1001264-89-6

Basic information

• Product Name: GDC-0068
• Synonyms: GDC-0068;GDC-0068(RG7440);RG7440;(2S)-2-(4-Chlorophenyl)-1-[4-[(5R,7R)-6,7-dihydro-7-hydroxy-5-methyl-5H-cyclopentapyrimidin-4-yl]-1-piperazinyl]-3-[(1-methylethyl)amino]-1-propanone;Ipatasertib (GDC-0068);Ipatasertib;(S)-2-(4-chlorophenyl)-1-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-3-(isopropylamino)propan-1-one;(2S)-2-(4-Chlorophenyl)-1-[4-[(5R,7R)-6,7-dihydro-7-hydroxy-5-methyl-5H-cyclopentapyrimidin-4-yl]-1-piperazinyl]-3-[(1-methylethyl)amino]-1-propanone Ipatasertib (GDC-0068)
• CAS NO: 1001264-89-6
• Molecular Formula: C24H32ClN5O2
• Molecular Weight: 457.99618
• Product Categories: Inhibitor;PI3K/Akt/mTOR;Inhibitors;Akt;mTOR;PI3K
• Mol File: 1001264-89-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 669.4±55.0 °C(Predicted)
• Appearance: Peach Solid
• Density: 1.254
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: Soluble in DMSO.
• PKA: 13.11±0.40(Predicted)
• CAS DataBase Reference: GDC-0068(CAS DataBase Reference)
• NIST Chemistry Reference: GDC-0068(1001264-89-6)
• EPA Substance Registry System: GDC-0068(1001264-89-6)

Safety Data

• Hazardous Substances Data: 1001264-89-6(Hazardous Substances Data)

Usage

Description

GDC-0068, also known as (2S)-2-(4-Chlorophenyl)-1-[4-[(5R,7R)-6,7-dihydro-7-hydroxy-5-methyl-5H-cyclopentapyrimidin-4-yl]-1-piperazinyl]-3-[(1-methylethyl)amino]-1-propanone, is a highly selective pan-Akt inhibitor that targets Akt1, Akt2, and Akt3 with IC50 values of 5 nM, 18 nM, and 8 nM, respectively. It is a promising pharmaceutical candidate for various applications, particularly in the treatment of hyperproliferative disorders such as cancer.

Uses

Used in Anticancer Applications:
GDC-0068 is used as a highly selective AKT inhibitor for the treatment of hyperproliferative disorders such as cancer. It targets Akt1, Akt2, and Akt3, which play a crucial role in cell proliferation and survival. Studies have shown that GDC-0068, in combination with vemurafenib (V118500), demonstrates therapeutic value in treating cancer by inhibiting the Akt signaling pathway, which is often dysregulated in various types of cancer.
Used in Drug Combination Therapy:
In the Pharmaceutical Industry, GDC-0068 is used as a component in drug combination therapy for enhancing the efficacy of cancer treatment. When combined with vemurafenib (V118500), it has shown to have a synergistic effect, improving the chemo-sensitivity and therapeutic outcomes in the treatment of hyperproliferative disorders such as cancer. This combination therapy approach aims to overcome drug resistance and improve patient outcomes by targeting multiple signaling pathways involved in cancer progression.

Biological Activity

gdc-0068 (rg7440) is a highly selective small molecule inhibitor of akt with ic50s of 5, 18 and 8 nm for akt1, akt2 and akt3. the pi3k-akt pathway regulates cell growth, survival and tumorigenesis. gdc-0068 binds to and blocks the activation of akt, which result in cell cycle arrest, inhibition of tumor cell proliferation and induction of tumor cell death. pi3k-akt is pathway frequently activated in tumors, thus tumors with pten or pi3k mutations, which lead to activation of akt are with high sensitivity to gdc-0068. gdc-0068 is now used for the treatment of human cancers.1. discovery and preclinical pharmacology of a selective atp-competitive akt inhibitor (gdc-0068) for the treatment of human tumors. jf blake, r xu, jr bencsik, d xiao… - journal of medicinal 20122. lin j, sampath d, nannini ma, et al: targeting activated akt with gdc-0068, a novel selective akt inhibitor that is efficacious in multiple tumor models. clin canc res 2013, 19:1760–1772.

Upstream product

• 65844-74-8 2-methylpropan-1,1,3-tricarboxylic acid trimethyl ester 
• 1001179-33-4 (S)-3-((tert-butoxycarbonyl)(isopropyl)amino)-2-(4-chlorophenyl)propionic acid 
• 1396256-89-5 tert-butyl (S)-(3-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2-(4-chlorophenyl)-3-oxopropyl)isopropylcarbamate 
• 220041-96-3 (R)-4-benzyl-3-(2-(4-chlorophenyl)acetyl)oxazolidin-2-one 
• 1878-66-6 4-chlorophenylacetic Acid 
• 1001180-45-5 tert-butyl 4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]-pyrimidin-4-yl)piperazine-1-carboxylate 
• 63473-60-9 (R)-3-methylpentanedioic acid monomethyl ester 
• 1001270-64-9 tert-butyl ((S)-2-(4-chlorophenyl)-3-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-3-oxopropyl)(isopropyl)carbamate 
• 1001269-75-5 (R)-1-oxo-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine 
• 1001179-27-6 potassium 3-(tert-butoxycarbonyl(isopropyl)amino)-2-(4-chlorophenyl)propanoate 
• 1001180-47-7 tert-butyl 4-((5R,7R)-5-methyl-7-((4-nitrobenzoyl)oxy)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-piperazine-1-carboxylate 
• 1001179-31-2 tert-butyl (S)-3-((S)-4-benzyl-2-oxooxazolidin-3-yl)-2-(4-chlorophenyl)-3-oxopropyl(isopropyl)carbamate 

Relevant articles and documents

Synthesis of Akt inhibitor ipatasertib. part 2. Total synthesis and first kilogram scale-up

Herein, the first-generation process to manufacture Akt inhibitor Ipatasertib through a late-stage convergent coupling of two challenging chiral components on multikilogram scale is described. The first of the two key components is a trans-substituted cyc

HYDROXYLATED AND METHOXYLATED CYCLOPENTA [D] PYRIMIDINES AS AKT PROTEIN KINASE INHIBITORS

The present invention provides compounds, including resolved enantiomers, resolved diastereomers, solvates and pharmaceutically acceptable salts thereof, comprising the Formula (I). Also provided are methods of using the compounds of this invention as AKT protein kinase inhibitors and for the treatment of hyperproliferative diseases such as cancer.