Osimertinib
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
Weitere Namen anzeigen
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
- Formalladung
- 0
- Komplexität
- 752
Experimentelle und physikochemische Eigenschaften
Human Drugs
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
- Farbe
- Pale Yellow to Beige
- InChIKey
- DUYJMQONPNNFPI-UHFFFAOYSA-N
- SMILES
- CN1C2=CC=CC=C2C(C2C=CN=C(NC3C=C(NC(=O)C=C)C(N(C)CCN(C)C)=CC=3OC)N=2)=C1
- CAS Datenbank
- 1421373 · 1421373-65-0
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
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
Toxikologische Informationen
Hepatotoxicity
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.
Sicherheitsdaten
- hs_code
- 29339900
Chemie und Industrie
Pharmakologische Informationen
ATC Code
L - Antineoplastic and immunomodulating agents
QL - Antineoplastic and immunomodulating agents
Mechanism of Action
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_.
Metabolism/Metabolites
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.
FDA Pharmacological Classification
3C06JJ0Z2O
OSIMERTINIB
Established Pharmacologic Class [EPC] - Kinase Inhibitor
Mechanisms of Action [MoA] - Kinase Inhibitors
Mechanisms of Action [MoA] - Cytochrome P450 3A Inhibitors
Mechanisms of Action [MoA] - Cytochrome P450 3A4 Inducers
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Protein kinase inhibitors that inhibit TYROSINE PROTEIN KINASES.
Absorption, Distribution and Excretion
The median time to Cmax was found to be 6 hours.
Osimertinib is primarily eliminated through excretion in the feces (68%), to a lesser extent through urine (14%), while only 2% is excreted unchanged.
The mean volume of distribution at steady state is 918 L.
Oral clearance is 14.3 L/hr.
Anwendungen
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]
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Ergänzende Hinweise
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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