U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C31H43N3O8
Molecular Weight 585.6884
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TANESPIMYCIN

SMILES

CO[C@H]1C[C@H](C)CC2=C(NCC=C)C(=O)C=C(NC(=O)\C(C)=C\C=C[C@H](OC)[C@@H](OC(N)=O)\C(C)=C\[C@H](C)[C@H]1O)C2=O

InChI

InChIKey=AYUNIORJHRXIBJ-TXHRRWQRSA-N
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

HIDE SMILES / InChI
Tanespimycin (17-allylamino-17-demethoxygeldanamycin, 17-AAG) is a synthetic analogue of geldanamycin, an antibiotic first purified in 1970 from Streptomyces hygroscopicus. Tanespimycin is an Hsp90 inhibitor that has demonstrated the potential to disrupt the activity of multiple oncogenes and cell signaling pathways implicated in tumor growth, including HER2, a key pathway in breast cancer. Tanespimycin was being under development by Kosan Biosciences. It was in phase 3 clinical development with bortezomib for the treatment of multiple myeloma (MM). However, in 2010 the company halted development of tanespimycin, during late-stage clinical trials as a potential treatment for multiple myeloma. While no definitive explanation was given, it has been suggested that Bristol-Myers Squibb halted development over concerns of the financial feasibility of tanespimycin development given the 2014 expiry of the patent on this compound, and the relative expense of manufacture.

CNS Activity

Curator's Comment: Studies on the tissue distribution of Tanespimycin (17-AAG) in mice showed that it penetrates the blood brain barrier.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
5.0 nM [IC50]
Conditions
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Cellular growth kinetics distinguish a cyclophilin inhibitor from an HSP90 inhibitor as a selective inhibitor of hepatitis C virus.
2012
Patents

Sample Use Guides

Solution, IV, 340mg/m2, twice weekly for 2 weeks (3 week cycle), 60 minutes infusion
Route of Administration: Intravenous
Tanespimycin (17-AAG) significantly inhibits cell proliferation in both synovial sarcoma cell lines Fuji and SYO-1 in a dose- and time-dependent manner. The 17-AAG IC50 values for synovial sarcoma monolayer models treated for 72 hours were both 0.038 uM/L. HER2 and FGFR3 were reduced to extremely low levels by 5 uM/L 17-AAG.
Name Type Language
TANESPIMYCIN
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
GELDANAMYCIN, 17-DEMETHOXY-17-(2-PROPENYLAMINO)-
Common Name English
KOS-953
Code English
(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
Systematic Name English
17-ALLYLAMINO 17-DEMETHOXYGELDANAMYCIN
Common Name English
17-AAG
Code English
17-DEMETHOXY-17-(2-PROPENYLAMINO)GELDANAMYCIN
Common Name English
CNF-1010
Code English
NSC-330507
Code English
BMS-722782
Code English
17-ALLYLAMINO-17-DEMETHOXYGELDANAMYCIN
Common Name English
TANESPIMYCIN [USAN]
Common Name English
Tanespimycin [WHO-DD]
Common Name English
CNF1010
Code English
17AAG
Common Name English
tanespimycin [INN]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 469915
Created by admin on Fri Dec 15 15:38:56 GMT 2023 , Edited by admin on Fri Dec 15 15:38:56 GMT 2023
NCI_THESAURUS C2516
Created by admin on Fri Dec 15 15:38:56 GMT 2023 , Edited by admin on Fri Dec 15 15:38:56 GMT 2023
FDA ORPHAN DRUG 191304
Created by admin on Fri Dec 15 15:38:56 GMT 2023 , Edited by admin on Fri Dec 15 15:38:56 GMT 2023
EU-Orphan Drug EU/3/04/256
Created by admin on Fri Dec 15 15:38:56 GMT 2023 , Edited by admin on Fri Dec 15 15:38:56 GMT 2023
FDA ORPHAN DRUG 191504
Created by admin on Fri Dec 15 15:38:56 GMT 2023 , Edited by admin on Fri Dec 15 15:38:56 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C37899
Created by admin on Fri Dec 15 15:38:56 GMT 2023 , Edited by admin on Fri Dec 15 15:38:56 GMT 2023
PRIMARY
CHEBI
64153
Created by admin on Fri Dec 15 15:38:56 GMT 2023 , Edited by admin on Fri Dec 15 15:38:56 GMT 2023
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EVMPD
SUB33510
Created by admin on Fri Dec 15 15:38:56 GMT 2023 , Edited by admin on Fri Dec 15 15:38:56 GMT 2023
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EPA CompTox
DTXSID5046352
Created by admin on Fri Dec 15 15:38:56 GMT 2023 , Edited by admin on Fri Dec 15 15:38:56 GMT 2023
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WIKIPEDIA
TANESPIMYCIN
Created by admin on Fri Dec 15 15:38:56 GMT 2023 , Edited by admin on Fri Dec 15 15:38:56 GMT 2023
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NSC
330507
Created by admin on Fri Dec 15 15:38:56 GMT 2023 , Edited by admin on Fri Dec 15 15:38:56 GMT 2023
PRIMARY
SMS_ID
100000127484
Created by admin on Fri Dec 15 15:38:56 GMT 2023 , Edited by admin on Fri Dec 15 15:38:56 GMT 2023
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DRUG BANK
DB05134
Created by admin on Fri Dec 15 15:38:56 GMT 2023 , Edited by admin on Fri Dec 15 15:38:56 GMT 2023
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USAN
SS-61
Created by admin on Fri Dec 15 15:38:56 GMT 2023 , Edited by admin on Fri Dec 15 15:38:56 GMT 2023
PRIMARY
MESH
C112765
Created by admin on Fri Dec 15 15:38:56 GMT 2023 , Edited by admin on Fri Dec 15 15:38:56 GMT 2023
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FDA UNII
4GY0AVT3L4
Created by admin on Fri Dec 15 15:38:56 GMT 2023 , Edited by admin on Fri Dec 15 15:38:56 GMT 2023
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ChEMBL
CHEMBL109480
Created by admin on Fri Dec 15 15:38:56 GMT 2023 , Edited by admin on Fri Dec 15 15:38:56 GMT 2023
PRIMARY
PUBCHEM
6505803
Created by admin on Fri Dec 15 15:38:56 GMT 2023 , Edited by admin on Fri Dec 15 15:38:56 GMT 2023
PRIMARY
CAS
75747-14-7
Created by admin on Fri Dec 15 15:38:56 GMT 2023 , Edited by admin on Fri Dec 15 15:38:56 GMT 2023
PRIMARY
INN
8815
Created by admin on Fri Dec 15 15:38:56 GMT 2023 , Edited by admin on Fri Dec 15 15:38:56 GMT 2023
PRIMARY