Osimertinib

HCID 71496458

Grundinformationen

CAS
1421373-65-0
Standard-SMILES
C=CC(=O)Nc1cc(Nc2nccc(-c3cn(C)c4ccccc34)n2)c(OC)cc1N(C)CCN(C)C
InChIKey
DUYJMQONPNNFPI-UHFFFAOYSA-N
Summenformel
C28H33N7O2
Durchschnittliche Molmasse
499,6 g/mol
Monoisotopische Masse
499,2695733

Überblick

Osimertinib is a member of the class of aminopyrimidines that is 4-(1-methylindol-3-yl)pyrimidin-2-amine in which one of the amino hydrogens is replaced by a 2-methoxy-4-[2-(dimethylamino)ethyl](methyl)amino-5-acrylamidophenyl group. Used (as the mesylate salt) for treatment of EGFR T790M mutation positive non-small cell lung cancer. It has a role as an antineoplastic agent and an epidermal growth factor receptor antagonist. It is a secondary carboxamide, a member of acrylamides, a member of indoles, a monomethoxybenzene, an aminopyrimidine, a substituted aniline, a secondary amino compound, a tertiary amino compound and a biaryl. It is a conjugate base of an osimertinib(1+).

Namen und Bezeichner

Bevorzugter Name
Osimertinib
IUPAC
N-[2-[2-(dimethylamino)ethyl-methylamino]-4-methoxy-5-[[4-(1-methylindol-3-yl)pyrimidin-2-yl]amino]phenyl]prop-2-enamide
Englischer Name
AZD-9291
Summenformel
C28H33N7O2
Molmasse
499.61

Namen und Synonyme

osimertinib1421373-65-0AZD-9291MereletinibAZD9291AZD 9291osimertinibumN-(2-{[2-(Dimethylamino)ethyl](Methyl)amino}-4-Methoxy-5-{[4-(1-Methyl-1h-Indol-3-Yl)pyrimidin-2-Yl]amino}phenyl)prop-2-Enamide3C06JJ0Z2OAZD-9291 FREE BASEN-[2-[2-(dimethylamino)ethyl-methylamino]-4-methoxy-5-[[4-(1-methylindol-3-yl)pyrimidin-2-yl]amino]phenyl]prop-2-enamideN-[2-[[2-(Dimethylamino)ethyl]methylamino]-4-methoxy-5-[[4-(1-methyl-1H-indol-3-yl)-2-pyrimidinyl]amino]phenyl]-2-propenamide
Weitere Namen anzeigen
ADZ9291N-(2-{2-dimethylaminoethyl-methylamino}-4-methoxy-5-{[4-(1-methylindol-3-yl)pyrimidin-2-yl]amino}phenyl)prop-2-enamideZAD9291AZD929/OsimertinibOsimertinib Intermediate 4N-(2-{[2-(Dimethylamino)ethyl](methyl)amino}-4-methoxy-5-{[4-(1-methyl-1H-indol-3-yl)pyrimidinosimCS-943Ochinib
CHEBI:90943DTXSID5010259612-Propenamide, N-(2-((2-(dimethylamino)ethyl)methylamino)-4-methoxy-5-((4-(1-methyl-1H-indol-3-yl)-2-pyrimidinyl)amino)phenyl)-2-Propenamide, N-[2-[[2-(dimethylamino)ethyl]methylamino]-4-methoxy-5-[[4-(1-methyl-1H-indol-3-yl)-2-pyrimidinyl]amino]phenyl]-N-(2-((2-(dimethylamino)ethyl)(methyl)amino)-4-methoxy-5-((4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl)amino)phenyl)prop-2-enamideN-(2-((2-(dimethylamino)ethyl)methylamino)-4-methoxy-5-((4-(1-methyl-1H-indol-3-yl)-2-pyrimidinyl)amino)phenyl)-2-propenamideN-(2-(2-(dimethylamino)ethyl-methylamino)-4-methoxy-5-((4-(1-methylindol-3-yl)pyrimidin-2-yl)amino)phenyl)prop-2-enamideRefChem:58257

Datenbank-Bezeichner

CAS
1421373-65-0
PubChem CID
71496458
DTXSID
DTXSID501025961
ChEMBL
CHEMBL3353410
ChEBI
CHEBI:90943
UNII
3C06JJ0Z2O
EC Number
108-168-8
Nikkaji
J3.291.102A

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,7
Polarare Oberfläche (TPSA)
87,6 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
7
Frei drehbare Bindungen
10
Schwere Atome
37

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
Human Drugs · 2 Einträge

Breast Feeding; Lactation; Antineoplastic Agents; Enzyme Inhibitors; Protein Kinase Inhibitors; Signal Transduction Inhibitors

EMA approved medicines: Human medicine

Physikochemische Eigenschaften

Schmelzpunkt
188 oC · >188oC (dec.)
Dichte
1.19 · 1.19±0.1 g/cm3(Predicted)
storage temp.
-20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
Löslichkeit
DMSO (Slightly, Heated), Methanol (Slightly, Heated)
pka
12.68 · 12.68±0.70(Predicted)
Aggregatzustand
Solid

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P260, P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P318, P319, P321, P330, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (50%)

Toxikologische Informationen

Hepatotoxicity · 1 Eintrag

Elevations in serum aminotransferase levels are uncommon during osimertinib therapy occurring in 4% to 5% of patients and rising above 5 times the upper limit of the normal range in only 1% or less. In preregistration trials, there was a single incidence of clinically apparent liver injury attributed to osimertinib therapy, but the clinical features and relatedness to therapy were not defined. Since its approval and more widespread use, there have been no published cases of liver injury due to osimertinib.

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Sicherheitsdaten

hs_code
29339900

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

L - Antineoplastic and immunomodulating agents

QL - Antineoplastic and immunomodulating agents

Protein BindingPlasma protein binding of osimertinib is 95%.
PharmacodynamicsA pharmacokinetic/pharmacodynamic analysis suggested a concentration-dependent QTc interval prolongation of 14 msec (upper bound of two-sided 90% CI: 16 msec) at a dose of osimertinib 80 mg.
Mechanism of Action · 1 Eintrag

Osimertinib is an epidermal growth factor receptor (EGFR) tyrosine kinase inhibitor (TKI) that binds to certain mutant forms of EGFR (T790M, L858R, and exon 19 deletion) that predominate in non-small cell lung cancer (NSCLC) tumours following treatment with first-line EGFR-TKIs. As a third-generation tyrosine kinase inhibitor, osimertinib is specific for the gate-keeper T790M mutation which increases ATP binding activity to EGFR and results in poor prognosis for late-stage disease. Furthermore, osimertinib has been shown to spare wild-type EGFR during therapy, thereby reducing non-specific binding and limiting toxicity. Compared to wild-type EGFR, osimertinib has 200 times higher affinity for EGFR molecules with the L858R/T790M mutation _in vitro_.

Biological Half-LifeThe population estimated mean half-life is 48 hours.
Metabolism/Metabolites · 1 Eintrag

Osimertinib is metabolized to at least two pharmacologically active metabolites, AZ7550 and AZ5104, that circulate at approximately 10% of the concentration of the parent compound. Biochemical assays have shown that AZ7550 has similar potency and efficacy to osimertinib, while AZ5104 is more potent against mutant and wild-type EGFR. The main metabolic pathways are oxidation (predominantly by CYP3A) and dealkylation.

Anwendungen · 2 Einträge

BeschreibungAZD-9291 (Mesylate), also known as Osimertinib, belongs to a third-generation EGFR (epidermal growth factor receptor) inhibitor. It can be used for the treatment of locally advanced or metastatic non-small cell lung cancer (NSCLC) in case when the cancer cells carry specific mutations (such as T790M) in the epidermal growth factor receptor. It takes effect through directly binding to the certain mutant forms of EGFR (T790M, L858R, and exon 19 deletions) that are frequently found in NSCLC, further causing poor prognosis for late-stage disease. Since it spares wild type EGFR during therapy, it has only limited toxicity.

VerwendenAZD 9291 is an irreversible inhibitor of epidermal growth factor receptor (EGFR) sensitizing and T790M resistance mutations (IC50s = 15-17 nM) while sparing the wild-type form of the receptor (IC50 = 480 nM). It binds the related IGF1R and hERG receptors with significantly reduced potency (IC50s = 2.9 and 16.2 μM, respectively). AZD 9291 has been shown to inhibit tumor growth in a xenograft mouse model at oral doses of 5-10 mg/kg and has been tested clinically in patients with advanced EGFR mutant non-small-cell lung cancer.[Cayman Chemical]

Anbieter100 Anbieter

上海波以尔化工有限公司[email protected]
广州市亿邦医药科技有限公司+86 (20) 28996708,29078958,28139708,29076128,28133708,28139728,28139738,28133718,021-31663278,021-31663578,021-60538387
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
希瓦生物科技(广州)有限公司13268215580 · [email protected]
上海柯维化学技术有限公司021-64609169 18901607656 · [email protected]
Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: A member of the class of aminopyrimidines that is 4-(1-methylindol-3-yl)pyrimidin-2-amine in which one of the amino hydrogens is replaced by a 2-methoxy-4-[2-(dimethylamino)ethyl](methyl)amino-5-acrylamidophenyl group. Used (as the mesylate salt) for treat ent of EGFR T790M mutation positive non-small cell lung cancer.

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