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Details

Stereochemistry ACHIRAL
Molecular Formula C20H22F3N5O
Molecular Weight 405.4168
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SGI-1776

SMILES

CN1CCC(CNC2=NN3C(C=C2)=NC=C3C4=CC=CC(OC(F)(F)F)=C4)CC1

InChI

InChIKey=MHXGEROHKGDZGO-UHFFFAOYSA-N
InChI=1S/C20H22F3N5O/c1-27-9-7-14(8-10-27)12-24-18-5-6-19-25-13-17(28(19)26-18)15-3-2-4-16(11-15)29-20(21,22)23/h2-6,11,13-14H,7-10,12H2,1H3,(H,24,26)

HIDE SMILES / InChI

Molecular Formula C20H22F3N5O
Molecular Weight 405.4168
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 http://astx.com/wp-content/uploads/2016/11/SUPG_News_2010_11_10_General_Releases.pdf

SGI-1776 is a PIM-kinase inhibitor, developed by SuperGen Inc. SGI-1176 was tested in clinical trials against relapsed/refractory leukemias, prostate cancer and Non Hodgkin's Lymphoma, but the dose limiting toxicity of cardiac QTc prolongation was identified and clinical development of SGI-1776 was terminated.

Originator

Curator's Comment: SuperGen Inc. was merged with Astex in 2011 http://www.fiercebiotech.com/biotech/supergen-and-astex-therapeutics-enter-definitive-merger-agreement-creating-a-financially

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
7.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
5%
SGI-1776 plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
PubMed

PubMed

TitleDatePubMed
Pim kinase inhibitor, SGI-1776, induces apoptosis in chronic lymphocytic leukemia cells.
2009 Nov 5
Patents

Sample Use Guides

In clinical trial SGI-1776 was administered orally at escalating dose levels ranging from 350 to 1600 mg/day. Clinical trial was prematurely terminated due to unacceptable toxicity of SGI-1776.
Route of Administration: Oral
CLL cells were treated with DMSO alone or with 0.3, 1, 3, or 10 μmol/L SGI-1776 for 24 hours. Cells (10^6) were washed, resuspended in 100 μL of annexin binding buffer, and mixed with 5 μL of annexin–fluorescein isothiocyanate (FITC) solution and 5 μL of propidium iodide solution with 2.5 μg/mL DNase-free RNase A (Roche). At least 10 000 cells were measured per sample by the use of a Becton Dickinson FACSCalibur flow cytometer. Caspase inhibitor N-benzyloxycarbonyl-valyl-alanyl-aspartyl-fluoromethylketone (ZVAD) was obtained from Alexis Biochemicals, and cells were treated with DMSO alone or 25 μmol/L ZVAD with or without 10 μmol/L SGI-1776 treatment for 24, 48, and 72 hours and then analyzed by flow cytometry. In vitro incubation of primary CLL cells (n = 7), with 1, 3, and 10 μmol/L SGI-1776 for 24 hours resulted in an average increase in apoptosis of 10%, 22%, and 38%, respectively, compared with untreated cells.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:43:25 GMT 2025
Edited
by admin
on Mon Mar 31 18:43:25 GMT 2025
Record UNII
72AUA0603W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
IMIDAZO(1,2-B)PYRIDAZIN-6-AMINE, N-((1-METHYL-4-PIPERIDINYL)METHYL)-3-(3-(TRIFLUOROMETHOXY)PHENYL)-
Preferred Name English
SGI-1776
Common Name English
N-((1-METHYLPIPERIDIN-4-YL)METHYL)-3-(3-(TRIFLUOROMETHOXY)PHENYL)IMIDAZO(1,2-B)PYRIDAZIN-6-AMINE
Systematic Name English
Code System Code Type Description
NCI_THESAURUS
C82404
Created by admin on Mon Mar 31 18:43:25 GMT 2025 , Edited by admin on Mon Mar 31 18:43:25 GMT 2025
PRIMARY
SMS_ID
300000052523
Created by admin on Mon Mar 31 18:43:25 GMT 2025 , Edited by admin on Mon Mar 31 18:43:25 GMT 2025
PRIMARY
CAS
1025065-69-3
Created by admin on Mon Mar 31 18:43:25 GMT 2025 , Edited by admin on Mon Mar 31 18:43:25 GMT 2025
PRIMARY
EPA CompTox
DTXSID10647329
Created by admin on Mon Mar 31 18:43:25 GMT 2025 , Edited by admin on Mon Mar 31 18:43:25 GMT 2025
PRIMARY
DRUG BANK
DB12494
Created by admin on Mon Mar 31 18:43:25 GMT 2025 , Edited by admin on Mon Mar 31 18:43:25 GMT 2025
PRIMARY
PUBCHEM
24795070
Created by admin on Mon Mar 31 18:43:25 GMT 2025 , Edited by admin on Mon Mar 31 18:43:25 GMT 2025
PRIMARY
ChEMBL
CHEMBL1952329
Created by admin on Mon Mar 31 18:43:25 GMT 2025 , Edited by admin on Mon Mar 31 18:43:25 GMT 2025
PRIMARY
FDA UNII
72AUA0603W
Created by admin on Mon Mar 31 18:43:25 GMT 2025 , Edited by admin on Mon Mar 31 18:43:25 GMT 2025
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
COMPETITIVE INHIBITOR
IC50
TARGET -> INHIBITOR
COMPETITIVE INHIBITOR
IC50
TARGET->WEAK INHIBITOR
IC50
Related Record Type Details
ACTIVE MOIETY