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

Details

Stereochemistry ACHIRAL
Molecular Formula C25H26N8O
Molecular Weight 454.5269
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIMITESPIB

SMILES

CCC1=CC(=CC=C1N2N=C(C(C)C)C3=C2N=CC=C3N4C=NC(=C4)C5=CN(C)N=C5)C(N)=O

InChI

InChIKey=NVVPMZUGELHVMH-UHFFFAOYSA-N
InChI=1S/C25H26N8O/c1-5-16-10-17(24(26)34)6-7-20(16)33-25-22(23(30-33)15(2)3)21(8-9-27-25)32-13-19(28-14-32)18-11-29-31(4)12-18/h6-15H,5H2,1-4H3,(H2,26,34)

HIDE SMILES / InChI
Molecular Formula C25H26N8O
Molecular Weight 454.5269
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/28062703

TAS-116 is a highly potent oral HSP90 inhibitor with unique tissue distribution properties. TAS-116 has the potential to demonstrate antitumor activity, while being designed to limit certain adverse events by unique tissue distribution. Phase-II clinical trials in gastrointestinal stromal tumours are ongoing in Japan.

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 34.7 nM [Ki]
Inhibitor
8504
 21.3 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase I
438
Unknown

Approved Use

Unknown
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3097 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/30679388
210.7 mg/m² single, oral
dose: 210.7 mg/m²
route of administration: Oral
experiment type: SINGLE
co-administered:
TAS-116 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2587 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/30679388
107.5 mg/m² single, oral
dose: 107.5 mg/m²
route of administration: Oral
experiment type: SINGLE
co-administered:
TAS-116 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
3080 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/30679388
107.5 mg/m² 1 times / day multiple, oral
dose: 107.5 mg/m²
route of administration: Oral
experiment type: MULTIPLE
co-administered:
TAS-116 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2756 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/30679388
210.7 mg/m² 1 times / 2 days multiple, oral
dose: 210.7 mg/m²
route of administration: Oral
experiment type: MULTIPLE
co-administered:
TAS-116 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
47365 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/30679388
210.7 mg/m² single, oral
dose: 210.7 mg/m²
route of administration: Oral
experiment type: SINGLE
co-administered:
TAS-116 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
36779 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/30679388
107.5 mg/m² single, oral
dose: 107.5 mg/m²
route of administration: Oral
experiment type: SINGLE
co-administered:
TAS-116 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
38923 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/30679388
107.5 mg/m² 1 times / day multiple, oral
dose: 107.5 mg/m²
route of administration: Oral
experiment type: MULTIPLE
co-administered:
TAS-116 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
33090 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/30679388
210.7 mg/m² 1 times / 2 days multiple, oral
dose: 210.7 mg/m²
route of administration: Oral
experiment type: MULTIPLE
co-administered:
TAS-116 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
13.32 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/30679388
210.7 mg/m² single, oral
dose: 210.7 mg/m²
route of administration: Oral
experiment type: SINGLE
co-administered:
TAS-116 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
13.21 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/30679388
107.5 mg/m² single, oral
dose: 107.5 mg/m²
route of administration: Oral
experiment type: SINGLE
co-administered:
TAS-116 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
12.76 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/30679388
107.5 mg/m² 1 times / day multiple, oral
dose: 107.5 mg/m²
route of administration: Oral
experiment type: MULTIPLE
co-administered:
TAS-116 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
9.91 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/30679388
210.7 mg/m² 1 times / 2 days multiple, oral
dose: 210.7 mg/m²
route of administration: Oral
experiment type: MULTIPLE
co-administered:
TAS-116 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
295 mg/m2 1 times / 2 days multiple, oral
Highest studied dose
Dose: 295 mg/m2, 1 times / 2 days
Route: oral
Route: multiple
Dose: 295 mg/m2, 1 times / 2 days
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
DLT: Platelet count decreased, Septic shock...
Disc. AE: Anemia...
Dose limiting toxicities:
Platelet count decreased (grade 3, 20%)
Septic shock (grade 4, 20%)
Respiratory failure (grade 4, 20%)
Pneumonia (grade 4, 20%)
Febrile neutropenia (grade 3, 20%)
AEs leading to
discontinuation/dose reduction:
Anemia (grade 3, 20%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
107.5 mg/m2 1 times / day multiple, oral
MTD
Dose: 107.5 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 107.5 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
DLT: Anorexia...
Disc. AE: Cystitis, Macular edema...
Dose limiting toxicities:
Anorexia (grade 3, 33.3%)
AEs leading to
discontinuation/dose reduction:
Cystitis (grade 2, 33.3%)
Macular edema (grade 2, 33.3%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
210.7 mg/m2 1 times / 2 days multiple, oral
MTD
Dose: 210.7 mg/m2, 1 times / 2 days
Route: oral
Route: multiple
Dose: 210.7 mg/m2, 1 times / 2 days
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
150.5 mg/m2 1 times / day multiple, oral
Studied dose
Dose: 150.5 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 150.5 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
DLT: AST increased, ALT increased...
Dose limiting toxicities:
AST increased (grade 3, 33.3%)
ALT increased (grade 3, 33.3%)
Gamma-glutamyltransferase increased (grade 3, 33.3%)
Night blindness (grade 3, 33.3%)
Visual impairment (grade 3, 33.3%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
AEs

AEs

AESignificanceDosePopulation
Febrile neutropenia grade 3, 20%
DLT
295 mg/m2 1 times / 2 days multiple, oral
Highest studied dose
Dose: 295 mg/m2, 1 times / 2 days
Route: oral
Route: multiple
Dose: 295 mg/m2, 1 times / 2 days
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
Platelet count decreased grade 3, 20%
DLT
295 mg/m2 1 times / 2 days multiple, oral
Highest studied dose
Dose: 295 mg/m2, 1 times / 2 days
Route: oral
Route: multiple
Dose: 295 mg/m2, 1 times / 2 days
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
Anemia grade 3, 20%
Disc. AE
295 mg/m2 1 times / 2 days multiple, oral
Highest studied dose
Dose: 295 mg/m2, 1 times / 2 days
Route: oral
Route: multiple
Dose: 295 mg/m2, 1 times / 2 days
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
Pneumonia grade 4, 20%
DLT, Disc. AE
295 mg/m2 1 times / 2 days multiple, oral
Highest studied dose
Dose: 295 mg/m2, 1 times / 2 days
Route: oral
Route: multiple
Dose: 295 mg/m2, 1 times / 2 days
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
Respiratory failure grade 4, 20%
DLT, Disc. AE
295 mg/m2 1 times / 2 days multiple, oral
Highest studied dose
Dose: 295 mg/m2, 1 times / 2 days
Route: oral
Route: multiple
Dose: 295 mg/m2, 1 times / 2 days
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
Septic shock grade 4, 20%
DLT, Disc. AE
295 mg/m2 1 times / 2 days multiple, oral
Highest studied dose
Dose: 295 mg/m2, 1 times / 2 days
Route: oral
Route: multiple
Dose: 295 mg/m2, 1 times / 2 days
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
Cystitis grade 2, 33.3%
Disc. AE
107.5 mg/m2 1 times / day multiple, oral
MTD
Dose: 107.5 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 107.5 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
Macular edema grade 2, 33.3%
Disc. AE
107.5 mg/m2 1 times / day multiple, oral
MTD
Dose: 107.5 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 107.5 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
Anorexia grade 3, 33.3%
DLT, Disc. AE
107.5 mg/m2 1 times / day multiple, oral
MTD
Dose: 107.5 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 107.5 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
ALT increased grade 3, 33.3%
DLT
150.5 mg/m2 1 times / day multiple, oral
Studied dose
Dose: 150.5 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 150.5 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
AST increased grade 3, 33.3%
DLT
150.5 mg/m2 1 times / day multiple, oral
Studied dose
Dose: 150.5 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 150.5 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
Gamma-glutamyltransferase increased grade 3, 33.3%
DLT
150.5 mg/m2 1 times / day multiple, oral
Studied dose
Dose: 150.5 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 150.5 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
Visual impairment grade 3, 33.3%
DLT
150.5 mg/m2 1 times / day multiple, oral
Studied dose
Dose: 150.5 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 150.5 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
Night blindness grade 3, 33.3%
DLT, Disc. AE
150.5 mg/m2 1 times / day multiple, oral
Studied dose
Dose: 150.5 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 150.5 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/30679388
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P000RAI
https://www.1pchem.com/search?query=1P000RAI
Chem Scene
CS-0009135
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0009135
ChemShuttle
140561
https://www.chemshuttle.com/catalogsearch/result/?q=140561
eMolecules
89940825
https://orderbb.emolecules.com/search/#?query=89940825
Excenen
EX-A2703
http://www.excenen.com/searchresultlist.php?id=EX-A2703
MedChem Express
HY-15785
https://www.medchemexpress.com/search.html?q=HY-15785&ft=&fa=&fp=
MolPort
MolPort-046-836-707
https://www.molport.com/shop/molecule-link/MolPort-046-836-707
MuseChem
I009711
https://www.musechem.com/product/I009711.html
Selleck Chemicals
S7716
http://www.selleckchem.com/search.html?searchDTO.searchParam=S7716
ShangHai Biochempartner
BCP25132
http://www.biochempartner.com/search_BCP25132
PubMed

PubMed

TitleDatePubMed
TAS-116, a Novel Hsp90 Inhibitor, Selectively Enhances Radiosensitivity of Human Cancer Cells to X-rays and Carbon Ion Radiation.
2017-01
TAS-116, a highly selective inhibitor of heat shock protein 90α and β, demonstrates potent antitumor activity and minimal ocular toxicity in preclinical models.
2015-01
Patents

Patents

20120108589
1
20140303162
1
8779142
1
WO2015050235A1
1

Sample Use Guides

In Vivo Use Guide
TAS-116 at 14.0 mg/kg/day was orally administered five times a week for four weeks
Route of Administration: Oral
In Vitro Use Guide
3 umol/L of TAS-116 does not inhibit GRP94, whereas 0.3 umol/L of TAS-116 inhibits HSP90a and b in HCT116 cells.
Substance Class Chemical
Created
by admin
on Tue Apr 01 18:17:51 GMT 2025
Edited
by admin
on Tue Apr 01 18:17:51 GMT 2025
Record UNII
PLO044MUDZ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TAS-116
Preferred Name English
PIMITESPIB
INN  
Official Name English
pimitespib [INN]
Common Name English
BENZAMIDE, 3-ETHYL-4-(3-(1-METHYLETHYL)-4-(4-(1-METHYL-1H-PYRAZOL-4-YL)-1H-IMIDAZOL-1-YL)-1H-PYRAZOLO(3,4-B)PYRIDIN-1-YL)-
Systematic Name English
PIMITESPIB [JAN]
Common Name English
Pimitespib [WHO-DD]
Common Name English
3-ETHYL-4-(3-(1-METHYLETHYL)-4-(4-(1-METHYL-1H-PYRAZOL-4-YL)-1H-IMIDAZOL-1-YL)-1H-PYRAZOLO(3,4-B)PYRIDIN-1-YL)BENZAMIDE
Systematic Name English
Code System Code Type Description
NCI_THESAURUS
C134448
Created by admin on Tue Apr 01 18:17:51 GMT 2025 , Edited by admin on Tue Apr 01 18:17:51 GMT 2025
PRIMARY
DRUG BANK
DB14876
Created by admin on Tue Apr 01 18:17:51 GMT 2025 , Edited by admin on Tue Apr 01 18:17:51 GMT 2025
PRIMARY
MANUFACTURER PRODUCT INFORMATION
TAS-116
Created by admin on Tue Apr 01 18:17:51 GMT 2025 , Edited by admin on Tue Apr 01 18:17:51 GMT 2025
PRIMARY Description: TAS-116 showed activity against orthotopically transplanted NCI-H1975 lung tumors. Together, these data suggest that TAS-116 has a potential to maximize antitumor activity while minimizing adverse effects such as visual disturbances that are observed with other compounds of this class. For the detailed information of TAS-116, the solubility of TAS-116 in water, the solubility of TAS-116 in DMSO, the solubility of TAS-116 in PBS buffer, the animal experiment (test) of TAS-116, the cell expriment (test) of TAS-116, the in vivo, in vitro and clinical trial test of TAS-116, the EC50, IC50, and affinity, of TAS-116, For the detailed information of TAS-116, the solubility of TAS-116 in water, the solubility of TAS-116 in DMSO, the solubility of TAS-116 in PBS buffer, the animal experiment (test) of TAS-116, the cell expriment (test) of TAS-116, the in vivo, in vitro and clinical trial test of TAS-116, the EC50, IC50, and affinity, of TAS-116, Please contact DC Chemicals.
PUBCHEM
67501411
Created by admin on Tue Apr 01 18:17:51 GMT 2025 , Edited by admin on Tue Apr 01 18:17:51 GMT 2025
PRIMARY
SMS_ID
300000038118
Created by admin on Tue Apr 01 18:17:51 GMT 2025 , Edited by admin on Tue Apr 01 18:17:51 GMT 2025
PRIMARY
FDA UNII
PLO044MUDZ
Created by admin on Tue Apr 01 18:17:51 GMT 2025 , Edited by admin on Tue Apr 01 18:17:51 GMT 2025
PRIMARY
CAS
1260533-36-5
Created by admin on Tue Apr 01 18:17:51 GMT 2025 , Edited by admin on Tue Apr 01 18:17:51 GMT 2025
PRIMARY
INN
11079
Created by admin on Tue Apr 01 18:17:51 GMT 2025 , Edited by admin on Tue Apr 01 18:17:51 GMT 2025
PRIMARY
Related Record Type Details
HEAT SHOCK PROTEIN 90KD ALPHA
TARGET -> INHIBITOR
Related Record Type Details
Structure of PIMITESPIB
ACTIVE MOIETY
Oral administration of TAS-116 led to tumor shrinkage in human tumor xenograft mouse models accompanied by depletion of multiple HSP90 clients, demonstrating that the inhibition of HSP90.ALPHA. and .BETA. alone was sufficient to exert antitumor activity in certain tumor models. One of the most notable HSP90-related adverse events universally observed to differing degrees in the clinical setting is visual disturbance. A two-week administration of the isoxazole resorcinol NVP-AUY922, an HSP90 inhibitor, caused marked degeneration and disarrangement of the outer nuclear layer of the retina and induced photoreceptor cell death in rats. In contrast, TAS-116 did not produce detectable photoreceptor injury in rats, probably due to its lower distribution in retinal tissue. Importantly, in a rat model, the antitumor activity of TAS-116 was accompanied by a higher distribution of the compound in subcutaneously xenografted NCI-H1975 non-small cell lung carcinoma tumors than in retina. Moreover, TAS-116 showed activity against orthotopically transplanted NCI-H1975 lung tumors.
NIH
NCATS
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