기본 정보
- CAS
144675-97-8- 표준 SMILES
NCCNc1ccc(NCCN)c2c1C(=O)c1ccncc1C2=O.O=C(O)C=CC(=O)O.O=C(O)C=CC(=O)O- InChIKey
SVAGFBGXEWPNJC-UHFFFAOYSA-N- 분자식
- C25H27N5O10
- 평균 분자량
- 557.5 g/mol
- 단동위원소 질량
- 557.17579208
개요
Pixantrone Dimaleate is the dimaleate salt of a synthetic, noncardiotoxic aza-anthracenedione analogue with potential antineoplastic activity. Pixantrone intercalates into DNA and induces topoisomerase II-mediated DNA strand crosslinks, resulting in inhibition of DNA replication and tumor cell cytotoxicity.
이름 및 식별자
- 우선 이름
- Benz(g)isoquinoline-5,10-dione, 6,9-bis((2-aminoethyl)amino)-, (2Z)-2-butenedioate (1:2)
- IUPAC
- 6,9-bis(2-aminoethylamino)benzo[g]isoquinoline-5,10-dione;bis(but-2-enedioic acid)
- 현지명
- 벤즈(g)이소퀴놀린-5,10-디온,6,9-비스((2-아미노에틸)아미노)-,(2Z)-2-부텐디오에이트(1:2)
- 영어명
- Pixantrone Dimaleate
- 분자식
- C21H23N5O6
- 분자량
- 441.44
이름 및 동의어
Pixantrone dimaleate144675-97-8Benz(g)isoquinoline-5,10-dione, 6,9-bis((2-aminoethyl)amino)-, (2Z)-2-butenedioate (1:2)6,9-bis(2-aminoethylamino)benzo[g]isoquinoline-5,10-dione;but-2-enedioic acidC25H27N5O106,9-bis(2-aminoethylamino)benzo[g]isoquinoline-5,10-dione;(Z)-but-2-enedioic acidBenz[g]isoquinoline-5,10-dione, 6,9-bis[(2-aminoethyl)amino]-, (2Z)-2-butenedioate (1:2)SCHEMBL7557069AKOS030241525SB16818벤즈(g)이소퀴놀린-5,10-디온,6,9-비스((2-아미노에틸)아미노)-,(2Z)-2-부텐디오에이트(1:2)Pixantrone maleate
이름 더 보기
CS-1295Bbr 2778Dimalate saltBBR 2778 dimaleatePixatrone dimaleatePixantrone dimaleate (BBR-2778)Pixantrone dimaleate, 10 mM in DMSOPixantrone-dimaleate, BBR2778 dimaleate
물성
구조 계산 물성
- 극성 표면적
- 272 Ų
- 수소 결합 공여자 수
- 8
- 수소 결합 수용자 수
- 15
- 회전 가능 결합 수
- 10
- 무거운 원자 수
- 40
- 형식 전하
- 0
- 복잡도
- 591
물리화학적 성질
- 녹는점
- 192 ° · 192°
- 저장 조건
- 2 · under inert gas (nitrogen or Argon) at 2-8°C
- 용해도
- 30 · DMSO:30.0(Max Conc. mg/mL);53.8(Max Conc. mM)H2O:5.0(Max Conc. mg/mL);9.0(Max Conc. mM)
- 물리적 상태
- 결정성 고체
- 색상
- Blue to dark blue
- 수용성
- 2 O: · H2O: 2mg/mL, clear
- InChIKey
- GORZTPPEWDXGBU-BTJKTKAUSA-N
- SMILES
- C(/C(=O)O)=C/C(=O)O.N(C1=CC=C(NCCN)C2C(C3=CN=CC=C3C(=O)C1=2)=O)CCN
화학적 성질
Blue Solid
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
GHS Classification
Danger
H300 (50%): Fatal if swallowed [Danger Acute toxicity, oral]
P203, P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P308+P316, P316, P318, P320, P321, P330, P361+P364, P403+P233, 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.
유해성 정보
Hazard Classes and CategoriesAcute Tox. 2 (50%)
안전 데이터
- wgk
- WGK 3
- Hazard Classifications
- Muta. 2Repr. 2
- 스토리지 클래스
- 13 - Non Combustible Solids
화학 및 산업
응용 분야
개요Pixantrone dimaleate was approved by European Medicine Agency (EMA) on May 10, 2012. It was developed and marketed as Pixuvri® by Cell Therapeutics in EU. (CTI Life Sciences).Pixantrone dimaleate is a DNA intercalating agent indicated as monotherapy for the treatment of adult patients with multiply relapsed or refractory aggressive Non-Hodgkin B-cell Lymphomas (NHL).Pixuvri® is available as lyophilised powder for infusion, containing 29 mg of free Pixantrone. The recommended dose is 50 mg/m2 of pixantrone on days 1, 8 and 15 of each 28-day cycle for up to 6 cycles.
출처Pixantrone dimaleate, also known as BBR 2778, was first synthesized by Professors Krapcho and Hacker at the University of Vermont. The University of Vermont and the Boehringer Mannheim Italia research center co-identified the in vitro tumor cell cytotoxicity.
용도Pixantrone is an antineoplastic drug belonging to group of antitumor antibiotics. Pixantrone is an anlogue of Mitoxantrone (M373425) and is just as potent in the treatment of multiple sclerosis with f ewer toxic effects on cardiac tissue. Studies suggest that Pixantrone significantly reduces amyloid beta (A beta(1-42)) neurotoxicity, a mechanism implicated in Alzheimer's disease.
제조 방법
The manufacturing scale synthesis of pixantrone dimaleate relies on several process modifications from the original synthesis reported by Krapcho in 1994. This modified procedure has provided active pharmaceutical ingredient (API) in high purity (>99%) and is acceptable for use in pharmaceutical applications (Scheme 25). Beginning with pyridine 3,4-dicarboxylic acid (129), generation of the corresponding anhydride 130 proceeded in 76% yield upon treatment with refluxing Ac2O. Next, an AlCl3-promoted Friedel–Crafts reaction of 1,4-difluorobenzene (131) with 130 under reflux conditions provided a mixture of nicotinic acid isomers 132a/132b in 84% yield, which were carried directly to the next step. Cyclization with fuming H2SO4 yielded the desired difluorobenzo-isoquinoline-dione core 133, which was further functionalized with ethylenediamine (134) to provide the free base of pixantrone. Subjection of the pixantrone free base to aqueous acetic anhydride and maleic acid provided pixantrone dimaleate (XX) in 92% yield over 3 steps.Synthesis of pixantrone dimaleate
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