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

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.
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
ACTIVE MOIETY
Structure of PIMITESPIB
NIH
NCATS
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