Tretazicar
Basic information
- CAS
21919-05-1- Standard SMILES
NC(=O)c1cc(N2CC2)c([N+](=O)[O-])cc1[N+](=O)[O-]- InChIKey
WOCXQMCIOTUMJV-UHFFFAOYSA-N- Molecular formula
- C9H8N4O5
- Average molar mass
- 252.18 g/mol
- Monoisotopic mass
- 252.04946937
Overview
Tretazicar is under investigation in clinical trial NCT00746590 (Study of Anti-tumour Effects and Safety of Prolarix™ in Hepatocellular Carcinoma).
Names & identifiers
- Preferred name
- Tretazicar
- IUPAC
- 5-(aziridin-1-yl)-2,4-dinitrobenzamide
- English name
- 5-Aziridino-2,4-dinitrobenzamide
- Molecular formula
- C9H8N4O5
- Molecular weight
- 252.18
Names & synonyms
Tretazicar21919-05-15-(AZIRIDIN-1-YL)-2,4-DINITROBENZAMIDE5-(1-Aziridinyl)-2,4-dinitrobenzamideCB-19545-Aziridinyl-2,4-dinitrobenzamideNSC-1158297865D5D01Maziridine dinitrobenzamide5-[aziridin-1-yl]-2,4-dinitrobenzamidetretazicarumRefChem:190772
Show more names
CB-954NSC 115829Tretazicar (>Tretazicar (>94%)CB1954(TRETAZICAR)Tretazicar (CB 1954)Tretazicar, 10 mM in DMSO
CB 1954CB19545-Aziridino-2,4-dinitrobenzamideTretazicar [INN]Benzamide,5-(1-aziridinyl)-2,4-dinitro-2,4-DinitroethyleneiminobenzamideTretazicar (>94%)MFCD00869490
Database identifiers
- CAS
21919-05-1- PubChem CID
- 89105
- DTXSID
DTXSID00176335- ChEMBL
CHEMBL23330- UNII
- 7865D5D01M
- EC Number
- 606-863-5
- Nikkaji
- J22.077I
Properties
Computed structural properties
- XLogP
- 0
- Topological polar surface area
- 138 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 2
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 385
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP0.2
Physicochemical properties
- Melting point
- 173 °C · 173 °C
- Boiling point
- 427.2 · 427.2±45.0 °C(Predicted)
- Density
- 1.671 · 1.671±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- Acetonitrile (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
- pka
- 14.23 · 14.23±0.50(Predicted)
- form
- solid
- color
- Yellow to Dark Yellow
- 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)
- InChIKey
- WOCXQMCIOTUMJV-UHFFFAOYSA-N
- SMILES
- NC(=O)c1cc(N2CC2)c(cc1[N+]([O-])=O)[N+]([O-])=O
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 2933.99.7500
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Precautionary statements
- P280-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Drugs used to potentiate the effectiveness of radiation therapy in destroying unwanted cells.
Applications
DescriptionCB-1954 is a prodrug that is enzymatically activated to generate an antitumor agent that forms DNA-DNA interstrand crosslinks. In rat Walker 256 carcinoma cells, CB-1954 is reduced by NAD(P)H:quinone oxidoreductase (NQO1) to the cytotoxic derivative 5-(aziridin-1-yl)-4-hydroxylamineo 2 nitrobenzamide, a bifunctional alkylating agent.
Uses5-Aziridino-2,4-dinitrobenzamide is an anticancer prodrug used in gene therapy research and is known to be activated by NAD(P)H Quinone Oxidoreductase 2.
UsesTretazicar is an anticancer prodrug used in gene therapy research and is known to be activated by NAD(P)H Quinone Oxidoreductase 2.
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