| Identification | Back Directory | [Name]
Alvespimycin | [CAS]
467214-20-6 | [Synonyms]
17-DMAG
CS-2382
DMAG-d6
17-DMAG-d6
Alvespimycin
NSC 707545-d6
AlvespiMycin-d6
Unii-001L2fe0m3
In-house Standard
DMAG Hydrochloride
17-DMAGhydrochloride
AlvespiMycin freebase
AlvespiMycin(17-DMAG)
17-DMAG (Alvespimycin)
NSC 707545 Hydrochloride
(150270-08-9) alvespimycin
17-DMAG;KOS-1022;NSC-707545
17-DIMETHYLAMINOETHYLAMINO-17-DEMETHOXYG
17-[2-(Dimethylamino)ethylamino]-17-desmethylgeldanamycin
17-N-(2-DiMethylaMinoethylaMino)-17-deMethoxy GeldanaMycin
17-Demethoxy-17-[[2-(dimethylamino)ethyl]amino]geldanamycin
17-N-[(diMethyl-d6)aMinoethylaMino]-17-deMethoxygeldanaMycin
17DMAG (17-diMethylaMinoethylaMino-17-deMethoxy-geldanaMycin)
17-N-(2-DiMethylaMinoethylaMino)-17-deMethoxy GeldanaMycin-d6
17-[2-[(DiMethyl-d6)aMino]ethylaMino]-17-desMethylgeldanaMycin
Geldanamycin, 17-demethoxy-17-[[2-(dimethylamino)ethyl]amino]-
17-DeMethoxy-17-[[2-[(diMethyl-d6)aMino]ethyl]aMino]geldanaMycin
17-[2-(DiMethylaMino)ethylaMino]-17-desMethylgeldanaMycin Hydrochloride
17-N-(2-DiMethylaMinoethylaMino)-17-deMethoxygeldanaMycin Hydrochloride
17-Demethoxy-17-[[2-(dimethylamino)ethyl]amino]geldanamycinhydrochloride
17-N-(2-DiMethylaMinoethylaMino)-17-deMethoxy GeldanaMycin Hydrochloride
17-DMAG/ Alvespimycin/ 17-Demethoxy-17-[[2-(dimethylamino)ethyl]amino]geldanamycin | [Molecular Formula]
C32H48N4O8 | [MDL Number]
MFCD08457919 | [MOL File]
467214-20-6.mol | [Molecular Weight]
616.75 |
| Chemical Properties | Back Directory | [Melting point ]
>270°C (dec.) | [Boiling point ]
810.5±65.0 °C(Predicted) | [density ]
1.20 | [storage temp. ]
Desiccate at -20°C | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
8.48±0.70(Predicted) | [color ]
Very Dark Purple | [InChIKey]
KUFRQPKVAWMTJO-NTPQRYOENA-N | [SMILES]
C1(NCCN(C)C)C(=O)C=C2NC(=O)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)CC=1C2=O)C |c:16,t:14,27,&1:18,21,29,31,33,37,r| |
| Hazard Information | Back Directory | [Description]
Geldanamycin is a potent inhibitor of Hsp90 that has poor water solubility. 17-DMAG is a water-soluble derivative of geldanamycin which potently inhibits Hsp90 (IC50 = 24 nM) and has excellent bioavailability and tissue distribution in animals. Like other Hsp90 inhibitors, 17-DMAG has diverse anti-tumor actions and has potential in treating certain types of cancer. This compound also suppresses inflammation by interfering with signaling through the NF-κB pathway. 17-DMAG also ameliorates high fat diet-induced renal failure in a mouse model of diabetes. | [Chemical Properties]
Solid | [Uses]
17-DMAG is a synthetic Geldanamycin derivative and inhibitor of Hsp90. | [Uses]
17-DMAG is an analogue of Gelamycin (G304500) and 17-(Allylamino)geldanamycin (A549650). 17-DMAG acts as a Hsp90 inhibitor and displays more potent antitumor activity than 17-AAG. | [Uses]
The labelled derivative of the analogue of Gelamycin (G304500) and 17-(Allylamino)geldanamycin (A549650). It acts as a Hsp90 inhibitor and displays more potent antitumor activity than 17-AAG. | [Definition]
ChEBI: A 19-membered macrocyle that is geldanamycin in which the methoxy group attached to the benzoquinone moiety has been replaced by a 2-(N,N-dimethylamino)ethylamino group. | [Biological Activity]
Water-soluble analog of 17-AAG (17-Demethoxy-17-(2-propenylamino)geldanamycin ) and 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 ). Binds the ATP binding site of Hsp90 and inhibits its chaperone activity. Displays more potent antitumor activity than 17-AAG (mean GI 50 values are 53 and 123 nM for 17-DMAG and 17-AAG respectively). | [References]
[1] M. EGORIN. Pharmacokinetics, tissue distribution, and metabolism of 17-(dimethylaminoethylamino)-17-demethoxygeldanamycin (NSC 707545) in CD2F1 mice and Fischer 344 rats[J]. Cancer Chemotherapy and Pharmacology, 2001, 49 1: 7-19. DOI: 10.1007/s00280-001-0380-8
[2] ELIZABETH E A BULL. Enhanced tumor cell radiosensitivity and abrogation of G2 and S phase arrest by the Hsp90 inhibitor 17-(dimethylaminoethylamino)-17-demethoxygeldanamycin.[J]. Clinical Cancer Research, 2004, 10 23: 8077-8084. DOI: 10.1158/1078-0432.ccr-04-1212
[3] TONY TALDONE Gabriela C Weilin Sun. Discovery and development of heat shock protein 90 inhibitors[J]. Bioorganic & Medicinal Chemistry, 2009, 17 6: Pages 2225-2235. DOI: 10.1016/j.bmc.2008.10.087
[4] CHRISTINA HACKL. Activating transcription factor-3 (ATF3) functions as a tumor suppressor in colon cancer and is up-regulated upon heat-shock protein 90 (Hsp90) inhibition.[J]. BMC Cancer, 2010, 10: 668. DOI: 10.1186/1471-2407-10-668
[5] RAMESH K RAMANATHAN. Phase I pharmacokinetic and pharmacodynamic study of 17-dimethylaminoethylamino-17-demethoxygeldanamycin, an inhibitor of heat-shock protein 90, in patients with advanced solid tumors.[J]. Journal of Clinical Oncology, 2010, 28 9: 1520-1526. DOI: 10.1200/jco.2009.25.0415
[6] NARUYUKI KOBAYASHI . The anti-proliferative effect of heat shock protein 90 inhibitor, 17-DMAG, on non-small-cell lung cancers being resistant to EGFR tyrosine kinase inhibitor[J]. Lung Cancer, 2012, 75 2: Pages 161-166. DOI: 10.1016/j.lungcan.2011.04.022
[7] JULIO MADRIGAL-MATUTE. Heat shock protein 90 inhibitors attenuate inflammatory responses in atherosclerosis.[J]. Cardiovascular Research, 2010, 86 2: 330-337. DOI: 10.1093/cvr/cvq046
[8] SAMUEL K SHIMP. HSP90 inhibition by 17-DMAG reduces inflammation in J774 macrophages through suppression of Akt and nuclear factor-κB pathways.[J]. Inflammation Research, 2012, 61 5: 521-533. DOI: 10.1007/s00011-012-0442-x
[9] HONG-MEI ZHANG. Geldanamycin derivative ameliorates high fat diet-induced renal failure in diabetes.[J]. PLoS ONE, 2012: e32746. DOI: 10.1371/journal.pone.0032746 |
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