Axitinib
Grundinformationen
- CAS
319460-85-0- Standard-SMILES
CNC(=O)c1ccccc1Sc1ccc2c(/C=C/c3ccccn3)n[nH]c2c1- InChIKey
RITAVMQDGBJQJZ-FMIVXFBMSA-N- Summenformel
- C22H18N4OS
- Durchschnittliche Molmasse
- 386,5 g/mol
- Monoisotopische Masse
- 386,12013238
Überblick
Axitinib is an indazole substituted at position 3 by a 2-(pyridin-2-yl)vinyl group and at position 6 by a 2-(N-methylaminocarboxy)phenylsulfanyl group. Used for the treatment of advanced renal cell carcinoma after failure of a first line systemic treatment. It has a role as an antineoplastic agent, a tyrosine kinase inhibitor and a vascular endothelial growth factor receptor antagonist. It is a member of benzamides, a member of pyridines, an aryl sulfide and a member of indazoles.
Namen und Bezeichner
- Bevorzugter Name
- Axitinib
- IUPAC
- N-methyl-2-[[3-[(E)-2-pyridin-2-ylethenyl]-1H-indazol-6-yl]sulfanyl]benzamide
- Englischer Name
- Axitinib
- Summenformel
- C22H18N4OS
- Molmasse
- 386.47
Namen und Synonyme
Axitinib319460-85-0InlytaaxitinibumAG-13736C9LVQ0YUXGDTXSID3049049AG013736NSC-757441N-methyl-2-((3-((1E)-2-(pyridin-2-yl)ethenyl)-1H-indazol-6-yl)sulfanyl)benzamideN-methyl-2-({3-[(E)-2-(pyridin-2-yl)ethenyl]-1H-indazol-6-yl}sulfanyl)benzamideDTXCID8028975
Weitere Namen anzeigen
(E)-N-Methyl-2-((3-(2-(pyridin-2-yl)vinyl)-1H-indazol-6-yl)thio)benzaMideN-Methyl-2-[[3-[(1E)-2-(2-pyridinyl)ethenyl]-1H-indazol-6-yl]thio]benzamide10mgCS-310AxtinibAxitinbAG 013736Axitinib Base
CHEBI:66910Benzamide, N-methyl-2-((3-((E)-2-(2-pyridinyl)ethenyl)-1H-indazol-6-yl)thio)-Benzamide, N-methyl-2-((3-((1E)-2-(2-pyridinyl)ethenyl)-1H-indazo)-6-yl)thio)-N-methyl-2-({3-[(1E)-2-(pyridin-2-yl)ethenyl]-1H-indazol-6-yl}sulfanyl)benzamideN-methyl-2-((3-((E)-2-(pyridin-2-yl)ethenyl)-1H-indazol-6-yl)sulfanyl)benzamideRefChem:58911L01XE17AG-013736
Datenbank-Bezeichner
- CAS
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 4,2
- Polarare Oberfläche (TPSA)
- 96 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 5
- Schwere Atome
- 28
- Formalladung
- 0
- Komplexität
- 557
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
LogP3.8
SolubilityIn aqueous media with a pH between 1.1 to 7.8, axitinib has a solubility of over 0.2 μg/mL.
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antineoplastic Agents; Enzyme Inhibitors; Protein Kinase Inhibitors; Signal Transduction Inhibitors; Tyrosine Kinase Inhibitors
FDA approved drugs -> Active ingredient
EMA approved medicines: Human medicine
EMA approved medicines: Human medicine
FDA approved drugs -> Active ingredient
Dissociation Constants4.8
Physikochemische Eigenschaften
- Schmelzpunkt
- 213 · 213-215°C
- Siedepunkt
- 668.9 · 668.9±55.0 °C(Predicted)
- Dichte
- 1.4 · 1.4
- storage temp.
- room temp
- Löslichkeit
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Warning
H302 (53.4%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P260, P264, P270, P273, P280, P301+P317, P318, P319, P330, P391, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 73 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 4 (53.4%)
Toxikologische Informationen
Hepatotoxicity
In large clinical trials of axitinib, elevations in serum aminotransferase levels were common, occurring in up to 22% of patients. Values greater than 5 times the upper limit of normal (ULN), however, were uncommon, occurring in 1% to 2% of recipients. Furthermore, no instances of clinically apparent liver injury from axitinib were reported in prelicensure studies. Nevertheless, periodic monitoring of liver tests during axitinib therapy was recommended.
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Axitinib
Ambiguous-DILI-concern
3
Warnings & precautions
DOI:10.1016/j.drudis.2016.02.015
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Sicherheitsdaten
Chemie und Industrie
Pharmakologische Informationen
ATC Code
L01XE17
L - Antineoplastic and immunomodulating agents
QL - Antineoplastic and immunomodulating agents
Protein BindingPlasma protein binding for axitinib is high at over 99% with most protein binding to albumin followed by α1-acid glycoprotein.
PharmacodynamicsAxitinib prevents the progression of cancer by inhibiting angiogenesis and blocking tumor growth.
Mechanism of ActionAxitinib selectively blocks the tyrosine kinase receptors VEGFR-1 (vascular endothelial growth factor receptor), VEGFR-2, and VEGFR-3.
Biological Half-LifeAxitinib has a half life of 2.5 to 6.1 hours.
Metabolism/MetabolitesAxitinib undergoes mainly hepatic metabolism. CYP3A4 and CYP3A5 are the main hepatic enzymes while CYP1A2, CYP2C19, and UGT1A1 enzymes are secondary.
FDA Pharmacological Classification
C9LVQ0YUXG
AXITINIB
Established Pharmacologic Class [EPC] - Kinase Inhibitor
Mechanisms of Action [MoA] - Receptor Tyrosine Kinase Inhibitors
Axitinib is a Kinase Inhibitor. The mechanism of action of axitinib is as a Receptor Tyrosine Kinase Inhibitor.
AXITINIB
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Agents that inhibit PROTEIN KINASES.
Absorption, Distribution and Excretion
After one 5 mg dose of axitinib, it takes about 2.5 to 4.1 hours to reach maximum plasma concentration.
Axitinib is mainly eliminated unchanged in the feces (41%) with 12% of the original dose as unchanged axitinib. There is also 23% eliminated in the urine, most of which are metabolites.
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