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曲他齐卡

曲他齐卡用途

CB1954(Tretazicar)是一种抗癌前体药物，在NQO2酶和共基质caricotamide(EP-0152R)存在的情况下转化为有效的、具有细胞毒性的双功能烷化剂。它可以被NQO2活化。

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曲他齐卡名称

[ CAS 号 ]:
21919-05-1

[ 中文名 ]:
5-(1-氮杂环丙基)-2,4-二硝基苯甲酰胺

[ 英文名 ]:
CB 1954

[中文别名 ]:

曲他齐卡

[英文别名 ]:

5-(1-Aziridinyl)-2,4-dinitrobenzamide
2,4-Dinitro-5-ethyleneiminobenzamide
2,4-Dinitroethyleneiminobenzamide
5-(aziridyn-1-yl)-2,4-dinitrobenzamide
Benzamide, 5-(1-aziridinyl)-2,4-dinitro-
5-Aziridinyl-2,4-dinitrobenzamide
CB-1954
5-(Aziridin-1-yl)-2,4-dinitrobenzamide
Tretazicar
1 (5 carbamoyl 2,4 dinitrophenyl)aziridine

曲他齐卡生物活性

[ 描述 ]:

Tretazicar (CB 1954) 是一种抗肿瘤前药,对 Walker 256 大鼠肿瘤细胞系具有很高的效力和选择性。Tretazicar 酶促活化后生成双功能试剂,该试剂可以形成 DNA-DNA 链间交联。大鼠细胞中的 Tretazicar 涉及通过酶 NAD(P)H：醌氧化还原酶1 (NQO1) 将其 4-硝基还原为 4-羟基胺。

[ 相关类别 ]:

研究领域 >> 癌症

信号通路 >> 细胞周期/DNA损伤 >> DNA烷基化剂/交联剂

[体外研究]

Tretazicar(CB 1954)(0.1-1000μM；3天)对逆转录病毒转导的AB22(AB22-nr)细胞具有敏感性,IC50为3μM[3]。受影响细胞中的DNA交联形成是Walker细胞中DT-心肌黄酶(NAD(P)H脱氢酶(醌))对药物的生物活化的结果,其还原了Tretazicar的4-硝基。该反应的产物是双官能烷化剂,5-氮丙啶-1-基-4-羟胺基-2-硝基苯甲酰胺[4]。

[体内研究]

Tretazicar(CB 1954)(80mg/kg；第2天和第9天腹膜内注射)导致存活率显着增加[3]。动物模型：雌性BALB/c小鼠(AB22 nr,SKOV3人卵巢肿瘤异种移植物)[3]剂量：80mg/kg给药：第2天和第9天腹膜内给药结果：AB22 nr的中位存活期为49天。导致生存率显着提高。

[参考文献]

[1]. Knox RJ,et al. Bioactivation of 5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB 1954) by human NAD(P)H quinone oxidoreductase 2: a novel co-substrate-mediated antitumor prodrug therapy. Cancer Res. 2000 Aug 1;60(15):4179-86.

[2]. Knox RJ, et al. CB 1954: from the Walker tumor to NQO2 and VDEPT. Curr Pharm Des. 2003;9(26):2091-104.

[3]. Green NK, et al. Immune enhancement of nitroreductase-induced cytotoxicity: studies using a bicistronicadenovirus vector. Int J Cancer. 2003 Mar 10;104(1):104-12.

[4]. Drabek D, et al. The expression of bacterial nitroreductase in transgenic mice results in specific cell killing by the prodrug CB1954. Gene Ther. 1997 Feb;4(2):93-100.

曲他齐卡物理化学性质

[ 密度 ]:
1.7±0.1 g/cm3

[ 沸点 ]:
427.2±45.0 °C at 760 mmHg

[ 熔点 ]:
173 °C

[ 分子式 ]:
C₉H₈N₄O₅

[ 分子量 ]:
252.184

[ 闪点 ]:
212.2±28.7 °C

[ 精确质量 ]:
252.049469

[ PSA ]:
137.74000

[ LogP ]:
1.28

[ 外观性状 ]:
固体;White to Yellow to Orange powder to crystal

[ 蒸汽压 ]:
0.0±1.0 mmHg at 25°C

[ 折射率 ]:
1.715

[ 储存条件 ]:
-20°C;存放于惰性气体之中;避免空气,加热

曲他齐卡MSDS

详细MSDS(安全技术说明书)

曲他齐卡毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CV2345000

CHEMICAL NAME :: Benzamide, 5-(1-aziridinyl)-2,4-dinitro-

CAS REGISTRY NUMBER :: 21919-05-1

LAST UPDATED :: 199612

DATA ITEMS CITED :: 10

MOLECULAR FORMULA :: C9-H8-N4-O5

MOLECULAR WEIGHT :: 252.21

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 29 mg/kg

TOXIC EFFECTS :: Gastrointestinal - gastritis Gastrointestinal - ulceration or bleeding from stomach Blood - hemorrhage

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 22 mg/kg

TOXIC EFFECTS :: Gastrointestinal - gastritis Gastrointestinal - ulceration or bleeding from stomach Blood - hemorrhage

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 22 mg/kg

TOXIC EFFECTS :: Gastrointestinal - gastritis Gastrointestinal - ulceration or bleeding from stomach Blood - hemorrhage

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraduodenal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 10 mg/kg

TOXIC EFFECTS :: Gastrointestinal - gastritis Gastrointestinal - ulceration or bleeding from stomach Blood - hemorrhage

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 176 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: DNA damage

TEST SYSTEM :: Rodent - hamster Lung

DOSE/DURATION :: 10 umol/L

REFERENCE :: BCPCA6 Biochemical Pharmacology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1- 1958- Volume(issue)/page/year: 37,4661,1988

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曲他齐卡安全信息

[ 个人防护装备 ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ 危险品运输编码 ]:
NONH for all modes of transport

[ 海关编码 ]:
2933990090

曲他齐卡海关

[ 海关编码 ]: 2933990090

[ 中文概述 ]:
2933990090. 其他仅含氮杂原子的杂环化合物. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:20.0%

[ 申报要素 ]: 品名, 成分含量, 用途, 乌洛托品请注明外观, 6－己内酰胺请注明外观, 签约日期

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

曲他齐卡文献

An unusually cold active nitroreductase for prodrug activations

Bioorg. Med. Chem. 20(11) , 3540-50, (2012)

A set of PCR primers based on the genome sequence were used to clone a gene encoding a hypothetical nitroreductases (named as Ssap-NtrB) from uropathogenic staphylococcus, Staphylococcus saprophyticus...

uvrB gene deletion enhances SOS chromotest sensitivity for nitroreductases that preferentially generate the 4-hydroxylamine metabolite of the anti-cancer prodrug CB1954.

J. Biotechnol. 150(1) , 190-4, (2010)

CB1954 is an anti-cancer prodrug that can be reduced at either of two nitro groups to form cytotoxic metabolites. We describe here two efficient and previously uncharacterized nitroreductases, YfkO fr...

CB 1954: from the Walker tumor to NQO2 and VDEPT.

Curr. Pharm. Des. 9(26) , 2091-104, (2003)

CB 1954 [5-(aziridin-1-yl)-2,4-dinitrobenzamide] has been the subject of continued interest for over 30 years. As an anti-cancer agent, it represents one of the very few examples of a compound that sh...

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