ChemicalBook > CAS DataBase List > GSK2110183B

GSK2110183B

Product Name: GSK2110183B
CAS No.: 1047645-82-8
Chemical Name: GSK2110183B
Synonyms: GSK2110183B;GSK 2110183B;GSK-2110183B;Afuresertib HCl;GSK2110183 hydrochloride;GSK-2110183 hydrochloride;GSK 2110183 hydrochloride;Afuresertib (hydrochloride);Afuresertib HCl (GSK2110183);Afuresertib hydrochloride GSK2110183
CBNumber: CB02667591
Molecular Formula: C18H18Cl3FN4OS
Formula Weight: 463.78
MOL File: 1047645-82-8.mol

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GSK2110183B Property

storage temp.: Store at -20°C, protect from light, stored under nitrogen
solubility: DMSO:65.0(Max Conc. mg/mL);140.15(Max Conc. mM)
DMF:50.0(Max Conc. mg/mL);107.81(Max Conc. mM)
Ethanol:50.0(Max Conc. mg/mL);107.81(Max Conc. mM)
Ethanol:PBS (pH 7.2) (1:1):0.5(Max Conc. mg/mL);1.08(Max Conc. mM)
form: A crystalline solid
color: Yellow to brown

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 17988
Product name: Afuresertib (hydrochloride)
Purity: ≥98%
Packaging: 1mg
Price: $40
Updated: 2024/03/01

Cayman Chemical

Product number: 17988
Product name: Afuresertib (hydrochloride)
Purity: ≥98%
Packaging: 5mg
Price: $138
Updated: 2024/03/01

Cayman Chemical

Product number: 17988
Product name: Afuresertib (hydrochloride)
Purity: ≥98%
Packaging: 10mg
Price: $254
Updated: 2024/03/01

Cayman Chemical

Product number: 17988
Product name: Afuresertib (hydrochloride)
Packaging: 25mg
Price: $583
Updated: 2024/03/01

ChemScene

Product number: CS-3385
Product name: Afuresertib(hydrochloride)
Purity: 98.02%
Packaging: 100mg
Price: $564
Updated: 2021/12/16

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GSK2110183B Chemical Properties,Usage,Production

Uses

Afuresertib is a selective, orally bioavailable inhibitor of Akt1, 2, and 3 with Ki values of 0.08, 2, and 2.6 nM, respectively. It preferentially inhibits the proliferation of human cancer cell lines with Akt pathway activation and various cell lines derived from hematologic malignancies with minimal effect on glucose homeostasis. Afuresertib demonstrates activity against multiple myeloma in both preclinical and clinical models.[Cayman Chemical]

Synthesis

1047644-62-1

1047645-82-8

The general procedure for the synthesis of N-((S)-1-amino-3-(3-fluorophenyl)propan-2-yl)-5-chloro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)thiophene-2-carboxamide as a hydrochloride salt was as follows: 5 mL of methyl tert-butyl ether (MTBE) was added to 213.9 mg (0.500 mmol) of the amorphous free base and the mixture was heated under magnetic The mixture was heated to 40 °C under magnetic stirring and maintained for 1 hour. Subsequently, a 1,4-dioxane solution of 4 M HCl was added in four additions (totaling 1 equiv, 125.1 μL). After the first addition of 0.25 equivalents of HCl solution, the mixture was heated to 42 °C and 1 mL of acetonitrile was added to completely dissolve the solid. After the remaining HCl solution was added, solid precipitation was observed. The slurry was stirred at 42°C for 4 hours, then held sequentially at 35°C, 30°C, and 25°C for 90 minutes each at a rate of 5°C per hour, and finally cooled slowly to 22°C overnight. The white solid was collected by filtration and dried under vacuum at 50 °C while slowly purged by passing nitrogen overnight. The yield of the resulting hydrochloride was 73.6% (0.3685 mmol, 170.90 mg). The product was confirmed to be HCl salt with stoichiometric ratio of 1:1 by ion chromatography analysis, and the powder X-ray diffraction (PXRD) pattern (Figure 1) showed it to be in the crystalline state, with the following characteristic diffraction peaks, and a melting point of 211 °C. The characteristic PXRD peaks (2θ values, with d-spacing in parentheses): 7.2° (12.20 ?) , 14.4° (6.16 ?) , 17.9° (4.94 ?) , 18.5° (4.79 ?) , 20.8° (4.26 ?) , 21.5° (4.12 ?) , 22.4° (3.96 ?) , 22.9° (3.88 ?) , 23.7° (3.75 ?) , 24.5° (3.63 ?) , 24.7° (3.61 ?) , 25.1° (4.12 ?) , 25.7° (3.46 ?) , 27.3° (3.26 ?) , 28.2° (3.16 ?) , 28.8° (3.10 ?) , 30.4° (2.94 ?) , 32.4° (2.76 ?) , 32.7° (2.73 ?) , 35.2° (2.55 ?) , 36.1° (2.48 ?) , 40.0° (2.25 ?) , 41.3° (2.18 ?) , 41.7° (2.16 ?) The Measuring instrument: Panaco X'Pert-Pro MPD diffractometer with Johansson monochromator (Cu Kα1 radiation, wavelength 1.540598 ?) and X'Celerator detector. Key test parameters: voltage 45 kV, current 40 mA, start angle 2.0° 2θ, end angle 52.0° 2θ, step size 0.02°, counting time per step 40.0 s, scanning speed 0.05°/sec. Incident beam configuration: 2° fixed anti-scattering slit, programmable divergence slit; diffraction beam configuration: 0.02 rad Soller slit, programmable anti-scattering slit. Samples were prepared on a silicon zero background sample holder.

in vivo

Mice bearing BT474 breast tumor xenografts are dosed orally with either vehicle or GSK2110183 at 10, 30 or 100 mg/kg daily for 21 days which result in 8, 37 and 61% TGI, respectively. Mice tolerated GSK2110183 well, with 1-3% body weight loss reported after 5 days of dosing which recover over the course of the study. Other tumor xenograft models which possess an activation of the Akt pathway are explored to further demonstrate compound efficacy. Mice treated with GSK2110183 at 10, 30 and 100 mg/kg result in 23, 37 and 97% TGI, respectively, of SKOV3 xenografts^[2].

IC 50

Akt1: 0.08 nM (Ki); Akt2: 2 nM (Ki); Akt3: 2.6 nM (Ki); Akt1 E17K mutant: 0.2 nM (IC₅₀); PKCη: 210 nM (IC₅₀); PKC-βI: 430 nM (IC₅₀); ROCK: 100 nM (IC₅₀); PKCθ: 510 nM (IC₅₀)

References

[1] Patent: US2010/197754, 2010, A1. Location in patent: Page/Page column 8-9
[2] Patent: WO2008/98104, 2008, A1. Location in patent: Page/Page column 191-192

GSK2110183B Preparation Products And Raw materials

Raw materials

Preparation Products

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1047645-82-8, GSK2110183BRelated Search:

Afuresertib (hydrochloride)

GSK 2110183B

GSK2110183B

GSK-2110183B

GSK 2110183 hydrochloride

GSK2110183 hydrochloride

GSK-2110183 hydrochloride

N-((S)-1-Amino-3-(3-fluorophenyl)propan-2-yl)-5-chloro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)thiophene-2-carboxamide hydrochloride

Afuresertib HCl

Afuresertib HCl (GSK2110183)

Afuresertib HCl salt, GSK-2110183 HCl salt, GSK-2110183B HCl salt

N-{(1S)-2-amino-1-[(3-fluorophenyl)methyl]ethyl}-5-chloro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxamide hydrochloride

2-Thiophenecarboxamide, n-[(1s)-2-amino-1-[(3-fluorophenyl)methyl]ethyl]-5-chloro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)-, hydrochloride (1:1)

AFURESERTIB;GSK 2110183;GSK2110183;GSK 2110183 HYDROCHLORIDE; GSK2110183 HYDROCHLORIDE; GSK-2110183 HYDROCHLORIDE

GSK 2110183 hydrochloride - Afuresertib hydrochloride

(S)-N-(1-amino-3-(3-fluorophenyl)propan-2-yl)-5-chloro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)thiophene-2-carboxamide hydrochloride

Afuresertib hydrochloride GSK2110183

Afuresertib,PKC,Protein kinase C,Akt,PKB,Rho-kinase,GSK2110183,ROK,Rho-associated protein kinase,Inhibitor,GSK-2110183,inhibit,Protein kinase B,Afuresertib hydrochloride,Rho-associated kinase,GSK 2110183,ROCK

(S)-N-(1-amino-3- (3-fluorophenyl) propan-2-yl)-5-chloro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl) thiophene-2-formamide, hydrochloride

Afuresertib hydrochloride, 10 mM in DMSO

N-[(2S)-1-amino-3-(3-fluorophenyl)propan-2-yl]-5-chloro-4-(4-chloro-2-methylpyrazol-3-yl)thiophene-2-carboxamide

1047645-82-8

C18H17Cl2FN4OSClH