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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H31N3O3.C3H6O3
Molecular Weight 499.5992
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ONALESPIB LACTATE

SMILES

C[C@H](O)C(O)=O.CC(C)C1=CC(C(=O)N2CC3=C(C2)C=C(CN4CCN(C)CC4)C=C3)=C(O)C=C1O

InChI

InChIKey=VYRWEWHOAMGLLW-WNQIDUERSA-N
InChI=1S/C24H31N3O3.C3H6O3/c1-16(2)20-11-21(23(29)12-22(20)28)24(30)27-14-18-5-4-17(10-19(18)15-27)13-26-8-6-25(3)7-9-26;1-2(4)3(5)6/h4-5,10-12,16,28-29H,6-9,13-15H2,1-3H3;2,4H,1H3,(H,5,6)/t;2-/m.0/s1

HIDE SMILES / InChI

Molecular Formula C24H31N3O3
Molecular Weight 409.5212
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C3H6O3
Molecular Weight 90.0779
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/?term=22181674

Onalespib (AT13387; (2,4-dihydroxy-5-isopropyl-phenyl)-[5-(4-methyl-piperazin-1-ylmethyl)-1,3-dihydro-isoindol-2-yl] methanone, l-lactic acid salt), is wholly owned by Astex, a novel, high-affinity HSP90 inhibitor, which is currently being clinically tested, has shown activity against a wide array of tumor cell lines, including lung cancer cell lines. As a targeted inhibitor of Hsp90, onalespib has the potential to control the proliferation of multiple solid tumors and hematological malignancies where uncontrolled cell growth is dependent on the interaction between Hsp90 and its client proteins. Astex is pursuing an approach based on the observation that addition of onalespib to a molecularly targeted agent may delay the emergence of resistance to the agent, and hence prolong the window of therapeutic benefit. Onalespib is currently being evaluated via a CRADA with the National Cancer Institute (NCI) in various tumor types, and in a Phase 1/2 clinical study in combination with AT7519, Astex CDK inhibitor.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.7 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Discovery of (2,4-dihydroxy-5-isopropylphenyl)-[5-(4-methylpiperazin-1-ylmethyl)-1,3-dihydroisoindol-2-yl]methanone (AT13387), a novel inhibitor of the molecular chaperone Hsp90 by fragment based drug design.
2010 Aug 26
Patents

Sample Use Guides

At 13387 (ONALESPIB) administered as a 1-hr IV infusion at a starting dose of 120 mg/m2 on Day 1 and Day 2 weekly for 3 weeks in a 4-week cycle.
Route of Administration: Intravenous
AT13387 (50 nM) ONALESPIB treatment resulted in G2/M-phase arrest and significantly reduced the migration capacity. The expression of selected proteins involved in DNA repair, cell-signaling and cell growth was downregulated in vitro, though the expression of most investigated proteins recurred after 8-24 h. AT13387 induces effective cytotoxic activity in all cancer cell lines (A431, HCT116, LS174T and H314) with an IC50 < 20 nM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:11:55 UTC 2023
Edited
by admin
on Fri Dec 15 18:11:55 UTC 2023
Record UNII
66226JUH2I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ONALESPIB LACTATE
USAN   WHO-DD  
USAN  
Official Name English
ONALESPIB L-LACTATE
Common Name English
ATI-13387A
Code English
ATI-13387AU
Code English
ONALESPIB LACTATE [USAN]
Common Name English
PROPANOIC ACID, 2-HYDROXY-, (2S)-, COMPD. WITH (1,3-DIHYDRO-5-((4-METHYL-1-PIPERAZINYL)METHYL)-2H-ISOINDOL-2-YL)(2,4-DIHYDROXY-5-(1-METHYLETHYL)PHENYL)METHANONE (1:1)
Systematic Name English
Onalespib lactate [WHO-DD]
Common Name English
ATI13387A
Code English
AT-13387 LACTATE
Code English
ATI13387AU
Code English
Classification Tree Code System Code
NCI_THESAURUS C74526
Created by admin on Fri Dec 15 18:11:56 UTC 2023 , Edited by admin on Fri Dec 15 18:11:56 UTC 2023
Code System Code Type Description
FDA UNII
66226JUH2I
Created by admin on Fri Dec 15 18:11:56 UTC 2023 , Edited by admin on Fri Dec 15 18:11:56 UTC 2023
PRIMARY
NCI_THESAURUS
C129425
Created by admin on Fri Dec 15 18:11:56 UTC 2023 , Edited by admin on Fri Dec 15 18:11:56 UTC 2023
PRIMARY
ChEMBL
CHEMBL1214827
Created by admin on Fri Dec 15 18:11:56 UTC 2023 , Edited by admin on Fri Dec 15 18:11:56 UTC 2023
PRIMARY
CAS
1019889-35-0
Created by admin on Fri Dec 15 18:11:56 UTC 2023 , Edited by admin on Fri Dec 15 18:11:56 UTC 2023
PRIMARY
SMS_ID
300000044548
Created by admin on Fri Dec 15 18:11:56 UTC 2023 , Edited by admin on Fri Dec 15 18:11:56 UTC 2023
PRIMARY
PUBCHEM
46915024
Created by admin on Fri Dec 15 18:11:56 UTC 2023 , Edited by admin on Fri Dec 15 18:11:56 UTC 2023
PRIMARY
USAN
BC-67
Created by admin on Fri Dec 15 18:11:56 UTC 2023 , Edited by admin on Fri Dec 15 18:11:56 UTC 2023
PRIMARY
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PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY