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Details

Stereochemistry ACHIRAL
Molecular Formula C22H27N5O4
Molecular Weight 425.4809
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PF-04691502

SMILES

COC1=CC=C(C=N1)C2=CC3=C(C)N=C(N)N=C3N([C@H]4CC[C@@H](CC4)OCCO)C2=O

InChI

InChIKey=XDLYKKIQACFMJG-WKILWMFISA-N
InChI=1S/C22H27N5O4/c1-13-17-11-18(14-3-8-19(30-2)24-12-14)21(29)27(20(17)26-22(23)25-13)15-4-6-16(7-5-15)31-10-9-28/h3,8,11-12,15-16,28H,4-7,9-10H2,1-2H3,(H2,23,25,26)/t15-,16-

HIDE SMILES / InChI

Molecular Formula C22H27N5O4
Molecular Weight 425.4809
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

PF-04691502 is a PI3K/mTOR dual inhibitor. It was tested in phase 2 clinical trials against endometrial cancer and breast cancer, but its development was discontinued due to unacceptable toxicity.

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Highly Selective and Potent Thiophenes as PI3K Inhibitors with Oral Antitumor Activity.
2011 Nov 10
PF-04691502 triggers cell cycle arrest, apoptosis and inhibits the angiogenesis in hepatocellular carcinoma cells.
2013 Jul 4
Patents

Sample Use Guides

In Vivo Use Guide
In clinical trials against endometrium cancer PF-04691502 was administred orally once daily (QD) at doses 6-8 mg
Route of Administration: Oral
In Vitro Use Guide
BT20, U87MG, and SKOV3 cells were plated at 3,000 cell/well in 96-well culture plates in growth medium with 10% FBS. Cells were incubated overnight and treated with DMSO (0.1% final) or serial diluted compound for 3 days. Resazurin (Sigma-Aldrich) was added to 0.1 mg/mL. Plates were incubated at 37°C in 5% CO2 for 3 hours. Fluorescence signals were read as emission at 590 nm after excitation at 530 nm. IC50 values were calculated by plotting fluorescence intensity to drug concentration in nonlinear curves. PF-04691502 inhibited cell proliferation of BT20, SKOV3, and U87MG with IC50 values of 313, 188, and 179 nmol/L
Substance Class Chemical
Created
by admin
on Tue Oct 22 15:34:35 UTC 2019
Edited
by admin
on Tue Oct 22 15:34:35 UTC 2019
Record UNII
4W39NS61KI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PF-04691502
Common Name English
PF-4691502
Code English
PYRIDO(2,3-D)PYRIMIDIN-7(8H)-ONE, 2-AMINO-8-(TRANS-4-(2-HYDROXYETHOXY)CYCLOHEXYL)-6-(6-METHOXY-3-PYRIDINYL)-4-METHYL-
Systematic Name English
Code System Code Type Description
PUBCHEM
25033539
Created by admin on Tue Oct 22 15:34:35 UTC 2019 , Edited by admin on Tue Oct 22 15:34:35 UTC 2019
PRIMARY
ChEMBL
CHEMBL1234354
Created by admin on Tue Oct 22 15:34:35 UTC 2019 , Edited by admin on Tue Oct 22 15:34:35 UTC 2019
PRIMARY
CAS
1013101-36-4
Created by admin on Tue Oct 22 15:34:35 UTC 2019 , Edited by admin on Tue Oct 22 15:34:35 UTC 2019
PRIMARY
Related Record Type Details
ACTIVE MOIETY