기본 정보
- CAS
319460-85-0- 표준 SMILES
CNC(=O)c1ccccc1Sc1ccc2c(/C=C/c3ccccn3)n[nH]c2c1- InChIKey
RITAVMQDGBJQJZ-FMIVXFBMSA-N- 분자식
- C22H18N4OS
- 평균 분자량
- 386.5 g/mol
- 단동위원소 질량
- 386.12013238
개요
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.
이름 및 식별자
- 우선 이름
- Axitinib
- IUPAC
- N-methyl-2-[[3-[(E)-2-pyridin-2-ylethenyl]-1H-indazol-6-yl]sulfanyl]benzamide
- 현지명
- 엑시티닙
- 영어명
- Axitinib
- 분자식
- C22H18N4OS
- 분자량
- 386.47
이름 및 동의어
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
이름 더 보기
엑시티닙(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
데이터베이스 식별자
- CAS
물성
구조 계산 물성
- XLogP
- 4.2
- 극성 표면적
- 96 Ų
- 수소 결합 공여자 수
- 2
- 수소 결합 수용자 수
- 4
- 회전 가능 결합 수
- 5
- 무거운 원자 수
- 28
- 형식 전하
- 0
- 복잡도
- 557
실험 및 물리화학적 성질
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
물리화학적 성질
- 녹는점
- 213 · 213-215°C
- 끓는 점
- 668.9 · 668.9±55.0 °C(Predicted)
- 밀도
- 1.4 · 1.4
- 저장 조건
- room temp
- 용해도
- 8 mg/mL · DMSO: ≥8mg/mL
- 물리적 상태
- 가루
- 산도 계수 (pKa)
- 12.7 · 12.70±0.40(Predicted)
- 색상
- 흰색에서 황갈색까지
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
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.
유해성 정보
Hazard Classes and CategoriesAcute Tox. 4 (53.4%)
독성 정보
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
안전 데이터
- wgk
- 3
- ridadr
- UN 3077 9 / PGIII
- HS 번호
- 29333990
화학 및 산업
약리 정보
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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