基本情報
- CAS
65271-80-9- 標準SMILES
O=C1c2c(O)ccc(O)c2C(=O)c2c(NCCNCCO)ccc(NCCNCCO)c21- InChIKey
KKZJGLLVHKMTCM-UHFFFAOYSA-N- 分子式
- C22H28N4O6
- 平均分子量
- 444.5 g/mol
- 単同位体質量
- 444.20088462
概要
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.
名称と識別子
- 優先名称
- Mitoxantrone
- IUPAC
- 1,4-dihydroxy-5,8-bis[2-(2-hydroxyethylamino)ethylamino]anthracene-9,10-dione
- 現地名
- ミトキサントロン
- 英語名
- Mitoxantrone
- 分子式
- C22H28N4O6
- 分子量
- 444.48
名称と別名
mitoxantrone65271-80-9MitozantroneMitoxanthroneDHAQMitoxantronMitoxantronaMitoxantronumMisostolNSC-279836NSC 279836BZ114NVM5P
名称をさらに表示
5,8-ジヒドロキシ-1,4-ビス[[2-[(2-ヒドロキシエチル)アミノ]エチル]アミノ]-9,10-アントラキノン1,4-ジヒドロキシ-5,8-ビス[2-(2-ヒドロキシエチルアミノ)エチルアミノ]-9,10-アントラキノン1,4-ジヒドロキシ-5,8-ビス[[2-[(2-ヒドロキシエチル)アミノ]エチル]アミノ]-9,10-アントラキノン1,4-ジヒドロキシ-5,8-ビス[2-(2-ヒドロキシエチルアミノ)エチルアミノ]-9,10-アントラセンジオンミトキサントロン1,4-ジヒドロキシ-5,8-ビス[[2-[(2-ヒドロキシエチル)アミノ]エチル]アミノ]-9,10-アントラセンジオン1,4-ジヒドロキシ-5,8-ビス[2-[(2-ヒドロキシエチル)アミノ]エチルアミノ]-9,10-アントラキノン1,4-ビス[[2-[(2-ヒドロキシエチル)アミノ]エチル]アミノ]-5,8-ジヒドロキシ-9,10-アントラキノン1,4-ジヒドロキシ-5,8-ビス({2-[(2-ヒドロキシエチル)アミノ]エチル}アミノ)-9,10-ジヒドロアントラセン-9,10-ジオン5,8-ジヒドロキシ-1,4-ビス(5-ヒドロキシ-3-アザペンタン-1-イルアミノ)アントラセン-9,10-ジオン1,4-ビス[2-(2-ヒドロキシエチルアミノ)エチルアミノ]-5,8-ジヒドロキシ-9,10-アントラキノンitoxantronedihydroxyanthraquinoneNSC-27983MitoxantroneBase
物性
構造計算による物性
- XLogP
- 1
- 極性表面積
- 163 Ų
- 水素結合供与体数
- 8
- 水素結合受容体数
- 10
- 回転可能結合数
- 12
- 重原子数
- 32
- 形式電荷
- 0
- 複雑度
- 571
実験および物理化学的性質
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals
LogP
-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]
物理化学的性質
- 融点
- 170 · 170-1740C
- 沸点
- 554.47 °C · 554.47°C (rough estimate)
- 比重(密度)
- 1.3049 · 1.3049 (rough estimate)
- 屈折率
- 1.65 · 1.6500 (estimate)
- 貯蔵温度
- 2 · Keep in dark place,Sealed in dry,2-8°C
- 溶解性
- DMSO（少々）、メタノール（少々）、水（少々）
- 酸解離定数(Pka)
- 5.99 · pKa 5.99 (Uncertain);8.13 (Uncertain)
- 外見
- 個体
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
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.
危険有害性情報
Regulatory InformationHazard Traits - Carcinogenicity
Hazard Classes and CategoriesCarc. 2 (100%)
毒性情報
Health EffectsCardiomyopathy is a particularly concerning effect as it is irreversible. [Wikipedia]
Hepatotoxicity
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.
化学と産業
薬理情報
ATC Code
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
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
Hepatic
Hepatic Half Life: 75 hours
FDA Pharmacological Classification
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
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.
関連反応
22 件
化合物ノート
読み込み中…