 1H), 4.18-4.08 (m, 2H), 3.55 (ddd, J=9.0, 6.5, 2.0 Hz, 1H), 3.43 (ddd, J=9.0, 3.0 , 3.0 Hz, 1H), 3.34 (s, 3H), 3.25 (s, 3H), 2.72 (dqd, J=9.5, 7.0, 2.0 Hz, 1H), 2.63 (d, J=14.0 Hz, 1H), 2.34 (dd, J=14.0, 11.0 Hz, 1H), 2.00 (bs, 3H), 1.78 (d, J= 1.0 Hz, 3H), 1.78-1.74 (m, 2H), 1.74-1.67 (m, 1H), 0.99-0.95 (m, 6H); 13C NMR (CDCl?, 125 MHz) δ 183.8 (18-C), 180.9 (21-C), 168.4 (1-C), 156.0 (7-O?CNH?), 144.6 (17-C), 141.2 (20-C), 135.8 (5-C), 134.9 (2-C), 133.7 (9-C), 132.7 (8-C), 132.5 (3'-C), 126.9 (4-C), 126.5 (3-C), 118.5 (3'-C), 108.8 (19-C), 108.7 (16-C), 81.6 (7-C), 81.4 (12-C), 81.2 (6-C), 72.6 (11-C), 57.1 (6- or 12-OCH?), 56.7 (6- or 12-OCH?), 47.8 (1'-C), 35.0 (13-C), 34.3 (15-C), 32.3 (10-C ), 28.4 (14-C), 22.9 (14-CH?), 12.8 (8-CH?), 12.6 (2-CH?), 12.3 (10-CH?); HRMS (FAB) m/z 586.3120 [M+H]? (calculated value of 586.3129 for C??H??N?O?).

storage

-20°C

References

[1] T W SCHULTE  L M N. The benzoquinone ansamycin 17-allylamino-17-demethoxygeldanamycin binds to HSP90 and shares important biologic activities with geldanamycin.[J]. Cancer Chemotherapy and Pharmacology, 1998, 42 4: 273-279. DOI:10.1007/s002800050817
[2] ADEELA KAMAL. A high-affinity conformation of Hsp90 confers tumour selectivity on Hsp90 inhibitors[J]. Nature, 2003, 425 6956: 407-410. DOI:10.1038/nature01913
[3] ADEELA KAMAL  Francis J B  Marcus F Boehm. Therapeutic and diagnostic implications of Hsp90 activation.[J]. Trends in molecular medicine, 2004, 10 6: 283-290. DOI:10.1016/j.molmed.2004.04.006

17-AAG Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 17-AAG manufacturers

Sinoway Industrial co., ltd.
Product
17-AAG 75747-14-7
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
20TONS
Release date
2025-02-10
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:

Telatinib Tilatinib Capecitabine Bismuth subcarbonate Bortezomib Selumetinib Luminespib Carfilzomib PLX4032 Olaparib Lithium diisopropylamide Allyl bromide Allyl glycidyl ether Sodium allylsulfonate Allyl chloride Tilatinib Allylamine Geldanamycin

  • 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-
  • Tanespimycin (17-AAG), HSP90 inhibitor
  • Tanespimycin, 10 mM in DMSO
  • Tanespimycin (17-AAG, KOS953)
  • 75747-14-7
  • C31H43N3O8
  • Antibiotics
  • Antibiotics A to Z
  • Antibiotics A-F
  • BioChemical
  • antibiotic
  • Amines
  • Heterocycles