Tanespimycin

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
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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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
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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
PubChem Compound
6505803
PubChem Substance
347827713
ChemSpider
21106220
BindingDB
50008057
ChEBI
64153
ChEMBL
CHEMBL109480
ZINC
ZINC000100014666
Wikipedia
Tanespimycin

Clinical Trials

Clinical Trials

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/MSsplash10-0006-0000920000-d7d2140fab3c1d4a9fff
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-02ai-2000090000-91bdbae484e39e124a63
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0007-0000890000-885edd075c17b790400f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ox-9000000000-dbcc55a912ad6b1bc7c8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01pc-0000490000-94e3d69e521c90f73daf
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000030000-2755c169247cef803833
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-250.1305485
predicted
DarkChem Lite v0.1.0
[M-H]-242.30763
predicted
DeepCCS 1.0 (2019)
[M+H]+250.2977485
predicted
DarkChem Lite v0.1.0
[M+H]+244.03136
predicted
DeepCCS 1.0 (2019)
[M+Na]+249.6190485
predicted
DarkChem Lite v0.1.0
[M+Na]+250.35945
predicted
DeepCCS 1.0 (2019)

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
  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. [Article]

Drug created at October 21, 2007 22:23 / Updated at November 18, 2022 07:07