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ChemicalBook--->CAS DataBase List--->2326521-71-3

2326521-71-3

2326521-71-3 Structure

2326521-71-3 Structure
IdentificationBack Directory
[Name]

MRTX-849
[CAS]

2326521-71-3
[Synonyms]

MRTX-849
Adagrasib
MRTX849(Adagrasib)
Adagrasib/MRTX-849
MRTX849;MRTX-849;MRTX 849
2-PIPERAZINEACETONITRILE, 4-[7-(8-CHLORO-1-NAPHTHALENYL)-5,6,7,8-TETRAHYDRO-2-[[(2S)-1-METHYL-2-PYRR
2-((S)-4-(7-(8-chloronaphthalen-1-yl)-2-(((S)-1-methylpyrrolidin-2-yl)methoxy)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl)-1-(2-fluoroacryloyl)piperazin-2-yl)acetonitrile
2-[(2S)-4-[7-(8-chloronaphthalen-1-yl)-2-[[(2S)-1-methylpyrrolidin-2-yl]methoxy]-6,8-dihydro-5H-pyrido[3,4-d]pyrimidin-4-yl]-1-(2-fluoroprop-2-enoyl)piperazin-2-yl]acetonitrile
2-Piperazineacetonitrile, 4-[7-(8-chloro-1-naphthalenyl)-5,6,7,8-tetrahydro-2-[[(2S)-1-methyl-2-pyrrolidinyl]methoxy]pyrido[3,4-d]pyrimidin-4-yl]-1-(2-fluoro-1-oxo-2-propen-1-yl)-, (2S)-
[Molecular Formula]

C32H35ClFN7O2
[MDL Number]

MFCD32263433
[MOL File]

2326521-71-3.mol
[Molecular Weight]

604.12
Chemical PropertiesBack Directory
[Boiling point ]

860.2±75.0 °C(Predicted)
[density ]

1.295±0.06 g/cm3(Predicted)
[storage temp. ]

Store at -20°C
[solubility ]

Soluble in DMSO:1.0(Max Conc. mg/mL);1.7(Max Conc. mM)
[form ]

A crystalline solid
[pka]

9.31±0.40(Predicted)
[color ]

White to yellow
[InChIKey]

PEMUGDMSUDYLHU-ZEQRLZLVSA-N
[SMILES]

N1(C(=O)C(F)=C)CCN(C2N=C(OC[C@@H]3CCCN3C)N=C3CN(C4=C5C(C=CC=C5Cl)=CC=C4)CCC3=2)C[C@@H]1CC#N
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P280-P301+P312-P302+P352-P305+P351+P338
Hazard InformationBack Directory
[Description]

MRTX-849 was identified as a potent, selective, and covalent KRASG12C inhibitor that exhibits favourable drug-like properties, modifies mutant cysteine 12 in GDP-bound KRASG12C, and inhibits KRAS-dependent signalling. MRTX-849 demonstrated pronounced tumour regression in 17 of 26 (65%) KRASG12C-positive cell line- and patient-derived xenograft models from multiple tumour types, and objective responses have been observed in patients with KRASG12C-positive lung and colon adenocarcinomas[1].
[Uses]

MRTX 849 is used as combination therapy for treatment of cancer.
[Brand name]

Krazati
[General Description]

Class: non-kinase; Treatment: KRAS(G12C) NSCLC; Other name: MRTX849; Elimination half-life: 24 h; Protein binding = 98.3%
[Biological Activity]

To minimize GSH metabolism, the development candidate MRTX-849 employed a 2-fluoroacrylamide warhead, imparting whole blood stability of >50 h t1/2 across species while maintaining tractable cellular potency (IC50 = 5–14 nM). Metabolism studies of MRTX-849 in hepatocytes showed that GSH conjugation of the 2-fluoroacrylamide was reduced compared to previous analogues containing the unsubstituted acrylamide. Favorable in vitro ADME and physical properties of MRTX-849 translated into moderate to high bioavailability of 26–63% across species tested. In a PK/PD experiment dosed at 10, 30, and 100 mg/kg to NCI-H358 tumor-bearing mice, MRTX-849 demonstrated dose-dependent protein modification with nearly maximal effect at the highest doses[2].
[Mechanism of action]

Adagrasib selectively modified mutant cysteine 12 in GDP-bound G12C and inhibited KRASdependent signaling.
[Clinical Use]

Adagrasib is an irreversible inhibitor of the RAS GTPase family. It is approved by the FDA for the treatment of adult patients with locally advanced or metastatic non-small cell lung cancer (NSCLC) who have been identified by testing as having a KRAS (G12C) mutation.
[target]

Primary target: KRAS(G12C)
[storage]

Store at -20°C
[References]

[1] Jay B. Fell. “Identification of the Clinical Development Candidate MRTX849, a Covalent KRASG12C Inhibitor for the Treatment of Cancer.” Journal of Medicinal Chemistry 63 13 (2020): 6679–6693.
[2] J. Christensen. “The KRASG12C Inhibitor, MRTX849, Provides Insight Toward Therapeutic Susceptibility of KRAS Mutant Cancers in Mouse Models and Patients.” Cancer discovery (2019).
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