GSK-690693

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H27N7O3
Molecular Weight	425.4842
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN1C(=NC2=C1C(OC[C@H]3CCCNC3)=CN=C2C#CC(C)(C)O)C4=NON=C4N

InChI

InChIKey=KGPGFQWBCSZGEL-ZDUSSCGKSA-N

InChI=1S/C21H27N7O3/c1-4-28-18-15(30-12-13-6-5-9-23-10-13)11-24-14(7-8-21(2,3)29)16(18)25-20(28)17-19(22)27-31-26-17/h11,13,23,29H,4-6,9-10,12H2,1-3H3,(H2,22,27)/t13-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C21H27N7O3
Molecular Weight	425.4842
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://adisinsight.springer.com/drugs/800026285
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26698230 | https://www.ncbi.nlm.nih.gov/pubmed/18800763 | https://www.ncbi.nlm.nih.gov/pubmed/18381444

GSK690693 is an aminofurazan derivative, a novel ATP-competitive, low-nanomolar pan-Akt kinase inhibitor. It is selective for the Akt isoforms versus the majority of kinases in other families; however, it does inhibit additional members of the AGC kinase family. GlaxoSmithKline was developing this compound for the treatment of lymphoma solid tumours but the clinical development of this compound was terminated due to the associated side-effect of transient hyperglycemia.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Serine/threonine-protein kinase AKT 31 Target ID: CHEMBL4282 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18800763	Inhibitor 8504	2.0 nM [IC50]
Serine/threonine-protein kinase AKT2 17 Target ID: CHEMBL2431 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18800763	Inhibitor 8504	13.0 nM [IC50]
Serine/threonine-protein kinase AKT3 17 Target ID: CHEMBL4816 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18800763	Inhibitor 8504	9.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 609 Sources: http://adisinsight.springer.com/drugs/800026285	Primary		Phase I 438	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Modulation of Akt/mTOR signaling overcomes sunitinib resistance in renal and prostate cancer cells.	2012-07	22532600
Comprehensive analysis of kinase inhibitor selectivity.	2011-10-30	22037378
Activation state-dependent binding of small molecule kinase inhibitors: structural insights from biochemistry.	2010-11-24	21095574
Personalized therapies in the cancer "omics" era.	2010-07-29	20670437
Identification of 4-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1-ethyl-7-{[(3S)-3-piperidinylmethyl]oxy}-1H-imidazo[4,5-c]pyridin-4-yl)-2-methyl-3-butyn-2-ol (GSK690693), a novel inhibitor of AKT kinase.	2008-09-25	18800763
Characterization of an Akt kinase inhibitor with potent pharmacodynamic and antitumor activity.	2008-04-01	18381444

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Intravenous

In Vitro Use Guide

GSK690693 effect on the proliferation was tested in 112 cell lines representing different hematologic neoplasia. Fifty-five percent of all cell lines tested were sensitive to AKT inhibitor (EC(50)<1 microM), with acute lymphoblastic leukemia (ALL), non-Hodgkin lymphoma, and Burkitt lymphoma showing 89%, 73%, and 67% sensitivity to GSK690693, respectively.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:27:49 GMT 2025` Edited by `admin` on `Mon Mar 31 21:27:49 GMT 2025`
Record UNII	GWH480321B
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GSK 690693

Preferred Name

English

GSK-690693

Common Name

English

(-)-4-(2-(4-AMINO-1,2,5-OXADIAZOL-3-YL)-1-ETHYL-7-((3S)-3-PIPERIDINYLMETHOXY)-1H-IMIDAZO(4,5-C)PYRIDIN-4-YL)-2-METHYL-3-BUTYN-2-OL

Systematic Name

English

3-BUTYN-2-OL, 4-(2-(4-AMINO-1,2,5-OXADIAZOL-3-YL)-1-ETHYL-7-((3S)-3-PIPERIDINYLMETHOXY)-1H-IMIDAZO(4,5-C)PYRIDIN-4-YL)-2-METHYL-

Systematic Name

English

4-(2-(4-AMINO-1,2,5-OXADIAZOL-3-YL)-1-ETHYL-7-((3S)-3-PIPERIDINYLMETHOXY)-1H-IMIDAZO(4,5-C)PYRIDIN-4-YL)-2-METHYL-3-BUTYN-2-OL, (-)-

Systematic Name

English

GSK690693

Code

English

Code System Code Type Description

CAS

937174-76-0