Identification

Name
Tanespimycin
Accession Number
DB05134
Description

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
Thumb
Weight
Average: 585.698
Monoisotopic: 585.305015357
Chemical Formula
C31H43N3O8
Synonyms
  • 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.

Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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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.

TargetActionsOrganism
UHeat shock protein HSP 90-alphaNot AvailableHumans
UHeat shock protein HSP 90-betaNot AvailableHumans
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
Learn about our commercial Adverse Effects data.
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Toxicity
Not Available
Affected organisms
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

Products

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)

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])/[[email protected]]([H])(OC)[[email protected]@]([H])(OC(O)=N)C(C)=C([H])[[email protected]]([H])(C)[[email protected]@]([H])(O)[[email protected]]([H])(C[[email protected]]([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
PubChem Compound
6505803
PubChem Substance
347827713
ChemSpider
21106220
BindingDB
50008057
ChEBI
64153
ChEMBL
CHEMBL109480
ZINC
ZINC000100014666
Wikipedia
Tanespimycin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentMultiple Myeloma (MM)1
2CompletedTreatmentAdenocarcinoma of the Pancreas / Recurrent Pancreatic Cancer / Stage IV Pancreatic Cancer1
2CompletedTreatmentAdenocarcinoma of the Prostate / Recurrent Prostate Cancer / Stage IV Prostate Cancer1
2CompletedTreatmentAdvanced Malignancies1
2CompletedTreatmentAnaplastic Large Cell Lymphoma / Anaplastic Large-Cell Lymphoma / Recurrent Adult Hodgkin's Lymphoma / Recurrent Mantle Cell Lymphoma1
2CompletedTreatmentChronic Myeloproliferative Disorders / Leukemias / Malignant Lymphomas / Nonneoplastic Condition / Precancerous Conditions1
2CompletedTreatmentHippel-Lindau Disease / Renal Cancers1
2CompletedTreatmentMalignant Melanoma of Skin / Melanoma (Skin)1
2CompletedTreatmentPrimary Peritoneal Cavity Cancer / Recurrent Ovarian Epithelial Cancer / Stage III Ovarian Epithelial Cancer / Stage IV Ovarian Epithelial Cancer1
2CompletedTreatmentRecurrent Thyroid Cancer / Stage IV Follicular Thyroid Cancer / Stage IV Papillary Thyroid Cancer / Thyroid Gland Medullary Carcinoma1

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
PropertyValueSource
Water Solubility0.00715 mg/mLALOGPS
logP2.53ALOGPS
logP1.52ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)-2.9ChemAxon
pKa (Strongest Basic)11.59ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area170.76 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity175.25 m3·mol-1ChemAxon
Polarizability61.3 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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
  1. 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. [PubMed:18393300]

Drug created on October 21, 2007 16:23 / Updated on June 12, 2020 10:52

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