Asciminib

HCID 72165228

기본 정보

CAS
1492952-76-7
표준 SMILES
O=C(Nc1ccc(OC(F)(F)Cl)cc1)c1cnc(N2CC[C@@H](O)C2)c(-c2ccn[nH]2)c1
InChIKey
VOVZXURTCKPRDQ-CQSZACIVSA-N
분자식
C20H18ClF2N5O3
평균 분자량
449.8 g/mol

개요

Asciminib is a tyrosine kinase inhibitor (TKI) used in the treatment of chronic-phase Philadelphia chromosome-positive chronic myeloid leukemia (Ph+ CML). More specifically, it is an inhibitor of the ABL1 kinase activity of the BCR-ABL1 fusion protein which serves as a driver of CML proliferation in most patients with the disease. It has also shown benefit in Ph+ CML with the T315I mutation, which produces a mutant BCR-ABL1 which is typically treatment-resistant as compared to wild-type BCR-ABL1. Existing inhibitors of ABL compete at the ATP binding sites of these proteins and can be classified into those that target the active conformation of the kinase domain ([dasatinib], [bosutinib]) and those that target the inactive kinase domain ([imatinib], [nilotinib], [ponatinib]). Asciminib is unique in that it acts as an allosteric inhibitor, binding at the myristoyl pocket of the BCR-ABL1 protein and locking it into an inactive conformation. Asciminib received FDA approval on October 29, 2021 (Scemblix, Novartis AG).

이름 및 식별자

우선 이름
Asciminib
IUPAC
N-[4-[chloro(difluoro)methoxy]phenyl]-6-[(3R)-3-hydroxypyrrolidin-1-yl]-5-(1H-pyrazol-5-yl)pyridine-3-carboxamide
영어명
Asciminib
분자식
C20H18ClF2N5O3
분자량
449.84

이름 및 동의어

asciminib1492952-76-7ABL-001ABL001-NXNVP-ABL001L1F3R18W77N-[4-[chloro(difluoro)methoxy]phenyl]-6-[(3R)-3-hydroxypyrrolidin-1-yl]-5-(1H-pyrazol-5-yl)pyridine-3-carboxamide3-Pyridinecarboxamide, N-[4-(chlorodifluoromethoxy)phenyl]-6-[(3R)-3-hydroxy-1-pyrrolidinyl]-5-(1H-pyrazol-3-yl)-3-Pyridinecarboxamide, N-(4-(chlorodifluoromethoxy)phenyl)-6-((3R)-3-hydroxy-1-pyrrolidinyl)-5-(1H-pyrazol-3-yl)-asciminibumN-(4-(chloro(difluoro)methoxy)phenyl)-6-((3R)-3-hydroxypyrrolidin-1-yl)-5-(1H-pyrazol-5-yl)pyridine-3-carboxamideRefChem:58302
이름 더 보기
(R)-N- (4-(CHLORODIFLUOROMETHOXY)PHENYL)- 6-(3- HYDROXYPYRROLIDIN-1- YL)-5- (1H-PYRAZOL- 5-YL)NICOTIAsiminiEOS-61420UNII-L1F3R18W772H4,15N]-Asciminib(R)-N-[4-(Chlorodifluoromethoxy)phenyl]-6-(3-hydroxy-1-pyrrolidinyl)-5-(3-pyrazolyl)nicotinamide
N-(4-(chlorodifluoromethoxy)phenyl)-6-((3R)-3-hydroxypyrrolidin-1-yl)-5-(1H-pyrazol-5-yl)pyridine-3-carboxamideABL001Asciminib free baseAsciminib [USAN]Asciminib (ABL001)(R)-N-(4-(Chlorodifluoromethoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)-5-(1H-pyrazol-5-yl)nicotinamideExample 9(R)-N-(4-(Chlorodifluoromethoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)-5-(1H-pyrazol-3-yl)nicotinamide

데이터베이스 식별자

CAS
1492952-76-7
PubChem CID
72165228
ChEMBL
CHEMBL4208229
UNII
L1F3R18W77
EC Number
841-613-0
Nikkaji
J3.737.613B

물성

구조 계산 물성

XLogP
3
극성 표면적
103 Ų
수소 결합 공여자 수
3
수소 결합 수용자 수
8
회전 가능 결합 수
6
무거운 원자 수
31

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Listed in ZINC15
Human Drugs · 2건

Breast Feeding; Lactation; Milk, Human; Antineoplastic Agents; Enzyme Inhibitors; Protein Kinase Inhibitors; Tyrosine Kinase Inhibitors

EMA approved medicines: Human medicine (Orphan designations)

물리화학적 성질

끓는 점
631.7 · 631.7±55.0 °C(Predicted)
밀도
1.518 · 1.518±0.06 g/cm3(Predicted)
저장 조건
-20 °C · Store at -20°C
용해도
93 · DMSO:93.0(Max Conc. mg/mL);206.74(Max Conc. mM)Ethanol:90.0(Max Conc. mg/mL);200.07(Max Conc. mM)
물리적 상태
결정성 고체
산도 계수 (pKa)
10.81 · 10.81±0.70(Predicted)

안전 및 규제

GHS 분류

GHS ClassificationNot Classified

유해성 정보

Hazard Classes and CategoriesNot Classified

독성 정보

Hepatotoxicity · 1건

In the prelicensure clinical trials of asciminib in patients with refractory and extensively treated CML, ALT elevations arose in 13% of patients but were usually self-limited and mild. ALT elevations above 5 times the upper limit of normal (ULN) were uncommon, being found in 3% of treated patients. The ALT elevations were typically transient and rarely required dose interruption or modification. In the open label and controlled trials supporting the approval of asciminib, there were no instances of clinically apparent liver injury, hepatic failure or deaths from liver injury. Furthermore, patients with aminotransferase elevations during therapy with first and second line BCR-ABL1 inhibitors did not have an increased rate of such elevations during asciminib therapy. Since its approval in the United States and Europe, there have been no reported cases of clinically apparent liver injury associated with asciminib therapy.

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

안전 데이터

신호 어
Warning
유해·위험 문구
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드 H302

화학 및 산업

약리 정보

ATC Code · 2건

L - Antineoplastic and immunomodulating agents

QL - Antineoplastic and immunomodulating agents

Protein Binding_In vitro_, asciminib is 97% bound to plasma proteins, although the specific protein(s) to which it binds are unclear.
Pharmacodynamics · 1건

Asciminib exerts its therapeutic activity by inhibiting an oncogenic protein responsible for the proliferation of CML. It may be administered orally once or twice a day depending on the condition being treated. By increasing the total daily dose 5-fold as compared to standard therapy (80mg daily vs. 400mg daily), it can be used to treat Ph+ CML with the T315I mutation, a typically treatment-resistant variant of the disease. As with many other chemotherapeutic agents, asciminib treatment can result in various forms of myelosuppression, including thrombocytopenia and neutropenia. Patients should receive frequent laboratory monitoring throughout therapy and dose adjustments may be required based on the severity of observed effects. Patients may also experience pancreatic and/or cardiovascular toxicity, both of which require frequent monitoring and may require dose adjustments as per prescribing information.

Mechanism of Action · 1건

In most patients with chronic myeloid leukemia (CML), progression of the disease is driven primarily by a translocation of the Philadelphia chromosome that creates an oncogenic fusion gene, _BCR-ABL1_, between the _BCR_ and _ABL1_ genes. This fusion gene produces a resultant fusion protein, BCR-ABL1, which exhibits elevated tyrosine kinase and transforming activities that contribute to CML proliferation. Asciminib is an allosteric inhibitor of the BCR-ABL1 tyrosine kinase. It binds to the myristoyl pocket of the ABL1 portion of the fusion protein and locks it into an inactive conformation, preventing its oncogenic activity.

Biological Half-LifeThe terminal elimination half-life asciminib is 5.5 hours when administered at 40mg twice daily and 9.0 hours when administered at 200mg twice daily.
Metabolism/Metabolites · 1건

Asciminib is negligibly metabolized, with unchanged parent drug comprising the main drug component in plasma (~93%) and following excretion (~57% in feces). The main circulating metabolites are M30.5, M44, and M29.5, accounting for approximately 5%, 2%, and 0.4% of the total administered dose, respectively. The oxidative metabolism of asciminib is mediated by CYP3A4, and the glucuronidation of asciminib is mediated by UGT2B7 and UGT2B17.

응용 분야

용도Asciminib comprises ABL kinase inhibitors and/or SLC7A11 inhibitors for the treatment of cancer and central nervous system (CNS) disorders.

공급사100 곳

天津欣康佑生物科技有限公司19922659386 · [email protected]
韶远科技(上海)有限公司021-50795510 4000665055 · [email protected]
安礼特(上海)医药科技有限公司18109805911 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]

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