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Mitoxantrone

HCID 4212
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
65271-80-9
표준 SMILES
O=C1c2c(O)ccc(O)c2C(=O)c2c(NCCNCCO)ccc(NCCNCCO)c21
InChIKey
KKZJGLLVHKMTCM-UHFFFAOYSA-N
분자식
C22H28N4O6
평균 분자량
444.5 g/mol
단동위원소 질량
444.20088462

개요

Mitoxantrone is a dihydroxyanthraquinone that is 1,4-dihydroxy-9,10-anthraquinone which is substituted by 6-hydroxy-1,4-diazahexyl groups at positions 5 and 8. It has a role as an analgesic and an antineoplastic agent.

이름 및 식별자

우선 이름
Mitoxantrone
IUPAC
1,4-dihydroxy-5,8-bis[2-(2-hydroxyethylamino)ethylamino]anthracene-9,10-dione
영어명
Mitoxantrone
분자식
C22H28N4O6
분자량
444.48

이름 및 동의어

mitoxantrone65271-80-9MitozantroneMitoxanthroneDHAQMitoxantronMitoxantronaMitoxantronumMisostolNSC-279836NSC 279836BZ114NVM5P
이름 더 보기
itoxantronedihydroxyanthraquinoneNSC-27983MitoxantroneBasePharmasubstanceEP4
NSC2798361,4-Bis(2-(2-hydroxyethylamino)ethyl)amino)-5,8-dihydroxyanthraquinone1,4-Dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-9,10-anthracenedioneDTXSID40469471,4-DIHYDROXY-5,8-BIS({2-[(2-HYDROXYETHYL)AMINO]ETHYL}AMINO)-9,10-ANTHRACENEDIONECHEBI:50729L01DB07Ralenova

데이터베이스 식별자

CAS
65271-80-9
PubChem CID
4212
DTXSID
DTXSID4046947
ChEMBL
CHEMBL58
ChEBI
CHEBI:50729
UNII
BZ114NVM5P
EC Number
833-758-3
Nikkaji
J19.969I、J710.751J

물성

구조 계산 물성

XLogP
1
극성 표면적
163 Ų
수소 결합 공여자 수
8
수소 결합 수용자 수
10
회전 가능 결합 수
12
무거운 원자 수
32
형식 전하
0
복잡도
571

실험 및 물리화학적 성질

Drugs · 2건

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals

LogP · 2건

-3.1

0.07

Solubility7.34e-01 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Antineoplastic Agents
Physical DescriptionLiquid
Collision Cross Section198.57 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

물리화학적 성질

녹는점
170 · 170-1740C
끓는 점
554.47 °C · 554.47°C (rough estimate)
밀도
1.3049 · 1.3049 (rough estimate)
굴절률
1.65 · 1.6500 (estimate)
저장 조건
2 · Keep in dark place,Sealed in dry,2-8°C
용해도
DMSO(약간 용해됨), 메탄올(약간 용해됨), 물(약간 용해됨)
산도 계수 (pKa)
5.99 · pKa 5.99 (Uncertain);8.13 (Uncertain)

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

Warning

H351 (100%): Suspected of causing cancer [Warning Carcinogenicity]

P203, P273, P280, P318, P391, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

유해성 정보

Regulatory InformationHazard Traits - Carcinogenicity
Hazard Classes and CategoriesCarc. 2 (100%)

독성 정보

Health EffectsCardiomyopathy is a particularly concerning effect as it is irreversible. [Wikipedia]
Hepatotoxicity · 1건

Chemotherapy with mitoxantrone alone is associated with serum enzyme elevations in up to 40% of patients, but these elevations are generally mild-to-moderate in severity, transient and not accompanied by symptoms or jaundice. Higher rates of liver enzyme elevations have been reported with combination chemotherapeutic regimens that include mitoxantrone. In high doses, mitoxantrone has been associated with a high rate of jaundice, but the degree of hyperbilirubinemia has been mild, transient and not associated with significant serum enzyme elevations or evidence of hepatitis. Rare instances of acute liver injury have been reported in patients taking mitoxantrone, including a single case of drug-rash with eosinophilia and systemic symptoms (DRESS). The latency to onset was 8 weeks and the pattern of serum enzyme elevations was cholestatic and later mixed. Immunoallergic features were prominent and appeared to respond to corticosteroid therapy. Other drugs were being taken and the association with mitoxantrone was not definite (Case 1). Thus, idiosyncratic and clinically apparent liver injury from mitoxantrone may occur but is quite rare.

화학 및 산업

약리 정보

ATC Code · 3건

L01DB07

L - Antineoplastic and immunomodulating agents

QL - Antineoplastic and immunomodulating agents

Protein Binding78%
PharmacodynamicsMitoxantrone has been shown in vitro to inhibit B cell, T cell, and macrophage proliferation and impair antigen presentation, as well as the secretion of interferon gamma, TNFa, and IL-2.
Mechanism of Action · 1건

Mitoxantrone, a DNA-reactive agent that intercalates into deoxyribonucleic acid (DNA) through hydrogen bonding, causes crosslinks and strand breaks. Mitoxantrone also interferes with ribonucleic acid (RNA) and is a potent inhibitor of topoisomerase II, an enzyme responsible for uncoiling and repairing damaged DNA. It has a cytocidal effect on both proliferating and nonproliferating cultured human cells, suggesting lack of cell cycle phase specificity.

Biological Half-Life75 hours
Metabolism/Metabolites · 2건

Hepatic

Hepatic Half Life: 75 hours

FDA Pharmacological Classification · 6건

BZ114NVM5P

MITOXANTRONE

Established Pharmacologic Class [EPC] - Topoisomerase Inhibitor

Mechanisms of Action [MoA] - Topoisomerase Inhibitors

Mitoxantrone is a Topoisomerase Inhibitor. The mechanism of action of mitoxantrone is as a Topoisomerase Inhibitor.

MITOXANTRONE

MeSH Pharmacological Classification · 3건

Compounds capable of relieving pain without the loss of CONSCIOUSNESS.

Substances that inhibit or prevent the proliferation of NEOPLASMS.

Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II.

관련 반응

22건
반응 기록 만들기
HRID 65397 반응식
HRID 65397반응물로uspto-grants-1986_09
HRID 65398 반응식
HRID 65398반응물로uspto-grants-1986_09
HRID 370432 반응식
HRID 370432생성물로uspto-grants-1985_07
HRID 370573 반응식
HRID 370573반응물로uspto-grants-1985_07
HRID 370574 반응식
HRID 370574반응물로uspto-grants-1985_07
HRID 477419 반응식
HRID 477419생성물로uspto-grants-1989_12
HRID 620290 반응식
HRID 620290반응물로uspto-grants-1989_04
HRID 647783 반응식
HRID 647783반응물로uspto-grants-1983_10
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화합물 노트

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이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
물리적 상태
고체
색상
진한 파란색에서 검정색까지
InChI
InChI=1S/C22H28N4O6/c27-11-9-23-5-7-25-13-1-2-14(26-8-6-24-10-12-28)18-17(13)21(31)19-15(29)3-4-16(30)20(19)22(18)32/h1-4,23-30H,5-12H2
InChIKey
KKZJGLLVHKMTCM-UHFFFAOYSA-N
SMILES
C1(O)=C2C(C(=O)C3=C(C2=O)C(NCCNCCO)=CC=C3NCCNCCO)=C(O)C=C1

화학적 성질

Dark Blue Crystalline Solid

Exposure Routes
Intravenous injection. Poorly absorbed following oral administration.
Toxicity Summary · 1건

Mitoxantrone, a DNA-reactive agent that intercalates into deoxyribonucleic acid (DNA) through hydrogen bonding, causes crosslinks and strand breaks. Mitoxantrone also interferes with ribonucleic acid (RNA) and is a potent inhibitor of topoisomerase II, an enzyme responsible for uncoiling and repairing damaged DNA. It has a cytocidal effect on both proliferating and nonproliferating cultured human cells, suggesting lack of cell cycle phase specificity.

Signs and SymptomsSevere leukopenia with infection.
Carcinogen Classification · 6건

Mitoxantrone

Group 2B: Possibly carcinogenic to humans

Volume 76: (2000) Some Antiviral and Antineoplastic Drugs, and Other Pharmaceutical Agents

2000

1999

2B, possibly carcinogenic to humans. (L135)

Drug Induced Liver Injury · 5건

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

mitoxantrone

DILI Positive

Intravenous

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

안전 데이터

wgk
3
rtecs
CB5748500
HS 번호
2922.50.2500
risk_code
46-61-26/27/28
hazard_code
T,T+
safety_code
53-36/37/39-45-22
Absorption, Distribution and Excretion · 3건

Poorly absorbed following oral administration

1000 L/m2

21.3 L/hr/m2 [Elderly patients with breast cancer receiving IV administration of 15-90 mg/m2]

Cellular LocationsCytoplasm

용도 및 제조

Uses · 2건

Use (kg) in USA (2002): 1

For the treatment of secondary (chronic) progressive, progressive relapsing, or worsening relapsing-remitting multiple sclerosis. Mitoxantrone is an Anthracenedione (not an anthracycline) antineoplastic agent.

응용 분야

용도Mitoxantrone is a DNA intercalating drug. Mitoxantrone inhibits DNA synthesis. Mitoxantrone is used as an anti-cancer agent.

상·하류 제품 정보

상류 원료

디히드로-1,4,5,8-테트라히드록시안트라퀴논아미노에틸 에탄올아민사염화-1,4-벤조퀴논테트라메틸 에틸렌디아민2,3-디하이드로-1,4,5,8-테트라하이드록시안트라퀴논

공급사100 곳

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