Drug Details

General Information of the Drug (ID: DR6066)
Name
Tanespimycin
Synonyms
Tanespimycin; 17-AAG; 75747-14-7; 17-(Allylamino)-17-demethoxygeldanamycin; 17-(Allylamino)geldanamycin; NSC-330507; 17-Allylaminogeldanamycin; KOS-953; 17-Demethoxy-17-allylamino geldanamycin; UNII-4GY0AVT3L4; Cp 127374; NSC 330507; 17AAG; CHEBI:64153; 17-AAG (Tanespimycin); BMS-722782; 4GY0AVT3L4; MFCD04973892; NCGC00163424-01; 17-N-allylamino-17-demethoxygeldanamycin; 17-demethoxy-17-(2-propenylamino)geldanamycin; Geldanamycin, 17-demethoxy-17-(2-propenylamino)-; NSC330507; (4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-19-(prop-2-en-1-ylamino)-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl carbamate; [(3S,5S,6R,7S,8E,10R,11S,12E,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-8,12,14,18,21-pentaen-10-yl] carbamate; Tanespimycin [USAN:INN]; tanespimycina; tanespimycine; tanespimycinum; CCRIS 9401; 17-Demethoxy-17-allylaminogeldanamycin; C31H43N3O8; Tanespimycin (USAN); Geldanamycin, 17-(Allylamino)-17-demethoxy-; DSSTox_CID_26352; DSSTox_RID_81555; DSSTox_GSID_46352; BSPBio_001434; SCHEMBL2604976; DTXSID5046352; SCHEMBL13037468; SCHEMBL16226295; CHEBI:94756; CNF-101; CNF1010; HMS1361H16; HMS1791H16; HMS1989H16; HMS3402H16; (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; CNF-1010; EX-A4668; NSC-330507D; Tox21_112054; BDBM50008057; s1141; AKOS024456643; ZINC100014666; BCP9000064; CCG-208039; CS-0161; DB05134; NSC-704057; IDI1_033904; NCGC00163424-02; NCGC00163424-04; NCGC00163424-05; NCGC00163424-06; NCGC00163424-07; HY-10211; Geldanamycin, des-O-methyl-17-allylamino-; CAS-75747-14-7; CP-127374; Geldanamycin, 17-allylamino-17-demethoxy-; X7553; D06650; W-5317; 747A147; Geldanamycin,17-demethoxy-17-(2-propenylamino)-; J-504153; BRD-K81473043-001-03-9; BRD-K81473043-001-08-8; 17-(Allylamino)-17-demethoxygeldanamycin, >=98% (HPLC), solid; (4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-Hydroxy-8,14-dimethoxy-4,10,12,16- tetramethyl-3,20,22-trioxo-19-(prop-2-enylamino)-2-azabicyclo(16.3.1)docosa- 1(21),4,6,10,18-penten-9-yl carbamate; [(3R,5S,6R,7S,8E,10S,11S,12Z,14E)-21-(allylamino)-6-hydroxy-5,11-dimethoxy-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; [(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-19-(prop-2-enylamino)-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl] carbamate; 17-AAG; ; ; 17-(Allylamino)-17-demethoxy-geldanamycin; ; ; [(3R,5S,6R,7S,8E,10S,11S,12Z,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
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Molecular Type
Small molecule
Disease Breast cancer [ICD-11: 2C60] Investigative [1]
Structure
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2D MOL

3D MOL

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Formula
C31H43N3O8
PubChem CID
6505803
Canonical SMILES
CC1CC(C(C(C=C(C(C(C=CC=C(C(=O)NC2=CC(=O)C(=C(C1)C2=O)NCC=C)C)OC)OC(=O)N)C)C)O)OC
InChI
1S/C31H43N3O8/c1-8-12-33-26-21-13-17(2)14-25(41-7)27(36)19(4)15-20(5)29(42-31(32)39)24(40-6)11-9-10-18(3)30(38)34-22(28(21)37)16-23(26)35/h8-11,15-17,19,24-25,27,29,33,36H,1,12-14H2,2-7H3,(H2,32,39)(H,34,38)/b11-9-,18-10+,20-15+/t17-,19+,24+,25+,27-,29+/m1/s1
InChIKey
AYUNIORJHRXIBJ-TXHRRWQRSA-N
CAS Number
CAS 75747-14-7
ChEBI ID
CHEBI:64153
TTD Drug ID
D0SC2J
DrugBank ID
DB05134
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Celastrol      Celastrus strigillosus     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Biological
                    Regulation		 Induction Proteotoxic stress
                    In-vitro Model U-251MG CVCL_0021 Astrocytoma Homo sapiens
U-343MG CVCL_S471 Glioblastoma Homo sapiens
                    Experimental
                    Result(s)		 celastrol targets proteostasis by disrupting sulfyhydryl homeostasis, independently of ROS, in human glioblastoma cells. Targeting proteotoxic stress responses by inhibiting HSP90 with 17-N-Allylamino-17-demethoxygeldanamycin sensitizes human glioblastoma to celastrol treatment, thereby serving as a novel synergism to overcome drug resistance.
          Sulforaphane      Brassica oleracea     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression HSP90A  Molecule Info 
Pathway MAP
                    In-vitro Model MIA PaCa-2 CVCL_0428 Pancreatic ductal adenocarcinoma Homo sapiens
PANC-1 CVCL_0480 Pancreatic ductal adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)		 Sulforaphane potentiates the efficacy of 17-AAG against pancreatic cancer through enhanced abrogation of Hsp90 function.
Target and Pathway
Target(s) Heat shock protein 90 alpha (HSP90A)  Molecule Info  [4]
KEGG Pathway Protein processing in endoplasmic reticulum Click to Show/Hide
2 PI3K-Akt signaling pathway
3 Antigen processing and presentation
4 NOD-like receptor signaling pathway
5 Progesterone-mediated oocyte maturation
6 Estrogen signaling pathway
7 Pathways in cancer
8 Prostate cancer
NetPath Pathway IL2 Signaling Pathway Click to Show/Hide
2 TCR Signaling Pathway
Pathway Interaction Database Signaling events mediated by HDAC Class II Click to Show/Hide
2 Validated targets of C-MYC transcriptional activation
3 Integrin-linked kinase signaling
4 LKB1 signaling events
5 Regulation of Telomerase
6 Glucocorticoid receptor regulatory network
7 Class I PI3K signaling events
8 IL2 signaling events mediated by PI3K
9 Regulation of Androgen receptor activity
10 Integrins in angiogenesis
11 Hypoxic and oxygen homeostasis regulation of HIF-1-alpha
12 ErbB receptor signaling network
13 VEGFR1 specific signals
14 Signaling events mediated by VEGFR1 and VEGFR2
15 Class I PI3K signaling events mediated by Akt
Reactome Constitutive Signaling by Ligand-Responsive EGFR Cancer Variants Click to Show/Hide
2 Tetrahydrobiopterin (BH4) synthesis, recycling, salvage and regulation
3 Regulation of actin dynamics for phagocytic cup formation
4 eNOS activation
5 Regulation of PLK1 Activity at G2/M Transition
6 Attenuation phase
7 HSF1-dependent transactivation
8 Loss of Nlp from mitotic centrosomes
9 Recruitment of mitotic centrosome proteins and complexes
10 Loss of proteins required for interphase microtubule organization?from the centrosome
11 EPHA-mediated growth cone collapse
12 VEGFA-VEGFR2 Pathway
13 VEGFR2 mediated vascular permeability
14 Anchoring of the basal body to the plasma membrane
15 Constitutive Signaling by EGFRvIII
WikiPathways NRF2 pathway Click to Show/Hide
2 Nuclear Receptors Meta-Pathway
3 Aryl Hydrocarbon Receptor Pathway
4 Binding and Uptake of Ligands by Scavenger Receptors
5 Signaling by ERBB2
6 Fcgamma receptor (FCGR) dependent phagocytosis
7 Influenza Life Cycle
8 EBV LMP1 signaling
9 Aryl Hydrocarbon Receptor
10 Corticotropin-releasing hormone
11 TNF alpha Signaling Pathway
12 Arylhydrocarbon receptor (AhR) signaling pathway
13 Signaling by EGFR
14 Semaphorin interactions
15 Mitotic G2-G2/M phases
16 Metabolism of nitric oxide
17 NOD pathway
References
Reference 1 A combination of Trastuzumab and 17-AAG induces enhanced ubiquitinylation and lysosomal pathway-dependent ErbB2 degradation and cytotoxicity in ErbB2-overexpressing breast cancer cells. Cancer Biol Ther. 2008 Oct;7(10):1630-40.
Reference 2 Celastrol targets proteostasis and acts synergistically with a heat-shock protein 90 inhibitor to kill human glioblastoma cells. Cell Death Dis. 2014 May 8;5(5):e1216.
Reference 3 Sulforaphane potentiates the efficacy of 17-allylamino 17-demethoxygeldanamycin against pancreatic cancer through enhanced abrogation of Hsp90 chaperone function. Nutr Cancer. 2011;63(7):1151-9.
Reference 4 Tanespimycin: the opportunities and challenges of targeting heat shock protein 90. Expert Opin Investig Drugs. 2009 Jun;18(6):861-8.
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