| Carbadox Basic information |
| Product Name: | Carbadox |
| Synonyms: | 2-formylquinoxaline1,4-dioxidecarbomethoxyhydrazone;3-(2-chinoxalinylmethylen-1,4-dioxid)methylkarbazat;carbazicacid,3-(2-quinoxalinylmethylene)-,methylester,n(sup1),n(sup4)-di;methyl3-(2-quinoxalinylmethylene)carbazate-n1,n4-dioxide;CARBADOX;LABOTEST-BB LT00771878;2-(2-quinoxalinylmethylene)hydrazine-carboxylic acid methyl ester n,n'-dioxide;3-[2-QUINOXALINYLMETHYLENE]CARBAZIC ACID METHYL ESTER N,N'-DIOXIDE |
| CAS: | 6804-07-5 |
| MF: | C11H10N4O4 |
| MW: | 262.22 |
| EINECS: | 229-879-0 |
| Product Categories: | Veterinaries;Intermediates & Fine Chemicals;Nitric Oxide Reagents;Pharmaceuticals |
| Mol File: | 6804-07-5.mol |
| Carbadox Chemical Properties |
| Melting point | 239-240°C |
| Boiling point | 405.47°C (rough estimate) |
| density | 1.3602 (rough estimate) |
| refractive index | 1.6000 (estimate) |
| Fp | 18°(64°F) |
| storage temp. | 2-8°C |
| solubility | DMSO (Slightly, Sonicated) |
| form | powder |
| pka | 10.51±0.46(Predicted) |
| color | Yellow to Dark Yellow |
| Water Solubility | Soluble in 1N NaOH (50 mg/ml), and water (partly). |
| Stability: | Light Sensitive |
| CAS DataBase Reference | 6804-07-5 |
| EPA Substance Registry System | Hydrazinecarboxylic acid, 2-[(1,4-dioxido-2-quinoxalinyl)methylene]-, methyl ester (6804-07-5) |
| Safety Information |
| Hazard Codes | F,T |
| Risk Statements | 45-11-22 |
| Safety Statements | 53-45 |
| RIDADR | UN 1325 4.1/PG 2 |
| WGK Germany | 3 |
| RTECS | FE2779000 |
| HazardClass | 4.1 |
| HS Code | 29339900 |
| Hazardous Substances Data | 6804-07-5(Hazardous Substances Data) |
| MSDS Information |
| Provider | Language |
|---|---|
| Carbadox | English |
| SigmaAldrich | English |
| Carbadox Usage And Synthesis |
| Chemical Properties | Yellow Crystalline Solid |
| Originator | Carbadox,Agrimex |
| Uses | Carbadox has been used to suppress aldosterone production, to study the spread of shiga toxin-producing Escherichia coli (STEC) strains, and to compare different antimicrobial activities. Carbadox is a quinoxaline-di-N-oxide antibiotic that is generally used in feed to swine to prevent dysentery and improve feed efficiency. It inhibits bacteria by intercalation and induction of mutations in bacterial genome. |
| Uses | Antimicrobial |
| Manufacturing Process | A solution of methylcarbazate (48.0 mg) in methanol (250 ml) is added all at once at room temperature to a well stirred solution of 2-formylquinoxaline- 1,4-dioxide (100 g) in methanol (2.5 liters). Two drops of concentrated hydrochloric acid are added. The mixture is stirred for 3 hours then filtered to remove the yellow crystalline product. The crystals of (2- quinoxalinylmethylene)hydrazinecarboxylic acid methyl ester are washed with methanol then air dried; M.P. 234.5-236°C (dec.). Yield=121.8 g. The product is purified by refluxing in chloroform for 2 hours, followed by filtration and air drying; M.P. 239.5-240°C (dec.).The ultraviolet absorption spectrum (water) exhibits maxima at 236, 251, 303, 366 and 373 nm with extinction coefficients of 11,000, 10,900, 36,400, 16,100 and 16,200, respectively. |
| Brand name | Mecadox (Pfizer). |
| Therapeutic Function | Antibacterial |
| Biochem/physiol Actions | Carbadox is a quinoxaline-di-N-oxide antibiotic that is generally used in feed to swine to prevent dysentery and improve feed efficiency. It inhibits bacteria by intercalation and induction of mutations in bacterial genome. |
| Safety Profile | Moderately toxic by ingestion. Questionable carcinogen with experimental carcinogenic effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of Nox. |
| Carbadox Preparation Products And Raw materials |
| Raw materials | Methyl carbazate-->2-Formylquinoxaline 1,4-dioxide |
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