Acalabrutinib

HCID 71226662

Grundinformationen

CAS
1420477-60-6
Standard-SMILES
CC#CC(=O)N1CCC[C@H]1c1nc(-c2ccc(C(=O)Nc3ccccn3)cc2)c2c(N)nccn12
InChIKey
WDENQIQQYWYTPO-IBGZPJMESA-N
Summenformel
C26H23N7O2
Durchschnittliche Molmasse
465,5 g/mol
Monoisotopische Masse
465,191323

Namen und Bezeichner

Bevorzugter Name
Acalabrutinib
IUPAC
4-[8-amino-3-[(2S)-1-but-2-ynoylpyrrolidin-2-yl]imidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide
Englischer Name
Acalabrutinib
Summenformel
C26H23N7O2
Molmasse
465.51

Namen und Synonyme

Acalabrutinib1420477-60-6ACP-196acalabrutinibumI42748ELQW4-[8-amino-3-[(2S)-1-but-2-ynoylpyrrolidin-2-yl]imidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamideBenzamide, 4-[8-amino-3-[(2S)-1-(1-oxo-2-butyn-1-yl)-2-pyrrolidinyl]imidazo[1,5-a]pyrazin-1-yl]-N-2-pyridinyl-CHEBI:167707DTXSID4010262094-[8-Amino-3-[(2S)-1-(1-oxo-2-butyn-1-yl)-2-pyrrolidinyl]imidazo[1,5-a]pyrazin-1-yl]-N-2-pyridinylbenzamide4-{8-amino-3-[(2S)-1-(but-2-ynoyl)pyrrolidin-2-yl]imidazo[1,5-a]pyrazin-1-yl}-N-(pyridin-2-yl)benzamideBenzamide, 4-(8-amino-3-((2S)-1-(1-oxo-2-butyn-1-yl)-2-pyrrolidinyl)imidazo(1,5-a)pyrazin-1-yl)-N-2-pyridinyl-
Weitere Namen anzeigen
ACP196CalquenceCS-1558EOS-60753D4-Acalabrutinibα-DimethylglycineACP196,Acalabrutinib
4-(8-Amino-3-((2S)-1-(1-oxo-2-butyn-1-yl)-2-pyrrolidinyl)imidazo(1,5-a)pyrazin-1-yl)-N-2-pyridinylbenzamide4-(8-amino-3-((2S)-1-(but-2-ynoyl)pyrrolidin-2-yl)imidazo(1,5-a)pyrazin-1-yl)-N-(pyridin-2-yl)benzamide4-(8-amino-3-((2S)-1-but-2-ynoylpyrrolidin-2-yl)imidazo(1,5-a)pyrazin-1-yl)-N-pyridin-2-ylbenzamideRefChem:57414L01XE51DTXCID401510462Bruton Tyrosine Kinase Inhibitor ACP-196814-272-0

Datenbank-Bezeichner

CAS
1420477-60-6
PubChem CID
71226662
DTXSID
DTXSID401026209
ChEMBL
CHEMBL3707348
ChEBI
CHEBI:167707
UNII
I42748ELQW
EC Number
814-272-0
Nikkaji
J3.695.616J

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3
Polarare Oberfläche (TPSA)
119 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
4
Schwere Atome
35

Experimentelle und physikochemische Eigenschaften

LogP0.49
SolubilityFreely soluble in water at pH values below 3 but is practically insoluble in water at pH values above 6

Physikochemische Eigenschaften

Schmelzpunkt
133 °C · >133°C (dec.)
Dichte
1.37 · 1.37±0.1 g/cm3(Predicted)
storage temp.
Refrigerator
Löslichkeit
Soluble in DMSO (up to at least 25 mg/ml)
pka
11.47 · 11.47±0.70(Predicted)
Aggregatzustand
solid

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.

Warning

H373 (66.7%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]

P260, P319, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory.;Reported as not meeting GHS hazard criteria per 1 of 3 reports by companies.;There are 2 notifications provided by 2 of 3 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Gefahrenhinweise

Hazard Classes and CategoriesSTOT RE 2 (66.7%)

Toxikologische Informationen

Hepatotoxicity · 1 Eintrag

In open label clinical trials of acalabrutinib in patients with CLL and mantle cell lymphoma, serum aminotransferase elevations occurred in 19% to 23% of patients during therapy and rose to above 5 times ULN in 2% to 3%. These elevations were transient and resolved spontaneously but occasionally led to early drug discontinuation. Among the 610 patients treated with acalabrutinib in pre-registration trials, there were no instances of clinically apparent liver injury attributed to its use, but there was a single instance of acute liver failure and death due to reactivation of hepatitis B. Similar cases of reactivation have been reported with ibrutinib, another small molecule inhibitor of Bruton's tyrosine kinase. Experience with acalabrutinib has been limited and the frequency of clinically apparent liver injury and reactivation of hepatitis B are not known. The majority of cases have occurred in patients taking multiple immunosuppressive agents and not just acalabrutinib alone.;Likelihood score: D (possible rare cause of reactivation of hepatitis B).

Drug Induced Liver Injury · 6 Einträge

Drug Induced Liver Injury Rank (DILIrank 2.0)

Acalabrutinib

Ambiguous-DILI-concern

4

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation · 1 Eintrag

◉ Summary of Use during Lactation;No information is available on the clinical use of acalabrutinib during breastfeeding. Because acalabrutinib is over 97% bound to plasma proteins, and the half-life of the drug and metabolite are less than 7 hours, the amount in milk is likely to be low. However, the protein binding of the active metabolite is not known and the manufacturer recommends that breastfeeding be discontinued during acalabrutinib therapy and for at least 2 weeks after the final dose.;◉ Effects in Breastfed Infants;Relevant published information was not found as of the revision date.;◉ Effects on Lactation and Breastmilk;Relevant published information was not found as of the revision date.

Sicherheitsdaten

Alarmwort
Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H302

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

L - Antineoplastic and immunomodulating agents;L01 - Antineoplastic agents;L01E - Protein kinase inhibitors;L01EL - Bruton's tyrosine kinase (btk) inhibitors;L01EL02 - Acalabrutinib

QL - Antineoplastic and immunomodulating agents;QL01 - Antineoplastic agents;QL01E - Protein kinase inhibitors;QL01EL - Bruton's tyrosine kinase (btk) inhibitors;QL01EL02 - Acalabrutinib

Protein Binding · 1 Eintrag

Reversible binding of acalabrutinib to human plasma protein is approximately 97.5%. The in vitro mean blood-to-plasma ratio is about 0.7. _In vitro_ experiments at physiologic concentrations show that acalabrutinib can be 93.7% bound to human serum albumin and 41.1% bound to alpha-1-acid glycoprotein.

Pharmacodynamics · 1 Eintrag

Acalabrutinib is a Bruton Tyrosine Kinase inhibitor that prevents the proliferation, trafficking, chemotaxis, and adhesion of B cells. It is taken every 12 hours and can cause other effects such as atrial fibrillation, other malignancies, cytopenia, hemorrhage, and infection.

Mechanism of Action · 1 Eintrag

Mantle Cell Lymphoma (MCL) is a rare yet aggressive type of B-cell non-Hodgkin lymphoma (NHL) with poor prognosis. Subsequently, relapse is common in MCL patients and ultimately represents disease progression. Lymphoma occurs when immune system lymphocytes grow and multiply uncontrollably. Such cancerous lymphocytes may travel to many parts of the body, including the lymph nodes, spleen, bone marrow, blood, and other organs where they can multiply and form a mass(es) called a tumor. One of the main kinds of lymphocytes that can develop into cancerous lymphomas are the body's own B-lymphocytes (B-cells). Bruton Tyrosine Kinase (BTK) is a signalling molecule of the B-cell antigen receptor and cytokine receptor pathways. Such BTK signaling causes the activation of pathways necessary for B-cell proliferation, trafficking, chemotaxis, and adhesion. Acalabrutinib is a small molecule inhibitor of BTK. Both acalabrutinib and its active metabolite, ACP-5862, act to form a covalent bond with a cysteine residue (Cys481) in the BTK active site, leading to inhibition of BTK enzymatic activity. As a result, acalabrutinib inhibits BTK-mediated activation of downstream signaling proteins CD86 and CD69, which ultimately inhibits malignant B-cell proliferation and survival Whereas ibrutinib is typically recognized as the first-in-class BTK inhibitor, acalabrutinib is considered a second generation BTK inhibitor primarily because it demonstrates highter selectivity and inhibition of the targeted activity of BTK while having a much greater IC50 or otherwise virtually no inhibition on the kinase activities of ITK, EGFR, ERBB2, ERBB4, JAK3, BLK, FGR, FYN, HCK, LCK, LYN, SRC, and YES1. In effect, acalabrutinib was rationally designed to be more potent and selective than ibrutinib, all the while demonstrating fewer adverse effects - in theory - because of the drug's minimized off target effects.

Biological Half-Life · 1 Eintrag

After administering a single oral dose of 100 mg acalabrutinib, the median terminal elimination half-life of the drug was found to be 0.9 (with a range of 0.6 to 2.8) hours. The half-life of the active metabolite, ACP-5862, is about 6.9 hours.

Metabolism/Metabolites · 1 Eintrag

Acalabrutinib is mainly metabolized by CYP3A enzymes. ACP-5862 is identified to be the major active metabolite in plasma with a geometric mean exposure (AUC) that is about 2-3 times greater than the exposure of acalabrutinib. ACP-5862 is about 50% less potent than acalabrutinib in regards to the inhibition of BTK.

Anwendungen · 1 Eintrag

BeschreibungAcalabrutinib (ACP-196) is a selective second-generation Bruton's tyrosine kinase (BTK) inhibitor with an IC50 of 3 nM, which prevents the activation of the B-cell antigen receptor (BCR) signaling pathway. ACP-196 has improved target specificity over ibrutinib with 323-, 94-, 19- and 9-fold selectivity over the other TEC kinase family members (ITK, TXK, BMX, and TEC, respectively) and no activity against EGFR.

Vor- und nachgelagerte Produkte

Anbieter100 Anbieter

合肥翰刚医药科技有限公司+8618062405514 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]
上海波以尔化工有限公司[email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]

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