Structure via PubChem · Public domain (PubChem)
geldanamycin
Sign in to saveGeldanamycin is a 1,4-benzoquinone ansamycin antitumor antibiotic that inhibits the function of Hsp90 (Heat Shock Protein 90) by binding to the unusual ADP/ATP-binding pocket of the protein. HSP90 client proteins play important roles in the regulation of the cell cycle, cell growth, cell survival, apoptosis, angiogenesis and oncogenesis.
Chemical data
- Formula
- C29H40N2O9
- Molecular weight
- 560.6 g/mol
- IUPAC name
- [(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-hydroxy-8,14,19-trimethoxy-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
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- kidney cancer, von Hippel-Lindau disease, Hodgkins lymphoma
via ChEMBL · EBI
Research
2,037 papers- Geldanamycin, a Naturally Occurring Inhibitor of Hsp90 and a Lead Compound for Medicinal Chemistry.Journal of medicinal chemistry · 2024
- Geldanamycin analogs.Journal of chemotherapy (Florence, Italy) · 2004
- Geldanamycin and its anti-cancer activities.Cancer letters · 2010
- Regulation of Geldanamycin Biosynthesis by Cluster-Situated Transcription Factors and the Master Regulator PhoP.Antibiotics (Basel, Switzerland) · 2019
- Geldanamycin and its derivatives as Hsp90 inhibitors.Frontiers in bioscience (Landmark edition) · 2012
via PubMed
Wikidata facts
- Mass
- 560.2733808599999
Show 3 more facts
- chemical formula
- C₂₉H₄₀N₂O₉
- isomeric SMILES
- C[C@H]1C[C@@H]([C@@H]([C@H](/C=C(/[C@@H]([C@H](/C=C\C=C(\C(=O)NC2=CC(=O)C(=C(C1)C2=O)OC)/C)OC)OC(=O)N)\C)C)O)OC
- canonical SMILES
- COC1=C2CC(C)CC(OC)C(O)C(C)C=C(C)C(OC(N)=O)C(OC)C=CC=C(C)C(=O)NC(=CC1=O)C2=O
via Wikidata · CC0
~2 min read
Article
4 sectionsContents
- Biosynthesis
- Notes
- References
- External links
Geldanamycin is a 1,4-benzoquinone ansamycin antitumor antibiotic that inhibits the function of Hsp90 (Heat Shock Protein 90) by binding to the unusual ADP/ATP-binding pocket of the protein. HSP90 client proteins play important roles in the regulation of the cell cycle, cell growth, cell survival, apoptosis, angiogenesis and oncogenesis.
thumb|Hsp90-geldanamycin complex. PDB Geldanamycin induces the degradation of proteins that are mutated or overexpressed in tumor cells such as v-Src, Bcr-Abl, p53, and ERBB2. This effect is mediated via HSP90. Despite its potent antitumor potential, geldanamycin presents several major drawbacks as a drug candidate such as hepatotoxicity, further, Jilani et al.. reported that geldanamycin induces the apoptosis of erythrocytes under physiological concentrations. These side effects have led to the development of geldanamycin analogues, in particular analogues containing a derivatisation at the 17 position: 17-AAG 17-DMAG