Identification
- Generic Name
- Tanespimycin
- DrugBank Accession Number
- DB05134
- Background
Tanespimycin, manufactured by Conforma Therapeutics is under development as a small molecule inhibitor of heat shock protein 90 (HSP90). It is developed for the treatment of several types of cancer, solid tumors or chronic myelogenous leukemia.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Tanespimycin (DB05134)
- Weight
- Average: 585.698
Monoisotopic: 585.305015357 - Chemical Formula
- C31H43N3O8
- Synonyms
- 17-allylamino-17-demethoxygeldanamycin
- 17-allylamino-17-demethoxygeldanamycin (17-AGG)
- 17AAG
- Tanespimycin
- tanespimycina
- External IDs
- 17-AAG
- BMS-722782
- CNF-1010
- CNF1010
- KOS-953
Pharmacology
- Indication
Investigated for use/treatment in leukemia (myeloid) and solid tumors.
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Tanespimycin is a small molecule inhibitor of heat shock protein 90 (HSP90). HSP90 is a molecular “chaperone” protein that controls protein shape or conformation, including that of key signaling molecules involved in the growth and survival of tumor cells.
Target Actions Organism UHeat shock protein HSP 90-alpha Not Available Humans UHeat shock protein HSP 90-beta Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Macrolactams
- Sub Class
- Not Available
- Direct Parent
- Macrolactams
- Alternative Parents
- Vinylogous amides / Carbamate esters / Secondary carboxylic acid amides / Secondary alcohols / Organic carbonic acids and derivatives / Lactams / Cyclic ketones / Enamines / Dialkylamines / Dialkyl ethers show 4 more
- Substituents
- Alcohol / Aliphatic heteropolycyclic compound / Amine / Amino acid or derivatives / Azacycle / Carbamic acid ester / Carbonic acid derivative / Carbonyl group / Carboxamide group / Carboxylic acid derivative show 20 more
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- secondary amino compound, lactam, macrocycle, benzoquinones (CHEBI:64153)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 4GY0AVT3L4
- CAS number
- 75747-14-7
- InChI Key
- AYUNIORJHRXIBJ-TXHRRWQRSA-N
- InChI
- 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
- IUPAC Name
- {[(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-20,22-dioxo-19-[(prop-2-en-1-yl)amino]-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid
- SMILES
- [H]/C1=C([H])/[C@]([H])(OC)[C@@]([H])(OC(O)=N)C(C)=C([H])[C@]([H])(C)[C@@]([H])(O)[C@]([H])(C[C@]([H])(C)CC2=C(NCC=C)C(=O)C=C(N=C(O)\C(C)=C\1/[H])C2=O)OC
References
- General References
- Not Available
- External Links
- PubChem Compound
- 6505803
- PubChem Substance
- 347827713
- ChemSpider
- 21106220
- BindingDB
- 50008057
- ChEBI
- 64153
- ChEMBL
- CHEMBL109480
- ZINC
- ZINC000100014666
- Wikipedia
- Tanespimycin
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Multiple Myeloma (MM) 1 2 Completed Treatment Adenocarcinoma of Prostate / Recurrent Prostate Cancer / Stage IV Prostate Cancer 1 2 Completed Treatment Advanced Malignant Neoplasm 1 2 Completed Treatment Anaplastic Large Cell Lymphoma / Recurrent Adult Hodgkin's Lymphoma / Recurrent Mantle Cell Lymphoma 1 2 Completed Treatment Chronic Myeloproliferative Disorders / Leukemias / Lymphoma / Non Neoplastic Condition / Precancerous Conditions 1 2 Completed Treatment Melanoma 1 2 Completed Treatment Pancreatic Adenocarcinoma / Recurrent Pancreatic Cancer / Stage IV Pancreatic Cancer 1 2 Completed Treatment Primary Peritoneal Cancer / Recurrent Epithelial Ovarian Cancer / Stage III Ovarian Epithelial Cancer / Stage IV Ovarian Epithelial Cancer 1 2 Completed Treatment Recurrent Thyroid Cancer / Stage IV Follicular Thyroid Cancer / Stage IV Papillary Thyroid Cancer / Thyroid Gland Medullary Carcinoma 1 2 Completed Treatment Renal Cancer 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00715 mg/mL ALOGPS logP 2.53 ALOGPS logP 1.52 Chemaxon logS -4.9 ALOGPS pKa (Strongest Acidic) -2.9 Chemaxon pKa (Strongest Basic) 11.59 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 11 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 170.76 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 175.25 m3·mol-1 Chemaxon Polarizability 61.3 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Tpr domain binding
- Specific Function
- Molecular chaperone that promotes the maturation, structural maintenance and proper regulation of specific target proteins involved for instance in cell cycle control and signal transduction. Under...
- Gene Name
- HSP90AA1
- Uniprot ID
- P07900
- Uniprot Name
- Heat shock protein HSP 90-alpha
- Molecular Weight
- 84659.015 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Utp binding
- Specific Function
- Molecular chaperone that promotes the maturation, structural maintenance and proper regulation of specific target proteins involved for instance in cell cycle control and signal transduction. Under...
- Gene Name
- HSP90AB1
- Uniprot ID
- P08238
- Uniprot Name
- Heat shock protein HSP 90-beta
- Molecular Weight
- 83263.475 Da
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Guo W, Siegel D, Ross D: Stability of the Hsp90 inhibitor 17AAG hydroquinone and prevention of metal-catalyzed oxidation. J Pharm Sci. 2008 Dec;97(12):5147-57. doi: 10.1002/jps.21394. [Article]
Drug created at October 21, 2007 22:23 / Updated at November 18, 2022 07:07