Sotorasib
- Product Name
- Sotorasib
- CAS No.
- 2296729-00-3
- Chemical Name
- Sotorasib
- Synonyms
- Sotorasib;AMG-510(Sotorasib);Storasib;Sotoracib;Sotolacib;rac AMG-510;CID 137278711;Sotolabu (AMG-510);Sotorasib AMG510 AMG-510;Sotorasib, 10 mM in DMSO
- CBNumber
- CB65475731
- Molecular Formula
- C30H30F2N6O3
- Formula Weight
- 560.61
- MOL File
- 2296729-00-3.mol
Sotorasib Property
- Boiling point:
- 730.5±70.0 °C(Predicted)
- Density
- 1.36±0.1 g/cm3(Predicted)
- storage temp.
- Store at -20°C, stored under nitrogen
- solubility
- DMSO : 100 mg/mL (178.38 mM; Need ultrasonic)|
- pka
- 6.52±0.35(Predicted)
- form
- Solid
- color
- White to yellow
- Water Solubility
- Water : 33.33 mg/mL (59.46 mM; ultrasonic and adjust pH to 11 with NaOH)
- InChIKey
- NXQKSXLFSAEQCZ-UHFFFAOYSA-N
- SMILES
- O=C1N=C(N2CCN(C(=O)C=C)CC2C)C2=CC(F)=C(C3C(=CC=CC=3F)O)N=C2N1C1C(=CC=NC=1C(C)C)C
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- CS-0081316
- Product name
- Sotorasib
- Purity
- 99.60%
- Packaging
- 5mg
- Price
- $90
- Updated
- 2021/12/16
- Product number
- CS-0081316
- Product name
- Sotorasib
- Purity
- 99.60%
- Packaging
- 10mg
- Price
- $160
- Updated
- 2021/12/16
- Product number
- CS-0081316
- Product name
- Sotorasib
- Purity
- 99.60%
- Packaging
- 50mg
- Price
- $480
- Updated
- 2021/12/16
- Product number
- CS-0081316
- Product name
- Sotorasib
- Purity
- 99.60%
- Packaging
- 100mg
- Price
- $840
- Updated
- 2021/12/16
- Product number
- DC22298
- Product name
- AMG-510(Sotorasib)
- Purity
- >99%,chiralpurity>99%
- Packaging
- 1g
- Price
- $1800
- Updated
- 2021/12/16
Sotorasib Chemical Properties,Usage,Production
Description
Sotorasib (AMG510) is a chiral compound and a potent KRAS G12C covalent inhibitor with potential antitumor activity.
Uses
Sotorasib (AMG510) is the first KRAS (G12C) inhibitor to enter clinical development. Having shown antitumor activity in clinical trials, AMG 510 represents a potentially transformative therapy.
Definition
ChEBI:Sotorasib is a pyridopyrimidine that is pyrido[2,3-d]pyrimidin-2(1H)-one substituted by 4-methyl-2-(propan-2-yl)pyridin-3-yl, (2S)-2-methyl-4-(prop-2-enoyl)piperazin-1-yl, fluoro and 2-fluoro-6-hydroxyphenyl groups at positions 1, 4, 6 and 7, respectively. It is approved for the treatment of patients with non-small cell lung cancer having KRAS(G12C) mutations. It has a role as an antineoplastic agent. It is a member of acrylamides, a N-acylpiperazine, a pyridopyrimidine, a member of monofluorobenzenes, a member of methylpyridines, a tertiary carboxamide, a tertiary amino compound and a member of phenols.
Indications
Sotorasib is an oral small molecule drug for the treatment of non-small cell lung cancer (NSCLC) patients with Kirsten rat sarcoma virus (KRAS) G12C mutation. It is the first approved inhibitor targeting KRAS G12C mutation for the treatment of patients with locally advanced or metastatic NSCLC whose disease has progressed after standard treatment.
brand name
Lumakras
General Description
Sotorasib, also known as AMG-510, is an acrylamide derived KRAS inhibitor developed by Amgen. It is indicated in the treatment of adult patients with KRAS G12C mutant non small cell lung cancer. This mutation makes up >50% of all KRAS mutations. Mutant KRAS discovered in 1982 but was not considered a druggable target until the mid-2010s. It is the first experimental KRAS inhibitor. The drug [MRTX849] is also currently being developed and has the same target. Sotorasib was granted FDA approval on 28 May 2021.
General Description
Class: non-kinase; Treatment: KRAS(G12C) NSCLC; Other name: AMG 510; Elimination half-life: 5.5 h; Protein binding = 89%
Side effects
Sotorasib may cause breathing problems that could lead to death. Get emergency medical help if you have new or worsening fever, cough, or shortness of breath.
Common side effects may include:
nausea, diarrhea;
cough;
liver problems;
pain in your bones, joints, or muscles;
tiredness;
abnormal lab tests.
For 28 patients (22%), side effects led to a pause, a reduction, or both, in the dose of sotorasib. Nine people (7%) stopped the treatment because of side effects.
www.everydayhealth.com/drugs/sotorasib
Synthesis
The synthetic route to sotorasib consists of nine steps. The synthetic route begins with the amidation of the nicotinic acid derivative 28.1 to form nicotinamide 28.2 (Figure 7.4.2). Subsequent treatment with oxalyl chloride and addition of aminopyridine 28.3 leads to urea 28.4 via an isocyanate intermediate. Urea 28.4 is not isolated but directly undergoes a base-mediated cyclization to give pyrimidinedione 28.5. At this point, classical resolution using (+)-2,3-dibenzoyl-D-tartaric acid ((+)-DBTA) in 2-methyltetrahydrofuran (2-MeTHF) and heptane allows the isolation of the desired isomeric cocrystals 28.6 (2-MeTHF solvent) in a ratio greater than 2000:1, and the free base can be isolated by adjusting the pH using disodium monophosphate and separating from MTBE and heptane. To improve the synthetic yield, the unwanted isomers can be recovered from the mother liquor after filtration of 28.6 by first decomposing the salt to remove the excess (+)-DBTA, and then treating the free base in anisole at 300°C to give the racemic 28.5.
Treatment of the diketone 28.6 with POCl3 gave the chloride 28.7, which was subsequently SNAr-reacted with the piperazine derivative 28.8 to give the pyrazoline 28.9 (Figure 7.4.3). Suzuki coupling with the boroxazine 28.10 gave the intermediate 28.11. Next, 28.11 was dissolved and treated with SiThiol scavaenger to remove the residual Pd, and trans fatty acids were added to cleave the Boc protecting group to give the amine 28.12, which was then amidated with acryloyl chloride to form the acrylamide in 28. Recrystallization from ethanol and water gave the final product, Sotorasib (28), with an overall yield of 65% for the intermediate 28.6.
target
Primary target: KRAS(G12C)
Mode of action
Sotorasib is an orally available inhibitor of the specific KRAS mutation, p.G12C, with potential antineoplastic activity. Upon oral administration, sotorasib selectively targets, binds to and inhibits the activity of the KRAS p.G12C mutant. This may inhibit growth in KRAS p.G12C-expressing tumor cells. The KRAS p.G12C mutation is seen in some tumor cell types and plays a key role in tumor cell proliferation.
Sotorasib Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Sotorasib manufacturers
- Product
- Sotorasib 2296729-00-3
- Price
- US $0.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 10000KGS
- Release date
- 2025-03-05