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Details

Stereochemistry ABSOLUTE
Molecular Formula C28H39N3O8
Molecular Weight 545.6246
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IPI-493

SMILES

CO[C@H]1C[C@H](C)CC2=C(N)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=XYFFWTYOFPSZRM-TWNAANEASA-N
InChI=1S/C28H39N3O8/c1-14-10-18-23(29)20(32)13-19(25(18)34)31-27(35)15(2)8-7-9-21(37-5)26(39-28(30)36)17(4)12-16(3)24(33)22(11-14)38-6/h7-9,12-14,16,21-22,24,26,33H,10-11,29H2,1-6H3,(H2,30,36)(H,31,35)/b9-7-,15-8+,17-12+/t14-,16+,21+,22+,24-,26+/m1/s1

HIDE SMILES / InChI
IPI-493 (17-AG, 17-Aminogeldanamycin) is the major metabolite of tanespimycin (17-AAG) and retaspimycin (17-DMAG) with potent antineoplastic activity. Hsp90 controls the proper folding, function, and stability of various "client" proteins within cells. Many of the clients of Hsp90 (such as Akt, Bcr-Abl, EGFR, Flt-3, c-Kit and PDGFR α) are oncoproteins or important cell-signaling proteins, and therefore are critical for tumor cell growth and survival. Inhibition of Hsp90 results in degradation of these proteins, which abrogates growth and survival signaling and leads to tumor cell death. IPI-493 has been used in trials studying the treatment of Advanced Malignancies.

Originator

Sources: Cancer Treatment Reports (1977), 61, (5), 815-24.

Approval Year

PubMed

PubMed

TitleDatePubMed
HSP90 inhibitor 17-AAG prevents apoptosis of cardiomyocytes via miR-93-dependent mitigation of endoplasmic reticulum stress.
2019 May
Patents

Patents

Sample Use Guides

IPI-504 at 400mg/m2, IV, 2 times a week for 2 weeks with 10 days off treatment. Twenty-one (21) day cycle
Route of Administration: Intravenous
Name Type Language
IPI-493
Common Name English
17-AMINOGELDANAMYCIN
Common Name English
GELDANAMYCIN, 17-AMINO-17-DEMETHOXY-
Common Name English
NSC-255109
Code English
IPI 493 [WHO-DD]
Common Name English
2-AZABICYCLO(16.3.1)DOCOSA-4,6,10,18,21-PENTAENE-3,20,22-TRIONE, 19-AMINO-9-((AMINOCARBONYL)OXY)-13-HYDROXY-8,14-DIMETHOXY-4,10,12,16-TETRAMETHYL-, (8R,9R,12R,13S,14R,16R)-
Systematic Name English
17AAG METABOLITE M8
Common Name English
17-AMINO-17-DEMETHOXYGELDANAMYCIN
Common Name English
Code System Code Type Description
FDA UNII
SLQ1AJG3VB
Created by admin on Fri Dec 15 19:21:57 GMT 2023 , Edited by admin on Fri Dec 15 19:21:57 GMT 2023
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NSC
255109
Created by admin on Fri Dec 15 19:21:57 GMT 2023 , Edited by admin on Fri Dec 15 19:21:57 GMT 2023
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NCI_THESAURUS
C78843
Created by admin on Fri Dec 15 19:21:57 GMT 2023 , Edited by admin on Fri Dec 15 19:21:57 GMT 2023
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CAS
64202-81-9
Created by admin on Fri Dec 15 19:21:57 GMT 2023 , Edited by admin on Fri Dec 15 19:21:57 GMT 2023
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PUBCHEM
9893658
Created by admin on Fri Dec 15 19:21:57 GMT 2023 , Edited by admin on Fri Dec 15 19:21:57 GMT 2023
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SMS_ID
100000175156
Created by admin on Fri Dec 15 19:21:57 GMT 2023 , Edited by admin on Fri Dec 15 19:21:57 GMT 2023
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DRUG BANK
DB13023
Created by admin on Fri Dec 15 19:21:57 GMT 2023 , Edited by admin on Fri Dec 15 19:21:57 GMT 2023
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