CAS Number21919-05-1
Synonyms5-(1-Aziridinyl)-2,4-dinitrobenzamide; 2,4-Dinitro-5-ethyleneiminobenzamide; 2,4-Dinitroethyleneiminobenzamide; 5-(aziridyn-1-yl)-2,4-dinitrobenzamide; 5-Aziridinyl-2,4-dinitrobenzamide; CB-1954; 5-(Aziridin-1-yl)-2,4-dinitrobenzamide; Tretazicar; 5-aziridino-2,4-dinitrobenzamide
Molecular FormulaC9H8N4O5
Molecular Weight252.184
Purity≥94 (HPLC)%
Density1.7±0.1 g/cm3
Boiling Point427.2±45.0 °C at 760 mmHg
Melting Point173 °C
Appearancesolid
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 21919-05-1 |
| Catalog No. | 2A-9038822 |
| Chinese Name | 曲他齐卡 |
| Synonyms | 5-(1-Aziridinyl)-2,4-dinitrobenzamide; 2,4-Dinitro-5-ethyleneiminobenzamide; 2,4-Dinitroethyleneiminobenzamide; 5-(aziridyn-1-yl)-2,4-dinitrobenzamide; 5-Aziridinyl-2,4-dinitrobenzamide; CB-1954; 5-(Aziridin-1-yl)-2,4-dinitrobenzamide; Tretazicar; 5-aziridino-2,4-dinitrobenzamide |
| Molecular Formula | C9H8N4O5 |
| Molecular Weight | 252.184 |
| Purity | ≥94 (HPLC) |
| Density | 1.7±0.1 g/cm3 |
| Boiling Point | 427.2±45.0 °C at 760 mmHg |
| Melting Point | 173 °C |
| Appearance | solid |
| Storage Condition | -20°C; store in inert gas; avoid air, heat |
| Application | Tretazicar (CB 1954) is an antineoplastic prodrug with high potency and selectivity against the Walker 256 rat tumor cell line. Enzymatic activation of Tretazicar generates a bifunctional reagent that |
| HTC | 2933990090 |
| PubChem ID | 24278301 |
| MDL Number | MFCD00869490 |
| SMILES | NC(=O)c1cc(N2CC2)c(cc1[N+]([O-])=O)[N+]([O-])=O |
| InChI | 1S/C9H8N4O5/c10-9(14)5-3-7(11-1-2-11)8(13(17)18)4-6(5)12(15)16/h3-4H,1-2H2,(H2,10,14) |
| InChI Key | WOCXQMCIOTUMJV-UHFFFAOYSA-N |
| NACRES Code | NA.32 |
| UNSPSC | 12352204 |
| Hazard Symbols | GHS |
| MSDS | msds/38822_1_21919_05_1.pdf |
| Bioactivity | Tretazicar (CB 1954), an antitumor prodrug, is highly selective against the Walker 256 rat tumour line. Tretazicar is enzymatically activated to generate a bifunctional agent, which can form DNA-DNA interstrand cross-links. Tretazicar in rat cells involves the reduction of its 4-nitro group to a 4-hydroxylamine by the enzyme NAD(P)H:quinone oxidoreductase 1 (NQO1)[1][2]. Related Catalog Research Areas >> Cancer Signaling Pathways >> Cell Cycle/DNA Damage >> DNA Alkylator/Crosslinker In Vitro Tretazicar (CB 1954) (0.1-1000 μM; 3 days) has sensitivity for retrovirally transduced AB22 (AB22-nr) cells with an IC50 of 3 μM[3]. DNA cross-link formation in affected cells is a result of the bioactivation of the drug by the enzyme DT diaphorase (NAD(P)H dehydro-genase (quinone)) in the Walker cells which reduces the 4-nitro group of Tretazicar. The product of this reaction is a difunctional alkylating agent, 5-aziridin-1-yl-4-hydroxylamino-2-nitrobenzamide[4]. In Vivo Tretazicar (CB 1954) (80 mg/kg; i.p. on days 2 and 9) results in a significant increase in survival[3]. Animal Model: Female BALB/c mice (AB22-nr, SKOV3 human ovarian tumour xenograft)[3] Dosage: 80 mg/kg Administration: i.p. on days 2 and 9 Result: The median survival of the AB22-nr was 49 days. Resulted in a significant increase in survival. References [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. Chemical & Physical Properties Density 1.7±0.1 g/cm3 Boiling Point 427.2±45.0 °C at 760 mmHg Melting Point 173 °C Molecular Formula C9H8N4O5 Molecular Weight 252.184 Flash Point 212.2±28.7 °C Exact Mass 252.049469 PSA 137.74000 LogP 1.28 Vapour Pressure 0.0±1.0 mmHg at 25°C Index of Refraction 1.715 InChIKey WOCXQMCIOTUMJV-UHFFFAOYSA-N SMILES NC(=O)c1cc(N2CC2)c([N+](=O)[O-])cc1[N+](=O)[O-] |
| Use of | Tretazicar (CB 1954), an antitumor prodrug, is highly selective against the Walker 256 rat tumour line. Tretazicar is enzymatically activated to generate a bifunctional agent, which can form DNA-DNA interstrand cross-links. Tretazicar in rat cells involves the reduction of its 4-nitro group to a 4-hydroxylamine by the enzyme NAD(P)H:quinone oxidoreductase 1 (NQO1)[1][2]. Properties Articles29 Name 5-(aziridin-1-yl)-2,4-dinitrobenzamide Synonym More Synonyms CB 1954 Biological Activity Description Tretazicar (CB 1954), an antitumor prodrug, is highly selective against the Walker 256 rat tumour line. Tretazicar is enzymatically activated to generate a bifunctional agent, which can form DNA-DNA interstrand cross-links. Tretazicar in rat cells involves the reduction of its 4-nitro group to a 4-hydroxylamine by the enzyme NAD(P)H:quinone oxidoreductase 1 (NQO1)[1][2]. Related Catalog Research Areas >> Cancer Signaling Pathways >> Cell Cycle/DNA Damage >> DNA Alkylator/Crosslinker In Vitro Tretazicar (CB 1954) (0.1-1000 μM; 3 days) has sensitivity for retrovirally transduced AB22 (AB22-nr) cells with an IC50 of 3 μM[3]. DNA cross-link formation in affected cells is a result of the bioactivation of the drug by the enzyme DT diaphorase (NAD(P)H dehydro-genase (quinone)) in the Walker cells which reduces the 4-nitro group of Tretazicar. The product of this reaction is a difunctional alkylating agent, 5-aziridin-1-yl-4-hydroxylamino-2-nitrobenzamide[4]. References [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. Chemical & Physical Properties Molecular Formula C9H8N4O5 Exact Mass 252.049469 PSA 137.74000 Index of Refraction 1.715 InChIKey WOCXQMCIOTUMJV-UHFFFAOYSA-N |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special precautions No data available |
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