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467214-21-7,MFCD09026908
Catalog No.:AA00D8YO

467214-21-7 | Alvespimycin hydrochloride

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25mg
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100mg
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  • Technical Information
  • Properties
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Technical Information
Catalog Number:
AA00D8YO
Chemical Name:
Alvespimycin hydrochloride
CAS Number:
467214-21-7
Molecular Formula:
C32H49ClN4O8
Molecular Weight:
653.2065
MDL Number:
MFCD09026908
SMILES:
COC1CC(C)CC2=C(NCCN(C)C)C(=O)C=C(C2=O)NC(=O)C(=CC=CC(C(C(=CC(C1O)C)C)OC(=O)N)OC)C.Cl
Properties
Computed Properties
 
Complexity:
1230  
Covalently-Bonded Unit Count:
2  
Defined Atom Stereocenter Count:
6  
Defined Bond Stereocenter Count:
3  
Heavy Atom Count:
45  
Hydrogen Bond Acceptor Count:
10  
Hydrogen Bond Donor Count:
5  
Rotatable Bond Count:
8  

Literature

Title: Heat shock protein 90 inhibitors induce functional inhibition of human natural killer cells in a dose-dependent manner.

Journal: Immunopharmacology and immunotoxicology 20160101

Title: 17-DMAG, an HSP90 Inhibitor, Ameliorates Multiple Organ Dysfunction Syndrome via Induction of HSP70 in Endotoxemic Rats.

Journal: PloS one 20160101

Title: The HSP90 inhibitor alvespimycin enhances the potency of telomerase inhibition by imetelstat in human osteosarcoma.

Journal: Cancer biology & therapy 20150601

Title: Exome sequencing of hepatocellular carcinomas identifies new mutational signatures and potential therapeutic targets.

Journal: Nature genetics 20150501

Title: A physiologically based pharmacokinetic model of alvespimycin in mice and extrapolation to rats and humans.

Journal: British journal of pharmacology 20140601

Title: The apoptotic effect and associated signalling of HSP90 inhibitor 17-DMAG in hepatocellular carcinoma cells.

Journal: Cell biology international 20121001

Title: A phase I dose-escalation trial of trastuzumab and alvespimycin hydrochloride (KOS-1022; 17 DMAG) in the treatment of advanced solid tumors.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20120915

Title: Population pharmacokinetic analysis of 17-dimethylaminoethylamino-17-demethoxygeldanamycin (17-DMAG) in adult patients with solid tumors.

Journal: Cancer chemotherapy and pharmacology 20120701

Title: HSP90 inhibition by 17-DMAG attenuates oxidative stress in experimental atherosclerosis.

Journal: Cardiovascular research 20120701

Title: Combination therapy with HSP90 inhibitor 17-DMAG reconditions the tumor microenvironment to improve recruitment of therapeutic T cells.

Journal: Cancer research 20120701

Title: Hsp90 inhibition overcomes HGF-triggering resistance to EGFR-TKIs in EGFR-mutant lung cancer by decreasing client protein expression and angiogenesis.

Journal: Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer 20120701

Title: The effect of inhibition of heat-shock proteins on thiram-induced tibial dyschondroplasia.

Journal: Poultry science 20120701

Title: AKT-aro and HER2-aro, models for de novo resistance to aromatase inhibitors; molecular characterization and inhibitor response studies.

Journal: Breast cancer research and treatment 20120701

Title: Expression and therapeutic relevance of heat-shock protein 90 in pancreatic endocrine tumors.

Journal: Endocrine-related cancer 20120601

Title: In vivo method to monitor changes in HER2 expression using near-infrared fluorescence imaging.

Journal: Molecular imaging 20120601

Title: Inhibition of heat shock protein (molecular weight 90 kDa) attenuates proinflammatory cytokines and prevents lipopolysaccharide-induced liver injury in mice.

Journal: Hepatology (Baltimore, Md.) 20120501

Title: HSP90 inhibition by 17-DMAG reduces inflammation in J774 macrophages through suppression of Akt and nuclear factor-κB pathways.

Journal: Inflammation research : official journal of the European Histamine Research Society ... [et al.] 20120501

Title: Heat shock protein 90 inhibition by 17-DMAG lessens disease in the MRL/lpr mouse model of systemic lupus erythematosus.

Journal: Cellular & molecular immunology 20120501

Title: Destabilization of PDK1 by Hsp90 inactivation suppresses hepatitis C virus replication through inhibition of PRK2-mediated viral RNA polymerase phosphorylation.

Journal: Biochemical and biophysical research communications 20120427

Title: Co-inhibition of HSP70/HSP90 synergistically sensitizes nasopharyngeal carcinoma cells to thermotherapy.

Journal: Integrative cancer therapies 20120301

Title: Quantitative proteomics reveals that Hsp90 inhibition preferentially targets kinases and the DNA damage response.

Journal: Molecular & cellular proteomics : MCP 20120301

Title: Optical imaging with her2-targeted affibody molecules can monitor hsp90 treatment response in a breast cancer xenograft mouse model.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20120215

Title: 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.

Journal: Lung cancer (Amsterdam, Netherlands) 20120201

Title: Expression profile of heat shock proteins in acute myeloid leukaemia patients reveals a distinct signature strongly associated with FLT3 mutation status--consequences and potentials for pharmacological intervention.

Journal: British journal of haematology 20120201

Title: Geldanamycin derivative ameliorates high fat diet-induced renal failure in diabetes.

Journal: PloS one 20120101

Title: Effect of inhibition of the ubiquitin-proteasome system and Hsp90 on growth and survival of rhabdomyosarcoma cells in vitro.

Journal: BMC cancer 20120101

Title: One-electron reduction of 17-(dimethylaminoethylamino)-17-demethoxygeldanamycin: a pulse radiolysis study.

Journal: The journal of physical chemistry. A 20110818

Title: Heat-shock protein 90 inhibition in autoimmunity to type VII collagen: evidence that nonmalignant plasma cells are not therapeutic targets.

Journal: Blood 20110609

Title: In vitro metabolism of 17-(dimethylaminoethylamino)-17-demethoxygeldanamycin in human liver microsomes.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20110401

Title: Dasatinib inhibits B cell receptor signalling in chronic lymphocytic leukaemia but novel combination approaches are required to overcome additional pro-survival microenvironmental signals.

Journal: British journal of haematology 20110401

Title: A phase I study of the heat shock protein 90 inhibitor alvespimycin (17-DMAG) given intravenously to patients with advanced solid tumors.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20110315

Title: Prolonged mechanical stretch is associated with upregulation of hypoxia-inducible factors and reduced contraction in rat inferior vena cava.

Journal: Journal of vascular surgery 20110301

Title: eNOS and Hsp90 interaction directly correlates with cord formation in human lymphatic endothelial cells.

Journal: Lymphatic research and biology 20110301

Title: Modulation of α(2C) adrenergic receptor temperature-sensitive trafficking by HSP90.

Journal: Biochimica et biophysica acta 20110201

Title: Blocking the chaperone kinome pathway: mechanistic insights into a novel dual inhibition approach for supra-additive suppression of malignant tumors.

Journal: Biochemical and biophysical research communications 20110107

Title: Autophagy inhibition sensitizes multiple myeloma cells to 17-dimethylaminoethylamino-17-demethoxygeldanamycin-induced apoptosis.

Journal: Leukemia research 20101101

Title: Down-regulation of heat shock protein 70 improves arsenic trioxide and 17-DMAG effects on constitutive signal transducer and activator of transcription 3 activity.

Journal: Cancer chemotherapy and pharmacology 20100901

Title: Heat shock protein 90 inhibition depletes TrkA levels and signaling in human acute leukemia cells.

Journal: Molecular cancer therapeutics 20100801

Title: 17-DMAG targets the nuclear factor-kappaB family of proteins to induce apoptosis in chronic lymphocytic leukemia: clinical implications of HSP90 inhibition.

Journal: Blood 20100708

Title: Reactive oxygen species mediate hepatotoxicity induced by the Hsp90 inhibitor geldanamycin and its analogs.

Journal: Free radical biology & medicine 20100601

Title: Novel HSP90 inhibitors, NVP-AUY922 and NVP-BEP800, radiosensitise tumour cells through cell-cycle impairment, increased DNA damage and repair protraction.

Journal: British journal of cancer 20100525

Title: Heat shock protein 90 inhibitors attenuate inflammatory responses in atherosclerosis.

Journal: Cardiovascular research 20100501

Title: The role of lysosomes in limiting drug toxicity in mice.

Journal: The Journal of pharmacology and experimental therapeutics 20100401

Title: Phase I study of the heat shock protein 90 inhibitor alvespimycin (KOS-1022, 17-DMAG) administered intravenously twice weekly to patients with acute myeloid leukemia.

Journal: Leukemia 20100401

Title: Down-regulation of RIP expression by 17-dimethylaminoethylamino-17-demethoxygeldanamycin promotes TRAIL-induced apoptosis in breast tumor cells.

Journal: Cancer letters 20100128

Title: Heat shock protein 90: inhibitors in clinical trials.

Journal: Journal of medicinal chemistry 20100114

Title: Phase I trial of 17-dimethylaminoethylamino-17-demethoxygeldanamycin (17-DMAG), a heat shock protein inhibitor, administered twice weekly in patients with advanced malignancies.

Journal: European journal of cancer (Oxford, England : 1990) 20100101

Title: Activating transcription factor-3 (ATF3) functions as a tumor suppressor in colon cancer and is up-regulated upon heat-shock protein 90 (Hsp90) inhibition.

Journal: BMC cancer 20100101

Title: Evidence for a role of heat shock protein-90 in toll like receptor 4 mediated pain enhancement in rats.

Journal: Neuroscience 20091229

Title: Heat shock protein 90 inhibitors: new mode of therapy to overcome endocrine resistance.

Journal: Cancer research 20091115

Title: Anti-proliferative activity of heat shock protein (Hsp) 90 inhibitors via beta-catenin/TCF7L2 pathway in adult T cell leukemia cells.

Journal: Cancer letters 20091018

Title: Monitoring therapeutic response of human ovarian cancer to 17-DMAG by noninvasive PET imaging with (64)Cu-DOTA-trastuzumab.

Journal: European journal of nuclear medicine and molecular imaging 20090901

Title: Heat shock protein 90 inhibitor 17-dimethylaminoethylamino-17-demethoxygeldanamycin enhances EphA2+ tumor cell recognition by specific CD8+ T cells.

Journal: Cancer research 20090901

Title: Geldanamycin analog 17-DMAG inhibits iNOS and caspases in gamma-irradiated human T cells.

Journal: Radiation research 20090901

Title: Co-treatment with heat shock protein 90 inhibitor 17-dimethylaminoethylamino-17-demethoxygeldanamycin (DMAG) and vorinostat: a highly active combination against human mantle cell lymphoma (MCL) cells.

Journal: Cancer biology & therapy 20090701

Title: Targeting focal adhesion kinase with dominant-negative FRNK or Hsp90 inhibitor 17-DMAG suppresses tumor growth and metastasis of SiHa cervical xenografts.

Journal: Cancer research 20090601

Title: Heat shock protein inhibitors, 17-DMAG and KNK437, enhance arsenic trioxide-induced mitotic apoptosis.

Journal: Toxicology and applied pharmacology 20090415

Title: 17-DMAG ameliorates polyglutamine-mediated motor neuron degeneration through well-preserved proteasome function in an SBMA model mouse.

Journal: Human molecular genetics 20090301

Title: Heat shock protein 90-binding agents protect renal cells from oxidative stress and reduce kidney ischemia-reperfusion injury.

Journal: American journal of physiology. Renal physiology 20080801

Title: Formulation of a geldanamycin prodrug in mPEG-b-PCL micelles greatly enhances tolerability and pharmacokinetics in rats.

Journal: Journal of controlled release : official journal of the Controlled Release Society 20080702

Title: Stage 1 testing and pharmacodynamic evaluation of the HSP90 inhibitor alvespimycin (17-DMAG, KOS-1022) by the pediatric preclinical testing program.

Journal: Pediatric blood & cancer 20080701

Title: 17-AAG and 17-DMAG-induced inhibition of cell proliferation through B-Raf downregulation in WT B-Raf-expressing uveal melanoma cell lines.

Journal: Investigative ophthalmology & visual science 20080601

Title: Efficacy of Hsp90 inhibition for induction of apoptosis and inhibition of growth in cervical carcinoma cells in vitro and in vivo.

Journal: Cancer chemotherapy and pharmacology 20080401

Title: Heat shock protein 90beta1 is essential for polyunsaturated fatty acid-induced mitochondrial Ca2+ efflux.

Journal: The Journal of biological chemistry 20080321

Title: Targeting Akt and heat shock protein 90 produces synergistic multiple myeloma cell cytotoxicity in the bone marrow microenvironment.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20080201

Title: Cancer stem cell heterogeneity in hereditary breast cancer.

Journal: Breast cancer research : BCR 20080101

Title: Humoral immune response upon mild heat-shock conditions in Galleria mellonella larvae.

Journal: Journal of insect physiology 20071101

Title: Targeting heat shock protein 90 in pancreatic cancer impairs insulin-like growth factor-I receptor signaling, disrupts an interleukin-6/signal-transducer and activator of transcription 3/hypoxia-inducible factor-1alpha autocrine loop, and reduces orthotopic tumor growth.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20071101

Title: Determination of 17-dimethylaminoethylamino-17-demethoxygeldanamycin in human plasma by liquid chromatography with mass-spectrometric detection.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20071015

Title: Mechanistic studies on Hsp90 inhibition by ansamycin derivatives.

Journal: Journal of molecular biology 20070914

Title: HIF-1alpha and HIF-2alpha play a central role in stretch-induced but not shear-stress-induced angiogenesis in rat skeletal muscle.

Journal: The Journal of physiology 20070901

Title: Perinecrotic hypoxia contributes to ischemia/reperfusion-accelerated outgrowth of colorectal micrometastases.

Journal: The American journal of pathology 20070401

Title: Synergism between arsenic trioxide and heat shock protein 90 inhibitors on signal transducer and activator of transcription protein 3 activity--pharmacodynamic drug-drug interaction modeling.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20070401

Title: Inhibition of heat shock protein 90 impairs epidermal growth factor-mediated signaling in gastric cancer cells and reduces tumor growth and vascularization in vivo.

Journal: Molecular cancer therapeutics 20070301

Title: Hsp90 inhibitors suppress HCV replication in replicon cells and humanized liver mice.

Journal: Biochemical and biophysical research communications 20070223

Title: STAT3 and MAPK signaling maintain overexpression of heat shock proteins 90alpha and beta in multiple myeloma cells, which critically contribute to tumor-cell survival.

Journal: Blood 20070115

Title: Small molecule inducers of heat-shock response reduce polyQ-mediated huntingtin aggregation. A possible therapeutic strategy.

Journal: Neuro-degenerative diseases 20070101

Title: Drug-mediated targeted disruption of multiple protein activities through functional inhibition of the Hsp90 chaperone complex.

Journal: Current medicinal chemistry 20070101

Title: Schedule-dependent synergy between the heat shock protein 90 inhibitor 17-(dimethylaminoethylamino)-17-demethoxygeldanamycin and doxorubicin restores apoptosis to p53-mutant lymphoma cell lines.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20061101

Title: Heat shock protein-90 inhibitors: a chronicle from geldanamycin to today's agents.

Journal: Current opinion in investigational drugs (London, England : 2000) 20060601

Title: Synergistic interactions between DMAG and mitogen-activated protein kinase kinase 1/2 inhibitors in Bcr/abl+ leukemia cells sensitive and resistant to imatinib mesylate.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20060401

Title: Benzoquinone ansamycin heat shock protein 90 inhibitors modulate multiple functions required for tumor angiogenesis.

Journal: Molecular cancer therapeutics 20060301

Title: Determination of the heat shock protein 90 inhibitor 17-dimethylaminoethylamino-17-demethoxygeldanamycin in plasma by liquid chromatography-electrospray mass spectrometry.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20060102

Title: Hsp90 inhibitors in the clinic.

Journal: Handbook of experimental pharmacology 20060101

Title: Inhibitors of the HSP90 molecular chaperone: current status.

Journal: Advances in cancer research 20060101

Title: Development and validation of a liquid chromatography/tandem mass spectrometry method for the determination of the novel anticancer agent 17-DMAG in human plasma.

Journal: Rapid communications in mass spectrometry : RCM 20060101

Title: Preclinical toxicity of a geldanamycin analog, 17-(dimethylaminoethylamino)-17-demethoxygeldanamycin (17-DMAG), in rats and dogs: potential clinical relevance.

Journal: Cancer chemotherapy and pharmacology 20051201

Title: Induction of the hypoxia-inducible factor system by low levels of heat shock protein 90 inhibitors.

Journal: Cancer research 20051201

Title: ZAP-70 is a novel conditional heat shock protein 90 (Hsp90) client: inhibition of Hsp90 leads to ZAP-70 degradation, apoptosis, and impaired signaling in chronic lymphocytic leukemia.

Journal: Blood 20051001

Title: In vivo antitumor efficacy of 17-DMAG (17-dimethylaminoethylamino-17-demethoxygeldanamycin hydrochloride), a water-soluble geldanamycin derivative.

Journal: Cancer chemotherapy and pharmacology 20050801

Title: Comparison of 17-dimethylaminoethylamino-17-demethoxy-geldanamycin (17DMAG) and 17-allylamino-17-demethoxygeldanamycin (17AAG) in vitro: effects on Hsp90 and client proteins in melanoma models.

Journal: Cancer chemotherapy and pharmacology 20050801

Title: 17-Allyamino-17-demethoxygeldanamycin and 17-NN-dimethyl ethylene diamine-geldanamycin have cytotoxic activity against multiple gynecologic cancer cell types.

Journal: Gynecologic oncology 20050201

Title: Enhanced tumor cell radiosensitivity and abrogation of G2 and S phase arrest by the Hsp90 inhibitor 17-(dimethylaminoethylamino)-17-demethoxygeldanamycin.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20041201

Title: Synthesis and biological activities of novel 17-aminogeldanamycin derivatives.

Journal: Bioorganic & medicinal chemistry 20041015

Title: Antiangiogenic properties of 17-(dimethylaminoethylamino)-17-demethoxygeldanamycin: an orally bioavailable heat shock protein 90 modulator.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20040715

Title: Clinical trials referral resource. Current clinical trials of 17-AG and 17-DMAG.

Journal: Oncology (Williston Park, N.Y.) 20040501

Title: Crystal structure and molecular modeling of 17-DMAG in complex with human Hsp90.

Journal: Chemistry & biology 20030401

Title: Ge J, et al. Design, synthesis, and biological evaluation of hydroquinone derivatives of 17-amino-17-demethoxygeldanamycin as potent, water-soluble inhibitors of Hsp90. J Med Chem. 2006 Jul 27;49(15):4606-15.

Title: Hertlein E, et al. 17-DMAG targets the nuclear factor-kappaB family of proteins to induce apoptosis in chronic lymphocytic leukemia: clinical implications of HSP90 inhibition. Blood. 2010 Jul 8;116(1):45-53.

Title: Henke A, et al. Reduced Contractility and Motility of Prostatic Cancer-Associated Fibroblasts after Inhibition of Heat Shock Protein 90. Cancers (Basel). 2016 Aug 24;8(9). pii: E77.

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Tags:467214-21-7 Molecular Formula|467214-21-7 MDL|467214-21-7 SMILES|467214-21-7 Alvespimycin hydrochloride